title: A new inhibitor of coupled oxidative phosphorylation, 5-hydroxynaphthalenedicarboxylic anhydride, a derivative of a carcinogenic polynuclear hydrocarbon.
abstract: 5-Hydroxy-1,2-naphthalenedicarboxylic anhydride is closely related to its precursor dibasic acid which is a metabolite of the carcinogenic polynuclear hydrocarbon dibenz[a,h]anthracene. The anhydride inhibited respiration of coupled mitochondria. This inhibition was relieved by 2,4-dinitrophenol. Several mitochondrial volume change processes energized by ATP were also inhibited by the anhydride. Both the mitochondrial ATPase activity induced by 2,4-dinitrophenol and the ATPase activity of submitochondrial particles induced by magnesium ion were inhibited by the anhydride. The spectrum of inhibitory activity was not associated with acetic anhydride, succinic anhydride, or phthalic anhydride. The data indicate that 5-hydroxy-1,2-naphthalenedicarboxylic anhydride inhibits the machinery of oxidative phosphorylation in a manner similar to rutamycin. 5-Hydroxy-1,2-naphthalenedicarboxylic anhydride is the first molecule derived from a carcinogen with such inhibitory properties.
mesh_terms: D000251:Adenosine Triphosphatases / Q000378:metabolism; D000812:Anhydrides / Q000494:pharmacology; D000818:Animals; D002273:Carcinogens; D003998:Dicarboxylic Acids / Q000494:pharmacology; D004140:Dinitrophenols / Q000494:pharmacology; D005663:Furans / Q000494:pharmacology; D006096:Gramicidin / Q000494:pharmacology; D008930:Mitochondria, Liver / Q000187:drug effects / Q000378:metabolism; D008933:Mitochondrial Swelling / Q000187:drug effects; D009284:Naphthols / Q000494:pharmacology*; D010085:Oxidative Phosphorylation / Q000187:drug effects*; D051381:Rats; D012427:Rutamycin / Q000494:pharmacology; D014475:Uncoupling Agents / Q000494:pharmacology
chemical_list: D000812:Anhydrides; D002273:Carcinogens; D003998:Dicarboxylic Acids; D004140:Dinitrophenols; D005663:Furans; D009284:Naphthols; D014475:Uncoupling Agents; D006096:Gramicidin; D012427:Rutamycin; C011485:5-hydroxynaphthalenedicarboxylic anhydride; D000251:Adenosine Triphosphatases