Effects of 3,5-dibromo-4-hydroxybenzaldehyde O-(2,4-dinitrophenyl)oxime on Reactions of Mitochondria and Chloroplasts

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Abstract
The effects of 3,5-dibromo-4-hydroxybenzaldehyde O-(2,4-dinitrophenyl)oxime (hereinafter referred to as C-9122), 3,5-dibromo-4-hydroxybenzonitrile (bromoxynil), 3,5-dibromo-4-hydroxybenzaldoxime (hereinafter referred to as bromoxime), and 2,4-dinitrophenol (hereinafter referred to as DNP) on phosphorylation and electron transport were measured in mitochondria isolated from white potato tubers (Solarium tuberosum L.) and in chloroplasts from spinach leaves (Spinacia oleracea L.). Mitochondrial oxygen utilization was monitored polarographically. All four chemicals stimulated ADP-limited oxygen utilization, inhibited non-ADP-limited oxygen uptake, and relieved oligomycin-inhibited oxygen uptake. C-9122 produced responses at lower molar concentrations than did bromoxynil, bromoxime, and DNP. The I50 value for inhibition of state 3 respiration by C-9122 was 2.7 × 10−6 M.In chloroplasts, C-9122, bromoxime, and DNP inhibited photoreduction and coupled photophosphorylation with water as the electron donor, and with ferricyanide and NADP as electron acceptors. Cyclic photophosphorylation, with phenazine methosulfate as the electron mediator under an argon gas phase, also was inhibited. With ascorbate-2,6-dichlorophenolindophenol (hereinafter referred to as DPIP) as the electron donor, phosphorylation coupled to NADP reduction was inhibited, but not the reduction of NADP. C-9122 was the strongest inhibitor, and bromoxime was the weakest inhibitor of the several reactions. The I50 value for inhibition of the coupled ferricyanide reduction was 4.6 × 10−6 M for C-9122. C-9122 appeared to act in two different ways by (a) inhibiting electron transport at or near photosystem II and the oxygen evolution pathway, and (b) interfering with energy transfer and the generation of ATP. Bromoxynil inhibited photoreduction and photophosphorylation reactions in which water served as the electron donor; but it was a very poor inhibitor of both cyclic photophosphorylation, and photophosphorylation coupled to NADP reduction with ascorbate-DPIP serving as the electron donor. Because of the pivotal role of ATP in cellular metabolism, it is conceivable that interference with ATP generation could be a major (but not necessarily the only) mechanism through which the herbicidal activity of C-9122 is expressed.