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Inhibitor of PP1 and PP2A
ALX-350-012-C100 100 µg 119.00 USD
ALX-350-012-C500 500 µg 352.00 USD
ALX-350-012-M001 1 mg 624.00 USD
Do you need bulk/larger quantities?
Replaces Prod. #: BML-EI193

Heptapeptide ester hepatotoxin. Tumor promoter. Equally potent and selective inhibitor of protein phosphatase 1 (PP1) and 2A (PP2A). PP2B is less sensitive and PP2C is not inhibited up to 4µM. Useful for affinity-purification of PP2A. The product is not cell permeable except in liver cells, which appear to have a functional uptake system. Is absorbed by hepatocytes via the multispecific organic anion transporter. Does not induce any effects on mouse skin or human fibroblasts due to cell membranes impermeability. Has no effect on protein kinases. Less toxic than the more hydrophobic analogs microcystin-LY, -LW and -LF. Frequently contaminates fresh-water lakes and ponds. Causes livestock poisonings. Ozonation did lead to complete loss of toxicity and toxins from contaminated samples.

Product Details

Source:Isolated from Microcystis aeruginosa.
Purity:≥95% (HPLC)
Identity:Identity determined by MS.
Appearance:Whitish film adhered to inside of the vial.
Solubility:Soluble in 100% ethanol, methanol or DMSO.
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: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 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;
Cerium exposure in Lake Taihu water aggravates microcystin pollution via enhancing endocytosis of Microcystis aeruginosa: Q. Yang, et al.; Environ. Pollut. 292, 118308 (2022), Abstract;
Crystal structure of human NADK2 reveals a dimeric organization and active site occlusion by lysine acetylation: C. Mary, et al.; Mol. Cell 82, 3299 (2022), Abstract;
Discovery of G2019S-selective leucine rich repeat protein kinase 2 inhibitors with in vivo efficacy: R.K. Lesniak, et al.; Eur. J. Med. Chem. 229, 114080 (2022), Abstract;
First Report on Microcystin-LR Occurrence in Water Reservoirs of Eastern Cuba, and Environmental Trigger Factors: J.C.R. Tito, et al.; Toxins (Basel) 14, 209 (2022), Abstract;
Higher sensitivity to hydrogen peroxide and light stress conditions of the microcystin producer Microcystis aeruginosa sp PCC7806 compared to non-producer strains: D. Latour, et al.; Harmful Algae 114, 102219 (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;
In Vitro Toxicity Evaluation of Cyanotoxins Cylindrospermopsin and Microcystin-LR on Human Kidney HEK293 Cells: L.D. Quijada, et al.; Toxins 14, 429 (2022), Abstract;
Microcystin-LR inhibits early pregnancy by impairing the vascular network of luteum: Involvement of the MEK/ERK/SP1/VEGFR2 axis: M. Guo, et al.; Food Chem. Toxicol. 170, 113454 (2022), Abstract;
mTORC1 regulates a lysosome-dependent adaptive shift in intracellular lipid species: A.M. Hosios, et al.; Nat. Metab. 4, 1792 (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
A temporal Ca 2+-desensitization of myosin light chain kinase in phasic smooth muscles induced by CaMKKß/PP2A pathways: T. Kitazawa, et al.; Am. J. Physiol. Cell Physiol. 321, C549 (2021), 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;
Chronic MC-LR exposure promoted Aβ and p-tau accumulation via regulating Akt/GSK-3β signal pathway: Y. Ma, et al.; Sci. Total Environ. 794, 148732 (2021), Abstract;
Comparative Assessment of Physical and Chemical Cyanobacteria Cell Lysis Methods for Total Microcystin-LR Analysis: K.E. Greenstein, et al.; Toxins 13, 596 (2021), Abstract;
Comparison of UV-A photolytic and UV/TiO 2 photocatalytic effects on Microcystis aeruginosa PCC7813 and four microcystin analogues: A pilot scale study: I. Menezes, et al.; J. Environ. Manage. 298, 113519 (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;
Impact of Type II LRRK2 inhibitors on signaling and mitophagy: A. Tasegian, et al.; Biochem. J. 478, 3555 (2021), Abstract; Full Text
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;
Mitochondrial NADP+ is essential for proline biosynthesis during cell growth: D.H. Tran, et al.; Nat. Metab. 3, 571 (2021), Abstract; Full Text
Multibiomarker-based assessment of toxicity of central European strains of filamentous cyanobacteria Aphanizomenon gracile and Raphidiopsis raciborskii to zebrafish Danio rerio: H. Falfushynska, et al.; Water Res. 194, 116923 (2021), Abstract;
Potential Impacts on Treated Water Quality of Recycling Dewatered Sludge Supernatant during Harmful Cyanobacterial Blooms: K. Pinkanjananavee, et al.; Toxins 13, 99 (2021), Abstract;
R1441G but not G2019S mutation enhances LRRK2 mediated Rab10 phosphorylation in human peripheral blood neutrophils: Y. Fan, et al.; Acta Neuropathol. 142, 475 (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;
Selective and easy detection of microcystin-LR in freshwater using a bioactivated sensor based on multiwalled carbon nanotubes on filter paper: M. Lee, et al.; Biosens. Bioelectron. 192, 113529 (2021), Abstract;
Selective interaction of microcystin congeners with zebrafish (Danio rerio) Oatp1d1 transporter: P. Marić, et al.; Chemosphere 283, 131155 (2021), Abstract;
The mechanisms of mitochondrial dysfunction and glucose intake decrease induced by Microcystin-LR in ovarian granulosa cells: J. Zhu, et al.; Ecotoxicol. Environ. Saf. 212, 111931 (2021), Abstract;
ULK1 phosphorylation of striatin activates protein phosphatase 2A and autophagy: Z. Hu, et al.; Cell Rep. 36, 109762 (2021), Abstract;
Distinct IL‐1α‐responsive enhancers promote acute and coordinated changes in chromatin topology in a hierarchical manner: S. Weiterer, et al.; EMBO J. 39, e101533 (2020), Abstract; Full Text
Endogenous Rab29 does not impact basal or stimulated LRRK2 pathway activity: A.F. Kalogeropulou, et al.; Biochem. J. 477, 4397 (2020), Abstract; Full Text
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
In vitro activity assays to quantitatively assess the endogenous reversible oxidation state of protein tyrosine phosphatases in cells: A.D. Londhe, et al.; Curr. Protoc. Chem. Biol. 12, e84 (2020), Abstract; Full Text
Kinetics of microcystin-LR removal in a real lake water by UV/H2O2 treatment and analysis of specific energy consumption: S. Sorlini, et al.; Toxins 12, 810 (2020), Abstract; Full Text
Lateral flow immunoassay (LFIA) for the detection of lethal amatoxins from mushrooms: C.S. Beyer, et al.; PLoS One 15, E0231781 (2020), Abstract; Full Text
Machine Learning Prediction of Cyanobacterial Toxin (Microcystin) Toxicodynamics in Humans: S. Altaner, et al.; ALTEX 37, 24 (2020), Abstract;
Microcystin-leucine-arginine induced neurotoxicity by initiating mitochondrial fission in hippocampal neurons: C. Zhang, et al.; Sci. Total Environ. 703, 134702 (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
A rapid extraction method combined with a monoclonal antibody-based immunoassay for the detection of amatoxins: C.S. Beyer, et al.; Toxins 11, 724 (2019), Abstract; Full Text
Blood-brain barrier disruption and inflammation reaction in mice after chronic exposure to Microcystin-LR: J. Wang, et al.; Sci. Total Environ. 689, 662 (2019), Abstract;
Chronic exposure to microcystin-LR reduces thyroid hormone levels by activating p38/MAPK and MEK/ERK signal pathway: J. Chen, et al.; Ecotoxicol. Environ. Saf. 173, 142 (2019), 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
Learning and memory deficits and alzheimer's disease-like changes in mice after chronic exposure to microcystin-LR: J. Wang, et al.; J. Hazard. Mater. 373, 504 (2019), Abstract;
Measuring the Kinase Activities of the LATS/NDR Protein Kinases: A. Hergovich; Methods Mol. Biol. 1893, 305 (2019), Abstract;
Microcystin-LR-Triggered Neuronal Toxicity in Whitefish Does Not Involve MiR124-3p: M. Florczyk, et al.; Neurotox. Res. 35, 29 (2019), Abstract; Full Text
PPM1H phosphatase counteracts LRRK2 signaling by selectively dephosphorylating Rab proteins: K. Berndsen, et al.; Elife 8, e50416 (2019), Abstract; Full Text
Single-Cell Analysis of Multiple Steps of Dynamic NF-κB Regulation in Interleukin-1α-Triggered Tumor Cells Using Proximity Ligation Assays: C. Mayr-Buro, et al.; Cancers (Basel) 11, 1199 (2019), Abstract; Full Text
The mechanism of Oatp1a5-mediated microcystin-leucine arginine entering into GnRH neurons: H. Jin, et al.; Ecotoxicol. Environ. Saf. 184, 109614 (2019), Abstract;
A new conjugation method used for the development of an immunoassay for the detection of amanitin, a deadly mushroom toxin: C.S. Beyer, et al.; Toxins 10, 265 (2018), Abstract; Full Text
A pathway for Parkinson's Disease LRRK2 kinase to block primary cilia and Sonic hedgehog signaling in the brain: H.S. Dhekne, et al.; Elife 7, e40202 (2018), 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;
Transgenerational effects of cyanobacterial toxins on a tropical micro-crustacean Daphnia lumholtzi across three generations: T.S. Dao, et al.; Environ. Pollut. 243, 791 (2018), Abstract;
Are We Underestimating Benthic Cyanotoxins? Extensive Sampling Results from Spain: E. A. Cantoral Uriza, et al.; Toxins (Basel) 9, 385 (2017), Abstract; Full Text
Electrochemical inactivation of Microcystis aeruginosa using BDD electrodes: Kinetic modeling of microcystins release and degradation: S. Zhou, et al.; J. Hazard. Mater. 346, 73 (2017), 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;
The role of IL-8/CXCR2 signaling in microcystin-LR triggered endothelial cell activation and increased vascular permeability: L. Chen, et al.; Chemosphere. 194, 43 (2017), Abstract;
Accumulation and detoxification dynamics of microcystin-LR and antioxidant responses in male red swamp crayfish Procambarus clarkii: J. Yuan, et al.; Aquatic Toxicology 177, 8 (2016), Application(s): MC-LR diffused into water with male crayfish, Abstract;
Cyanotoxins at low doses induce apoptosis and inflammatory effects in murine brain cells: potential implications for neurodegenerative diseases: L. Takser, et al.; Toxicol. Rep. 3, 180 (2016), Application(s): Cell culture, Abstract;
Intraperitoneal exposure of whitefish to microcystin-LR induces rapid liver injury followed by regeneration and resilience to subsequent exposures: M. Wozny, et al.; Toxicol. Appl. Pharmacol. 313, 68 (2016), Application(s): Solution for fish maintenance, exposure, and collection of samples, Abstract;
Microcystin-LR causes sexual hormone disturbance in male rat by targeting gonadotropin-releasing hormone neurons: X. Wang, et al.; Toxicon. 123, 45 (2016), Application(s): Determining intraperitoneal (i.p.) lethal dose 50 in rats, Abstract;
Microcystin-LR promotes epithelial-mesenchymal transition in colorectal cancer cells through PI3-K/AKT and SMAD2: Y. Ren, et al.; Toxicol. Lett. 265, 53 (2016), Abstract;
Oxidative stress responses in the animal model, Daphnia pulex exposed to a natural bloom extract versus artificial cyanotoxin mixtures: M. Esterhuizen-Londt, et al.; Aquat. Toxicol. 179, 151 (2016), Abstract;
Selective cytotoxicity of microcystins LR, LW and LF in rat astrocytes: K. Bulc Rozman, et al.; Toxicol. Lett. 15, 1 (2016), Abstract;
Activity and Transcriptional Responses of Hepatopancreatic Biotransformation and Antioxidant Enzymes in the Oriental River Prawn Macrobrachium nipponense Exposed to Microcystin-LR: J. Yuan, et al.; Toxins 7, 4006 (2015), Application(s): Cell Culture, Abstract; Full Text
Biodegradation of multiple microcystins and cylindrospermopsin in clarifier sludge and a drinking water source: Effects of particulate attached bacteria and phycocyanin: E. Maghsoudi, et al.; Ecotoxicol. Environ. Saf. 120, 409 (2015), Abstract;
Effects of Microcystin-LR Exposure on Spermiogenesis in Nematode Caenorhabditis elegans: Y. Li, et al.; Int. J. Mol. Sci. 16, 22927 (2015), Application(s): Cell Culture in nematodes, Abstract; Full Text
Microcystin-LR altered mRNA and protein expression of endoplasmic reticulum stress signaling molecules related to hepatic lipid metabolism abnormalities in mice: W. Qin, et al.; Environ. Toxicol. Pharmacol. 40, 114 (2015), Application(s): Injection into mice, Abstract;
Naringin attenuates the cytotoxicity of hepatotoxin microcystin-LR by the curious mechanisms to OATP1B1- and OATP1B3-expressing cells: S. Takumi, et al.; Environ. Toxicol. Pharmacol. 39, 974 (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;
Role of nitric oxide in the genotoxic response to chronic microcystin-LR exposure in human-hamster hybrid cells: X. Wang, et al.; J. Environ. Sci. (China) 29, 210 (2015), Application(s): Cell Culture, Abstract;
Roles of miRNAs in microcystin-LR-induced Sertoli cell toxicity: Y. Zhou, et al.; Toxicol. Appl. Pharmacol. 287, 1 (2015), Application(s): Cell Culture, Abstract;
Subacute Microcystin-LR Exposure Alters the Metabolism of Thyroid Hormones in Juvenile Zebrafish (Danio Rerio): Z. Liu, et al.; Toxins 7, 337 (2015), Application(s): MC-LR in aquarium water of Zebrafish, Abstract; Full Text
Toxin Resistance in Aquatic Fungi Poses Environmentally Friendly Remediation Possibilities: A Study on the Growth Responses and Biosorption Potential of Mucor hiemalis EH5 against Cyanobacterial Toxins: E. Balsano, et al.; Int. J. Water Wastewater Treat. 1, (2015), Application(s): Cell Culture, Full Text
Reproductive toxicity on female mice induced by microcystin-LR: J. Wu, et al.; Environ. Toxicol. Pharmacol. 37, 1 (2013), Abstract;
Decline of sperm quality and testicular function in male mice during chronic low-dose exposure to microcystin-LR: Y. Chen, et al.; Reprod. Toxicol. 31, 551 (2011), Abstract;
Global Gene Expression Profiling in Larval Zebrafish Exposed to Microcystin-LR and Microcystis Reveals Endocrine Disrupting Effects of Cyanobacteria: E.D. Rogers, et al; Environ. Sci. Technol. 45, 1962 (2011), 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;
Investigation of microcystin congener-dependent uptake into primary murine neurons: D. Feurstein, et al.; Environ. Health Perspect. 118, 1370 (2010), Abstract; Full Text
Analysis of dissolved microcystins in surface water samples from Kovada Lake, Turkey: F. Gurbuz, et al.; Sci. Total Environ. 407, 4038 (2009), Abstract;
Mitochondria a key role in microcystin-LR kidney intoxication: R. La-Salete, et al.; J. Appl. Toxicol. 28, 55 (2008), Abstract;
Decrease in toxicity of microcystins LA and LR in drinking water by ozonation: S. Brooke, et al.; Toxicon. 48, 1054 (2006), Abstract;
Negative regulation of ERK and Elk by protein kinase B modulates c-Fos transcription: I. Galetic, et al.; J. Biol. Chem. 278, 4416 (2003), Abstract; Full Text
The toxicology of microcystin-LR: occurrence, toxicokinetics, toxicodynamics, diagnosis and treatment: K. Bischoff; Vet. Hum. Toxicol. 43, 294 (2001), Review, Abstract;
Comparative toxicity of four microcystins of different hydrophobicities to the protozoan, Tetrahymena pyriformis: C.J. Ward & G.A. Codd; J. Appl. Microbiol. 86, 874 (1999), Abstract;
Unique features of the okadaic acid activity class of tumor promoters: H. Fujiki & M. Suganuma; J. Cancer Res. Clin. Oncol. 125, 150 (1999), Review, Abstract;
Microcystin uptake and inhibition of protein phosphatases: effects of chemoprotectants and self-inhibition in relation to known hepatic transporters: M. Runnegar, et al.; Toxicol. Appl. Pharmacol. 134, 264 (1995), Abstract;
Two significant aspects of microcystin-LR: specific binding and liver specificity: R. Nishiwaki, et al.; Cancer Lett. 83, 283 (1994), Abstract;
Evidence for the regulation of exocytic transport by protein phosphorylation: H.W. Davidson, et al.; J. Cell. Biol. 116, 1343 (1992), Abstract;
Liver tumor promotion by the cyanobacterial cyclic peptide toxin microcystin-LR: R. Nishiwaki-Matsushima, et al.; J. Cancer Res. Clin. Oncol. 118, 420 (1992), Abstract;
Protein phosphatase 2A is a specific protamine-kinase-inactivating phosphatase: G.D. Amick, et al.; Biochem. J. 287, 1019 (1992), Abstract;
Increased synthase phosphatase activity is responsible for the super-activation of glycogen synthase in hepatocytes from fasted obese Zucker rats: L. Lavoie, et al.; Endocrinology 129, 2674 (1991), Abstract;
Characterization of microcystin-LR, a potent inhibitor of type 1 and type 2A protein phosphatases: R.E. Honkanen, et al.; J. Biol. Chem. 265, 19401 (1990), Abstract; Full Text
Cyanobacterial microcystin-LR is a potent and specific inhibitor of protein phosphatases 1 and 2A from both mammals and higher plants: C. MacKintosh, et al.; FEBS Lett. 264, 187 (1990), Abstract;
Nodularin, microcystin, and the configuration of Adda: K.L. Rinehart, et al.; JACS 110, 8557 (1988),
Structural studies on cyanoginosins-LR, -YR, -YA, and -YM, peptide toxins from Microcystis aeruginosa: D.P. Botes, et al.; J. Chem. Soc., Perkin Trans. 1 1985, 2747 (1985), Abstract;

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