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Bioorg Med Chem. 2013 Apr 15;21(8):2346-2354. doi: 10.1016/j.bmc.2013.01.075. Epub 2013 Feb 13.

Effects of alkyl side chain modification of coenzyme Q10 on mitochondrial respiratory chain function and cytoprotection.

Author information

1
Center for BioEnergetics, Biodesign Institute, and Department of Chemistry and Biochemistry, Arizona State University, Tempe, AZ 85287, USA.
2
Department of Molecular Biosciences, University of California, Davis, CA 95616, USA.
3
Department of Molecular Biosciences, University of California, Davis, CA 95616, USA. Electronic address: gcortopassi@ucdavis.edu.
4
Center for BioEnergetics, Biodesign Institute, and Department of Chemistry and Biochemistry, Arizona State University, Tempe, AZ 85287, USA. Electronic address: sidney.hecht@asu.edu.

Abstract

The effect of the alkyl side chain length of coenzyme Q10 on mitochondrial respiratory chain function has been investigated by the use of synthetic ubiquinone derivatives. Three analogues (3, 4 and 6) were identified that exhibited significantly improved effects on mitochondrial oxygen consumption and mitochondrial membrane potential, and also conferred significant cytoprotection on cultured mammalian cells in which glutathione had been depleted by treatment with diethyl maleate. The analogues also exhibited lesser inhibition of the electron transport chain than idebenone. The results obtained provide guidance for the design of CoQ10 analogues with improved activity compared to that of idebenone (1), the latter of which is undergoing evaluation in the clinic as a therapeutic agent.

PMID:
23473946
DOI:
10.1016/j.bmc.2013.01.075
[Indexed for MEDLINE]

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