Cited in several environment-related research articles
Microcystin-LA (MC-LA) is an analog of microcystin-LR (Prod. No. ALX-350-012) with Ala substituted in place of Arg. MC-LA inhibits protein phosphatase 2A (PP2A) and calcineurin/protein phosphatase 3 (PP3) more potently than protein phosphatase 1 (PP1).
Product Details
Alternative Name:
MC-LA
Formula:
C46H67N7O12
MW:
910.0
Source:
Isolated from Microcystis aeruginosa.
CAS:
96180-79-9
RTECS:
GT2805000
Purity:
≥95% (HPLC)
Identity:
Identity determined by MS.
Appearance:
Whitish film adhered to inside of the vial.
Solubility:
Soluble in 100% ethanol or methanol.
Shipping:
Ambient Temperature
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:
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
A Feasibility Study into the Production of a Mussel Matrix Reference Material for the Cyanobacterial Toxins Microcystins and Nodularins: A.D. Turner, et al.; Toxins 15, 27 (2023), Abstract;
Novel one-point calibration strategy for high-throughput quantitation of microcystins in freshwater using LC-MS/MS: H. Zhang, et al.; Sci. Total Environ. 858, 159345 (2023), Abstract;
Year-Round Presence of Microcystins and Toxin-Producing Microcystis in the Water Column and Ice Cover of a Eutrophic Lake Located in the Continuous Permafrost Zone (Yakutia, Russia): V. Gabyshev, et al.; Toxins 15, 467 (2023), Abstract;
A Summer of Cyanobacterial Blooms in Belgian Waterbodies: Microcystin Quantification and Molecular Characterizations: W.H.R. Van Hassel, et al.; Toxins 14, 61 (2022), Abstract;
Adsorption of cyanotoxins on polypropylene and polyethylene terephthalate: Microplastics as vector of eight microcystin analogues: D.S. Moura, et al.; Environ. Pollut. 303, 119135 (2022), Abstract;
Confirmation Using Triple Quadrupole and High-Resolution Mass Spectrometry of a Fatal Canine Neurotoxicosis following Exposure to Anatoxins at an Inland Reservoir: A.D. Turner, et al.; Toxins 14, 804 (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;
Improving the Quantification of Cyanotoxins Using a Mass Balance-Based Effective Concentration-Equivalent Concentration Approach: A. Jia, et al.; Environ. Sci. Technol. 56, 14418 (2022), Abstract;
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;
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;
Selective interaction of microcystin congeners with zebrafish (Danio rerio) Oatp1d1 transporter: P. Marić, et al.; Chemosphere 283, 131155 (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;
Exposure to aerosolized algal toxins in South Florida increases short- and long-term health risk in Drosophila model of aging: J. Hu, et al.; Toxins 12, 787 (2020), Abstract; Full Text
Machine Learning Prediction of Cyanobacterial Toxin (Microcystin) Toxicodynamics in Humans: S. Altaner, et al.; ALTEX 37, 24 (2020), Abstract;
Microcystins and Microcystis aeruginosa PCC7806 extracts modulate steroidogenesis differentially in the human H295R adrenal model: V. Mallia, et al.; PLoS One 15, 12 (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
An Innovative Portable Biosensor System for the Rapid Detection of Freshwater Cyanobacterial Algal Bloom Toxins: S.R. Bickman, et al.; Environ. Sci. Technol. 52, 11691 (2018), Abstract;
First observation of microcystin- and anatoxin-a-producing cyanobacteria in the easternmost part of the Gulf of Finland (the Baltic Sea): E. Chernova, et al.; Toxion 157, 18 (2018), Abstract;
Simple, high efficiency detection of microcystins and nodularin-R in water by fluorescence polarization immunoassay: H. Zhang, et al.; Anal. Chim. Acta 992, 119 (2017), Abstract;
Effect of chlorination on the protein phosphatase inhibition activity for several microcystins: H. Mash, et al.; Water Res. 95, 230 (2016), Abstract;
Hepatotoxic Microcystin Removal Using Pumice Embedded Monolithic Composite Cryogel as an Alternative Water Treatment Method: F. Gurbuz, et al.; Water Res. 90, 337 (2016), Application(s): Injection, Abstract;
Acyloxymethyl esterification of nodularin-R and microcystin-LA produces inactive protoxins that become reactivated and produce apoptosis inside intact cells: L. Herfindal, et al.; J. Med. Chem. 52, 5758 (2009), Abstract;
Decrease in toxicity of microcystins LA and LR in drinking water by ozonation: S. Brooke, et al.; Toxicon 48, 1054 (2006), Abstract;
Treatment options for microcystin toxins: similarities and differences between variants: G. Newcombe, et al.; Environ. Technol. 24, 299 (2003), Abstract;
The design, synthesis, and biological evaluation of analogues of the serine-threonine protein phosphatase 1 and 2A selective inhibitor microcystin LA: rational modifications imparting PP1 selectivity: J.B. Aggen, et al.; Bioorg. Med. Chem. 7, 543 (1999), Abstract;
Microcystin composition of an axenic clonal strain of Microcystis viridis and Microcystis viridis - containing waterblooms in Japanese freshwaters: K. Kaya & M.M. Watanabe; J. Appl. Phycol. 2007, 173 (1990),
The structure of cyanoginosin-LA, a cyclic heptapeptide toxin from the cyanobacterium Microcystis aeruginosa: D.P. Botes et al.; J. Chem. Soc. 1, 2311 (1984),
