Microycystin-LR is a naturally occuring heptapeptide ester hepatotoxin and has been seen to be one of the most toxic within the Microcystin family. Studies have also revealed this toxin can act as a tumor promoter by selectively inhibiting protein phosphatase 1 (PP1) and 2A (PP2A). PP2B is less sensitive and PP2C is not inhibited up to 4µM. This product is useful for affinity-purification of PP2A. It 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.
Microcystin-LR has been frequently found as a contaminate to fresh-water lakes and ponds causing a major negative impact. This product can be used as an analytical standard (reference substance) for water testing. The product can also be used a very pure Microcystin-LR in studying its interaction with the protein phosphatases.
Product Details
Formula:
C49H74N10O12
MW:
995.2
Source:
Isolated from Microcystis aeruginosa.
CAS:
101043-37-2
RTECS:
GT2810000
Excitation maximum:
239nm
Purity:
≥99% (HPLC)
Purity Detail:
Flash Chromatography followed by HPLC
Identity:
Identity determined by MS.
Appearance:
Whitish film adhered to inside of the vial.
Solubility:
Soluble in 100% ethanol, methanol or DMSO.
Shipping:
Shipped on Dry Ice
Short Term Storage:
-20°C
Long Term Storage:
-20°C
Use/Stability:
Preparation of stock solution:
Thaw vial. Centrifuge the vial for maximum recovery.
Using a sterile syringe, draw the desired solvent (suggested solvent is methanol). Make sure that no bubbles are drawn.
Inject 1.0ml of the desired solvent into the septum to obtain a concentration of 10µg/ml.
Make sure that all the solvent has been injected prior to removing the syringe from the septum.
Gently swirl the vial to get toxin into solution.
If required, gently tap the bottom of the vial.
Material is ready for analysis.
Stock solutions are stable for up to 6 months when stored at -20°C. Unstable at pH >7.7.
Handling:
Warm to room temperature before opening. Keep sterile. 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.
Regulatory Status:
RUO - Research Use Only
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Product Literature References
In Vitro Toxicity Evaluation of Cyanotoxins Cylindrospermopsin and Microcystin-LR on Human Kidney HEK293 Cells: L.D. Quijada, et al.; Toxins 14, 429 (2022), Abstract;
Comparison of UV-A photolytic and UV/TiO 2 photocatalytic effects on Microcystis aeruginosa PCC7813 and four microcystin analogues: A pilot scale study: I. Menezes, et al.; J. Environ. Manage. 298, 113519 (2021), Abstract;
Ecotoxicological profiling of selected cyanobacterial strains using multi-endpoint effect-directed analysis: P. Marić, et al.; Ecotoxicology 29, 535 (2020), Application(s): Used as standards, 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;
Uptake and accumulation of Microcystin-LR based on exposure through drinking water: An animal model assessing the human health risk: B. Greer, et al.; Sci. Rep. 8, 4913 (2018), Abstract; Full Text
Comparative effects of nodularin and microcystin-LR in zebrafish: 1. Uptake by organic anion transporting polypeptide Oatp1d1 (Slco1d1): S. Faltermann, et al.; Aquat. Toxicol. 171, 69 (2016), Application(s): Cellular uptake and immunoblotting, Abstract;
Comparative effects of nodularin and microcystin-LR in zebrafish: 2. Uptake and molecular effects in eleuthero-embryos and adult liver with focus on endoplasmic reticulum stress: S. Faltermann, et al.; Aquat. Toxicol. 171, 77 (2016), Application(s): Induced ER-stress and TNFα in liver organ cultures of zebrafish, Abstract;
Pulsed galvanostatic control of a solid-contact ion-selective electrode for potentiometric biosensing of microcystin-LR: N. Yu, et al.; Sens. Actuators B Chem. 230, 785 (2016), Application(s): Inhibition of protein phosphatase,
Variation in the synthesis of microcystin in response to saline and osmotic stress in Microcystis aeruginosa PCC7806: B. Martín-Luna, et al.; Limnetica 34, 205 (2015), Application(s): Standards, Full Text
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;
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;
