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N,N-dichlorotaurine: chemical and bactericidal properties
Waldemar Gottardi1, Magdalena Hagleitner, Markus Nagl
1Department of Hygiene, Microbiology and Social Medicine, Division of Hygiene and Medical Microbiology, Innsbruck Medical University, Austria. waldemar.gottardi@uibk.ac.at
Archiv Der Pharmazie
|October 8, 2005
Summary
N-chlorotaurine (NCT) converts to N,N-dichlorotaurine (NDCT) in acidic conditions. NDCT is less effective than NCT in chlorinating amines but shows increased bactericidal activity against Gram-negative bacteria, though not suitable for medical use.
Area of Science:
- Antimicrobial agents
- Chemical synthesis
- Biochemistry
Background:
- N-chlorotaurine (NCT) is a biogenous antimicrobial agent.
- NCT disproportionates to N,N-dichlorotaurine (NDCT) in acidic environments.
- NDCT formation occurs in weakly acidic biological systems.
Purpose of the Study:
- Investigate the properties of the undescribed compound N,N-dichlorotaurine (NDCT).
- Determine NDCT's stability, reactivity, and antimicrobial efficacy.
- Assess NDCT's potential as a substitute for NCT in medical applications.
Main Methods:
- Synthesis of NDCT using trichloroisocyanuric acid in an aqueous system.
- Characterization of NDCT sodium and potassium salts, including melting points and stability.
- Evaluation of NDCT's efficacy in chlorinating amines and its bactericidal activity against various bacterial strains.
Main Results:
- NDCT sodium and potassium salts were synthesized and characterized; the sodium salt showed good stability.
- NDCT was less effective than NCT in chlorinating amines, particularly at pH < 7.
- NDCT exhibited greater molar bactericidal activity than NCT against Gram-negative bacteria (E. coli, P. aeruginosa, P. mirabilis) but not Gram-positive bacteria (S. aureus, S. epidermidis).
Conclusions:
- NDCT is synthesized and characterized, with its sodium salt demonstrating notable stability.
- NDCT's reduced efficacy in amine chlorination and its specific bactericidal profile suggest it is not a suitable replacement for NCT in medical practice.