Abstract
1. The ability of a series of compounds to uncouple oxidative phosphorylation of rat-liver mitochondria has been investigated. 2. The compounds were: 2-amino-1,1,3-tricyanopropene; carbonyl cyanide phenylhydrazone and its m-chloro and p-trifluoromethoxy derivatives; 4,5,6,7-tetrachloro-, 5-chloro-4-nitro-, 5-nitro-and 4,5,6,7-tetrachloro-1-methyl-benzotriazole; 4-hydroxy-3,5-di-iodo-, 3,5-di-bromo-4-hydroxy- and 3,5-dichloro-4-hydroxy-benzonitrile; and pentafluorophenol. 3. In a medium the components and physical condition of which were, as far as possible, kept constant, each compound was tested for ability to stimulate adenosine triphosphatase, to stimulate respiration in the presence of pyruvate as substrate, to inhibit phosphate uptake and to prevent swelling by trimethyltin. 4. Each compound was also examined with respect to its ability to produce rapid rigor mortis in mice. 5. The biological properties were compared with the dissociation constant and the hexane–water partition coefficient for each compound. 6. With the exception of 4,5,6,7-tetrachloro-1-methylbenzotriazole, all the compounds behaved qualitatively as 2,4-dinitrophenol. 7. Within each class of compound there is a relation between biological activity and the physical attributes measured. 8. The most efficient uncouplers were the most acidic and the most hydrophobic.
Full text
PDFSelected References
These references are in PubMed. This may not be the complete list of references from this article.
- ALDRIDGE W. N. Liver and brain mitochondria. Biochem J. 1957 Nov;67(3):423–431. doi: 10.1042/bj0670423. [DOI] [PMC free article] [PubMed] [Google Scholar]
- ALDRIDGE W. N., PARKER V. H. Barbiturates and oxidative phosphorylation. Biochem J. 1960 Jul;76:47–56. doi: 10.1042/bj0760047. [DOI] [PMC free article] [PubMed] [Google Scholar]
- ALDRIDGE W. N., STONER H. B. The behaviour of liver mitochondria isolated from rats with different body temperatures after limb ischaemia or after injection of 3:5-dinitro-ocresol. Biochem J. 1960 Jan;74:148–154. doi: 10.1042/bj0740148. [DOI] [PMC free article] [PubMed] [Google Scholar]
- ALDRIDGE W. N. The biochemistry of organotin compounds: trialkyltins and oxidative phosphorylation. Biochem J. 1958 Jul;69(3):367–376. doi: 10.1042/bj0690367. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Aldridge W. N., Street B. W. Oxidative phosphorylation. Biochemical effects and properties of trialkyltins. Biochem J. 1964 May;91(2):287–297. doi: 10.1042/bj0910287. [DOI] [PMC free article] [PubMed] [Google Scholar]
- HEYTLER P. G., PRICHARD W. W. A new class of uncoupling agents--carbonyl cyanide phenylhydrazones. Biochem Biophys Res Commun. 1962 May 4;7:272–275. doi: 10.1016/0006-291x(62)90189-4. [DOI] [PubMed] [Google Scholar]
- MITCHELL P. Coupling of phosphorylation to electron and hydrogen transfer by a chemi-osmotic type of mechanism. Nature. 1961 Jul 8;191:144–148. doi: 10.1038/191144a0. [DOI] [PubMed] [Google Scholar]
- PARKER V. H., BARNES J. M., DENZ F. A. Some observations on the toxic properties of 3:5-dinitro-ortho-cresol. Br J Ind Med. 1951 Oct;8(4):226–235. doi: 10.1136/oem.8.4.226. [DOI] [PMC free article] [PubMed] [Google Scholar]
- PARKER V. H. Effect of nitrophenols and halogenophenols on the enzymic activity of rat-liver mitochondria. Biochem J. 1958 Jun;69(2):306–311. doi: 10.1042/bj0690306. [DOI] [PMC free article] [PubMed] [Google Scholar]
- RACKER E. Mechanisms of synthesis of adenosine triphosphate. Adv Enzymol Relat Subj Biochem. 1961;23:323–399. doi: 10.1002/9780470122686.ch7. [DOI] [PubMed] [Google Scholar]
- TERNER C. The effect of p-nitrophenol on the Pasteur reaction and on aerobic phosphorylation in suspensions of the mammary gland. Biochem J. 1954 Mar;56(3):471–480. doi: 10.1042/bj0560471. [DOI] [PMC free article] [PubMed] [Google Scholar]
- WEINBACH E. C. Pentachlorophenol and mitochondrial adenosinetriphosphatase. J Biol Chem. 1956 Aug;221(2):609–618. [PubMed] [Google Scholar]
- WEINBACH E. C. The effect of pentachlorophenol on oxidative phosphorylation. J Biol Chem. 1954 Oct;210(2):545–550. [PubMed] [Google Scholar]
- Webster G. R., Smith A. T. A note on the construction of a modified tissue homogenizer. Biochem J. 1964 Jan;90(1):64–65. doi: 10.1042/bj0900064. [DOI] [PMC free article] [PubMed] [Google Scholar]