Aplidine
Title: Aplidine
CAS Registry Number: 137219-37-5
CAS Name: N-[1-(1,2-Dioxopropyl)-L-prolyl]-didemnin A
Additional Names: dehydrodidemnin B; DDB
Trademarks: Aplidin (PharmaMar)
Molecular Formula: C57H87N7O15
Molecular Weight: 1110.34
Percent Composition: C 61.66%, H 7.90%, N 8.83%, O 21.61%
Literature References: Cyclic depsipeptide analog of the didemnins, q.v., isolated from the marine tunicate, Aplidum albicans. Induces rapid apoptotic death with or without previous cell cycle arrest. Isoln and synthesis: K. Rinehart, A. M. Lithgow-Bertelloni, WO 9104985 (1991 to PharmaMar); G. Jou et al., J. Org. Chem. 62, 354 (1997). Antiproliferative effects on Ehrlich carcinoma: J. L. Urdiales et al., Cancer Lett. 102, 31 (1996); cytotoxic effect on acute lymphoblastic leukemia cells: E. Erba et al., Br. J. Cancer 89, 763 (2003). Mechanism of action study: idem et al., ibid. 86, 1510 (2002). Degradation kinetics in solution: J. C. M. Waterval et al., J. Chromatogr. B 754, 161 (2001). 2D-NMR conformational analysis in solution: F. Cárdenas et al., J. Org. Chem. 68, 9554 (2003). LC/MS/MS determn in plasma: J. Yin et al., Rapid Commun. Mass Spectrom. 17, 1909 (2003). In vitro toxicity on hematopoietic progenitors and stem cells: S. G. Gomez et al., Exp. Hematol. 31, 1104 (2003). Clinical pharmacokinetics and evaluation in advanced malignancies: S. Faivre et al., J. Clin. Oncol. 23, 7871 (2005).
Properties: White solid, mp 152-160°. [a]D -95.9° (c = 1.8 in CHCl3).
Melting point: mp 152-160°
Optical Rotation: [a]D -95.9° (c = 1.8 in CHCl3)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Alkaloids/Natural Products.

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