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. 1981 Oct;20(4):558–562. doi: 10.1128/aac.20.4.558

Mode of antibiotic action of 4-hydroxy-3-nitrosobenzaldehyde from Streptomyces viridans.

C C Yang, J Leong
PMCID: PMC181746  PMID: 6805420

Abstract

The free ligand, deferroviridomycin A, and its iron(II) complex, viridomycin A, were detected in culture supernatant fluids of Streptomyces viridans 1671 and were structurally characterized as 4-hydroxy-3-nitrosobenzaldehyde and tris(4-hydroxy-3-nitrosobenzaldehydato-N3,O4)ferrate(II), respectively. We investigated the antibiotic activity of the above compounds and of the chemically synthesized bis copper(II), tris cobalt(III), and tris nickel(II) complexes against Escherichia coli NIHJ, Salmonella typhimurium LT-2Z, Staphylococcus aureus 209P, Streptococcus faecium 10541, and Bacillus cereus, T. The free ligand and its kinetically labile copper(II) and nickel(II) complexes displayed activity against all of the above organisms, whereas the kinetically inert iron(II) and cobalt(III) complexes displayed activity only against S. aureus and B. cereus. The antibiotic activity of the substitutionally labile metal complexes was attributed to dissociation of the free ligand. The mode of antibiotic action of the free ligand against E. coli appears to be interference with the structural and functional integrity of the cell membrane.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Candeloro S., Grdenic D., Taylor N., Thompson B., Viswamitra M., Hodgkin D. C. Structure of ferroverdin. Nature. 1969 Nov 8;224(5219):589–591. doi: 10.1038/224589a0. [DOI] [PubMed] [Google Scholar]
  2. FEW A. V., SCHULMAN J. H. The absorption of polymyxin E by bacteria and bacterial cell walls and its bactericidal action. J Gen Microbiol. 1953 Dec;9(3):454–466. doi: 10.1099/00221287-9-3-454. [DOI] [PubMed] [Google Scholar]
  3. Hassan H. M., Fridovich I. Mechanism of the antibiotic action pyocyanine. J Bacteriol. 1980 Jan;141(1):156–163. doi: 10.1128/jb.141.1.156-163.1980. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Luckey M., Pollack J. R., Wayne R., Ames B. N., Neilands J. B. Iron uptake in Salmonella typhimurium: utilization of exogenous siderochromes as iron carriers. J Bacteriol. 1972 Sep;111(3):731–738. doi: 10.1128/jb.111.3.731-738.1972. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Marchenko I. V., Egorova S. A., Blinov N. O., Krassilnikov N. A. The role of iron in the formation of green pigments by actinomycetes. Z Allg Mikrobiol. 1968;8(5):437–439. [PubMed] [Google Scholar]
  6. Molin S., Von Meyenburg K., Maaloe O., Hansen M. T., Pato M. L. Control of ribosome synthesis in Escherichia coli: analysis of an energy source shift-down. J Bacteriol. 1977 Jul;131(1):7–17. doi: 10.1128/jb.131.1.7-17.1977. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Nazar R. N., Wong J. T. Inhibitor-induced shift-downs in Escherichia coli. J Bacteriol. 1969 Nov;100(2):956–961. doi: 10.1128/jb.100.2.956-961.1969. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Olenick J. G., Cook T. M., Hahn F. E. Bactericidal action of 2-hydroxy-3-(cyclohexylpropyl)-1,4-naphthoquinone on Bacillus megaterium. J Bacteriol. 1971 Aug;107(2):528–534. doi: 10.1128/jb.107.2.528-534.1971. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Pollack J. R., Ames B. N., Neilands J. B. Iron transport in Salmonella typhimurium: mutants blocked in the biosynthesis of enterobactin. J Bacteriol. 1970 Nov;104(2):635–639. doi: 10.1128/jb.104.2.635-639.1970. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Reid G. A., Ingledew W. J. Characterization and phenotypic control of the cytochrome content of Escherichia coli. Biochem J. 1979 Aug 15;182(2):465–472. doi: 10.1042/bj1820465. [DOI] [PMC free article] [PubMed] [Google Scholar]

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