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Microcystin-LR

Inhibitor of PP1 and PP2A
 
ALX-350-012-C050 50 µg 50.00 USD
 
ALX-350-012-C100 100 µg 64.00 USD
 
ALX-350-012-C500 500 µg 245.00 USD
 
ALX-350-012-M001 1 mg 435.00 USD
 
Replaces Prod. #: BML-EI193

Heptapeptide ester hepatotoxin. Tumor promoter. Equally potent and selective inhibitor of protein phosphatase 1 (PP1) and 2A (PP2A). PP2B is less sensitive and PP2C is not inhibited up to 4µM. Useful for affinity-purification of PP2A. The product is not cell permeable except in liver cells, which appear to have a functional uptake system. Is absorbed by hepatocytes via the multispecific organic anion transporter. Does not induce any effects on mouse skin or human fibroblasts due to cell membranes impermeability. Has no effect on protein kinases. Less toxic than the more hydrophobic analogs microcystin-LY, -LW and -LF. Frequently contaminates fresh-water lakes and ponds. Causes livestock poisonings. Ozonation did lead to complete loss of toxicity and toxins from contaminated samples.

Product Specification

Formula:C49H74N10O12
 
MW:995.2
 
Source:Isolated from Microcystis aeruginosa.
 
CAS:101043-37-2
 
RTECS:GT2810000
 
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.
 
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.
 
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

Reproductive toxicity on female mice induced by microcystin-LR: J. Wu, et al.; Environ. Toxicol. Pharmacol. 37, 1 (2013), Abstract;
Decline of sperm quality and testicular function in male mice during chronic low-dose exposure to microcystin-LR: Y. Chen, et al.; Reprod. Toxicol. in press, (2011), Abstract;
Global Gene Expression Profiling in Larval Zebrafish Exposed to Microcystin-LR and Microcystis Reveals Endocrine Disrupting Effects of Cyanobacteria: E.D. Rogers, et al; Environ. Sci. Technol. 45, 1962 (2011), Abstract;
Investigation of microcystin congener-dependent uptake into primary murine neurons: D. Feurstein, et al.; Environ. Health Perspect. 118, 1370 (2010), Abstract; Full Text
Analysis of dissolved microcystins in surface water samples from Kovada Lake, Turkey: F. Gurbuz, et al.; Sci. Total Environ. 407, 4038 (2009), Abstract;
Mitochondria a key role in microcystin-LR kidney intoxication: R. La-Salete, et al.; J. Appl. Toxicol. 28, 55 (2008), Abstract;
Decrease in toxicity of microcystins LA and LR in drinking water by ozonation: S. Brooke, et al.; Toxicon. 48, 1054 (2006), Abstract;
Negative regulation of ERK and Elk by protein kinase B modulates c-Fos transcription: I. Galetic, et al.; J. Biol. Chem. 278, 4416 (2003), Abstract; Full Text
The toxicology of microcystin-LR: occurrence, toxicokinetics, toxicodynamics, diagnosis and treatment: K. Bischoff; Vet. Hum. Toxicol. 43, 294 (2001), Review, Abstract;
Comparative toxicity of four microcystins of different hydrophobicities to the protozoan, Tetrahymena pyriformis: C.J. Ward & G.A. Codd; J. Appl. Microbiol. 86, 874 (1999), Abstract;
Unique features of the okadaic acid activity class of tumor promoters: H. Fujiki & M. Suganuma; J. Cancer Res. Clin. Oncol. 125, 150 (1999), Review, Abstract;
Microcystin uptake and inhibition of protein phosphatases: effects of chemoprotectants and self-inhibition in relation to known hepatic transporters: M. Runnegar, et al.; Toxicol. Appl. Pharmacol. 134, 264 (1995), Abstract;
Two significant aspects of microcystin-LR: specific binding and liver specificity: R. Nishiwaki, et al.; Cancer Lett. 83, 283 (1994), Abstract;
Evidence for the regulation of exocytic transport by protein phosphorylation: H.W. Davidson, et al.; J. Cell. Biol. 116, 1343 (1992), Abstract;
Liver tumor promotion by the cyanobacterial cyclic peptide toxin microcystin-LR: R. Nishiwaki-Matsushima, et al.; J. Cancer Res. Clin. Oncol. 118, 420 (1992), Abstract;
Protein phosphatase 2A is a specific protamine-kinase-inactivating phosphatase: G.D. Amick, et al.; Biochem. J. 287, 1019 (1992), Abstract;
Increased synthase phosphatase activity is responsible for the super-activation of glycogen synthase in hepatocytes from fasted obese Zucker rats: L. Lavoie, et al.; Endocrinology 129, 2674 (1991), Abstract;
Characterization of microcystin-LR, a potent inhibitor of type 1 and type 2A protein phosphatases: R.E. Honkanen, et al.; J. Biol. Chem. 265, 19401 (1990), Abstract; Full Text
Cyanobacterial microcystin-LR is a potent and specific inhibitor of protein phosphatases 1 and 2A from both mammals and higher plants: C. MacKintosh, et al.; FEBS Lett. 264, 187 (1990), Abstract;
Nodularin, microcystin, and the configuration of Adda: K.L. Rinehart, et al.; JACS 110, 8557 (1988),
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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