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2-Anilino-1.3.4-thiadiazole, Hemmstoffe der oxidativen und photosynthetischen Phosphorylierung : 2-Anilino-l,3,4-Thiadiazoles, Inhibitors of Oxidative and Photosynthetic Phosphorylation

Schäfer, G., Trebst, A., Büchel, K. H.
Zeitschrift für Naturforschung 2014 v.30 no.3-4 pp. 183-189
Spinacia oleracea, acids, chloroplasts, electron transfer, mitochondria, phosphorylation, photophosphorylation, spinach
2-anilino-1,3,4-thiadiazoles carrying various substituents in the 5-position as well as in the benzene-ring were synthesized.The compounds were tested with rat-liver-mitochondria and with spinach-chloroplasts and revealed to be potent uncouplers of both, oxidative and photosynthetic phosphorylation, with p I₅₀-values rangeing from 6.79 to 4.05. At higher concentration all compounds are inhibitors of the Hillreaction.In mitochondria a fair correlation exists between pKa of the acidic NH-group and the uncoupling activity; a maximum is obtained around pKa= 6 .8 , whereas in chloroplasts activity is shifted to more acid pKa-values.The compounds meet the requirements for uncouplers according to the chemi-osmotic theory, being lipophilic weak acids. N-methylation causes total loss of activity in mitochondrial oxidative phosphorylation.The inhibitory action on photosynthetic electron transport is located within photosystem II. This latter activity is almost independent of substituent effects in contrast to uncoupling of either respiratory- or photo-phosphorylation