475815-M

Microcystin-LR

from Microcystis aeruginosa, ≥95% (HPLC), protein phosphatase inhibitor, lyophilized solid

• Synonym(s): Microcystin-LR, Microcystis aeruginosa, MCYST-LR
• Empirical Formula (Hill Notation): C₄₉H₇₄N₁₀O₁₂
• CAS Number: 101043-37-2
• Molecular Weight: 995.17
• UNSPSC Code: 12352200
• MDL number: MFCD01774058
• Assay: ≥95% (HPLC)
• Form: lyophilized solid
• Storage condition: OK to freeze

Properties

• Product Name: Microcystin-LR, Microcystis aeruginosa, Cyclic heptapeptide toxin isolated from the freshwater cyanobacteria Microcystis aeruginosa.
• Quality Segment: 100
• description: RTECS - GT2810000
• assay: ≥95% (HPLC)
• form: lyophilized solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: pale yellow
• solubility: methanol: 2 mg/mL, DMSO: 2.5 mg/mL
• storage temp.: −20°C
• SMILES string: N1[C@H]([C@@H](C(=O)N[C@H](CCC(=O)N(C(=C)C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H]([C@@H](C(=O)N[C@H](C1=O)CCCN=C(N)N)C)C(=O)O)CC(C)C)C)C)C(=O)O)C)\C=C\C(=C\[C@@H]([C@@H](OC)Cc2ccccc2)C)\C
• InChI: 1S/C49H74N10O12/c1-26(2)23-37-46(66)58-40(48(69)70)30(6)42(62)55-35(17-14-22-52-49(50)51)45(65)54-34(19-18-27(3)24-28(4)38(71-10)25-33-15-12-11-13-16-33)29(5)41(61)56-36(47(67)68)20-21-39(60)59(9)32(8)44(64)53-31(7)43(63)57-37/h11-13,15-16,18-19,24,26,28-31,34-38,40H,8,14,17,20-23,25H2,1-7,9-10H3,(H,53,64)(H,54,65)(H,55,62)(H,56,61)(H,57,63)(H,58,66)(H,67,68)(H,69,70)(H4,50,51,52)/b19-18+,27-24+/t28-,29-,30-,31+,34-,35-,36+,37-,38-,40+/m0/s1
• InChI key: ZYZCGGRZINLQBL-GWRQVWKTSA-N

Description

General description

Cyclic heptapeptide toxin isolated from the freshwater cyanobacteria Microcystis aeruginosa. Potent inhibitor of protein phosphatase 1 (PP1) and protein phosphatase 2A (PP2A). Unlike Okadaic Acid (Cat. No. 495604), microcystin-LR is effective on both PP1 (IC₅₀ = 1.7 nM) and PP2A (IC₅₀ = 40 pM). Reacts with phosphatase in a two-step mechanism involving rapid binding and inactivation of the catalytic subunit followed by slower covalent interactions. Has no effect on protein kinases, making it useful for reducing the effect of contaminating phosphatase activities in protein kinase assays. A 2.5 mM (250 µg/100 µl) solution of Microcystin-LR, Microcystis aeruginosa (Cat. No. 475821) in DMSO is also available.

Biochem/physiol Actions

Target IC₅₀: 1.7 nM and 40 pM against PP1 and PP2A, respectively

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C. Unstable at > pH 7.7.

Further dilute with aqueous buffer just prior to use.

Other Notes

Craig, M., et al. 1996. Biochem. Cell Biol. 74, 569.
Nishiwaki, R., et al. 1994. Cancer Lett. 83, 283.
Amick, G.D., et al. 1992. Biochem. J.287, 1019.
Davidson, H.W., et al. 1992. J. Cell Biol.116, 1343.
Nishiwaki-Matsushima, R., et al. 1992. J. Cancer Res. Clin. Oncol. 118, 420.
Cohen, P., et al. 1990. Trends Biochem. Sci.15, 98.
MacKintosh, C., et al. 1990. FEBS Lett.264, 187.
Cohen, P., et al. 1989. FEBS Lett.250, 596.
Carmichael, W.W. 1988. in Handbook of Natural Toxins3: Marine Toxins and Venoms(Tu, A.T., Ed.) p. 121, Decker, New York.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Highly Toxic (H)

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Codes: H300 + H310,H315,H317,H319,H335
• Precautionary Statements: P261 - P262 - P280 - P301 + P310 - P302 + P352 + P310 - P305 + P351 + P338
• 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: WGK 3
• Flash Point (°F): No data available
• Flash Point (°C): No data available