Advertisement

Folia Microbiologica

, Volume 31, Issue 1, pp 19–31 | Cite as

Mode of action of the antimicrobial compound 5-Bromo-5-nitro-1,3-dioxane (Bronidox)

  • M. Ghannoum
  • M. Thomson
  • W. Bowman
  • S. Al-Khalil
Article

Abstract

The mode of action of the antimicrobial agent, 5-bromo-5-nitro-l,3-dioxane (bronidox), was studied in detail for gram-positive and gram-negative bacteria, yeast and fungi. The studies included MIC testing, thiol inhibition of activity, intracellular leakage, oxygen consumption, incorporation of3H-uridine, scanning electron microscopy, inhibition of enzyme activity (papain) andin vitro oxidation of thiols to disulfides. It appears that the primary mode of action of bronidox is the same as, or similar to, that of bronopol,i.e. the oxidation of essential protein thiol causing inhibition of enzyme activity and subsequent inhibition of microbial growth.

Keywords

Thiol Dioxane Papain Tryptic Soya Agar Mercaptoacetic Acid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Abbreviations

PCMB

4-chloromercuribenzoic acid

PMSF

phenylmethanesulfonyl fluoride

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Al-Khalil S.I., Bow’man W.R.: Effects of methanol solvation on the nucleophilic reactions of thiolates with 2-substituted 2-nitropropanes.Tetrahedron Lett. 25, 461 (1984).CrossRefGoogle Scholar
  2. Arson R., Shpira E.: Antibodies to papains, a selective fractionation according to inhibitory capacity.Biochemistry 6, 3942 (1967).CrossRefGoogle Scholar
  3. Bowman W.R., Stretton R.J.: Antimicrobial activity of a series of halo-nitro compounds.Antimicrob.Agents Chemother. 2, 504 (1972).PubMedGoogle Scholar
  4. Bryce D.M., Croshaw B., Hall J.E., Holland V.R., Lessel B.: The activity and safety of the antimicrobial agent bronopol (2-bromo-2-nitropropan-l,3-diol).J. Soc.Cosmet.Chem. 29, 3 (1978).Google Scholar
  5. Clark N.G., Croshaw N.M., Leggetter B.E., Spooner D.F.: Synthesis and antimicrobial activity of aliphatic nitro compounds.J. Med.Chem. 17, 977 (1974).PubMedCrossRefGoogle Scholar
  6. Dawes E.A.:Quantitative Problems in Biochemistry. E. and S. Livingstone Ltd., New York 1967.Google Scholar
  7. Fersht A.:Enzyme Structure and Mechanism, p. 16. W.H.Freeman, Reading 1977.Google Scholar
  8. Ghannoum M.A.: The effect of selected steroids on the growth, morphology and sterol contentsof Candida albicans. PhD Thesis, University of Technology, Loughborough (UK) 1977.Google Scholar
  9. Ghannoum M.A.,Bowman W.R.,Valmas M.: Antimicrobial activity of some heteroeyche derivatives of 1-inethyl-l-nitroethyl sulphides.Microbios, in press (1984).Google Scholar
  10. Hugo W.B.,Russell A.D.: Types of antimicrobial agents, in Principles and Practice of Disinfection, Preservation and Sterilisation (D. Russell, B. Hugo, G. Ayliffe , eds). Blackwell Scientific Publication 1982.Google Scholar
  11. Jocelyn P.C.:Biochemistry of the SH Group, p. 83. Academic Press, London 1972.Google Scholar
  12. Kunitz M.: Crystalline soybean trypsin inhibitor II.J.Gen. Physiol. 30, 291 (1947).CrossRefGoogle Scholar
  13. Lappas L.C., Hiksch CA., Winely C.L.: Substituted 5-nitio-l,.3-dioxanes: Corrolation of chemical structure and antimicrobial activity.J. Pharm. Sci. 65, 1301 (1976).PubMedCrossRefGoogle Scholar
  14. Lorenz P.: 5-Bromo-5-nitro-l,3-dioxane, a preservative for cosmetics.Cosmet.Toiletr. 92. S9 (1977a).Google Scholar
  15. Lorenz P.: 5-Bromo-5-nitro-l,3-dioxane, ein neues Konservierungsmittel für dio Kosmetik.J.Soc.Cosmet.Chem. 28, 427 (1977b).Google Scholar
  16. Maccaro G.A.: The assessment of the interaction between anti-bacterial drugs.Prog. L 1. Microbiol. 3, 173 (1961).Google Scholar
  17. Newton B.A.: The release of soluble constituents from washed cells ofPseudomonas aeruginosa by the action of polymyxin.J.Gen. Microbiol. 9, 54 (1953).PubMedGoogle Scholar
  18. Rajgopalan T.G., Mooee S., Stein W.H.: Pepsin from pepsinogen. Preparation and properties.J.Biol.Chem. 241, 4940 (1966).Google Scholar
  19. Salton M.R.J.:The Bacterial Cell Wall. Elsevier, Amsterdam 1964.Google Scholar
  20. Sokolovsky M., Harell D., Riobdan J.F.: Reaction of tetranitromethane with sulfhydryl groups in proteins.Biochemistry 8, 4740 (1969).PubMedCrossRefGoogle Scholar
  21. Strbtton R.J., Manson T.W.: Some aspects of the mode of action of the antibacterial compound bronopol (2-bromo-2-nitro-propan-l,3-diol).J. Appl. Bact. 36, 61 (1973).Google Scholar
  22. Umbrett W.W., Burris R.A., Stauffer J.F.:Manometric Techniques. Burgess Publ. Co., Minneapolis 1957.Google Scholar

Copyright information

© Institute of Microbiology, Academy of Sciences of the Czech Republic 1986

Authors and Affiliations

  • M. Ghannoum
    • 1
  • M. Thomson
    • 2
  • W. Bowman
    • 3
  • S. Al-Khalil
    • 3
  1. 1.Department of Botany and MicrobiologyKuwait University, Faculty of ScienceKuwait
  2. 2.Department of BiochemistryKuwait University, Faculty of ScienceKuwait
  3. 3.Department of ChemistryUniversity of TechnologyLoughboroughUK

Personalised recommendations