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Microcystin-YR

Inhibitor of PP1 and PP2A
 
ALX-350-044-C025 25 µg 161.00 USD
 
ALX-350-044-C100 100 µg 305.00 USD
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Analog of microcystin-LR (Prod. No. ALX-350-012) with Tyr substituted in place of Leu. As for all microcystins the conjugated double bonds in the ADDA moiety cause a characteristic absorption maximum at 238nm. The Tyr residue in position 2 of microcystin-YR confers an absorption maximum at 232nm. Potent inhibitor of eukaryotic protein phosphatases 1 and 2A. Useful as a reference compound in environmental analysis. The hydroxyl group of the Tyr residue may prove useful for linking microcystin-YR via conjugation to other chemicals. Inhibits the synthesis of proteases such as cathepsin D and L, and arginine aminopeptidase.

Product Specification

Formula:C52H72N10O13
 
MW:1045.2
 
Source:Isolated from Microcystis aeruginosa.
 
CAS:101064-48-6
 
Purity:≥95% (HPLC)
 
Identity:Identity determined by MS.
 
Appearance:Whitish film adhered to inside of the vial.
 
Solubility:Soluble in 100% ethanol, methanol or DMSO.
 
Shipping:Ambient
 
Long Term Storage:-20°C
 
Handling:For maximum product recovery after thawing, centrifuge the vial before opening the cap.
 
Scientific Background:Microcystins are a group of cyclic heptapeptide hepatotoxins produced by a number of cyanobacterial genera. The most notable of which, and namesake, is the widespread genus Microcystis. Structurally, all microcystins consist of the generalized structure cyclo(-D-Ala1-X2-D-MeAsp3-Y4-Adda5-D-Glu6-Mdha7-). X and Y are variable L-amino acids, D-MeAsp is D-erythro-β-methylaspartic acid and Mdha is N-methyldehydroalanine. Adda is the cyanobacteria unique C20 β-amino acid 3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoic acid. Substitutions of the variable L-amino acids at positions 2 and 4 give rise to at least 21 known primary microcystin analogs and alterations in the other constituent amino acids result in more than 90 reported mycrocystins to date.
 
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Product Literature References

An Innovative Portable Biosensor System for the Rapid Detection of Freshwater Cyanobacterial Algal Bloom Toxins: S.R. Bickman, et al.; Environ. Sci. Technol. (2018), Abstract;
Development and single-laboratory validation of a UHPLC-MS/MS method for quantitation of microcystins and nodularin in natural water, cyanobacteria, shellfish and algal supplement tablet powders: A.D. Turner, et al.; J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 1074-1075, 111 (2018), Abstract;
Are We Underestimating Benthic Cyanotoxins? Extensive Sampling Results from Spain: E. A. Cantoral Uriza, et al.; Toxins (Basel) 9, 385 (2017), Abstract; Full Text
Simple, high efficiency detection of microcystins and nodularin-R in water by fluorescence polarization immunoassay: H. Zhang, et al.; Anal. Chim. Acta 992, 119 (2017), Abstract;
Effect of chlorination on the protein phosphatase inhibition activity for several microcystins: H. Mash, et al.; Water Res. 95, 230 (2016), Abstract;
Hepatotoxic Microcystin Removal Using Pumice Embedded Monolithic Composite Cryogel as an Alternative Water Treatment Method: F. Gurbuz, et al.; Water Res. 90, 337 (2016), Application(s): Injection, Abstract;
Biodegradation of multiple microcystins and cylindrospermopsin in clarifier sludge and a drinking water source: Effects of particulate attached bacteria and phycocyanin: E. Maghsoudi, et al.; Ecotoxicol. Environ. Saf. 120, 409 (2015), Abstract;
Cardiotoxic injury caused by chronic administration of microcystin-YR: D. Suput, et al.; Folia Biol. (Praha) 56, 14 (2010), Abstract;
Acute and subacute toxic effects produced by microcystin-YR on the fish cell lines RTG-2 and PLHC-1: S. Pichardo, et al.; Toxicol. In Vitro 21, 1460 (2007), Abstract;
Detection of the cyanobacterial hepatotoxins microcystins: J. McElhiney and L.A. Lawton; Toxicol. Appl. Pharmacol. 203, 219 (2005), Abstract;
Genetic contributions to the risk assessment of microcystin in the environment: E. Dittmann and T. Borner; Toxicol. Appl. Pharmacol. 203, 192 (2005), Abstract;
Guidance values for microcystins in water and cyanobacterial supplement products (blue-green algal supplements): a reasonable or misguided approach?: D. Dietrich and S. Hoeger; Toxicol. Appl. Pharmacol. 203, 273 (2005), Abstract;
Production of secondary metabolites by freshwater cyanobacteria: K. Harada; Pharm. Bull. 52, 889 (2004), Abstract;
Molecular enzymology underlying regulation of protein phosphatase-1 by natural toxins: C.F. Holmes, et al.; Curr. Med. Chem. 9, 1981 (2002), Abstract;
The microcystins and nodularins: cyclic polypeptide inhibitors of PP1 and PP2A: B.M. Gulledgea, et al.; Curr. Med. Chem. 9, 1991 (2002), Abstract;
Influence of microcystin-YR and nodularin on the activity of some proteolytic enzymes in mouse liver: A. Lankoff & A. Kolataj; Toxicon. 39, 419 (2001), Abstract;
Isolation and detection of microcystins and nodularins, cyanobacterial peptide hepatotoxins: J. Meriluoto, et al.; Methods Mol. Biol. 145, 65 (2000), Abstract;
Toxicology and evaluation of microcystins: P.K. Lam, et al.; Ther. Drug. Monit. 22, 69 (2000), Abstract;
Molecular mechanisms underlying inhibition of protein phosphatases by marine toxins: J.F. Dawson and C.F. Holmes; Front. Biosci. 4, D646 (1999), Abstract;
The toxicology of microcystins: R.M. Dawson; Toxicon 36, 953 (1998), Abstract;
The cyanotoxins: W.W. Carmichael; Adv. Bot. Res. 27, 211 (1997),
Isolation and characterization of microcystins from laboratory cultures and environmental samples of Microcystis aeruginosa and from an associated animal toxicosis: L.A. Lawton, et al.; Nat. Toxins 3, 50 (1995), Abstract;
Characterization of natural toxins with inhibitory activity against serine/threonine protein phosphatases: R.E. Honkanen, et al.; Toxicon 32, 339 (1994), Abstract;
Extraction and high-performance liquid chromatographic method for the determination of microcystins in raw and treated waters: L.A. Lawton, et al.; Analyst 119, 1525 (1994), Abstract;
Cyanobacteria secondary metabolites - the cyanotoxins: W.W. Carmichael; J. Appl. Bacteriol. 72, 445 (1992), Abstract;
Structural studies on cyanoginosins-LR, -YR, -YA, and -YM, peptide toxins from Microcystis aeruginosa: D.P. Botes, et al.; JCS Perkin Trans. I, 2747 (1985),

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