title: Design, synthesis and biological activity of 7-O-(4-O-acetyl-3-iodo-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl) daunomycinone and 7-O-(3-chloro-2,3,6-trideoxy-4-O-propanoyl-alpha-L-lyxo- hexopyranosyl)daunomycinone.
abstract: The synthesis and pharmacological evaluation of 7-O-(4-O-acetyl-3-iodo-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl) daunomycinone and 7-O-(3-chloro-2,3,6-trideoxy-4-O-propanoyl-alpha-L-lyxo-hexopyrano syl) daunomycinone are described. Their cytotoxic activity was evaluated against normal and resistant cell lines. Both compounds exhibited activity against the adriamycin resistant cell line KB-A1. These results support the hypothesis that the increased lipophilicity of the sugar part of anthracyclines is associated with their ability to overcome multidrug resistance (MDR).
authors.affiliation: University of Athens, Department of Pharmacy, Panepistimiopolis-Zografou, Greece.
authors.forename: N
authors.initials: N
authors.lastname: Aligiannis
authors.forename: N
authors.initials: N
authors.lastname: Pouli
authors.forename: P
authors.initials: P
authors.lastname: Marakos
authors.forename: S
authors.initials: S
authors.lastname: Mitaku
authors.forename: A L
authors.initials: AL
authors.lastname: Skaltsounis
authors.forename: S
authors.initials: S
authors.lastname: Leonce
authors.forename: A
authors.initials: A
authors.lastname: Pierre
authors.forename: G
authors.initials: G
authors.lastname: Atassi
mesh_terms: D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000494:pharmacology; D002453:Cell Cycle / Q000187:drug effects; D003630:Daunorubicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004317:Doxorubicin / Q000494:pharmacology; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor; D019450:Genes, MDR; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D014407:Tumor Cells, Cultured
chemical_list: C406443:7-O-(3-chloro-2,3,6-trideoxy-4-O-propanoyl-lyxo-hexopyranosyl)daunomycinone; C406442:7-O-(4-O-acetyl-3-iodo-2,3,6-trideoxy-arabino-hexopyranosyl)daunomycinone; D000903:Antibiotics, Antineoplastic; D004317:Doxorubicin; D003630:Daunorubicin