Title: Okadaic Acid
CAS Registry Number: 78111-17-8
CAS Name: 9,10-Deepithio-9,10-didehydroacanthifolicin
Additional Names: halochondrine A
Molecular Formula: C44H68O13
Molecular Weight: 805.00
Percent Composition: C 65.65%, H 8.51%, O 25.84%
Literature References: First ionophoric polyether identified in marine organisms; isolated from marine black sponges, Halichondria (okadai or melanodocia). Tumor promoting cytotoxin associated with diarrhetic seafood poisoning. Isoln: K. Tachibana et al., J. Am. Chem. Soc. 103, 2469 (1981). Total synthesis: M. Isobe et al., Tetrahedron 43, 4767 (1987). Contractile effects: S. Shibata et al., J. Pharmacol. Exp. Ther. 223, 135 (1982). Inhibition of protein phosphatases: A. Takai et al., FEBS Lett. 217, 81 (1987); C. Bialojan, A. Takai, Biochem. J. 256, 283 (1988). Tumor promoting activity: M. Suganuma et al., Proc. Natl. Acad. Sci. USA 85, 1768 (1988). Review of mechanism of action and use as a probe for cellular regulation: P. Cohen et al., Trends Biochem. Sci. 15, 98-102 (1990); A. Schönthal, New Biol. 4, 16-21 (1992). Review of tumor promoting activity: H. Fujiki, M. Suganuma, J. Biochem. 115, 1-5 (1994).
Properties: Crystals from dichloromethane/hexane, mp 171-175°. [a]D20 +21° (c = 0.33 in CHCl3). Also reported as crystals from benzene-CHCl3, mp 164-166°. [a]D25 +25.4° (c = 0.24 in CHCl3). LD50 i.p. in mice: 192 mg/kg (Shibata).
Melting point: mp 171-175°; mp 164-166°
Optical Rotation: [a]D20 +21° (c = 0.33 in CHCl3); [a]D25 +25.4° (c = 0.24 in CHCl3)
Toxicity data: LD50 i.p. in mice: 192 mg/kg (Shibata)
Use: Biochemical tool as tumor promoter and probe of cellular regulation. |