Inhibition of Succinoxidase and Reduced Nicotinamide Adenine Dinucleotide (NADH) Oxidase by 2,3-Ethylenedioxy-1,4-benzoquinones Having Alkylthio and Arylthio Side Chains

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A series of 2,3-ethylenedioxy-1,4-benzoquinones having an alkylthio or arylthio side chain at the 5-position or two alkylthio or arylthio side chains at the 5,6-positions was synthesized. These compounds were tested for inhibition of the succinoxidase and reduced nicotinamide adenine dinucleotide (NADH) oxidase systems in the mitochondrial respiratory chain. 5-Arylthio- and 5,6-diarylthio-2,3-ethylenedioxy-1,4-benzoquinones were found to show potent inhibitory activities toward both enzyme systems. However, 5-alkylthio- and 5,6-dialkylthio-2,3-ethylenedioxy-1,4-benzoquinones showed weak inhibitory activities. The substitution of a 2,3-ethylenedioxy group in place of the 2,3-dimethoxy group of coenzyme Q (CoQ) was found to be more favorable than the previously reported 2,3-dimethyl compound or 1,4-naphthoquinones for the inhibition of both enzyme systems. The effects of 2,3-ethylenedioxy-1,4-benzoquinones on the reduced minus oxidized difference spectra of submitochondrial particles with succinate or NADH as a substrate were investigated to identify their inhibitory sites in the respiratory chain. The spectral changes suggested that 5-arylthio- and 5,6-diarylthio-2,3-ethylenedioxy-1,4-benzoquinones inhibit some sites between succinate and CoQ, as well as after cytochrome a+a_3. On the other hand, 5,6-dialkylthio-2,3-ethylenedioxy-1,4-benzoquinones were found to inhibit some sites between NADH and CoQ, as well as after chrochrome a+a_3.
公益社団法人日本薬学会の論文
1989-01-25

Inhibition of Succinoxidase and Reduced Nicotinamide Adenine Dinucleotide (NADH) Oxidase by 2,3-Ethylenedioxy-1,4-benzoquinones Having Alkylthio and Arylthio Side Chains

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