Microcystin-YR

Inhibitor of PP1 and PP2A



ALX-350-044-C025	25 µg	131.00 USD

ALX-350-044-C100	100 µg	228.00 USD

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.

Identity:	Identity determined by MS.

Formula:	C₅₂H₇₂N₁₀O₁₃

MW:	1045.2

Purity:	≥95% (HPLC)

Appearance:	Whitish film adhered to inside of the vial.

CAS:	101064-48-6

Source/Host:	Isolated from Microcystis aeruginosa.

Solubility:	Soluble in 100% ethanol, methanol or DMSO.

Long Term Storage:	-20°C

Hazard:	HIGHLY IRRITANT. MAY BE CARCINOGENIC. VERY TOXIC.

Handling:	For maximum product recovery after thawing, centrifuge the vial before opening the cap.

Background / Technical Information:	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

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),