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Comparative Analysis of Microbicidal and Anti-inflammatory Properties of Novel Taurine Bromamine Derivatives and Bromamine T

  • Conference paper
Taurine 10

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 975))

Abstract

Taurine, the most abundant free amino acid in leukocyte cytosol traps hypohalous acids (HOCl and HOBr) to produce N-chlorotaurine (taurine chloramine, NCT and N-bromotaurine (taurine bromamine, Tau-NHBr,) respectively. Both haloamines show anti-inflammatory and antimicrobial properties. However, the therapeutic applicability of Tau-NHBr is limited due to its relatively poor stability. To overcome this disadvantage, we have synthesized the stable N-bromotaurine compounds N-monobromo-2,2-dimethyltaurine (Br-612) and N-dibromo-2,2-dimethyltaurine (Br-422). The aim of this study was to compare anti-inflammatory and microbicidal properties of Br-612 and Br-422 with that of Tau-NHBr and bromamine T (BAT). We have shown that all the tested compounds show similar anti-inflammatory properties. Importantly, the stable N-bromotaurine compounds exerted even stronger microbicidal activity than Tau-NHBr. Finally, for the purpose of topical application of these compounds we have developed a carbomer-based bioadhesive solid dosage form of BAT and Br-612, featuring sustained release of the active substance.

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Abbreviations

BAT:

Bromamine T

C. albicans :

Candida albicans

CFU:

Colony forming units

HOBr:

Hypobromous acid

HOCl:

Hypochlorous acid

LCL:

Luminol dependent chemiluminescence

LPS:

Lipopolysaccharide

MRI:

Magnetic Resonance Imaging

NCT:

N-chlorotaurine, taurine chloramine

OZ:

Opsonized zymosan

P. acnes :

Propioniobacterium acnes

P. aeruginosa :

Pseudomonas aeruginosa

PGE2 :

Prostaglandins

ROS:

Reactive oxygen species

S. aureus :

Staphylococcus aureus

Tau-NHBr:

N-bromotaurine, taurine bromamine

References

  • Albrecht K, Greindl M, Kremser C, Wolf C, Debbage P, Bernkop-Schnürch A (2006) Comparative in vivo mucoadhesion studies of thiomer formulations using magnetic resonance imaging and fluorescence detection. J Control Release 115:78–84

    Article  CAS  PubMed  Google Scholar 

  • Ding AH, Nathan CF, Stuehr DJ (1988) Release of reactive nitrogen intermediates from mouse peritoneal macrophages: comparison of activating cytokines and evidence for independent production. J Immunol 141:2407–2412

    CAS  PubMed  Google Scholar 

  • Dorozynski P, Jamroz W, Niwinski K, Kurek M, Weglarz WP, Jachowicz R, Kulinowski P (2013) Novel method for screening of enteric film coatings properties with magnetic resonance imaging. Int J Pharm 456(2):569–571

    Article  CAS  PubMed  Google Scholar 

  • Ekberg O (2012) Dysphagia (Saliva and the control of its secretion). Springer-Verlag, Berlin, Heidelberg

    Google Scholar 

  • Fejerskov O, Kidd E (2008) Dental caries: the disease and its clinical. Management Blackwell, Munsgaard

    Google Scholar 

  • Gaut JP, Yeh GC, Tran HD, Byun J, Henderson JP, Richter GM, Brennan ML, Lusis AJ, Belaaouaj A, Hotchkiss RS, Heinecke JW (2001) Neutrophils employ the myeloperoxidase systemto generate antimicrobial brominating and chlorinating oxidants during sepsis. Proc Natl Acad Sci U S A 98(21):11961–11966

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Gottardi W, Nagl M (2010) N-chlorotaurine, a natural antiseptic with outstanding tolerability. J Antimicrob Chemother 65:399–409

    Article  CAS  PubMed  Google Scholar 

  • Gottardi W, Debabov D, Nagl M (2013) N-chloramines: a promising class of well-tolerated topical antiinfectives. Antimicrob Agents Chemother 9:1107–1114

    Article  Google Scholar 

  • Gottardi W, Klotz S, Nagl M (2014) Superior bactericidal activity of N-bromine compounds compared to their N-chlorine analogues can be reversed under protein load. J Appl Microbiol 116:1427–1437

    Article  CAS  PubMed  Google Scholar 

  • Gstöttner M, Nagl M, Pototschnig C et al (2003) Refractory rhinosinusitis complicating immunosuppression: application of N-chlorotaurine, a novel endogenous antiseptic agent. ORL J Otorhinolaryngol Relat Spec 65:303–305

    Article  PubMed  Google Scholar 

  • Jamróz W, Jachowicz R, Cul J, Marcinkiewicz J (2014) Evaluation of poloxamer in situ gelling system as a carrier of bromamine taurine. XIX Taurine Meeting, Kraków, Poland

    Google Scholar 

  • Klebanoff SJ (2005) Myeloperoxidase: friend and foe. J Leukoc Biol 77:598–625

    Article  CAS  PubMed  Google Scholar 

  • Koprowski M, Marcinkiewicz J (2002) Taurine chloramine—its role in immunity and new perspectives for clinical use. Centr Eur J Immunol 27(2):69–74

    CAS  Google Scholar 

  • Kyriakopoulos AM, Logotheti S, Marcinkiewicz J, Nagl M (2016) N-chlorotaurine and N-bromotaurine combination regimen for the cure of valacyclovir-unresponsive herpes zoster comorbidity in a multiple sclerosis patient. Int J Med Pharm Case Reports 7(2):1–6

    Article  Google Scholar 

  • Marcinkiewicz J (2009) Taurine bromamine: a new therapeutic option in inflammatory skin diseases. Pol Arch Med Wewn 119(10):673–676

    CAS  PubMed  Google Scholar 

  • Marcinkiewicz J (2010) Taurine bromamine (TauBr)-its role in immunity and new perspectives for clinical use. J Biomed Sci 17(Suppl 1):S3

    Article  PubMed  PubMed Central  Google Scholar 

  • Marcinkiewicz J, Chain B, Nowak B et al (2000) Antimicrobial and cytotoxic activity of hypochlorous acid: interactions with taurine and nitrite. Inflamm Res 49:280–289

    Article  CAS  PubMed  Google Scholar 

  • Marcinkiewicz J, Mak M, Bobek M, Biedroń R, Białecka A, Koprowski M, Kontny E, Maśliński W (2005) Is there a role of taurine bromamine in inflammation? Interactive effects with nitrite and hydrogen peroxide. Inflamm Res 54(1):42–49

    Article  CAS  PubMed  Google Scholar 

  • Marcinkiewicz J, Biedroń R, Białecka A, Kasprowicz A, Mak M, Targosz M (2006) Susceptibility of Propionibacterium acnes and Staphylococcus epidermidis to killing by MPO-halide system products. Implication for taurine bromamine as a new candidate for topical therapy in treating acne vulgaris. Arch Immunol Ther Exp 54(1):61–68

    Article  CAS  Google Scholar 

  • Marcinkiewicz J, Wojas-Pelc A, Walczewska M et al (2008) Topical taurine bromamine, a new candidate in the treatment of moderate inflammatory acne vulgaris: a pilot study. Eur J Dermatol 18(4):433–439

    CAS  PubMed  Google Scholar 

  • Marcinkiewicz J, Strus M, Walczewska M, Machul A, Mikołajczyk D (2013) Influence of taurine haloamines (TauCl and TauBr) on the development of pseudomonas aeruginosa biofilm: a preliminary study. Adv Exp Med Biol 775:269–283

    Article  CAS  PubMed  Google Scholar 

  • Mendyk A, Jachowicz R et al (2012) KinetDS: an open source software for dissolution test data analysis. Dissolut Technol 19(1):6–11

    Article  Google Scholar 

  • Müller G, Kramer A (2008) Biocompatibility index of antiseptic agents by parallel assessment of antimicrobial activity and cellular cytotoxicity. J Antimicrob Chemother 61:1281–1287

    Article  PubMed  Google Scholar 

  • Nagl M, Hess MW, Pfaller K et al (2000) Bactericidal activity of micromolar N chlorotaurine: evidence for its antimicrobial function in the human defense system. Animicrob Agents Chemother 44(9):2507–2513

    Article  CAS  Google Scholar 

  • Nagl M, Nguyen VA, Gottardi W et al (2003) Tolerability and efficacy of N chlorotaurine in comparison with chloramine T for treatment of chronic leg ulcers with a purulent coating: a randomized phase II study. Br J Dermatol 149:590–597

    Article  CAS  PubMed  Google Scholar 

  • Nair CG, Lalithakumari R, Senan PI (1978) Bromamine-T as a new oxidimetric ti-trant. Talanta 25:525–527

    Article  CAS  PubMed  Google Scholar 

  • Neher A, Nagl M, Appenroth E et al (2004) Acute otitis externa: efficacy and tolerability of N-chlorotaurine, a novel endogenous antiseptic agent. Laryngoscope 114:850–854

    Article  PubMed  Google Scholar 

  • Olszanecki R, Marcinkiewicz J (2004) Taurine chloramine and taurine bromamine induce heme oxygenase-1 in resting and LPS-stimulated J774.2 macrophages. Amino Acids 27(1):29–35

    Article  CAS  PubMed  Google Scholar 

  • Olszanecki R, Kurnyta M, Biedroń R, Chorobik P, Bereta M, Marcinkiewicz J (2008) The role of heme oxygenase-1 in down regulation of PGE2 production by taurine chloramine and taurine bromamine in J774.2 macro-phages. Amino Acids 35(2):359–364

    Article  CAS  PubMed  Google Scholar 

  • Park E, Schuller-Levis G, Jia JH et al (1997) Preactivation exposure of RAW 264.7 cells to taurine chloramines attenuates subsequent production of nitric oxide and expression of iNOS mRNA. J Leukoc Biol 61:161–166

    CAS  PubMed  Google Scholar 

  • Pasich E, Walczewska M, Białecka A, Peruń A, Kasprowicz A, Marcinkiewicz J (2015) Taurine Haloamines and Biofilm: II. Efficacy of Taurine Bromamine and Chlorhexidine against selected microorganisms of oral biofilm. Adv Exp Med Biol 803:133–143

    Article  PubMed  Google Scholar 

  • Schleupner CJ, Glasgow LA (1978) Peritoneal macrophage activation indicated by enhanced chemiluminescence. Infect Immun 21:886–895

    CAS  PubMed  PubMed Central  Google Scholar 

  • Schuller-Levis GB, Park E (2003) Taurine: new implications for an old amino acid. FEMS Microbiol Lett 226(2):195–202

    Article  CAS  PubMed  Google Scholar 

  • Strus M, Walczewska M, Machul A, Mikołajczyk D, Marcinkiewicz J (2015) Taurine haloamines and biofilm. Part I: antimicrobial activity of taurine bromamine and chlorhexidine against biofilm forming pseudomonas aeruginosa. Adv Exp Med Biol 803:121–132

    Article  PubMed  Google Scholar 

  • Thomas EL, Grisham MB, Jefferson MM (1985) Preparation and characterization of chloramines. Methods Enzymol 132:569–585

    Article  Google Scholar 

  • Thomas EL, Bozeman PM, Jefferson MM, King CC (1995) Oxidation of bromide by the human leukocyte enzymes myeloperoxidase and eosinophil peroxidase. Formation of bromamines. J Biol Chem 270(7):2906–2913

    Article  CAS  PubMed  Google Scholar 

  • Weiss SJ, Klein R, Slivka A et al (1982) Chlorination of taurine by human neutrophils: evidence for hypochlorous acid generation. J Clin Invest 70:598–603

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Yazdanbakhsh M, Eckmann CM, Roos D (1987) Killing of schistosomula by taurine chloramine and taurine bromamine. AmJTrop Med Hyg 37:106–110

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This study was supported by Jagiellonian University Medical College Grant K/ZDS/005454. We are grateful to Johanna Stocker and Dieter Klammer for quantitative killing tests with Br-612 and Br-422.

Author information

Authors and Affiliations

  1. Department of Immunology, Jagiellonian University Medical College, Krakow, Poland

    M. Walczewska, A. Peruń, M. Śróttek & J. Marcinkiewicz

  2. Center of Microbiological research and Autovaccines Ltd., Krakow, Poland

    A. Białecka

  3. Faculty of Pharmacy, Department of Pharmaceutical Technology and Biopharmaceutics, Jagiellonian University Medical College, Krakow, Poland

    W. Jamróz, P. Dorożyński & R. Jachowicz

  4. Institute of Technology, Pedagogical University of Cracow, Krakow, Poland

    P. Kulinowski

  5. Department of Hygiene, Microbiology and Social Medicine, Division of Hygiene and Medical Microbiology, Medical University of Innsbruck, Innsbruck, Austria

    M. Nagl & W. Gottardi

Authors
  1. M. Walczewska
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  2. A. Peruń
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  3. A. Białecka
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  4. M. Śróttek
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  6. P. Dorożyński
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  7. R. Jachowicz
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  8. P. Kulinowski
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  9. M. Nagl
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  10. W. Gottardi
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  11. J. Marcinkiewicz
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Corresponding author

Correspondence to J. Marcinkiewicz .

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Editors and Affiliations

  1. Department of Life Sciences, University of Seoul, Seoul, South Korea

    Dong-Hee Lee  & Ha Won Kim  & 

  2. College of Medicine, University of South Alabama, Mobile, Alabama, USA

    Stephen W. Schaffer

  3. Department of Developmental Neurobiology, NY State Institute for Basic Research in Developmental Disabilities, New York, USA

    Eunkyue Park

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Walczewska, M. et al. (2017). Comparative Analysis of Microbicidal and Anti-inflammatory Properties of Novel Taurine Bromamine Derivatives and Bromamine T. In: Lee, DH., Schaffer, S.W., Park, E., Kim, H.W. (eds) Taurine 10. Advances in Experimental Medicine and Biology, vol 975. Springer, Dordrecht. https://doi.org/10.1007/978-94-024-1079-2_41

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