Isolated from Microcystis aeruginosa. Microcystin containing a homotyrosine (Hty) in position 2 and arginine (R) in position 4. Hepatotoxic.
Product Details
Alternative Name:
[Hil2]microcystin-IR, [Hil2]MC-IR
Formula:
C50H76N10O12
MW:
1009.2
Source:
Isolated from Microcystis aeruginosa.
Purity:
≥95% (HPLC)
Identity:
Identity determined by MS.
Appearance:
White to off-white powder or oily film adhered to inside of the vial.
Solubility:
Soluble in DMSO or 100% methanol.
Shipping:
Ambient
Long Term Storage:
-20°C
Handling:
For maximum product recovery after thawing, centrifuge the vial before opening the cap.
Scientific Background:
Cyanobacteria are photosynthetic prokaryotes mostly present in freshwater ecosystems. The increasingly frequent appearance of cyanobacteria blooms in lakes and rivers is linked to climate changes and human activities. 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
7-epi-cylindrospermopsin and microcystin producers among diverse Anabaena/Dolichospermum/Aphanizomenon CyanoHABs in Oregon, USA: T.W. Dreher, et al.; Harmful Algae 116, 102241 (2022), Abstract;
Identification of Novel Microcystins Using High-Resolution MS and MSn with Python Code: D. Baliu-Rodriguez, et al.; Environ. Sci. Technol. 56, 1652 (2022), Abstract;
An ELISA-based Method for Variant-independent Detection of Total 3 Microcystins and Nodularins via Multi-immunogen Approach: J. Liu, et al.; Environ. Sci. Technol. 55, 12984 (2021), Abstract;
Remediation Strategies to Control Toxic Cyanobacterial Blooms: Effects of Macrophyte Aqueous Extracts on Microcystis aeruginosa (Growth, Toxin Production and Oxidative Stress Response) and on Bacterial Ectoenzymatic Activities: Z. Tazart, et al.; Microorganisms 9, 1782 (2021), Abstract;
Machine Learning Prediction of Cyanobacterial Toxin (Microcystin) Toxicodynamics in Humans: S. Altaner, et al.; ALTEX 37, 24 (2020), 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
Dhb Microcystins Discovered in USA Using an Online Concentration LC-MS/MS Platform: J.A. Birbeck, et al.; Toxins (Basel) 11, 653 (2019), Abstract; Full Text
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;
Detection of the cyanobacterial hepatotoxins microcystins: J. McElhiney and L.A. Lawton; Toxicol. Appl. Pharmacol. 203, 219 (2005), Abstract;
Production of secondary metabolites by freshwater cyanobacteria: K. Harada; Pharm. Bull. 52, 889 (2004), Abstract;
The toxicology of microcystins: R.M. Dawson; Toxicon 36, 953 (1998), Abstract;
The cyanotoxins: W.W. Carmichael; Adv. Bot. Res. 27, 211 (1997),
