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

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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.

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Abbreviations

PCMB:

4-chloromercuribenzoic acid

PMSF:

phenylmethanesulfonyl fluoride

References

  • 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).

    Article  CAS  Google Scholar 

  • Arson R., Shpira E.: Antibodies to papains, a selective fractionation according to inhibitory capacity.Biochemistry 6, 3942 (1967).

    Article  Google Scholar 

  • Bowman W.R., Stretton R.J.: Antimicrobial activity of a series of halo-nitro compounds.Antimicrob.Agents Chemother. 2, 504 (1972).

    PubMed  CAS  Google Scholar 

  • 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).

    CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • Dawes E.A.:Quantitative Problems in Biochemistry. E. and S. Livingstone Ltd., New York 1967.

    Google Scholar 

  • Fersht A.:Enzyme Structure and Mechanism, p. 16. W.H.Freeman, Reading 1977.

    Google Scholar 

  • 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 

  • Ghannoum M.A.,Bowman W.R.,Valmas M.: Antimicrobial activity of some heteroeyche derivatives of 1-inethyl-l-nitroethyl sulphides.Microbios, in press (1984).

  • 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.

  • Jocelyn P.C.:Biochemistry of the SH Group, p. 83. Academic Press, London 1972.

    Google Scholar 

  • Kunitz M.: Crystalline soybean trypsin inhibitor II.J.Gen. Physiol. 30, 291 (1947).

    Article  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • Lorenz P.: 5-Bromo-5-nitro-l,3-dioxane, a preservative for cosmetics.Cosmet.Toiletr. 92. S9 (1977a).

    Google Scholar 

  • Lorenz P.: 5-Bromo-5-nitro-l,3-dioxane, ein neues Konservierungsmittel für dio Kosmetik.J.Soc.Cosmet.Chem. 28, 427 (1977b).

    CAS  Google Scholar 

  • Maccaro G.A.: The assessment of the interaction between anti-bacterial drugs.Prog. L 1. Microbiol. 3, 173 (1961).

    Google Scholar 

  • Newton B.A.: The release of soluble constituents from washed cells ofPseudomonas aeruginosa by the action of polymyxin.J.Gen. Microbiol. 9, 54 (1953).

    PubMed  CAS  Google Scholar 

  • Rajgopalan T.G., Mooee S., Stein W.H.: Pepsin from pepsinogen. Preparation and properties.J.Biol.Chem. 241, 4940 (1966).

    Google Scholar 

  • Salton M.R.J.:The Bacterial Cell Wall. Elsevier, Amsterdam 1964.

    Google Scholar 

  • Sokolovsky M., Harell D., Riobdan J.F.: Reaction of tetranitromethane with sulfhydryl groups in proteins.Biochemistry 8, 4740 (1969).

    Article  PubMed  CAS  Google Scholar 

  • 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 

  • Umbrett W.W., Burris R.A., Stauffer J.F.:Manometric Techniques. Burgess Publ. Co., Minneapolis 1957.

    Google Scholar 

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We would like to thank Miss F. Kayed and Mr. M. Al Samawi for their technical assistance. The cooperation of staff at the E.M. Unit,Faculty of Science, Kuwait University, is appreciated.

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Ghannoum, M., Thomson, M., Bowman, W. et al. Mode of action of the antimicrobial compound 5-Bromo-5-nitro-1,3-dioxane (Bronidox). Folia Microbiol 31, 19–31 (1986). https://doi.org/10.1007/BF02928676

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  • DOI: https://doi.org/10.1007/BF02928676

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