Molecules - Fascinating Facts

In this section we present some of the chemical substances in our catalog - with entertaining stories, scientific background, interesting applications and literature references. Almost every molecule has a lot to tell!

 Luc-B.cereus Na
  

      

Luc-B.cereus Na
(L-8275)

Bacillus cereus is a rod-shaped beta hemolytic bacterium commonly found in food and soil. Some strains can be associated with food intoxications, mainly from raw meat and poultry products. One example is the so called “fried rice syndrome”, that occurs when dishes containing cooked rice are left for several hours at room temperature. Typical symptoms of the infection include severe nausea, vomiting and diarrhea. Some strains of Bacillus cereus on the contrary are not harmful at all and they are used as probiotics food additives in animal farming to reduce the presence of other pathogens like Salmonella in the cecum end intestine. Bacillus cereus expresses phosphatidyl-choline specific phospholipase C (PC-PLC), encoded by the plc gene, which is regulated by PlcR. In addition, the expression of PlcR is dependent on the growth medium. Luc-B.cereus Na (L-8275) is a synthetic chemiluminescent substrate for the phosphatidyl-choline specific phospholipase C. The enzyme cleaves off phosphocholine from L-8275, leading to the release of D-Luc, and consequent strong light emission B. cereus culture exhibited strong luminescence, while RLU values were much lower for samples with B. thuringiensis.

Harmane (H-1150) and Norharmane (N-8700)

Norharmane and Harmane are both members of the class of beta-carbolines. They are known to be endogenously formed body constituents, but external sources have also been identified. For example, tobacco smoke and certain processed meat contain small amounts of the compounds (J. Chromatogr. B). Plants containing these alkaloids are originally used in hallucinogenic drinks or snuffs in religious ceremonies particularly in the Amazon basin. The neurological effects of beta-carbolines are well characterized at the molecular level. In addition, Norharmane and Harmane show molecular similarity to Parkinson-inducing neurotoxins and as a result these compounds have been studied extensively to identify their connection to idiopathic Parkinson’s disease. Indeed, it has been noted that the concentration of Harmane in the blood seems to be elevated in Parkinson’s disease patients. (NeuroToxicology)

           





Apstatin
  

      

Apstatin
(J-009728)

The concentration of hormones in the body is highly regulated. For example, the peptide hormone Bradykinin (Bk) is almost completely inactivated during a single circulation through the lung. The Bk half-life is controlled by two enzymes: the angiotensin-converting enzyme (ACE) and aminopeptidase P (APP). Several specific ACE inhibitors are known, e.g. Enalapril (Biosynth Cat.No. J-032735) and Lisinopril (Cat.No. Q-201310). But studies to determine the role of APP have been hampered by the lack of a specific APP inhibitor. With the introduction of Apstatin an APP inhibitor became available (Prechel et al. 1995). Together with ACE inhibitors, Apstatin can completely block the degradation of Bk in the pulmonary circulation. Today, a number of studies demonstrate that Apstatin reduces myocardial infarcts in vivo by a Bk-dependent pathway. Buy Apstatin for your research in the Biosynth online store.

Melatonin (M-1200)

Melatonin is a neurotransmitter produced by the pineal gland that is involved in the regulation of sleep-wake cycles. It can be used to treat several conditions like shift work disorders, insomnia, jet-lag and alterations of the circadian rhythm. Some authors also proposed the use of melatonin against cognitive
disorders. In an interesting research conducted on zebrafish (Science, 2007, 1144-1146) it was found that memory formation occurs better during daytime compared to nighttime, suggesting a role of melatonin in this process. When melatonin was administered during daytime it caused reduced memory formation. On the contrary, removing the pineal gland or treating the
fish with a melatonin antagonist significantly improves nighttime memory
formation.

           






  

      

L-Malic acid
(M-0850)


Malic acid is the most abundant carboxylic acid in apple, apricots, grapes and many other fruits and it is responsible for the characteristic taste of green apple. The function of this peculiar taste is that a certain amount of malic acid in unripe fruits prevents animals to eat the fruits spreading immature seeds, ensuring the reproduction of the plant. Indeed, the malic acid concentration decreases when the fruit ripens. In cider production, the malolactic fermentation (MLF) is, besides the alcoholic fermentation, the main biochemical pathway. During the MLF, malic acid is converted into the much milder lactic acid influencing the taste of the cider. Every producer of cider has his own unique taste, therefore the MLF is either desirable, suppressed or regulated depending on the desired results. Interestingly, some cider manufacturers even add external malic acid at the end of the process to adjust taste and acidity and also for its preserving properties.

DMNPE-caged Luciferin (L-8300)

DMNPE-caged Luciferin is a photoactivatable probe that can easily penetrate the cell membrane, and by exposure to UV light it undergoes a photochemical decomposition liberating a Luciferin molecule. Once exposed to Luciferase enzyme expressed by the cells, Luciferin emits visible (and measurable) light. Using
this technique, imaging of luciferase activity was performed both in living cells and in mouse tumor xenograft, by intraperitoneal injection of the caged DMNPE luciferin (Chem. Commun., 2009, 0, 4028-4030).

           






  

      

Ac-DEVD-6-Amino-D-Luciferin
(L-8282)


Caspases are a family of protease enzymes playing essential roles in programmed cell death and inflammation. The acronym caspase stands for Cysteine Aspartic Acid Specific Protease due to their specific cleavage of an aspartic acid residue, by mean of a cysteine in the catalytic site of the enzyme.
About 11 or 12 different caspases are known in humans and 10 in mice, participating in numerous different cellular functions. Caspase deficiency, for example, has been identified as a cause of tumor development, while over-activation of some caspases such as caspase-3 can lead to excessive apoptosis that can be observed in several neurodegenerative diseases. Caspases cleave proteins at specific peptide recognition sequences. Ac-DEVD-6-Amino-D-Luciferin (Ac-Asp-Glu-Val-Asp-6-Amino-D-Luciferin, Cat.No
L-8282) is a synthetic chemiluminescent peptide for the determination of caspase-3 and caspase-7activity.

6-Azauracil (A-9700)

Purine and pyrimidine analogues have been extensively studied for their wide therapeutic potential as antimetabolites and their ability to inhibit the growth of various microorganisms, viruses and cancer cells. Modified nucleic acid bases act by replacing the organisms own bases and consequently disrupting the nucleic acid replication, inhibiting the cellular multiplication. The pyrimidine analogue 6-Azauracil has been known since many years for its bacteriostatic and tumor growth inhibition effects, even though it did not enter clinical use. Rather, 6-Azauracil is frequently used in yeast sensitivity assays where it causes a reduction of intracellular GTP levels inhibiting the yeast’s growth.

           






  

      

APTS
(J-100021)

APTS (8-Aminopyrene-1,3,6-trisulfonic acid, trisodium salt) is a fluorescent amine that is frequently used in the detection and differentiation of sugars or glycoconjugates like glycoproteins or certain hormones. Conjugation of the APTS with carbohydrates for example is performed by reductive amination of the aldehyde (or ketone) group of the sugar with APTS to form an imine, which is then reduced with sodium cyanoborohydride (NaBH3CN). The fluorophore remains stable under the reaction conditions described and provides a very sensitive detection method for the APTS-coupled molecule using laser-induced fluorescence. Find a number of example protocols and comprehensive technical data in our corresponding APTS Product info sheet.

Anthrone(A-8100)

Anthrone is a reagent used for qualitative assays and for the quantitative colorimetric determination of carbohydrates. Numerous assay kits based on Anthrone are available on the market. The Anthrone assay allows the estimation of the total amount of sugars in a given sample. Initially the sample is treated with concentrated sulfuric acid to hydrolyze polysaccharides into monosaccharides and to dehydrate the monosaccharides to a furfuraldehyde derivative. The latter reacts with Anthrone forming a blue-greenish colored complex which can be analyzed by UV spectroscopy. Interestingly, Anthrone can be extracted from some plants, and it is also known for its sweet-smelling characteristics. An early report on the use of Anthrone for sugar determination can be found here: Nature,1952, 626–627.

           






  

      

Atropine sulfate anhydrous
(Q-200660)

Atropine occurs in various plants of the nightshade (or Solanaceae) family which also includes the famous belladonna (deadly nightshade) and jimson weed. Since Atropine works by reducing the activity of the parasympathetic nervous system, this propane-alkaloid can be used in a number of applications, for example to treat bradycardia and to inhibit excessive secretions of the salivary and mucous glands. It can also be used to treat hyperhidrosis. Another typical use of atropine is in eye drops used to dilate the pupils, eliminate the eye's accommodation ability in order to facilitate eye examination, or treat eye conditions like uveitis. Furthermore, Atropine is an effective antidote against cholinesterase inhibitors, which are found in pesticides, venoms and poisons. Interestingly during the renaissance period, ladies used eye drops based on belladonna extracts to look even more beautiful (due to the dilation of pupils caused by atropine) – hence the name of the plant Atropa Belladonna (belladonna = beautiful woman).

Caffeic acid phenethyl ester (C-1400)

Caffeic acid phenethyl ester (CAPE) is an active phenolic compound found in honeybee propolis that has the potential to downregulate inflammation in mammals. Studies demonstrated that CAPE specifically inhibits the protein complex NFƙB - a key player in inflammation, associated with the pathogenesis of chronic inflammatory diseases. Moreover, CAPE inhibits the activity of the enzyme cyclooxygenase and the production of nitric oxide by macrophages, also responsible for inflammation. By acting on T cells, CAPE can reduce the production of pro-inflammatory cytokines and increase the production of anti-inflammatory ones, leading to a less overwhelming immune response to allergens. Buy CAPE for your research at the Biosynth online store Cat. No. C-1400

           






  

      

Coelenterazine, native
(C-7001)

Coelenterazine is the substrate for the enzymes Renilla luciferase, Gaussia luciferase and other luciferase enzymes. Marine organisms like squids, shrimps, fish and jellyfish use coelenterazine to produce spectacular bioluminescence (in analogy with insects which utilize firefly luciferine). Today, coelenterazine is used in numerous applications like immunoassays, ELISA, and protein based calcium indicators. The isolation and structure determination of coelenterazine was reported independently by two different groups in the seventies who discovered the molecule in sea pansy (Renilla reniformis) and in the cnidarian Aequorea victoria, respectively. Interestingly (PNAS 98 (20): 11148–51) it was also found that the luminescent jellyfish Aequorea victoria does not produce coelenterazine itself but it rather assimilates it through ingestion of small preys like shrimps and copepods. Browse Biosynth’s catalogue to find all major coelenterazine derivatives.

WST-8
(J-012505)

Tetrazolium compounds such as WST-1 and WST-8 are sensitive chromogenic indicators for NADH. Quantification of cell proliferation, cell viability test as well as cytotoxicity assays are also routinely performed using WSTs, which are known to be more sensitive than traditional tetrazolium salts, such as NBT, XTT and MTT. Additionally, since the classic formazan dyes are water-insoluble, when they are used in assays a solubilization step is usually required, which may lead to reduced reproducibility. To overcome this problem, the Water Soluble Tetrazolium salts (WST) a new generation of tetrazolium salts have been developed. Get Biosynth foramzan dyes, both the classical and the new ones.

           





  

      

EDOT
(Q-200346)

EDOT is a colorless viscous liquid used as a precursor for the synthesis of the PEDOT polymer, a conductive material frequently used in the production of displays, photovoltaics and sensors. Recent studies revealed that PEDOT doped with heparin and dodecyl benzyl sulfonate (DBS) can modulate the Salmonella biofilm formation on electrochemically active surfaces. By applying a small voltage, the polymer’s surface can either favor bacterial adhesion and growth or to inhibit it. As a result, Bacteria form a dense biofilm at the anodic pole, while at the cathode the biofilm formation is not observed. Favoring biofilm growth can be useful for example in the production of microbial fuel cells, while PEDOT derivatives can be applied as an antifouling coating for medical devices or to prevent the formation of biofilms whenever necessary. (Gomez-Carretero, S.; Libberton, B.; Rhen, M.; Richter-Dahlfors, A., npj Biofilms and Microbiomes 2017, 3 (1), 19.)

Corydaline
(C-7350)

Inhibition of acetylcholinesterase (AChE) leads to accumulation of acetylcholine in the synaptic cleft causing overstimulation of nicotinic and muscarinic receptors and alteration for the neurotransmission signal. Molecules that can inhibit acetylcholinesterase have important pharmacological and toxicological properties. For example reversible inhibitors of AChE are commonly employed for the treatment of cognitive and neurodegenerative disorders (Alzheimer’s disease), while irreversible inhibitors are used as pesticides, insecticides and nerve agents. Corydaline is a well known alkaloid found in the plant Corydalis yanhusuo which displays significant AChe inhibition properties. Recently, (Biological & Pharmaceutical Bulletin, 2010, 958-62) it was found that Corydaline can also accelerate gastric emptying and gastric relaxation in animal model.

           





  

      

Chrysanthemin
(Q-100788)

Anthocyanins are a group of pigments responsible for blue, red or purple colors of flowers, leafs and fruits like blueberry, raspberry and grapes. The color of anthocyanins depends largely on their structure (for example on the position and type of sugars attached), as well as on external factors like pH. Recently, a new blue wine product was invented, which was made adopting anthocyanins and some indole-type compounds in the wine making process. Interestingly, anthocyanins are generally thought to have the function to protect the plant from excessive sun exposure, and in addition they are considered to be healthy for human consumption. Read more here. Biosynth’s Chrysanthemin (one of the most abundant antocyanins in plants) is available online.

 

n-Octyl-beta-D-thioglucopyranoside (OTG)
(O-2710)

OTG is applied for the solubilization and purification of membrane and membrane-associated proteins. It allows for the isolation of intact macromolecular complexes without affecting protein-protein interactions. The non-ionic detergent belongs to the top 20 detergents employed for membrane protein purification and crystallization. The solubilizing power of OTG for E.coli membrane proteins is similar to that of another frequently used substance, octyl glucoside (Cat. No. O-2000). For the best results protocols and detergent concentrations need to be adapted to the respective target protein and sample source. Find example protocols in our Product info sheet.

           




  

      

Geosmin
(J-012735)

Geosmin is an “earth” smelling substance that is produced by soil bacteria like Streptomyces.
Together with other substances, geosmin is a  key constituent of petrichor, the pleasant scent released in the air from soil during a rain fall. The mechanism for the liberation of geosmin and other substances after the impact of rain droplets with the soil was demonstrated only recently (Nature Commun., 2015, 6083). Interestingly, Geosmin is responsible for the characteristic muddy taste of certain fish like carp and catfish. Fortunately, however, the molecule decomposes under acidic conditions and the unpleasant taste can be reduced by simple treatment with vinegar.

 

Betanin
(J-926108)

The decoration of eggs is a popular tradition during Easter time, particularly appreciated among children. In order to prepare the eggs for the coloring, they have to be treated first with a weak acid, typically vinegar. In this pretreatment, the shell is slightly roughened and the proteins contained in the deeper layers are protonated so that the dye can be better absorbed giving a more intense color tone. One of the many natural substances used to color eggs is betanin, an intense glycoconjugate dye from beetroot, which is commonly used as a food additive (E162). Interestingly, betanin is also well known for the fact that its color is pH-dependent, ranging from red to blue-violet at increasing pH values.

           





  

      

alpha-Naphthaleneacetic acid, NAA
(N-1420)

NAA is a plant growth regulator of the auxin family that promotes cell division. The procedures to apply NAA are fairly simple and it is widely used in plant biotechnology today. For example, seedlings of flowering plants are soaked for 24 hours in the dark in a NAA solution. At a concentration of 0.1 ppm NAA this procedure shortens the time of inducing flowering by approximately one week. In addition, the same treatment increased the number of flowers significantly. This growth regulator may be simply added to the culture media as well; e.g. NAA is an ingredient of orchid callus media. Find the full composition of these orchid media and 100 more media recipes on Biosynth's plant biotechnology page. Biosynth offers NAA at a great price - Buy NAA (Cat.No. N-1420) online in our web store.

L-Albizziine
(A-4650 )

Asparagus is “the” spring vegetable. Apart from being highly nutritious and rich in vitamines C and B9, it is also rich in the important amino acid Asparagine which was indeed firstly discovered in asparagus extracts. The biosynthesis of Asparagine from Aspartate is mediated by the enzyme asparagine synthetase, which can be inhibited by the amino acid Albizziin . Recently, (Nature 2018 doi:10.1038/nature25465) a correlation between asparagine synthetase expression and risk of later metastatic relapse, as well as the influence of asparagine bioavailability on metastatic potential were evaluated.

           





  

      

 Indican
(I-6045)

The Blue Jeans – started 150 years ago as workwear, found nowadays in almost every wardrobe. Their renowned indigo color tone is truly unique; nevertheless, the high demand for the dye poses serious sustainability and environmental problems connected with its manufacturing process. Recently, a group of scientists presented an alternative indigo dyeing method inspired by the indoxyl glucoconjugate present in the plant P.tinctorium. The researchers proposed as an alternative approach a biocatalytic process using recombinant E.coli to access water soluble β-gluco-indoxyl (indican). At the point of coloring, indican gets hydrolyzed by β-glucosidase enzymes forming indoxyl, which suddenly undergoes oxidation to leucoindigo and further crystallizes to indigo giving the typical blue denim its peculiar character. Read More on www.nature.com

D-Trehalose dihydrate
(T-5000)

Trehalose is a naturally occurring disaccharide found in many organisms - except from mammals. Its role in nature is as versatile as its applications in the laboratory. Trehalose is synthesized by cells in response to stress and helps retaining the cellular integrity under tough conditions: An important function of Trehalose is to stabilize protein structures and to prevent proteins from their degradation. Researchers use Trehalose for instance as a carbon source in selective microbiological media, as desiccation protectant and for cryoprotection. Buy high quality D-Trehalose dihydrate here

           





  

      

 N-Acetylneuraminic acid
(A-1600)

N-Acetylneuraminic acid (Neu5Ac or NANA) belongs to the family of sialic acids, carbohydrates with a rather unusual structure which can be found in almost every cell. Sialic acids are present in the cell surface as glycoconjugates functioning as important cellular recognition elements. Neu5Ac is also involved in the attachment of viruses to the host cell surface and in the virus spread after multiplication through the action of neuraminidase. Several neuraminidase inhibitors have been marketed indeed against viral infections. An account on virus-sialic acid interactions can be found here: Nat Rev Microbiol. doi:
10.1038/nrmicro3346.

L-Carnosine
(C-2000)

L-Carnosine is a dipeptide consisting of beta-Alanine and L-Histidine which is abundant in brain and muscles. This simple dipeptide is considered to act as an antioxidant and as a neutralizing agent for excess lactic acid generated during exercise, which can explain the elevated L-Carnosine concentration in 400m sprinter’s muscles. Additionally, the dipeptide is able to chelate copper and zinc ions, which are ubiquitous in the nervous system and are also thought to be involved in the clinical course of Alzheimer’s disease and Autistic Spectrum Disorders, although the mechanism of action is not fully understood. A study including children with Autistic Spectrum Disorder suggests that the supplementation with carnosine can significantly improve speech and behavior. (https://www.ncbi.nlm.nih.gov/pubmed/12585724).

           



  

      

D-Arabitol
(A-8270)

D-Arabitol (or D-Arabinitol) is the reduced alcohol form of Arabinose. Arabitol is a commonly used food supplement, it is comparably sweet to sucrose but the oral flora cannot metabolize Arabitol, and hence protects from caries. Arabitol plays also an important role in energy controlled diets since it is absorbed slowly by the human digestive tract and has a low caloric content. The differential metabolism of the Arabitol D- and L-forms suggested its use in microbiological diagnostics (Bernard, E.M. et al. 1981) and became a routine urine laboratory test: L-Arabitol is metabolized by a variety of different bacteria and fungi utilizing an arabitol dehydrogenase enzyme. Therefore, it serves as a biomarker for, e.g., invasive candidiasis, since an infection results in an elevated urine D-Arabitol/L-Arabitol (DA/LA) ratio. Biosynth offers both isomers in research grade: D-Arabitol (A-8270) and L-Arabitol (A-8280).

Deferoxamine
(D-0675)

Deferoxamine is a very well known drug for the treatment of iron excess occurring in patients with thalassemia who are receiving regular transfusions. Excessive iron intake from diet may also cause accumulation of the metal ions which result in several symptoms such as metabolic acidosis and hypovolemic shock. The mechanism of action of Deferoxamine is based on its ability to chelate iron and other metal ions (i.e. aluminum) permitting their rapid urinary elimination. Recently, another potential therapeutic uses of Deferoxamine for treating diabetic neuropathy was suggested since it was observed that the drug could activate the production of pro-angiogenic, neuroprotective and anti inflammatory factors. Read the full story here:  http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0178011
Get Biosynth’s high quality deferoxamine mesylate here

           



  

      

Sinigrin
(Q-100458)

Sinigrin is a glucosinolate which is found in a broad range of green vegetables (for example Brassica), which plays a role in defining their tasting characteristics. The glucosinolate and the enzyme myrosinase are separated in the plant tissues but through damaging the cells (cooking or chewing), the enzyme gets released to catalyze the cleavage of sinigrin to glucose and an isothiocyanate (ITC). These ITC species display diverse biological properties including anti-bacterial, anti-fungal and even may reduce the risk of developing cancer (Read More). To humans, the ITC’s have a characteristic bitter taste, which can be loved or detested or is not even detectable by some people, depending on genetic factors.

3,3',5,5'-Tetramethylbenzidine (TMB), dihydrochloride hydrate 
(T-2150)

HRP and TMB – it takes two to tango! The enzyme horseradish peroxidase (HRP) has been isolated from the roots of the plant in commercially useful quantities since the nineteen-sixties. Today, HRP-coupled antibodies have become indispensable in immunoassays. The most popular chromogenic substrate for HRP is Tetramethylbenzidine (TMB), in particular in enzyme-linked Immunosorbent assays (ELISA). HRP converts TMB into a blue color that can be read spectrophotometrically at 650 nm. The HRP reaction can be stopped by adding sulfuric or phosphoric acid. This yields a yellow color that can be read at 450 nm. Biosynth supplies research grade TMB dihydrochloride (Cat.No. T-2150)

           



  

      

3,5-Diiodo-L-tyrosine dihydrate
(D-3800)

There are many good reasons to eat fish and seafood, one of them is certainly the fact that they are rich in iodine salts, which are a fundamental for the endocrine activity of the thyroid gland. Iodine salts are enzymatically converted into molecular iodine, which adds to tyrosine residues in thyroglobulin forming diiodotyrosine. This is the first step towards the biosynthesis of thyroid hormones triodityronine T3 and tetraiodotyronine T4 which serve important regulatory functions in body metabolism and energy expenditure. Recently, the dietary introduction of potassium iodide and diiodotyrosine were compared in mice showing that diiodotyrosine can also be used effectively as food supplement preventing the potential damage from excessive intake of inorganic iodine salts. Liu, D., Lin, X., Yu, F. et al. Biol Trace Elem Res (2015) 168: 447.

Mogroside V
(Q-100878)

In recent years consumers have become more concerned about their nutrition, particularly about sugar consumption. For this reason, natural sweeteners having a good taste while being also healthier than sucrose are increasingly demanded. Mogroside V is about 300-400 times sweeter than cane sugar and is found to be the most abundant sweetening component in the Luo Han Guo fruit cultivated in southern Asia. Siraitia grosvenorii (Luo Han Guo) fruits were used for centuries as ingredients in cooling drinks and in traditional Chinese medicine. In a recent study the ability of these terpenoid glucosides on pancreatic beta cells to stimulate insulin secretion was also reported.

           



  

      

n-Dodecyl-beta-D-maltoside 
(D-8823)

Dodecyl maltoside (DDM) is a non-ionic detergent that consists of a hydrophilic maltose head and a hydrophobic long chain alkyl tail. It has a relatively low critical micelle concentration of 0.17 mM and is considered a gentle but powerful detergent. DDM is often the best tool for solubilizing/ crystallizing membrane proteins. Membrane proteins usually have alpha-helical structures that are easily destroyed when the protein is released from its membrane environment. DDM can often preserve these structures during the solubilization. In addition, membrane proteins can often be renatured when isolated with DDM.
    DDM has been used as a model detergent in the development of a new method for detergent quantification. Detergents are indispensable for the solubilization, functional tests and structure analysis of membrane-bound proteins. But the determination of actual detergent concentrations has been extremely difficult, especially in mixtures of different detergents or detergent-protein complexes. Without knowing the actual concentration, experiments involving detergents are hardly systematically practicable. Solubilization problems are therefore often solved by trial and error. To answer this common problem, Chaptal et al. developed a MALDI-TOF MS-based method that allows quantification of pure or mixed detergents in complex with membrane proteins. Their work also allows to precisely estimate the detergent corona diameter that promotes best the membrane protein crystallization or to visualize the detergent belt for Cryo-EM studies. Reference: Chaptal, V. et al. (2017) Quantification of Detergents Complexed with Membrane Proteins. Sci. Rep. 7, 41751.

Chenodeoxycholic acid
(C-2900)
Ursodeoxycholic acid
(U-9000)

Chenodeoxycholic acid is a human primary bile acid which is also found the bile of geese. Its C-7 epimer, Ursodeoxycholic acid is found in bear’s bile. Both bile acids are used for the treatment of gallstones, although Ursodeoxycholic acid has shown superior efficacy (bear’s bile extracts are also used in Chinese medicine). An interesting discussion on how the structure of bile acids correlates with the evolutionary path of vertebrates can be found in this review:  Journal of Lipid Research,
2010, 226-246.

           

  

      

Guaiacol (Q-100002)

Whiskies produced on the Scottish island of Isley are known for their typical smoky taste. Several different phenols are known to be responsible for this particular characteristic. For example guaiacol can be “detected” even at very the low concentrations of approximately 4 mgL-1. According to a recently published computational study from Kalmar, Sweden, the relative amounts of water, alcohol and guaiacol have been looked at in order to understand why these factors enhance the taste of whisky. Alcohol and guaiacol are predominantly found at the air-water interface in mixtures containing up to 45 % ethanol while at concentrations higher than 59 vol-%, guaiacol is increasingly surrounded by ethanol molecules which prevent the molecule from being diffused in air. (https://www.nature.com/articles/s41598-017-06423-5)

trans-Zeatin Riboside (Z-3000)

Cytokinins are plant hormones involved in developmental processes and in the modulation of plant immune system. Zeatin was identified as the first naturally occurring cytokinin from the endosperm of corn (latin: Zea mays). Water-soluble trans-Zeatin Riboside is a major long-distance signaling molecule in xylem vessels and its action depends on metabolic conversion in proximity to the site of action. Trans-Zeatin Riboside is a powerful agent used in horticulture to improve shoot growth or to induce callus formation (e.g. in tomato). It is used for plant regeneration from leaf explants (e.g. in potato) and for the direct initiation of shoot cultures from bract axils of many plant species.

           

trans-Zeatin Riboside

  

      

Quinine (J-100237)

Quinine is a well-known fluorescent compound found in Cinchona trees, which are native to the high altitudes of South America. The extracts of the Cinchona bark have been used to treat malaria for hundreds of years, usually administered as a suspension in wine or spirits. This may have promoted the discovery of gin and tonic, initially consumed daily by the British across their global Empire. Isolated in 1820, quinine became one of the first pure chemical compounds treating a disease. The importance of quinine as a second-line malaria treatment remains until today.

Chlorindazone DS (C-4120)

Chlorindazone DS is a red water-soluble azo dye used as an analytical tool to detect heavy metal ions including cadmium, nickel, copper and zinc. A particularly interesting application is for the detection of copper and zinc in forensics for the visualization of gunshot residues, by forming purple and blue complexes, respectively. Since zinc is widespread in many commercial products, such as some types of gloves, these tests need to be carried out with highest precautions in order to avoid artifacts.

           

CybLuc

  

      

Vitamin K1 (Q-201934)

During his seminal studies on the metabolism of cholesterol, the Danish biochemist Henrik Dam noticed the tendency of bleeding spontaneously in chicks receiving a cholesterol- and fat-free diet. He postulated that in addition to the already known ones, a novel fat-soluble group of vitamins, namely Vitamin K had to be a regulator of the blood coagulation process. The Nobel Price winning discovery (Medicine,1943) involving the structural elucidation of Vitamin K was awarded to the two scientists Dam and Doisy. Interestingly, Vitamin K1 (Phyllochinon) is an element of the photosynthesis, present in certain green leafy vegetables and fruits.

CybLuc (C-8790)

In vivo bioluminescence imaging (BLI) is limited by the fact that the luminescence signal from native D-Luciferin (maximum emission at about 560 nm) is attenuated in the animal due to absorption and scattering of light below 600 nm in blood and tissues. These shortcomings can be avoided using a red-shifted luciferin derivative (max. em. at 600 nm) like CybLuc. In addition to red shift properties, CybLuc also displays higher lipophilicity and metabolic stability. This make it the ideal luciferin for in vivo studies. Biosynth is the only supplier of commercial CybLuc – Now available online. To learn more visit our download section.

           

CybLuc

  

      

CCVJ (J-100084)

 

Molecular rotors are fascinating tools for a wide variety of applications such as the detection of biomolecular interactions (J. Am. Chem. Soc., 2014, 136 (17), pp 6159–6162) and viscosity testing in polymer chemistry and food sciences. These molecules, including 9-(2-Carboxy-2-cyanovinyl)julolidine (CCVJ) are highly sensitive to their environment, showing viscosity-dependent emitting properties. Fluorescence can be observed when the molecule is in its planar conformation, while when the molecule is rotating it relaxes in a non radiative manner. Effective molecular rotors generally comprise an electron-donating, an electron-accepting and a π-conjugated linking moiety.

 

Isoalantolactone (Q-100495)

 

Isoalantolactone and the corresponding isomer Alantolactone are sesquiterpene lactones from plants of the elecampane species. These two natural products and their synthetic analogues are known to possess several biological activities, such as antifungal and antibacterial. Recently there has been a renewed interest in alantolactone, as highlighted on Nature Scientific Reports. The pro-apoptotic activity and the ability of alantolactone to increase chemosensitivity of lung adenocarcinoma cells resulting in cell death have been evaluated.

           

Isoalantolactone

  

      

Eugenol (Q-201105)

 

Most chemists probably remember their very first experiences in the lab making practice with the extraction of Eugenol. Eugenol is the main component of clove oil with a strong spicy fragrance. It’s used in a number of oriental perfumes and also as flavoring food additive. In addition, Eugenol is a powerful phenol with many biological activities including antibacterial, fungicidal and anti-inflammatory. It has also been suggested as a naturally derived pesticide. Another use of Eugenol is in dentistry as a mild analgesic and a component of non-prescription medicines for toothache targeting ion channels of the trigeminal ganglion neurons sensing dental pain. Another interesting application to the many uses of Eugenol, is as a fish anesthetic, in order to avoid manipulation stress.

 

Chalcogran (J-640439)

 

Several different Bark Beetle species are known to attack trees to reproduce inside their trunk. This causes significant damage to the plant, as mentioned recently in the news about the spruces in Bialowieza forest in Poland (Nature, 2017). Once the male beetles are nested in the tree, they secrete Chalcogran to attract females. Chalcogran and other insect pheromones can be used in special traps in order to minimize the application of insecticides or the constant monitoring of the insect population. To guarantee a supply of Chalcogran, Biosynth recently developed an efficient process for its production.

           

Chalcogran

(+)-trans-Chrysanthemic acid   

      

(+)-trans-Chrysanthemic acid (J-023366)

 

Chrysanthemic acid is the carboxylic acid moiety of Pyrethrin I, which is found in the flowers of the Chrysanthemums family. Thanks to the fast degradation of Pyrethrins, the crushed flowers were used for centuries as environmentally benign insecticides. Special precautions are required when using Pyrethrins, since these insecticides are highly toxic to honey bees, and in some cases also for humans. Since the first synthesis reported by Ruzicka and Staudinger in 1924, a large number of synthetic Pyrethrin derivatives were obtained and tested, providing the basis to identify new compounds with lower toxicity and side-effects. (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1568513/)

 

Brucine (Q-100426)

 

Brucine is the 10, 11-dimethoxy derivative of Strychnine; both substances are found in the seeds of Strychnos nux-vomica, the strychnine tree, which is widespread in southern Asia. These Indole-Alkaloids are mainly known for their poisonous properties and they are responsible for the intense bitter taste of the plant extracts. Brucine’s toxicity however is lower compared to the one of Strychnine. Interestingly, some attempts of using Brucine for asymmetric decarboxylations have been reported by Marckwald as early as in 1904. In this context, Brucine can be considered an ancestral organocatalyst (W. Marckwald, 1904).

           

Brucine

Pinoresinol diglucopyranoside  

      

Pinoresinol diglucopyranoside (Q-100734)

 

Lignans are secondary plant metabolites which serve as starting materials for the biosynthesis of Lignin, one of the most abundant natural products. In particular, Pinoresinol is a highly valuable Lignan, occurring in many different legumes and vegetables, showing higher concentrations in flax and sesame seeds. Due to their phytoestrogenic activity, Lignans have been studied for the prevention of certain hormone-dependent cancer types. An interesting account on the biosynthesis of Lignans can be found here.

 

Clindamycin hydrochloride (Q-200874)

 

Lincomycin and its chlorinated analogue Clindamycin are Lycosamide antibiotics. Both molecules are highly active against anaerobic species and their mechanism of action consists in the inhibition of protein biosynthesis. Lincomycin is mostly used in veterinary medicine, while the more potent Clindamycin finds many clinical uses, for example as an alternative treatment to penicillin for allergic patients. Interestingly, Clindamycin has also been proposed as a treatment for malaria in combination with quinine and other known antimalarial agents (Antimicrob. Agents Chemother. 2002, 2315-2320).

           

Clindamycin hydrochloride

Esculin  

      

Esculin (E-3600)

 

Sugars formed by photosynthesis are essential for plant’s nutrition and they can be carried by a sophisticated system called phloem from the leaves to the root tips. Since the phloem is a delicate tissue composed of various specialized cell types, the study of its structure and functions remains a challenging task. Recently, fluorescent coumarin glucoside derivatives, including esculin (Plant Physiology 2015, 1211-1220) have been used as phloem probes. Among the probes tested, only esculin and fraxin are transported, while skimmin is not, suggesting a certain specifity of natural coumarin glucosides for the transporter AtSUC2 .

 

Thioflavin T (T-3730)

 

Amyloid fibrils are insoluble proteinaceous materials found in a wide range of protein-misfolding diseases, including Alzheimer’s and prion diseases. Thioflavin T is a benzothiazole dye that exhibits enhanced fluorescence upon binding to amyloid. Upon binding of fibrils, Thioflavin T displays a dramatic shift of the excitation maximum (from 385 nm to 450 nm) and the emission maximum (from 445 nm to 482 nm). A strong increase in Thioflavin T fluorescence intensity upon fibril binding makes it a sensitive and efficient marker of amyloid in histology. Read more about the Molecular Mechanism here.

           

Thioflavin T

Quercetin  

      

Quercetin (J-200114)

 

Eating food which is rich in flavonoids can protect from influenza through the action of our gut microbiota. According to a recent research, desaminotyrosine, a bacterial metabolite originating from flavonoids, modulates the immune response to viral infection by augmenting type I interferon signaling. The study provides interesting insights on how microbiota can influence the host response to influenza, which can be a potential approach for prevention of viral infections. Read the full story here: Science 2017, 498-502.

 

Khellin (K-3400)

 

Khellin is a natural product isolated from Bishop’s Weed, which is particularly abundant in the Mediterranean regions. Ancient Egyptians already used the herb for the treatment of asthma and kidney stones. Nowadays Khellin is used in medicine as well, e.g. against arrhythmia and as a photosensitizer in UVA Vitiligo treatment. Recently, furanochromones like Khellin and Visnagin have also been found to have phytotoxic properties (J. Agric. Food Chem., 2016, 64(50), 9475-9487). For this reasons these natural compounds can be used as effective and environmentally benign herbicides.

           

Khellin

  

      

3,4,5-Tricaffeoylquinic acid (Q-100870)

 

Caffeoylquinic acid derivatives are taxonomically widespread metabolites in plants. These secondary metabolites are produced by plants under stress to provide pathogen defence, antiherbivory and a general plant response to oxidative stress. 3,4,5-Tricaffeoylquinic acid (TCQA) is found for example in sweetpotato or in different herbs. But also in mammalian cell models this compound demonstrates anti-oxidant (and anti-inflammatory) effects: TCQA reduces proteasome inhibition-mediated programmed cell death in differentiated PC12 cells (Nam et al. 2014). This may direct to new approaches in the prevention of neuronal degeneration, as the dysfunction of the proteasome system is involved in neuronal degeneration. In addition, the powerful TCQA inhibits lipopolysaccharide-stimulated production of inflammatory mediators and is also an anti-HIV agent inhibiting HIV type 1 integrase.

 

Dodecylguanidine hydrochloride (Q-100979)

 

DGH is a cationic surfactant with a guanidine group. It is a unique cationic surfactant as it exhibits a strong tendency for self-assembly when compared with common ionic surfactants. The self-assembly is due to the hydrogen bonding between its guanidine groups in addition to the hydrophobic interaction between its alkyl chains (Miyake et al. 2008). DGH is an effective biocidal agent and successfully used to control fungi, bacteria and algae. The compound is effective against Gram-negative bacteria and other common water contaminating bacteria; it is also effective against sulfur reducing bacteria. Mixtures of quaternary ammonium compounds with DGH show particularly high activity. For example, DGH is used as an ingredient in disinfectants to fight Legionella pneumophila in water cooling systems.

           

Dodecylguanidine hydrochloride

  

      

N-Nonyldeoxygalactonojirimycin (W-201929)

 

N-Nonyldeoxygalactonojirimycin is an alkylated iminosugar analogue. The introduction of a long fatty chain at the nitrogen atom favors chaperone activity on mutant glucosidases (P. Natl. Acad. Sci., 2002, 99, 24, 15428), showing potential for an alternative treatment of Gaucher’s disease.
Recently N-Nonyldeoxygalactonojirimycin and its derivatives have been proposed for the preparation of stabilizing platelet media for prolonged room temperature storage (US 2016/0143269 Al). Indeed it is well known that storage at low temperatures is not an option because it deactivates the platelets.

 

(+) Spartein Surrogate (J-023575)

 

As anticipated in our previous post, both enantiomers of Spartein are important ligands for asymmetric synthesis. Traditionally (-) Spartein has been much easier to find on the market than its enantiomer encouraging the development of simplified synthetic analogues known as (+) Spartein Surrogates. Interestingly enough, in recent years (-) Spartein has suddenly disappeared from the market, and the hunt for a reliable continuous supply is still open nowadays. Read the full mysterious story here: C&EN 2017, 95, 18-20.

           

(+) Spartein Surrogate

      

(+) Spartein (S-6999)

 

Sparteines are alkaloids extracted from Legumes of the gender Lupinus acting as sodium channel blockers and antiarrhythmic agents. Interestingly, different Lupinus species can produce opposite enantiomers of Sparteine; for instance the (-) enantiomer is found in Lupinus luteus and the (+) enantiomer is found in Lupinus pusillus, respectively. Sparteine alkaloids find numerous applications in synthetic chemistry, especially in asymmetric lithiation reactions. Suggested readings can be found here: ACIE, 1997, 36, 2282-2316.

 

Bergapten (Q-100536)

is a 5-methoxyfurocoumarin that is psoralen substituted by a methoxy group at position 5. Bergapten occurs naturally in plants and is one of the main non-volatile components of Bergamot essential oil. Psoralens extracted from Bergamot have photosensitizing effects on the skin and have been used in sunscreens in the past. But these substances have been found to be photocarcinogenic and were banned in sunscreen formulations. Today Bergapten is used in combination with UV light irradiation only in certain therapies to manage psoriasis and vitiligo. In addition, Bergapten can inhibit proliferation in the human hepatocellular carcinoma cell line.

           

Bergapten




      

Saxitoxin (S-1900)

Saxitoxin is a potent neurotoxin produced by certain species of dinoflagellates and cyanobacteria which accumulates in bivalve shellfish during toxic algal blooms, sometimes appearing as the spectacular phenomenon of red tides. Ingestion of Saxitoxin contaminated food causes a serious illness known as paralytic shellfish poisoning. Several methods for rapid detection and quantification of Saxitoxin are available on the market, for example an ELISA test has been also developed
recently: (DOI:10.1016/j.toxicon.2017.05.009).

Glutathione reduced ethyl ester (W-200037)

As described in our previous post, Glutathione is a key antioxidant in the body. Glutathione reduced monoethyl ester (GSH-MEE) is a membrane-permeable form of glutathione (GSH) that undergoes hydrolysis by intracellular esterases to release GSH. Inside cells GSH deploys its antioxidant properties. GSH is also known to be essential for pheomelanin formation which may provide a powerful strategy for skin whitening. Chung et al. reported that GSH-MEE could have de-pigmenting efficacy superior to GSH itself, but has significantly lower cytotoxic potential as seen in Melan-A mouse melanocytes. The full article is available at PubMed Central

         

GSH-MEE

      

Glutathione (G-3980)

Glutathione is a tripeptide with strong antioxidant properties. The oxidation of the cysteine amino acidic residue to form a disulfide bond prevents cellular damage caused by free radicals, metals and oxidants. The ratio between reduced and oxidized forms of glutathione is also an indication of cellular oxidative stress and low levels of glutathione are observed during excessive training and starvation. A correlation between glutathione levels and risk of hearth failure has also been reported recently https://doi.org/10.1371/journal.pone.0004871. Biosynth’s glutathione is available here: https://www.biosynth.com/en/products/biochemistry/other-biochemicals/products/G-3980.html

Amphotericin B (A-7680)

is a potent antifungal agent produced by the bacteria Streptomyces  nodosus. By binding Ergosterol, it forms pores in the cell membrane causing cell death. The mechanism of action of Amphotericin B unfortunately is also responsible for its toxicity because it can interact with Cholesterol (the mammalian steroid having analogous function of Ergosterol). This beautiful molecule has certainly stimulated great synthetic chemistry and also interesting biological studies, for example we recommend reading: Angew. Chem. 2008, 47, 4335-4338.

   

 




      

Ergosterol (J-015387)

is a naturally occurring steroid found in fungi. When exposed to light, Ergosterol undergoes a pericyclic reaction which converts it into vitamin D2. This topic is inevitably linked to the Woodward-Hoffmann rules, which provide full rationale for these transformations:   (doi:10.1021/ja01080a054).
The development of the theory resulted in Nobel prize in 1981 to Hoffmann shared with Kenichi Fukui, and to what it would have been a second Nobel prize to Woodward (already winner in 1965), who unfortunately died two years before.

Brassinolide (Q-200747)

During spring yellow colored fields make the Swiss countryside looking even more beautiful, thanks to the flowering of Rapeseed.
While everyone knows about rapeseed, rapeseed oil and its uses, it is certainly worth mentioning Brassinolide: an intriguing steroidal plant hormone (and a potent stem elongation and cell division promoter) firstly isolated from
Rapeseed pollen. Inerestingly, in a recent paper J. Agric. Food Chem., 2017, 575. Brassinolide was found also in honey, together with 49 well known phytohormones. A nice synthetic work on Brassinolide which we have selected for your readings can be found here: Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-OrganicChemistry (1972-1999), 379-82.

       

 3-Hydroxybutyrate_liver      

The D-isomer of 3-hydroxybutyric acid (H-4001)

(also termed beta-hydroxybutyrate, βOHB) is an important ketone body in the metabolism of humans and animals. (Chemically speaking it is not a ketone but is simply converted into a keton by dehydrogenase activity). βOHB has been looked upon as a carrier of energy from the liver to peripheral tissues (heart and kidneys) during fasting and exercise. Historically, the association with diabetes and starvation have given the ketone bodies a morbid connotation. Only more recently, βOHB is also recognized as a potentially powerful nutritional supplement and a signaling molecule.
Since D-3-hydroxybutyrate can supply a great deal of energy, it is added to the diet to treat a variety of diseases and to support a ketogenic diet, for example in the treatment of infant’s epilepsy or diabetes. Newman and Verdin presented a model of how ketone bodies and βOHB in particular might turn off genes that otherwise accelerate aging.

Pentosidine (J-005087)

is a fluorescent compound which forms by reaction of a sugar with one molecule of Lysine and one of Arginine. An amazing feature of this reaction (The Journal Of Biological Chemistry, 1991, 11649-11653) is that the formation of Pentosidine does not depend on the sugar present: D- Glucose, D-Fructose, D-Ribose or L-ascorbate undergo a similar reaction pathway. Pentosidine can be quantified by HPLC using a fluorescence detector or by ELISA (several kits are available on the market). High levels of Pentosidine correlate with several pathological conditions, including diabetes, neurodegenerative diseases and neuropathy. Ask a quotation for Pentosidine here.

       

fructosyl lysine

       

Fructosyl Lysine (J-200245)

The acronym AGEs stands for Advanced Glycation End-products. These interesting molecules form spontaneously by reaction of sugars with amino acids and peptides. Their levels in the human body can be correlated with various conditions like diabetes. Interestingly enough, AGEs formation in the body occurs with the very same reaction (the Maillard reaction) that can be observed when certain foods are cooked (and they become brown, especially bread and meat). Fructosyl lysine is a good example of AGEs and in a recent paper (2017-DOI: 10.1002/prot.25015) it was used to study enzymatic activity of Amadoridase I, an enzyme that can reverse the formation of AGEs.

Tacrolimus (Q-101412)

(also known FK 506) is a macrocyclic lactone which is used to prevent the risk of rejection after organ transplant due to its strong immunosuppressant activity. After being approved in 1994 byFDA, Tacrolimus is a valuable alternative to the well know anti-rejection drug Cyclosporin C and it can also be used for the treatment of ulcerative cholitis and for the topical treatment of eczema, showing an effect similar to steroidal anti-inflammatory drugs. Special care should be taken however when prescribing  tacrolimus according to arecent paper which describes inhibitor effects of tacrolimus on bone reconstruction and fixation on titanium implants: Eur. Journal. of Oral Sciences 2017DOI:10.1111/eos.12320.

       

Tacrolimus

 Agaric acid

Agaric acid (A-3920)

is a tricarboxylic fatty acid found in several fungi species including Amanita muscaria (fly agaric). Due to its ability to block the nervous transmission to sweat glands, agaric acid is useful in any pathological condition in which excessive sweating is involved. This effects of Agaric acid were discussed aready in a review of The British Medical Journal in 1889. Link to the original publication: PubMedCentral

Ferene S (P-8300)

The colorimetric test for iron deficiency in blood using Ferene S is a widely used procedure today. Before methods of iron determination became available, there were many misunderstandings about the symptoms related to iron deficiency in history. Patients were treated inappropriately for centuries, due to a lack of methods for iron detection and improper diagnosis in the past. Read more about chromogenic reagents used in the determination of blood iron.

Ferene_S
Rapamycin

Rapamycin (Q-201659)

Rapamycin’s name is derived from Rapa Nui, the traditional name of Easter Island. This fascinating macrolide was isolated from bacteria of the species Streptomyces hygroscopicus collected in the island. Initially found to be an antifungine and antibiotic agent, it is now used in medicine to prevent transplant rejection due to its potent immunosuppressant activity. Another interesting application is in the coating of coronary stents. Rapamycin showed the property to extend lifespan expectations in mouse model (Nature 460, 2009).

Quercitrin (Q-100588)

is an intense yellow colored natural dye. Its name combines the words quercus (the latin word for oak), and citron, lemon. The main chemical constituent of the dye is Quercitrin, a water soluble flavonoid conjugated with a molecule of rhamnose. Acidic hydrolysis followed by precipitation converts Quercitrin into Quercetin which instead is soluble in organic solvents while keeping its yellow color. Quercitron and other natural dyes impacted the color industry of the US since approximately the beginning of the 1800 until the post second-world war.


Quercitrin

Bilirubin

Bilirubin (B-2500)

Insoluble bilirubin can be turned into water soluble iso-bilirubin by blue-light irradiation. This is the molecular basis of the standard treatment of neonatal hyperbilirubinemia by a fairly simple phototherapy . In a new study by Lee et al., the solubility switch of bilirubin was used in a new type of bilirubin-based carriers for anti-cancer drugs.
Lee Y, Lee S, Lee DY, Yu B, Miao W, Jon S. Multistimuli-Responsive Bilirubin Nanoparticles for Anticancer Therapy. Angew Chem Int Ed Engl. 2016, 55: 10676-80

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