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Microcystin-LR

Inhibitor of PP1 and PP2A
 
ALX-350-012-C050 50 µg 53.00 USD
 
ALX-350-012-C100 100 µg 67.00 USD
 
ALX-350-012-C500 500 µg 259.00 USD
 
ALX-350-012-M001 1 mg 459.00 USD
Do you need bulk/larger quantities?
 
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.
 
Shipping:Ambient
 
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.
 
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

Accumulation and detoxification dynamics of microcystin-LR and antioxidant responses in male red swamp crayfish Procambarus clarkii: J. Yuan, et al.; Aquatic Toxicology 177, 8 (2016), Application(s): MC-LR diffused into water with male crayfish, Abstract;
Cyanotoxins at low doses induce apoptosis and inflammatory effects in murine brain cells: potential implications for neurodegenerative diseases: L. Takser, et al.; Toxicol. Rep. 3, 180 (2016), Application(s): Cell culture,
Intraperitoneal exposure of whitefish to microcystin-LR induces rapid liver injury followed by regeneration and resilience to subsequent exposures: M. Wozny, et al.; Toxicol. Appl. Pharmacol. 313, 68 (2016), Application(s): Solution for fish maintenance, exposure, and collection of samples, Abstract;
Microcystin-LR causes sexual hormone disturbance in male rat by targeting gonadotropin-releasing hormone neurons: X. Wang, et al.; Toxicon. 123, 45 (2016), Application(s): Determining intraperitoneal (i.p.) lethal dose 50 in rats, Abstract;
Activity and Transcriptional Responses of Hepatopancreatic Biotransformation and Antioxidant Enzymes in the Oriental River Prawn Macrobrachium nipponense Exposed to Microcystin-LR: J. Yuan, et al.; Toxins 7, 4006 (2015), Application(s): Cell Culture, Abstract; Full Text
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;
Effects of Microcystin-LR Exposure on Spermiogenesis in Nematode Caenorhabditis elegans: Y. Li, et al.; Int. J. Mol. Sci. 16, 22927 (2015), Application(s): Cell Culture in nematodes, Abstract; Full Text
Microcystin-LR altered mRNA and protein expression of endoplasmic reticulum stress signaling molecules related to hepatic lipid metabolism abnormalities in mice: W. Qin, et al.; Environ. Toxicol. Pharmacol. 40, 114 (2015), Application(s): Injection into mice, Abstract;
Naringin attenuates the cytotoxicity of hepatotoxin microcystin-LR by the curious mechanisms to OATP1B1- and OATP1B3-expressing cells: S. Takumi, et al.; Environ. Toxicol. Pharmacol. 39, 974 (2015), Application(s): Cell Culture, Abstract;
Rapid and Sensitive Analysis of Microcystins using Ionic Liquid-based in situ Dispersive Liquid-Liquid Microextraction: H. Yu, et al.; J. Chromatogr. A 1406, 10 (2015), Application(s): Cell Culture, Abstract;
Role of nitric oxide in the genotoxic response to chronic microcystin-LR exposure in human-hamster hybrid cells: X. Wang, et al.; J. Environ. Sci. (China) 29, 210 (2015), Application(s): Cell Culture, Abstract;
Roles of miRNAs in microcystin-LR-induced Sertoli cell toxicity: Y. Zhou, et al.; Toxicol. Appl. Pharmacol. 287, 1 (2015), Application(s): Cell Culture, Abstract;
Toxin Resistance in Aquatic Fungi Poses Environmentally Friendly Remediation Possibilities: A Study on the Growth Responses and Biosorption Potential of Mucor hiemalis EH5 against Cyanobacterial Toxins: E. Balsano, et al.; Int. J. Water Wastewater Treat. 1, (2015), Application(s): Cell Culture, Full Text
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. 31, 551 (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;
Similar uptake profiles of microcystin-LR and-RR in an in vitro human intestinal model: P. Zeller, et al.; Toxicology 290, 7 (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.; J. Chem. Soc., Perkin Trans. 1 1985, 2747 (1985), Abstract;

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