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Chemical characterization and biological properties of NVC-422, a novel, stable N-chlorotaurine analog.

ABSTRACT: During oxidative burst, neutrophils selectively generate HOCl to destroy invading microbial pathogens. Excess HOCl reacts with taurine, a semi-essential amino acid, resulting in the formation of the longer-lived biogenerated broad-spectrum antimicrobial agent, N-chlorotaurine (NCT). In the presence of an excess of HOCl or under moderately acidic conditions, NCT can be further chlorinated, or it can disproportionate to produce N,N-dichlorotaurine (NNDCT). In the present study, 2,2-dimethyltaurine was used to prepare a more stable N-chlorotaurine, namely, N,N-dichloro-2,2-dimethyltaurine (NVC-422). In addition, we report on the chemical characterization, in vitro antimicrobial properties, and cytotoxicity of this compound. NVC-422 was shown effectively to kill all 17 microbial strains tested, including antibiotic-resistant Staphylococcus aureus and Enterococcus faecium. The minimum bactericidal concentration of NVC-422 against Gram-negative and Gram-positive bacteria ranged from 0.12 to 4 ?g/ml. The minimum fungicidal concentrations against Candida albicans and Candida glabrata were 32 and 16 ?g/ml, respectively. NVC-422 has an in vitro cytotoxicity (50% cytotoxicity = 1,440 ?g/ml) similar to that of NNDCT. Moreover, our data showed that this agent possesses rapid, pH-dependent antimicrobial activity. At pH 4, NVC-422 completely killed both Escherichia coli and S. aureus within 5 min at a concentration of 32 ?g/ml. Finally, the effect of NVC-422 in the treatment of an E. coli-infected granulating wound rat model was evaluated. Treatment of the infected granulating wound with NVC-422 resulted in significant reduction of the bacterial tissue burden and faster wound healing compared to a saline-treated control. These findings suggest that NVC-422 could have potential application as a topical antimicrobial.

SUBMITTER: Wang L

PROVIDER: S-EPMC3101424 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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Chemical characterization and biological properties of NVC-422, a novel, stable N-chlorotaurine analog.

Wang Lu L Belisle Barbara B Bassiri Mansour M Xu Ping P Debabov Dmitri D Celeri Chris C Alvarez Nichole N Robson Martin C MC Payne Wyatt G WG Najafi Ramin R Khosrovi Behzad B

Antimicrobial agents and chemotherapy 20110321 6

During oxidative burst, neutrophils selectively generate HOCl to destroy invading microbial pathogens. Excess HOCl reacts with taurine, a semi-essential amino acid, resulting in the formation of the longer-lived biogenerated broad-spectrum antimicrobial agent, N-chlorotaurine (NCT). In the presence of an excess of HOCl or under moderately acidic conditions, NCT can be further chlorinated, or it can disproportionate to produce N,N-dichlorotaurine (NNDCT). In the present study, 2,2-dimethyltaurine ...[more]

PMID: 21422212

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Chemical characterization and biological properties of NVC-422, a novel, stable N-chlorotaurine analog.

Publications

Chemical characterization and biological properties of NVC-422, a novel, stable N-chlorotaurine analog.

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