title: Cytotoxic effect of novel dehydroepiandrosterone derivatives on different cancer cell lines.
abstract: The aim of this study was to determine the cytotoxic effect of human cancer cells on three series of novel dehydroepiandrosterone derivatives containing triazole or pyrazole rings at C-17 and an ester moiety at C-3 of the androstane skeleton. The panel cancer cells used in this study were the following: PC-3, MCF-7 and SKLU-1. The results from this study indicated that the steroidal derivatives 4a-4e and 4f-4k showed the highest cytotoxic potency. This difference in this activity could be attributed to the ability of the triazole (three nitrogen atoms) to form stronger hydrogen bonds with the active site of the cell as compared to the pyrazole group having two nitrogen atoms. Compounds 4f-4k having an aromatic ester at C-3 showed an enhanced cytotoxic activity as compared to their aliphatic counterparts 4a-4e. Apparently the electronegative phenyl ring increased the polarity of the molecule, thus increasing the dipole-dipole association of the steroidal molecule with the reactive site of the cell.
authors.affiliation: Department of Pharmacy, Faculty of Chemistry, National University of Mexico, Mexico, D.F., Mexico.
authors.forename: Mariana
authors.initials: M
authors.lastname: Garrido
authors.forename: Marisa
authors.initials: M
authors.lastname: Cabeza
authors.forename: Francisco
authors.initials: F
authors.lastname: Cortés
authors.forename: José
authors.initials: J
authors.lastname: Gutiérrez
authors.forename: Eugene
authors.initials: E
authors.lastname: Bratoeff
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003687:Dehydroepiandrosterone / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity*; D006801:Humans; D009369:Neoplasms / Q000188:drug therapy*; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D003687:Dehydroepiandrosterone
keywords: Cancer cell lines; Cytotoxic effect; MCF-7; PC-3; Pyrazole ring; SKLU-1; Synthesis of dehydroepiandrosterone derivatives; Triazole ring