Microcystin-LA

Inhibitor of PP2A and calcineurin



ALX-350-096-C025	25 µg	152.00 USD

ALX-350-096-C100	100 µg	234.00 USD

Analog of microcystin-LR (Prod. No. ALX-350-012) with Ala substituted in place of Arg. Inhibits protein phosphatase 2A (PP2A) and protein phosphatase 3 (PP3) more potently than protein phosphatase 1 (PP1). Ozonation of toxic water samples does lead to a complete loss of the microcystins and their toxicity.

Product Specification

Identity:	Identity determined by MS.

Formula:	C₄₆H₆₇N₇O₁₂

MW:	910.0

Purity:	≥95% (HPLC)

Appearance:	Whitish film adhered to inside of the vial.

CAS:	96180-79-9

RTECS:	GT2805000

Source/Host:	Isolated from Microcystis aeruginosa.

Solubility:	Soluble in 100% ethanol or methanol.

Long Term Storage:	-20°C

Use/Stability:	Stock solutions are stable for up to 6 months when stored at -20°C. Unstable at pH>7.7.

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-ß-methylaspartic acid and Mdha is N-methyldehydroalanine. Adda is the cyanobacteria unique C₂₀ ß-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

Acyloxymethyl esterification of nodularin-R and microcystin-LA produces inactive protoxins that become reactivated and produce apoptosis inside intact cells: L. Herfindal. et al.; J.Med.Chem. 52, 5758 (2009), Abstract;

Decrease in toxicity of microcystins LA and LR in drinking water by ozonation: S. Brooke, et al.; Toxicon. 48, 1054 (2006), Abstract;

Treatment options for microcystin toxins: similarities and differences between variants: G. Newcombe, et al.; Environ. Technol. 24, 299 (2003), Abstract;

The design, synthesis, and biological evaluation of analogues of the serine-threonine protein phosphatase 1 and 2A selective inhibitor microcystin LA: rational modifications imparting PP1 selectivity: J.B. Aggen, et al.; Bioorg. Med. Chem. 7, 543 (1999), Abstract;

Microcystin composition of an axenic clonal strain of Microcystis viridis and Microcystis viridis - containing waterblooms in Japanese freshwaters: K. Kaya and M.M. Watanabe; J. App. Phycol. 2007, 173 (1990),

The structure of cyanoginosin-LA, a cyclic heptapeptide toxin from the cyanobacterium Microcystis aeruginosa: D.P. Botes et al.; J. Chem. Soc. 1, 2311 (1984),