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Chemical Compound Review:

CHEMBL527817 2-heptyl-1H-quinolin-4-one

Synonyms: SureCN170164, SureCN472759, TCMDC-132026, AG-J-77329, CHEBI:62219, ...

Laszlo, D.J. et al., Machan, Z.A. et al., Kenimer, E.A. et al., Singh, A.P. et al., Hogarth, C. et al., et al.

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Disease relevance of MY 12-62c

2-Heptyl-4-hydroxyquinoline N-oxide, an antistaphylococcal agent produced by Pseudomonas aeruginosa [1].
2-Heptyl-4-hydroxyquinoline was identified in a sample of human bronchial secretions from a patient with cystic fibrosis who was heavily colonized with P. aeruginosa [1].
Aerotaxis (migration towards oxygen) of Bacillus cereus M63, a motile strain, was inhibited by potassium cyanide and 2-heptyl-4-hydroxyquinoline N-oxide, indicating a requirement for both the terminal oxidase (cytochrome aa3) and the cytochrome b segment of the electron transport system [2].

High impact information on MY 12-62c

1. Cytochrome spectra of the liver and heart mitochondria incubated under various conditions are presented to compare the effects of antimycin, colletotrichin and 2-heptyl-4-hydroxyquinoline N-oxide (HQNO) additions [3].
Antimycin A and 2-heptyl-4-hydroxyquinoline N-oxide (HQNO), both of which bind to the same site of complex III, prevented U937 cell killing promoted by tert-butylhydroperoxide (tB-OOH) [4].
Generation of the membrane potential required Na+ and was inhibited by 2-heptyl-4-hydroxyquinoline N-oxide, a specific inhibitor of the Na+-dependent NADH oxidase [5].
In contrast, a particulate NADH oxidase, which was sensitive to inhibition by antimycin A and 2-heptyl-4-hydroxyquinoline N-oxide, was induced by aerobic growth in the presence of haematin [6].
Comparison of the effects of various respiratory inhibitors reveals that the difference in cyanide sensitivity between these membranes is located on the oxidase side of the 2-heptyl-4-hydroxyquinoline N-oxide-sensitive step [7].

Associations of MY 12-62c with other chemical compounds

The effects of selected electron transport inhibitors (amytal, rotenone, 2-heptyl-4-hydroxyquinoline, antimycin A1, and potassium cyanide [KCN]) on electron transfer in whole-cell and sonically treated whole-cell preparations of N. gonorrhoeae were examined [8].
Inhibition was also produced by the ATPase inhibitors N,N'-dicyclohexylcarbodimide (DCCD) and diphenyl phosphorazidate (DPA), and by the respiratory chain inhibitors piericidin A, 2-heptyl-4-hydroxyquinoline N-oxide, and An2+ [9].

References

2-Heptyl-4-hydroxyquinoline N-oxide, an antistaphylococcal agent produced by Pseudomonas aeruginosa. Machan, Z.A., Taylor, G.W., Pitt, T.L., Cole, P.J., Wilson, R. J. Antimicrob. Chemother. (1992) [Pubmed]
Bacillus cereus electron transport and proton motive force during aerotaxis. Laszlo, D.J., Niwano, M., Goral, W.W., Taylor, B.L. J. Bacteriol. (1984) [Pubmed]
The pathway of electron flow through ubiquinol:cytochrome c oxidoreductase in the respiratory chain. Evidence from inhibition studies for a modified 'Q cycle'. Halestrap, A.P. Biochem. J. (1982) [Pubmed]
Mitochondrial formation of hydrogen peroxide is causally linked to the antimycin A-mediated prevention of tert-butylhydroperoxide-induced U937 cell death. Brambilla, L., Cantoni, O. FEBS Lett. (1998) [Pubmed]
Generation of the electrochemical potential of Na+ by the Na+-motive NADH oxidase in inverted membrane vesicles of Vibrio alginolyticus. Tokuda, H., Udagawa, T., Unemoto, T. FEBS Lett. (1985) [Pubmed]
Growth of Streptococcus faecalis var. zymogenes on glycerol: the effect of aerobic and anaerobic growth in the presence and absence of haematin on enzyme synthesis. Pugh, S.Y., Knowles, C.J. J. Gen. Microbiol. (1982) [Pubmed]
Cyanide-resistant electron transport in sporulating Bacillus megaterium KM. Hogarth, C., Wilkinson, B.J., Ellar, D.J. Biochim. Biophys. Acta (1977) [Pubmed]
Effects of selected inhibitors on electron transport in Neisseria gonorrhoeae. Kenimer, E.A., Lapp, D.F. J. Bacteriol. (1978) [Pubmed]
ATP-dependent proton translocation and quenching of 9-aminoacridine fluorescence in inside-out membrane vesicles of a cytochrome-deficient mutant of Escherichia coli,. Singh, A.P., Bragg, P.D. Biochim. Biophys. Acta (1977) [Pubmed]

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