Kahalalide F
Structural Formula Vector Image
Title: Kahalalide F
CAS Registry Number: 149204-42-2
Manufacturers' Codes: PM-92102
Molecular Formula: C75H124N14O16
Molecular Weight: 1477.87
Percent Composition: C 60.95%, H 8.46%, N 13.27%, O 17.32%
Literature References: One of a family of cyclic depsipeptides isolated from the Hawaiian marine mollusk, Elysia rufescens. First reported diet-derived chemical defense peptide; production of which depends on consumption of the green alga, Bryopsis sp. Isoln: P. J. Schauer et al., EP 610078 (1994 to Pharma Mar); M. T. Hamann, P. J. Scheuer, J. Am. Chem. Soc. 115, 5825 (1993); of the family: M. T. Hamann et al., J. Org. Chem. 61, 6594 (1996). Synthesis: A. López-Macià et al., J. Am. Chem. Soc. 123, 11398 (2001). Stereochemistry: G. Goetz et al., Tetrahedron 55, 7739 (1999). Updated stereochemistry: I. Bonnard et al., J. Nat. Prod. 66, 1466 (2003). Identification as defensive peptide: M. A. Becerro et al., J. Chem. Ecol. 27, 2287 (2001). LC/MS/MS determ in plasma: E. Stokvis et al., J. Mass Spectrom. 37, 992 (2002). Toxicology: A. P. Brown et al., Cancer Chemother. Pharmacol. 50, 333 (2002). In vitro cytotoxic activity: Y. Suárez et al., Mol. Cancer Ther. 2, 863 (2003). Mechanism of cytotoxicity: J. M. Sewell et al., Eur. J. Cancer 41, 1637 (2005). Clinical pharmacology in prostate cancer: J. M. Rademaker-Lakhai et al., Clin. Cancer Res. 11, 1854 (2005). Review of development and therapeutic potential: M. T. Hamann, Curr. Opin. Mol. Ther. 6, 657-665 (2004).
Properties: White amorphous powder. [a]D -8° (c = 4.32 in CH3OH). LD50 in male, female rats (mg/kg): 375, 600 i.v. (Brown).
Optical Rotation: [a]D -8° (c = 4.32 in CH3OH)
Toxicity data: LD50 in male, female rats (mg/kg): 375, 600 i.v. (Brown)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Alkaloids/Natural Products.

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