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M2912

Sigma-Aldrich

Microcystin LR from Microcystis aeruginosa

≥95% (HPLC), solid film

Synonym(s):

5-L-Arginine-microcystin LA

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About This Item

Empirical Formula (Hill Notation):
C49H74N10O12
CAS Number:
101043-37-2
Molecular Weight:
995.17
MDL number:
MFCD00131607
UNSPSC Code:
12352200
PubChem Substance ID:
24896778

assay

≥95% (HPLC)

form

solid film

solubility

ethanol: 1 mg/mL
DMSO: soluble

storage temp.

−20°C

SMILES string

CO[C@H](Cc1ccccc1)[C@H](C)\C=C(C)\C=C\[C@@H]2NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)C2C)C(O)=O)C(O)=O

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Biochem/physiol Actions

Potent inhibitor of protein phosphatase Types 1 and 2A; has no effect on protein kinase. Hepatic tumor promoter in experimental animal model.[1]

Other Notes

Hepatotoxic cyclic heptapeptide.

Reconstitution

Stock solutions can be diluted in 50 mM Tris-HCl, pH 7.0, containing 0.03% Brij 35; phosphatase inhibition will be retained for up to 1 month when stored at concentrations up to 0.01 nM.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Oral - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
128K1478
098K1495
068K1343
048K1602
038K1345

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J F Dawson et al.
Frontiers in bioscience : a journal and virtual library, 4, D646-D658 (1999-09-30)
The protein serine/threonine phosphatases constitute a unique class of enzymes that are critical regulatory enzymes as they must counteract the activities of thousands of protein kinases in human cells. Uncontrolled inhibition of phosphatase activity by toxic inhibitors can lead to
Chronic Microcystin Exposure Induces Hepatocyte Proliferation with Increased Expression of Mitotic and Cyclin-associated Genes in P53-deficient Mice.
Clark, S. P., et al.
Toxicologic Pathology (2008)
R E Guzman et al.
Toxicologic pathology, 27(5), 582-588 (1999-10-21)
Microcystin LR (MCLR) is a naturally occurring protein phosphatase inhibitor and potent hepatotoxin produced by strains of Microcystis aeruginosa. Although its acute toxicity has been well characterized, little is known about its chronic effects. In this study, we sought to
Zhenyu Lin et al.
Talanta, 103, 371-374 (2012-12-04)
In this study, an electrochemical impedance biosensor for cyanobacterial toxin microcystin-LR (MC-LR) detection has been developed. MC-LR aptamers were immobilized on the gold electrode through Au-S interaction, in the presence of target (MC-LR); the binding of MC-LR and aptamers probe
Andrea Ziková et al.
Aquatic toxicology (Amsterdam, Netherlands), 128-129, 25-33 (2012-12-26)
Cyanobacteria are the primary biomass producers and some species synthesize remarkable amounts of secondary metabolites, the so-called cyanotoxins. Several reports deal with the most common cyanotoxins, microcystins (MCs), and their effects on fishes but only a few studies investigated a
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