Skip to main content

Anti-Inflammatory Effects of Taurine Derivatives (Taurine Chloramine, Taurine Bromamine, and Taurolidine) are Mediated by Different Mechanisms

  • Conference paper
Taurine 6

5. Summary

In this study, in an animal model of zymosan-induced peritonitis we have tested antiinflammatory properties of Taurolidine (TRD), a synthetic derivative of taurine. In vitro, the effect of TRD and HOCl treated TRD on peritoneal macrophages was compared with that of TauCl. We report that locally administered TRD (Taurolin) shows strong antiinflammatory properties. TRD inhibits vascular permeability increased by inflammatory stimuli; it also significantly attenuates the influx of neutrophils into the peritoneal cavity, as well as the production of pro-inflammatory cytokines (TNF-α, IL-6) by peritoneal exudate cells. Chlorination of TRD resulted in the formation of chloramine (TRD-Cl), as confirmed by characteristic UV spectra. Both TRD and TRD-Cl, more effectively than TauCl, inhibited the production of IL-6 by stimulated macrophages. The effect was not dependent on its well-known anti-endotoxin activity since TRD inhibited cytokine production by macrophages stimulated with either LPS or IFN-γ.

Finally, we report that anti-inflammatory activities of TRD and taurine haloamines are mediated by different mechanisms. TRD, in contrast to TauCl and TauBr, does not induce expression of HO-1, a stress inducible enzyme with strong anti-inflammatory properties.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

7. References

  • Abraham, N. G., Lin, J. H., Schwartzman, M. L., Levere, R.D., and Shibahara, S., 1988, The physiological significance of heme oxygenase, Int. J. Biochem. 20:543.

    Article  PubMed  CAS  Google Scholar 

  • Baker, D. M., Jones, J. A., Nguyen-Van-Tam, J. S., Lloyd, J. H., Morris, D. L., Bourke, J. B., Steele, R. J., and Hardcastle, J. D., 1994, Taurolidine peritoneal lavage as prophylaxis against infection after elective colorectal surgery, Br. J. Surg. 8:1054.

    Google Scholar 

  • Barua, M., Liu, Y., and Quinn, M. R., 2001, Taurine chloramine inhibits inducible nitric oxide synthase and TNF-alpha gene expression in activated alveolar macrophages: decreased NF-kappaB activation and IkappaB kinase activity, J. Immunol. 167:2275.

    PubMed  CAS  Google Scholar 

  • Bedrosian, I., Sofia, R. D., Wolff, S. M., and Dinarello, C. A., 1991, Taurolidine, an analogue of the amino acid taurine, suppresses interleukin 1 and tumor necrosis factor synthesis in human peripheral blood mononuclear cells, Cytokine 3:568.

    Article  PubMed  CAS  Google Scholar 

  • Browne, M. K., Leslie, G. B., and Pfirrmann, R. W., 1976, Taurolin, a new chemotherapeutic agent, J. Appl. Bacteriol. 41:363.

    PubMed  CAS  Google Scholar 

  • Darnowski, J. W., Goulette, F. A., Cousens, L. P., Chatterjee, D., and Calabresi, P., 2004, Mechanistic and antineoplastic evaluation of taurolidine in the DU145 model of human prostate cancer, Cancer Chemother. Pharmacol. 54:249.

    Article  PubMed  CAS  Google Scholar 

  • Gorman, S. P., McCafferty, D. F., Woolfson, A. D., and Jones, D. S., 1987, Reduced adherence of microorganisms to human mucosal epithelial cells following treatment with Taurolin, a novel antimicrobial agent, J. Appl. Bacteriol. 62:315.

    PubMed  CAS  Google Scholar 

  • Kanayama, A., Inoue, J., Sugita-Konishi, Y., Shimizu, M., and Miyamoto, Y., 2002, Oxidation of Ikappa Balpha at methionine 45 is one cause of taurine chloramine-induced inhibition of NF-kappa B activation, J. Biol. Chem. 277:24049.

    Article  PubMed  CAS  Google Scholar 

  • Kirsch, L. E. and Sihn, Y. S., 1997, The effect of polyvinylpyrrolidine on the stability of taurolidine, Pharm. Dev. Technol. 2:345.

    PubMed  CAS  Google Scholar 

  • Klebanoff, S. J. and Hamon, C. B., 1992, Role of myeloperoxidase-mediated antimicrobial systems in intact leukocytes, J. Reticuloendothel. Soc. 12:170.

    Google Scholar 

  • Kontny, E., Szczepanska, K., Kowalczewski, J., Kurowska, M., Janicka, I., Marcinkiewicz, J., and Maslinski, W., 2000, The mechanism of taurine chloramine inhibition of cytokine (interleukin-6, interleukin-8) production by rheumatoid arthritis fibroblast-like synoviocytes, Arthritis Rheum. 43:2169.

    Article  PubMed  CAS  Google Scholar 

  • Kushida, T., Li Volti, G., Quan, S., Goodman, A., and Abraham, N. G., 2002, Role of human heme oxygenase-1 in attenuating TNF-alpha-mediated inflammation injury in endothelial cells, J. Cell Biochem. 87:377.

    Article  PubMed  CAS  Google Scholar 

  • Learn, D. B., Fried, V. A., and Thomas, E. L., 1990, Taurine and hypotaurine content of human leukocytes, J. Leukoc. Biol. 48:174.

    PubMed  CAS  Google Scholar 

  • Lee, T. S. and Chau, L. Y., 2002, Heme oxygenase-1 mediates the anti-inflammatory effect of interleukin-10 in mice, Nat. Med. 8:240.

    Article  PubMed  CAS  Google Scholar 

  • Marcinkiewicz, J., Grabowska, A., Bereta, J., and Stelmaszynska, T., 1995, Taurine chloramine, a product of activated neutrophils, inhibits in vitro the generation of nitric oxide and other macrophage inflammatory mediators, J Leukoc Biol. 58:667.

    PubMed  CAS  Google Scholar 

  • Marcinkiewicz, J., Mak, M., Bobek, M., Biedron, R., Bialecka, A., Koprowski, M., Kontny, E., and Maslinski, W., 2005, Is there a role of taurine bromamine in inflammation? Interactive effects with nitrite and hydrogen peroxide, Inflamm. Res. 54:42.

    Article  PubMed  CAS  Google Scholar 

  • Marcinkiewicz, J., Nowak, B., Grabowska, A., Bobek, M, Petrovska, L., and Chain, B., 1999, Regulation of murine dendritic cell functions in vitro by taurine chloramine, a major product of the neutrophil myeloperoxidase-halide system, Immunology 98:371.

    Article  PubMed  CAS  Google Scholar 

  • Marcinkiewicz, J., 1997, Neutrophil chloramines: missing links between innate and acquired immunity, Immunol. Today 18:677.

    Article  Google Scholar 

  • McCourt, M., Wang, J. H., Sookhai, S., and Redmond, H. P., 2000, Taurolidine inhibits tumor cell growth in vitro and in vivo, Ann. Surg. Oncol. 7:685.

    Article  PubMed  CAS  Google Scholar 

  • Myers, E. and Allwood, M. C., 1980, The interaction between taurolin and endotoxin, Microbios Lett. 13:141.

    CAS  Google Scholar 

  • Nagl, M., Hess, M. W., Pfaller, K., Hengster, P., and Gottardi, W., 2000, Bactericidal activity of micromolar Nchlorotaurine: evidence for its antimicrobial function in the human defense system, Antimicrob. Agents Chemother. 44:2507.

    Article  PubMed  CAS  Google Scholar 

  • Nici, L., Monfils, B., and Calabresi, P., 2004, The effects of taurolidine, a novel antineoplastic agent, on human malignant mesothelioma, Clin. Cancer Res. 10:7655.

    Article  PubMed  CAS  Google Scholar 

  • Olszanecki, R. and Marcinkiewicz, J., 2004, Taurine chloramine and taurine bromamine induce heme oxygenase-1 in resting and LPS-stimulated J774.2 macrophages, Amino Acids 27:29.

    Article  PubMed  CAS  Google Scholar 

  • Park, E., Schuller-Lewis, G., and Quinn, M. R., 1995, Taurine chloramine inhibits production of nitric oxide and the TNF-α in activated RAW 264.7 cells by mechanisms that involve transcriptional and translational events, J. Immunol. 154:4778.

    PubMed  CAS  Google Scholar 

  • Schuller-Levis, G. B. and Park, E., 2003, Taurine: new implications for an old amino acid, FEMS Microbiol. Lett. 226:195.

    Article  PubMed  CAS  Google Scholar 

  • Staubach, K. H., 1997, Adjuvant therapy of peritonitis with taurolidine. Modulation of mediator liberation, Langenbecks Arch. Chir. 382:S26.

    Article  PubMed  CAS  Google Scholar 

  • Thomas, E. L., Bozeman, P. M., Jefferson, M. M., and King, C. C., 1995, Oxidation of bromide by the human leukocyte enzymes myeloperoxidase and eosinophil peroxidase. Formation of bromamines, J. Biol. Chem. 270:2906.

    Article  PubMed  CAS  Google Scholar 

  • Thomas, E. L., Grisham, M. B., and Jefferson, M. M., 1986, Preparation and characterization of chloramines, Methods Enzymol. 132:569.

    Article  PubMed  CAS  Google Scholar 

  • Torres-Viera, C., Thauvin-Eliopoulos, C., Souli, M., DeGirolam, P., Farris, M. G., Wennersten, C. B., Sofia, R.D., and Eliopoulos, G. M., 2000, Activities of taurolidine in vitro and in experimental enterococcal endocarditis, Antimicrob Agents Chemother. 44:1720.

    Article  PubMed  CAS  Google Scholar 

  • Traub, W. H., Leonhard, B., and Bauer, D., 1993, Taurolidine: in vitro activity against multiple-antibioticresistant, nosocomially significant clinical isolates of Staphylococcus aureus, Enterococcus faecium, and diverse Enterobacteriaceae, Chemotherapy 39:322.

    Article  PubMed  CAS  Google Scholar 

  • Vicente, A. M., Guillen, M. I., Habib, A., and Alcaraz, M. J., 2003, Beneficial effects of heme oxygenase-1 upregulation in the development of experimental inflammation induced by zymosan, J. Pharmacol. Exp. Ther. 307:1030

    Article  PubMed  CAS  Google Scholar 

  • Watson, R. W, Redmond, H. P., McCarthy, J., and Bouchier-Hayes, D., 1995, Taurolidine, an antilipopolysaccharide agent, has immunoregulatory properties that are mediated by the amino acid taurine, J. Leukoc. Biol. 58:299.

    PubMed  CAS  Google Scholar 

  • Willatts, S. M., Radford, S., and Leitermann, M., 1995, Effect of the antiendotoxic agent, taurolidine, in the treatment of sepsis syndrome: a placebo-controlled, double-blind trial, Crit. Care Med. 23:1033.

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2006 Springer Science+Business Media, LLC

About this paper

Cite this paper

Marcinkiewicz, J., Kurnyta, M., Biedroń, R., Bobek, M., Kontny, E., Maśliński, W. (2006). Anti-Inflammatory Effects of Taurine Derivatives (Taurine Chloramine, Taurine Bromamine, and Taurolidine) are Mediated by Different Mechanisms. In: Oja, S.S., Saransaari, P. (eds) Taurine 6. Advances in Experimental Medicine and Biology, vol 583. Springer, Boston, MA . https://doi.org/10.1007/978-0-387-33504-9_54

Download citation

Publish with us

Policies and ethics