Title: Filipin
CAS Registry Number: 11078-21-0
Additional Names: Filimarisin
Manufacturers' Codes: U-5956; NSC-3364
Literature References: Polyene antibiotic complex containing at least eight pentaene compounds, which has been resolved into three pure components, filipin II, III (major), and IV, which differ in the number of hydroxyl groups present (8, 9, 9, resp.) and filipin I, a mixture of at least 5 components. Described as a single entity in the earlier literature. Initial isolation from Streptomyces filipenensis in Philippine soil: Whitfield et al., J. Am. Chem. Soc. 77, 4799 (1955). Early structural work: Dhar et al., Proc. Chem. Soc. London 1960, 310; Djerassi et al., Tetrahedron Lett. 1961, 383; Golding, Rickards, ibid. 1964, 2615; Dhar et al., J. Chem. Soc. 1964, 842; Ceder, Ryhage, Acta Chem. Scand. 18, 588 (1964). Separation of filipin complex into components: Bergy, Eble, J. Antibiot. 23, 414 (1970); see also Rickards et al., ibid. 603. Mechanism of action: R. W. Holz in Antibiotics vol. 5, pt. 2, F. E. Hahn, Ed. (Springer-Verlag, New York, 1979) pp 313-340. Filipin also interacts specifically with 3b-hydroxysterols (e.g. cholesterol): P. M. Elias et al., J. Histochem. Cytochem. 27, 1247 (1979); see also N. J. Severs, H. J. Simons, Nature 303, 637 (1983).
Properties: Yellow, feathery needles from chloroform, mp 195-205°. Sensitive to air. [a]D22 -148.3° (c = 0.89 in methanol). uv max (methanol): 322, 338, 355 nm (E1%1cm 910, 1360, 1330). Freely sol in DMF, pyridine. Also sol in 95% ethanol, methanol, butanol, isopropanol, glacial acetic acid, ether. Practically insol in water, chloroform.
Melting point: mp 195-205°
Optical Rotation: [a]D22 -148.3° (c = 0.89 in methanol)
Absorption maximum: uv max (methanol): 322, 338, 355 nm (E1%1cm 910, 1360, 1330)
Derivative Type: Filipin III
CAS Registry Number: 480-49-9
Additional Names: 4,6,8,10,12,14,16,27-Octahydroxy-3- (1-hydroxyhexyl)-17,28-dimethyloxacyclooctacosa-17,19,21,23,25-pentaen-2-one; 15-deoxylagosin
Molecular Formula: C35H58O11
Molecular Weight: 654.83
Percent Composition: C 64.20%, H 8.93%, O 26.88%
Properties: Isomeric with filipin IV. Crystals from propanol, mp 163-180° (Bergy, Eble). [a]D25 -245° (c = 0.8 in DMF). uv max (methanol): 243, 308, 321, 337, 354 nm (E1%1cm 62, 413, 851, 1368, 1343).
Melting point: mp 163-180° (Bergy, Eble)
Optical Rotation: [a]D25 -245° (c = 0.8 in DMF)
Absorption maximum: uv max (methanol): 243, 308, 321, 337, 354 nm (E1%1cm 62, 413, 851, 1368, 1343)
Use: Produces arthritis rapidly in rabbits: Pras, Weissman, Drug Trade News, July 4, 1966, p 40; as a sterol probe in freeze-fracture cytochemistry.
Therap-Cat: Antifungal.
Keywords: Antifungal (Antibiotics); Polyenes. |