PMID- 8766706 OWN - NLM STAT- MEDLINE DCOM- 19960923 LR - 20191210 IS - 0014-5793 (Print) IS - 0014-5793 (Linking) VI - 389 IP - 3 DP - 1996 Jul 8 TI - 2-Nitrosofluorene and N-hydroxy-2-aminofluorene react with the ubiquinone-reduction center (center N) of the mitochondrial cytochrome bc1 complex. PG - 233-7 AB - We determined the sites of artificial electron transfer onto 2-nitrosofluorene (NOF), a metabolite of carcinogenic 2- acetylaminofluorene in mitochondria and isolated cytochrome bc1 complex. NOF-induced O2 consumption in mitochondria was sensitive to antimycin A, but insensitive to myxothiazol. In the isolated cytochrome bc1 complex, NOF induced rapid MOA-stilbene-insensitive reoxidation of cytochrome b, whereas in the presence of antimycin A, reoxidation was very slow. The corresponding hydroxylamine, N-hydroxy-2-aminofluorene (N-OH-AF), reduced cytochrome b specifically through center N of the cytochrome bc1 complex. We conclude that NOF and N-OH-AF bind to center N of the cytochrome bc1 complex and act as electron acceptor and donor, respectively. The N-OH-AF/NOF interconversion is considered to be involved in the cytotoxicity of 2-acetylaminofluorene in vivo. FAU - Klohn, P C AU - Klohn PC AD - Institut fur Toxikologie, Universitat Wurzburg, Germany. FAU - Brandt, U AU - Brandt U FAU - Neumann, H G AU - Neumann HG LA - eng PT - Journal Article PT - Research Support, Non-U.S. Gov't PL - England TA - FEBS Lett JT - FEBS letters JID - 0155157 RN - 0 (Cytochrome b Group) RN - 0 (Fluorenes) RN - 0 (Methacrylates) RN - 0 (Nitroso Compounds) RN - 0 (Stilbenes) RN - 0 (Thiazoles) RN - 0 (Uncoupling Agents) RN - 103455-29-4 (3-methoxy-2-(2-styrylphenyl)propenic acid methyl ester) RN - 1339-63-5 (Ubiquinone) RN - 14844-07-6 (Dithionite) RN - 34E9V9B29K (2-nitrosofluorene) RN - 61M94X4V24 (N-hydroxy-2-aminofluorene) RN - 642-15-9 (Antimycin A) RN - 6VY98BQ7NB (myxothiazol) RN - EC 7.1.1.8 (Electron Transport Complex III) RN - MQD255M2ZO (Potassium Cyanide) RN - P4P3AC32ZB (Tetramethylphenylenediamine) SB - IM MH - Animals MH - Antimycin A/pharmacology MH - Cytochrome b Group/metabolism MH - Dithionite/pharmacology MH - Electron Transport Complex III/antagonists & inhibitors/*metabolism MH - Fluorenes/*metabolism/pharmacology MH - Male MH - Methacrylates MH - Mitochondria, Liver/drug effects/*metabolism MH - Nitroso Compounds/*metabolism/pharmacology MH - Oxidation-Reduction MH - Oxygen Consumption/drug effects MH - Potassium Cyanide/pharmacology MH - Rats MH - Rats, Wistar MH - Stilbenes/pharmacology MH - Tetramethylphenylenediamine/pharmacology MH - Thiazoles/pharmacology MH - Ubiquinone/*metabolism MH - Uncoupling Agents/pharmacology EDAT- 1996/07/08 00:00 MHDA- 1996/07/08 00:01 CRDT- 1996/07/08 00:00 PHST- 1996/07/08 00:00 [pubmed] PHST- 1996/07/08 00:01 [medline] PHST- 1996/07/08 00:00 [entrez] AID - 0014-5793(96)00592-3 [pii] AID - 10.1016/0014-5793(96)00592-3 [doi] PST - ppublish SO - FEBS Lett. 1996 Jul 8;389(3):233-7. doi: 10.1016/0014-5793(96)00592-3.