title: N-deacetyl-N-aminoacylthiocolchicine derivatives: synthesis and biological evaluation on MDR-positive and MDR-negative human cancer cell lines.
abstract: A new series of N-deacetyl-N-(N-trifluoroacetylaminoacyl)thiocolchicine derivatives 9-15 have been synthesized starting from the corresponding N-deacetylthiocolchicine (3) and the N-trifluoroacetylamino acids 5-8 which were used as a racemic mixture. The trifluoroacetyl protecting group has been removed easily, giving the corresponding N-deacetyl-N-aminoacylthiocolchicines 16-22. Optical pure compounds 9-22 were isolated from the diastereoisomeric mixture or were prepared starting from compound 3 and an optical pure amino acid derivative; the configuration of each compound was assigned unequivocally. The diastereoisomeric couples of amino acids synthesized were tested, and their antiproliferative activity on MDR-positive and MDR-negative human cancer cell lines was evaluated.
authors.affiliation: Dipartimento di Ostetricia e Ginecologia, Università Cattolica, Roma, Italy.
authors.forename: M L
authors.initials: ML
authors.lastname: Gelmi
authors.forename: S
authors.initials: S
authors.lastname: Mottadelli
authors.forename: D
authors.initials: D
authors.lastname: Pocar
authors.forename: A
authors.initials: A
authors.lastname: Riva
authors.forename: E
authors.initials: E
authors.lastname: Bombardelli
authors.forename: R
authors.initials: R
authors.lastname: De Vincenzo
authors.forename: G
authors.initials: G
authors.lastname: Scambia
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002455:Cell Division / Q000187:drug effects; D003078:Colchicine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D018432:Drug Resistance, Multiple; D019008:Drug Resistance, Neoplasm; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D003078:Colchicine