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2136212 
Journal Article 
A new inhibitor of coupled oxidative phosphorylation, 5-hydroxynaphthalenedicarboxylic anhydride, a derivative of a carcinogenic polynuclear hydrocarbon 
Hadler, HI; Demetriou, JM 
1975 
Yes 
Biochemistry
ISSN: 0006-2960
EISSN: 1520-4995 
HEEP/76/05599 
Biochemistry. 
14 
24 
5374-5378 
English 
53070 
WOS:A1975AX94000022 
HEEP COPYRIGHT: BIOL ABS. 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)antrhacene. The anhydrode 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. The mitochondrial ATPase activity induced by 2,4-dinitrophenol and the ATPase activity of submitochondrial particles induced by Mg-++ 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 1st molecule derived from a carcinogen with such inhibitory properties. 
Adenosine Triphosphatases/metabolism; Anhydrides/pharmacology; Animals; Carcinogens; Dicarboxylic Acids/pharmacology; Dinitrophenols/pharmacology; Furans/pharmacology; Gramicidin/pharmacology; Mitochondria, Liver/drug effects/metabolism; Mitochondrial Swelling/drug effects; Naphthols/pharmacology; Oxidative Phosphorylation/drug effects; Rutamycin/pharmacology; Uncoupling Agents/pharmacology; 1405-97-6; 4736R46V0G