Effects of 4,4-dimethyl-5,8-dihydroxynaphtalene-1-one and 4,4-dimethyl-5,8-dihydroxytetralone derivatives on tumor cell respiration.
A set of structurally related compounds incorporating a carbonyl group in the ortho position with regard to a phenol function were tested against the TA3 mouse carcinoma cell line and its multidrug-resistant variant TA3-MTX-R. The series consists of 2'-hydroxyacetophenone, 4'-hydroxyacetophenone 2',5'-dihydroxyacetophenone, 4-acetyl-3,3-dimethyl-5-hydroxy-2-morpholino-2,3-dihydrobenzobfuran, five 4,4-dimethyl-5,8-dioxygenated naphtalene-1-ones and three 4,4-dimethyl-5,8-dioxygenated tetralones. A tentative structure-activity relationship was found for this family of substances, suggesting that a coplanar ortho-carbonyl-1,4-hydroquinone motif is able to cause inhibition of cellular respiration.
Department of Organic and Physical Chemistry, Faculty of Chemical and Pharmaceutical Sciences, University of Chile, Casilla 233, Santiago 1, Chile. raraya@ciq.uchile.cl
Ramiro
R
Araya-Maturana
Tomás
T
Delgado-Castro
Mario
M
Gárate
Jorge
J
Ferreira
Mario
M
Pavani
Hernán
H
Pessoa-Mahana
Bruce K
BK
Cassels
D000818:Animals; D019069:Cell Respiration / Q000187:drug effects*; D018432:Drug Resistance, Multiple; D007659:Ketones / Q000138:chemical synthesis / Q000494:pharmacology; D051379:Mice; D010101:Oxygen Consumption / Q000187:drug effects; D010636:Phenols / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D007659:Ketones; D010636:Phenols