Microcystin-RR is the Arg-Arg analog of microcystin-LR (Prod. No. ALX-350-431). Hepatotoxic, although found to be up to 10-fold less toxic than microcystin-LR on i.p. injection in mice. Potent inhibitor of protein phosphatase 2A (PP2A). This product can be used as an analytical standard for water testing or for molecular studies when high purity is required.
Product Details
Formula:
C49H75N13O12
MW:
1038.2
Source:
Isolated from Microcystis aeruginosa.
CAS:
111755-37-4
Purity:
≥99% (HPLC)
Purity Detail:
Flash Chromatography followed by HPLC
Identity:
Identity determined by MS.
Appearance:
Clear to whitish film adhered to inside of vial.
Shipping:
Dry Ice
Short Term Storage:
-20°C
Long Term Storage:
-20°C
Use/Stability:
Preparation of stock solution:
Thaw vial. Centrifuge vial for maximum product recovery.
Use a syringe, draw the desired solvent (suggested solvent is 80% methanol). Make sure that no bubbles are drawn.
Inject 1.0ml of desired solvent into the septum to obtain an concentration of 10µg/ml.
Make sure that all the solvent has been injected prior to removing the syringe.
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
LC-MS/MS Validation and Quantification of Cyanotoxins in Algal Food Supplements from the Belgium Market and Their Molecular Origins: W.H.R. Van Hassel, et al.; Toxins 14, 513 (2022), 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;
Microcystin Toxins at Potentially Hazardous Levels in Algal Dietary Supplements Revealed by a Combination of Bioassay, Immunoassay, and Mass Spectrometric Methods: T. Miller, et al.; J. Agric. Food Chem. 68, 8016 (2020), Abstract; Full Text
The apoptotic effect of oral administration of microcystin-RR on mice liver: P. Huang, et al.; Environ. Toxicol. 26, 443 (2010), Abstract;
Microcystin-RR-induced accumulation of reactive oxygen species and alteration of antioxidant systems in tobacco BY-2 cells: L. Yin, et al.; Toxicon. 46, 507 (2005), Abstract;
Physiological and biochemical analyses of microcystin-RR toxicity to the cyanobacterium Synechococcus elongatus: Z.Q. Hu, et al.; Environ. Toxicol. 19, 571 (2004), Abstract;
Determination of some physicochemical parameters of microcystins (cyanobacterial toxins) and trace level analysis in environmental samples using liquid chromatography: C. Rivasseau, et al.; J. Chromatogr. A 799, 155 (1998), 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;
Inhibition of protein phosphatases activates glucose-6-phosphatase in isolated rat hepatocytes: S. Claeyssens, et al.; FEBS Lett. 315, 7 (1993), Abstract;
Toxicity and toxins of natural blooms and isolated strains of Microcystis spp. (Cyanobacteria) and improved procedure for purification of cultures: M. Shirai, et al.; Appl. Environ. Microbiol. 57, 1241 (1991), Abstract;
The structure of a cyclic peptide toxin, cyanogenosin-RR from Microcystis aeruginosa: P. Painuly, et al.; THL 29, 11 (1988),
