Cited in several water quality-related research articles
Microcystin-RR (MC-RR) is an Arg-Arg analog of Microcystin-LR (Prod. No. ALX-350-012). Although MC-RR was found to be up to 10-fold less toxic than MC-LR after intra-peritoneal injection in mice, it is both hepatotoxic and carcinogenic. It is a potent inhibitor of protein phosphatase 2A (PP2A).
Product Details
Alternative Name:
MC-RR
Formula:
C49H75N13O12
MW:
1038.2
Source:
Isolated from Microcystis aeruginosa.
CAS:
111755-37-4
Purity:
≥95% (HPLC)
Identity:
Identity determined by MS.
Appearance:
Clear to whitish film adhered to inside of vial.
Solubility:
Soluble in 80% aqueous 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
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;
Adsorption behavior of polyamide microplastics as a vector of the cyanotoxin microcystin-LR in environmental freshwaters: N. Kim, et al.; J. Hazard. Mater. 446, 130683 (2023), Abstract;
Bioinspired polydopamine-mediated metal-organic framework click-grafting aptamers functionalized fabric for highly-specific recognition of microcystin-leucine arginine: Q. Xie, et al.; J. Chromatogr. A 1688, 463728 (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;
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;
Effect of cold food storage techniques on the contents of Microcystins and Cylindrospermopsin in leaves of spinach (Spinacia oleracea) and lettuce (Lactuca sativa): A.C. Rodríguez, et al.; Food Chem. Toxicol. 170, 113507 (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;
Microcystin-LR exposure enhances toxin-degrading capacity and reduces metabolic diversity of sediment microbial communities: Q. Ding, et al.; Environ. Pollut. 311, 119947 (2022), Abstract;
Multiclass cyanotoxin analysis in reservoir waters: Tandem solid-phase extraction followed by zwitterionic hydrophilic interaction liquid chromatography-mass spectrometry: M.M. Aparicio-Muriana, et al.; Talanta 237, 122929 (2022), Abstract;
Renoprotection of microcystin-RR in unilateral ureteral obstruction-induced renal fibrosis: targeting the PKM2-HIF-1α pathway: Y. Ren, et al.; Front. Pharmacol. 13, 830312 (2022), Abstract; Full Text
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;
Degradation of Multiple Peptides by Microcystin-Degrader Paucibacter toxinivorans (2C20): A.A. Santos, et al.; Toxins (Basel) 13, 265 (2021), Abstract; Full Text
Development and field evaluation of the organic-diffusive gradients in thin-films (o-DGT) passive water sampler for microcystins: P. Wong, et al.; Chemosphere 287, 132079 (2021), Abstract;
Energy-effective elimination of harmful microcystins by a non-thermal plasma process: H. Kim, et al.; Chemosphere 284, 131338 (2021), Abstract;
Health risk assessment related to cyanotoxins exposure of a community living near Tri An Reservoir, Vietnam: T.A.D. Nguyen, et al.; Environ. Sci. Pollut. Res. Int. 28, 56079 (2021), Abstract;
Influence of refrigeration and freezing in Microcystins and Cylindrospermopsin concentrations on fish muscle of tilapia (Oreochromis niloticus) and tench (Tinca tinca): L. Diez-Quijada, et al.; Food Chem. Toxicol. 158, 112673 (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;
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
Are We Underestimating Benthic Cyanotoxins? Extensive Sampling Results from Spain: E. A. Cantoral Uriza, et al.; Toxins (Basel) 9, 385 (2017), Abstract; Full Text
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;
Microcystin-RR exposure results in growth impairment by disrupting thyroid endocrine in zebrafish larvae: L. Xie, et al.; Aquat. Toxicol. 164, 16 (2015), Application(s): Cell Culture, Abstract;
Rapid and Sensitive Analysis of Microcystins using Ionic Liquid-based in situ Dispersive Liquid-Liquid Microextraction: H. Yu, et al.; J. Chromatogr. A 1406, 10 (2015), Application(s): Cell Culture, Abstract;
Similar uptake profiles of microcystin-LR and-RR in an in vitro human intestinal model: P. Zeller, et al.; Toxicology 290, 7 (2011), Abstract;
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),
