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

Overview

Journal Adv Exp Med Biol

Specialties Biology
General Medicine

Date 2017 Aug 30

PMID 28849479

Citations 7

Authors

M Walczewska

A Perun

A Bialecka

M Srottek

W Jamroz

P Dorozynski

R Jachowicz

P Kulinowski

M Nagl

W Gottardi

J Marcinkiewicz

Affiliations

Soon will be listed here.

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.

Citing Articles

Taurine and N-Bromotaurine in Topical Treatment of Psoriasis.

Kyriakopoulos A, Nagl M, Gupta R, Marcinkiewicz J Adv Exp Med Biol. 2022; 1370:99-111.

PMID: 35882785 DOI: 10.1007/978-3-030-93337-1_9.

Current Opinion on the Therapeutic Capacity of Taurine-Containing Halogen Derivatives in Infectious and Inflammatory Diseases.

Marcinkiewicz J, Nagl M, Kyriakopoulos A, Walczewska M, Skora M, Skalska P Adv Exp Med Biol. 2022; 1370:83-98.

PMID: 35882784 DOI: 10.1007/978-3-030-93337-1_8.

Bromamine T, a stable active bromine compound, prevents the LPS‑induced inflammatory response.

Baliou S, Sofopoulos M, Goulielmaki M, Spandidos D, Ioannou P, Kyriakopoulos A Int J Mol Med. 2021; 47(4).

PMID: 33537817 PMC: 7891821. DOI: 10.3892/ijmm.2021.4870.

Bromamine T (BAT) Exerts Stronger Anti-Cancer Properties than Taurine (Tau).

Baliou S, Goulielmaki M, Ioannou P, Cheimonidi C, Trougakos I, Nagl M Cancers (Basel). 2021; 13(2).

PMID: 33430276 PMC: 7825693. DOI: 10.3390/cancers13020182.

Successful treatment of a unique chronic multi-bacterial scalp infection with -chlorotaurine, -bromotaurine and bromamine T.

Kyriakopoulos A, Nagl M, Orth-Holler D, Marcinkiewicz J, Baliou S, Zoumbourlis V Access Microbiol. 2020; 2(7):acmi000126.

PMID: 32974590 PMC: 7497830. DOI: 10.1099/acmi.0.000126.

References

Albrecht K, Greindl M, Kremser C, Wolf C, Debbage P, Bernkop-Schnurch A . Comparative in vivo mucoadhesion studies of thiomer formulations using magnetic resonance imaging and fluorescence detection. J Control Release. 2006; 115(1):78-84. DOI: 10.1016/j.jconrel.2006.06.023. View

Ding A, Nathan C, Stuehr D . Release of reactive nitrogen intermediates and reactive oxygen intermediates from mouse peritoneal macrophages. Comparison of activating cytokines and evidence for independent production. J Immunol. 1988; 141(7):2407-12. View

Dorozynski P, Jamroz W, Niwinski K, Kurek M, Weglarz W, Jachowicz R . Novel method for screening of enteric film coatings properties with magnetic resonance imaging. Int J Pharm. 2013; 456(2):569-71. DOI: 10.1016/j.ijpharm.2013.08.004. View

Gaut J, Yeh G, Tran H, Byun J, Henderson J, Richter G . Neutrophils employ the myeloperoxidase system to generate antimicrobial brominating and chlorinating oxidants during sepsis. Proc Natl Acad Sci U S A. 2001; 98(21):11961-6. PMC: 59821. DOI: 10.1073/pnas.211190298. View

Gottardi W, Nagl M . N-chlorotaurine, a natural antiseptic with outstanding tolerability. J Antimicrob Chemother. 2010; 65(3):399-409. DOI: 10.1093/jac/dkp466. View

Gottardi W, Klotz S, Nagl M . Superior bactericidal activity of N-bromine compounds compared to their N-chlorine analogues can be reversed under protein load. J Appl Microbiol. 2014; 116(6):1427-37. DOI: 10.1111/jam.12474. View

Gstottner M, Nagl M, Pototschnig C, Neher A . Refractory rhinosinusitis complicating immunosuppression: application of N-chlorotaurine, a novel endogenous antiseptic agent. ORL J Otorhinolaryngol Relat Spec. 2004; 65(5):303-5. DOI: 10.1159/000075231. View

Klebanoff S . Myeloperoxidase: friend and foe. J Leukoc Biol. 2005; 77(5):598-625. DOI: 10.1189/jlb.1204697. View

Marcinkiewicz J . Taurine bromamine: a new therapeutic option in inflammatory skin diseases. Pol Arch Med Wewn. 2009; 119(10):673-6. View

10.

Marcinkiewicz J . Taurine bromamine (TauBr)--its role in immunity and new perspectives for clinical use. J Biomed Sci. 2010; 17 Suppl 1:S3. PMC: 2994406. DOI: 10.1186/1423-0127-17-S1-S3. View

11.

Marcinkiewicz J, Chain B, Nowak B, Grabowska A, Bryniarski K, Baran J . Antimicrobial and cytotoxic activity of hypochlorous acid: interactions with taurine and nitrite. Inflamm Res. 2000; 49(6):280-9. DOI: 10.1007/PL00000208. View

12.

Marcinkiewicz J, Mak M, Bobek M, Biedron R, Bialecka A, Koprowski M . Is there a role of taurine bromamine in inflammation? Interactive effects with nitrite and hydrogen peroxide. Inflamm Res. 2005; 54(1):42-9. DOI: 10.1007/s00011-004-1322-9. View

13.

Marcinkiewicz J, Wojas-Pelc A, Walczewska M, Lipko-Godlewska S, Jachowicz R, Maciejewska A . Topical taurine bromamine, a new candidate in the treatment of moderate inflammatory acne vulgaris: a pilot study. Eur J Dermatol. 2008; 18(4):433-9. DOI: 10.1684/ejd.2008.0460. View

14.

Marcinkiewicz J, Strus M, Walczewska M, Machul A, Mikolajczyk D . Influence of taurine haloamines (TauCl and TauBr) on the development of Pseudomonas aeruginosa biofilm: a preliminary study. Adv Exp Med Biol. 2013; 775:269-83. DOI: 10.1007/978-1-4614-6130-2_23. View

15.

Muller G, Kramer A . Biocompatibility index of antiseptic agents by parallel assessment of antimicrobial activity and cellular cytotoxicity. J Antimicrob Chemother. 2008; 61(6):1281-7. DOI: 10.1093/jac/dkn125. View

16.

Nagl M, Nguyen V, Gottardi W, Ulmer H, Hopfl R . Tolerability and efficacy of N-chlorotaurine in comparison with chloramine T for the treatment of chronic leg ulcers with a purulent coating: a randomized phase II study. Br J Dermatol. 2003; 149(3):590-7. DOI: 10.1046/j.1365-2133.2003.05432.x. View

17.

Nair C, Lalithakumari R, Senan P . Bromamine-T as a new oxidimetric titrant. Talanta. 1978; 25(9):525-7. DOI: 10.1016/0039-9140(78)80089-7. View

18.

Neher A, Nagl M, Appenroth E, Gstottner M, Wischatta M, Reisigl F . Acute otitis externa: efficacy and tolerability of N-chlorotaurine, a novel endogenous antiseptic agent. Laryngoscope. 2004; 114(5):850-4. DOI: 10.1097/00005537-200405000-00011. View

19.

Olszanecki R, Marcinkiewicz J . Taurine chloramine and taurine bromamine induce heme oxygenase-1 in resting and LPS-stimulated J774.2 macrophages. Amino Acids. 2004; 27(1):29-35. DOI: 10.1007/s00726-004-0097-1. View

20.

Olszanecki R, Kurnyta M, Biedron R, Chorobik P, Bereta M, Marcinkiewicz J . The role of heme oxygenase-1 in down regulation of PGE2 production by taurine chloramine and taurine bromamine in J774.2 macrophages. Amino Acids. 2007; 35(2):359-64. DOI: 10.1007/s00726-007-0609-x. View