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About This Item

Empirical Formula (Hill Notation):
C49H74N10O12
CAS Number:
101043-37-2
Molecular Weight:
995.17
MDL number:
MFCD01774058
UNSPSC Code:
12352200
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Product Name

Microcystin-LR, Microcystis aeruginosa, Cyclic heptapeptide toxin isolated from the freshwater cyanobacteria Microcystis aeruginosa.

Quality Level

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

Related Categories

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)

Pictograms

Skull and crossbones
GHS06

Signal Word

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 Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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