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Chemical Compound Review:

Malonoben 2-[(4-hydroxy-3,5-ditert- butyl...

Synonyms: Tyrphostin 9, tyrphostin A9, Lopac-T-182, CHEMBL78150, T182_SIGMA, ...

Terada, H. et al., Mountfort, D.O. et al., Friedberg, I. et al., Hori, H. et al., Hitchens, G.D. et al.

Hori, Noguchi, Yokoyama, Ise, Jin, Kasai, Goto, Taira,

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High impact information on Malonoben

5. Photophosphorylation is completely inhibited by the uncoupler SF 6847 at a concentration corresponding to 0.31 molecules per electron transport chain [1].
Addition of the protonophore 3,5-di-tert-butyl-4-hydroxybenzylidenemalononitrile (SF-6847) to protoplast suspensions resulted in a dissipation of the membrane potential (delta psi), and this was accompanied by a parallel decrease in the rates of ATP synthesis and methanogenesis [2].
Titration with electrogenic ionophores, such as carbonylcyanide m-chlorophenylhydrazone (CCCP), SF-6847 and gramicidin D, markedly increased the membrane permeability within a very narrow range of ionophore concentration [3].
This report also supports the notion that the inhibition of tumor cell growth of inhibitor of protein tyrosine kinase AG17, which is identical to SF 6847, may be due to its mitochondrial cytotoxicity [4].
Unique action of a modified weakly acidic uncoupler without an acidic group, methylated SF 6847, as an inhibitor of oxidative phosphorylation with no uncoupling activity: possible identity of uncoupler binding protein [5].

Biological context of Malonoben

Thus, O-methylated SF 6847 is a unique inhibitor of oxidative phosphorylation [5].

Anatomical context of Malonoben

The O-methylated SF 6847 at 20 microM did, however, inhibit state 3 respiration of mitochondria, although it did not inhibit electron-flow through the respiratory chain, ATPase activated by weakly acidic uncouplers or Pi-ATP exchange [5].
The potent weakly acidic uncoupler SF 6847 was modified by methylation of its phenolic OH group, and the effect of the resulting derivative, with no acid-dissociable group, on oxidative phosphorylation in rat liver mitochondria was examined [5].

References

On the extent of localization of the energized membrane state in chromatophores from Rhodopseudomonas capsulata N22. Hitchens, G.D., Kell, D.B. Biochem. J. (1982) [Pubmed]
Methanogenesis and ATP synthesis in a protoplast system of Methanobacterium thermoautotrophicum. Mountfort, D.O., Mörschel, E., Beimborn, D.B., Schönheit, P. J. Bacteriol. (1986) [Pubmed]
Permeability change in transformed mouse fibroblasts caused by ionophores, and its relationship to membrane permeabilization by exogenous ATP. Friedberg, I., Weisman, G.A., De, B.K. J. Membr. Biol. (1985) [Pubmed]
Design and synthesis of new mitochondrial cytotoxin N-thiadiazolylanilines that inhibit tumor cell growth. Hori, H., Noguchi, N., Yokoyama, H., Ise, H., Jin, C.Z., Kasai, S., Goto, T., Taira, Z. Bioorg. Med. Chem. (1996) [Pubmed]
Unique action of a modified weakly acidic uncoupler without an acidic group, methylated SF 6847, as an inhibitor of oxidative phosphorylation with no uncoupling activity: possible identity of uncoupler binding protein. Terada, H., Fukui, Y., Shinohara, Y., Ju-ichi, M. Biochim. Biophys. Acta (1988) [Pubmed]

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