Partition and Ion-pair Partition of 2,4-Dinitrophenol, an Uncoupler of Oxidative Phosphorylation

概要

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The partition of 2,4-dinitrophenol (DNP) between n-octanol and water was studied under various conditions. It was found that DNP is transferred to the organic phase in three forms : in the neutral form, in the form of an ion-pair complex with cations in the aqueous phase, and directly in the anionic form. The values of the ion-pair partition coefficient, the ion-pair complex formation constants of the DNP anion with K^+ and the n-butyltrimethylammonium ion, and the partition coefficients of the neutral and anionic forms of DNP, indicated that upon partition at pH 7,most DNP is present in n-octanol in the form of the ion-pair complex with the quaternary ammonium ion, and the relative amount of the neutral form of DNP in n-octanol is about the same as that of the ion-pair with K^+. Above pH 8,direct transfer of the DNP anion to n-octanol became significant, while the transfer of the neutral form of DNP became very small. These results are discussed in relation to the uncoupling activity of DNP in mitochondria.
社団法人日本薬学会の論文
1981-01-25