title: Synthesis of new 2-galactosylthiazolidine-4-carboxylic acid amides. Antitumor evaluation against melanoma and breast cancer cells.
abstract: A set of 2-galactosylthiazolidine-4-carboxylic acid amides was synthesized with different length for the carbon chain amide moiety. The cytotoxicity of the molecules was evaluated against A375 melanoma and MCF7 breast cancer cell lines. For the derivatives tested, the one that contains a C(16) amide carbon chain is the most active with an IC(50) of 17.0 μM for A375 and 5.8 μM for MCF7. This compound also shows cytotoxicity in the triple negative cancer cell line HCC1806. The selectivity of the compounds was assessed by comparing the cytotoxicity in cancer cell line versus in a fibroblast cell line. Flow cytometry studies show the activation of apoptotic pathways and also DNA damages with blockage of the cell cycle in the S-phase and appearance of peaks in G0/G1-phase.
authors.affiliation: Departamento de Química, Universidade de Coimbra, Rua Larga, 3004 535 Coimbra, Portugal. armenio.serra@gmail.com
authors.forename: Arménio C
authors.initials: AC
authors.lastname: Serra
authors.forename: António M d'A
authors.initials: AM
authors.lastname: Rocha Gonsalves
authors.forename: Mafalda
authors.initials: M
authors.lastname: Laranjo
authors.forename: Ana M
authors.initials: AM
authors.lastname: Abrantes
authors.forename: Ana C
authors.initials: AC
authors.lastname: Gonçalves
authors.forename: Ana B
authors.initials: AB
authors.lastname: Sarmento-Ribeiro
authors.forename: M Filomena
authors.initials: MF
authors.lastname: Botelho
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001943:Breast Neoplasms / Q000473:pathology*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D004305:Dose-Response Relationship, Drug; D006801:Humans; D008545:Melanoma / Q000473:pathology*
chemical_list: D000970:Antineoplastic Agents; D002264:Carboxylic Acids