[D-Asp3]microcystin-RR is isolated from Microcystis aeruginosa. This microcystin contains arginine (R) in positions 2 and 4. Additionally, the D-MeAsp at position 3 is demethylated to Asp. [D-Asp3]microcystin-RR is hepatotoxic.
White to off-white powder or oily film adhered to inside of the vial.
Solubility:
Soluble in DMSO or 100% methanol.
Shipping:
Ambient Temperature
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
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;
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;
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;
Degradation of Multiple Peptides by Microcystin-Degrader Paucibacter toxinivorans (2C20): A.A. Santos, et al.; Toxins (Basel) 13, 265 (2021), Abstract; Full Text
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;
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;
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;
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;
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;
Development of an analytical method for the unambiguous structure elucidation of cyclic peptides with special appliance for hepatotoxic desmethylated microcystins: T. Kruger, et al.; Toxicon 54, 302 (2009), Abstract;
