The effect of α-N-substituted histidine derivatives on bimolecular lipid membranes as related to their ability to uncouple oxidative phosphorylation |
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Authors: | William Stillwell Harry C Winter |
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Institution: | Department of Biochemistry, Pennsylvania State University, University Park, Pennsylvania 16802 USA |
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Abstract: | A series of α-N-alkyl and α-N-aryl histidines was synthesized. Several of the more lipophilic derivatives were shown to be uncouplers of oxidative phosphorylation. A direct relationship was noted for the α-N-alkyl series between carbon chain length on the α-nitrogen of histidine, organic/water partition coefficient, efflux rate from liposomes, ability to lower electrical resistance of bimolecular lipid membranes, ability to increase respiration in coupled mitochondria, and ability to lower P/O ratios in coupled mitochondria. The aromatic derivative α-N-salicyl histidine was the best uncoupler in the series but was still not as effective an uncoupler as 2,4-dinitrophenol. |
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