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Advanced Research on N-chlorotaurine and Other Active Halogen Taurine Derivatives

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Molecular Pharmacology".

Deadline for manuscript submissions: closed (20 June 2025) | Viewed by 5040

Special Issue Editors


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Guest Editor
Institute of Hygiene and Medical Microbiology, Medical University of Innsbruck, 6020 Innsbruck, Austria
Interests: antimicrobial agents; chlorotaurine; taurine derivatives; active halogen compounds; antiseptics

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Guest Editor
Department of Research and Development, Nasco AD Biotechnology Laboratory, 11 Sachtouri Str, 18536 Piraeus, Greece
Interests: antibiotics; taurine

Special Issue Information

Dear Colleagues,

N-chlorotaurine (NCT, also designated as taurine chloramine) was discovered by researchers in Poland in 1971 as a product of the oxidative burst of human neutrophilic granulocytes and monocytes. It was formed by the reaction of hypochlorous acid with taurine and the leading substance of long-lived oxidants (chloramines) produced by these cells. The reactivity of NCT is low, so its formation can be regarded as a detoxification of hypochlorous acid. Due to its anti-inflammatory properties, for instance, the downregulation of nuclear factor kappaB, tumour necrosis factor-alpha, several cytokines and chemokines, and the upregulation of hemoxygenase-1, its additional function is to contribute to the termination of inflammation. In 1989, the synthesis of the sodium salt of NCT was successful in Austria, and, in the following, the broad-spectrum microbicidal activity of the substance was investigated, including biofilms. Preclinical and clinical studies have demonstrated the tolerability of high concentrations of topical NCT in different body regions and its efficacy as a body-own antiseptic and anti-infective. Thereby, NCT has proved superior to synthetic analogues taking together tolerability and efficacy. Treating upper and lower airway infections, including inhalation, has become a crucial research topic in recent years with several indications, for instance, chronic bronchitis, cystic fibrosis and COVID-19.

N-bromotaurine (NBrT, also designated as taurine bromamine) has broad-spectrum microbicidal and anti-inflammatory activity, and has been applied successfully against acne and skin infections in studies and cases. More stable dimethylated derivatives and bromamine T have similar properties, and recent activity against cancers in in vitro and in animal models has been found.

Furthermore, publications in recent years have comprised the interaction of NCT, NBrT, and their derivatives with innate and adaptive immunity; for instance, their influence on neutrophil degranulation, lymphocytes, leukocyte migration, and osteoclastogenesis. The inhibition of LPS-induced neuroinflammatory responses and inhibition of inflammation in LPS-induced pneumonia by NCT via the upregulation of Nrf2 and hemoxygenase-1 has been described, while efferocytosis was stimulated. Moreover, specific targets of NCT in certain pathogens and specific reactions of pathogens to NCT have been elucidated.

This issue aims to collect publications on N-chlorotaurine, N-bromotaurine and further halogenated taurine derivatives for stimulating research on these compounds in preclinical and clinical studies.

Scope: Both in vitro and in vivo studies and reviews on their mechanisms of action, their properties, their role in immunity and their application as anti-infective, anti-tumour, or other medications are welcome.

Dr. Markus Nagl
Dr. Anthony M. Kyriakopoulos
Guest Editors

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Keywords

  • N-chlorotaurine
  • N-bromotaurine
  • halogenated taurine derivatives
  • anti-infective
  • antiseptic
  • antimicrobial
  • immunity
  • inflammation
  • cancer

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Published Papers (3 papers)

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Research

10 pages, 2763 KiB  
Communication
Long-Term Stability and Efficacy of NCT Solutions
by Gabriel J. Staudinger, Zach M. Thomas, Sarah E. Hooper, Jeffrey F. Williams and Lori I. Robins
Int. J. Mol. Sci. 2024, 25(16), 8745; https://doi.org/10.3390/ijms25168745 - 10 Aug 2024
Viewed by 1621
Abstract
To realize the potential for the use of N-chlorotaurine (NCT) in healthcare, a better understanding of the long-term stability of the compound in water is needed. An array of analytical procedures is required that can measure changes in NCT concentration over time [...] Read more.
To realize the potential for the use of N-chlorotaurine (NCT) in healthcare, a better understanding of the long-term stability of the compound in water is needed. An array of analytical procedures is required that can measure changes in NCT concentration over time and allow for the detection and identification of contaminants and likely degradation end products. We used UV-Vis and NMR spectroscopy, HPLC, and LCMS to establish the stability of NCT in solutions subjected to prolonged ambient and elevated temperatures. Stability proved to be dependent on concentration with half-lives of ~120 days and ~236 days for 1% and 0.5% solutions of NCT at ~20 °C. Regardless of initial pH, all solutions shifted toward and maintained a pH of ~8.3 at 20 °C and 40 °C. NCT at 500 µg/mL and 250 µg /mL inhibited biofilm formation by Pseudomonas aeruginosa and Staphylococcus aureus but did not disperse established biofilms. NCT exposure to the biofilms had profound effects on the viability of both bacteria, reducing live organisms by >90%. Exposure of Interleukin-6 (IL-6) to 11 µM NCT reduced the binding of IL-6 to an immobilized specific antibody by ~48%, which is 5× the amount required for HOCl to bring about the same effect in this test system. Our data demonstrate the potency of the compound as an antimicrobial agent with potential benefits in the management of infected chronic wounds and suggest that NCT may contribute to anti-inflammatory processes in vivo by direct modification of cytokine mediators. Full article
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13 pages, 2648 KiB  
Article
Activity of N-Chlorotaurine against Periodontal Pathogens
by Kacper Kowalczyk, Débora C. Coraça-Huber, Walter Wille-Kollmar, Michael Berktold and Markus Nagl
Int. J. Mol. Sci. 2024, 25(15), 8357; https://doi.org/10.3390/ijms25158357 - 30 Jul 2024
Cited by 1 | Viewed by 1357
Abstract
Dental plaque bacteria play an important role in the pathogenicity of periodontitis and peri-implantitis. Therefore, antimicrobial agents are one means of treatment. N-chlorotaurine (NCT) as an endogenous well-tolerated topical antiseptic could be of advantage for this purpose. Accordingly, its microbicidal activity against [...] Read more.
Dental plaque bacteria play an important role in the pathogenicity of periodontitis and peri-implantitis. Therefore, antimicrobial agents are one means of treatment. N-chlorotaurine (NCT) as an endogenous well-tolerated topical antiseptic could be of advantage for this purpose. Accordingly, its microbicidal activity against some dental plaque bacteria was investigated at therapeutic concentrations in vitro. In quantitative killing assays, the activity of NCT against planktonic bacteria and against biofilms grown for 48 h on implantation screws was tested. Electron microscopy was used to demonstrate the formation of biofilm and its morphological changes. The killing of planktonic bacteria of all tested species, namely Streptococcus sanguinis, Streptococcus salivarius, Streptococcus oralis, Streptococcus cristatus, Rothia aeria, and Capnocytophaga ochracea, was shown within 10–20 min by 1% NCT in 0.01 M phosphate-buffered saline at 37 °C. Bacteria grown on screws for 24 h were inactivated by 1% NCT after 15–20 min as well, but the formation of biofilm on the screws was visible in electron microscopy not before 48 h. The killing of biofilms by 1% NCT was demonstrated after 30 min (streptococci) and 40 min (R. aeria). As expected, NCT has broad activity against dental plaque bacteria as well and should be further investigated on its clinical efficacy in periodontitis and peri-implantitis. Full article
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21 pages, 2049 KiB  
Article
N-Chlorotaurine Solutions as Agents for Infusion Detoxification Therapy: Preclinical Studies
by Bohdan Murashevych, Gennadii Bilenkyi, Dmitry Girenko and Emil Bilenkyi
Int. J. Mol. Sci. 2024, 25(15), 8345; https://doi.org/10.3390/ijms25158345 - 30 Jul 2024
Cited by 1 | Viewed by 1330
Abstract
N-chlorotaurine (NCT) is a broad-spectrum antimicrobial agent with outstanding tolerability, effective for topical and inhalation use. This paper presents the results of studies of single and repeated intravenous infusions of NCT to laboratory animals. The studies were conducted on female Wistar Han [...] Read more.
N-chlorotaurine (NCT) is a broad-spectrum antimicrobial agent with outstanding tolerability, effective for topical and inhalation use. This paper presents the results of studies of single and repeated intravenous infusions of NCT to laboratory animals. The studies were conducted on female Wistar Han rats. The effect of NCT infusions on the general condition, behavioral reactions, main biochemical and hematological parameters, hemocoagulation system, cardiovascular system, and on the condition of the internal organs was studied. It was found that NCT infusions do not reveal deviations in the studied parameters that could indicate a toxic effect. The estimated LD50 is more than 80 mg/kg. In a subchronic experiment, a statistically significant decrease in cholesterol (by up to 11%), glucose (by up to 15%) and excess bases (up to four times) in the blood, and an increase in heart rate (by up to 31%) and frequency of defecations (by up to 35%), as well as pronounced antiplatelet effect, were found. In animals with simulated endotoxicosis, a decrease in the cytolysis and oxidative stress markers was observed. Such effects are caused by both chlorine-active compounds and taurine.The results obtained indicate broad prospects for the use of NCT solutions as an infusion detoxifying agent. Full article
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