Taurine Chloramine and Hydrogen Peroxide as a Potential Source of Singlet Oxygen for Topical Application

Singlet oxygen (1O2) is the “active principle” in photodynamic therapy. Taurine chloramine (Tau‐NHCl) and hydrogen peroxide (H2O2) are well‐tolerated and widely used antiseptics. Due to its mild oxidizing features and stability, Tau‐NHCl can be directly used to treat skin diseases. We found that a d...

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Bibliographic Details
Published in:Photochemistry and photobiology 2021-09, Vol.97 (5), p.963-970
Main Authors: Ximenes, Valdecir F., Ximenes, Thomaz P., Morgon, Nelson H., de Souza, Aguinaldo R.
Format: Article
Language:English
Subjects:
Alanine
Antiseptics
Chemiluminescence
Deuterium
Heavy water
Hydrogen peroxide
Oxidation
Oxygen
Photodynamic therapy
Singlet oxygen
Skin diseases
Sodium azide
Sodium azides
Solvent effect
Stability
Taurine
Topical application
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Summary:Singlet oxygen (1O2) is the “active principle” in photodynamic therapy. Taurine chloramine (Tau‐NHCl) and hydrogen peroxide (H2O2) are well‐tolerated and widely used antiseptics. Due to its mild oxidizing features and stability, Tau‐NHCl can be directly used to treat skin diseases. We found that a diluted aqueous mixture of Tau‐NHCl and H2O2 acts as a slow and long‐lasting potential source of 1O2. The reactions were studied by luminol‐enhanced chemiluminescence. Evidence of the formation of 1O2 was obtained using deuterium oxide, sodium azide and 9,10‐Anthracenediyl‐bis(methylene)dimalonic acid, a chemical trap of 1O2. The reaction was optimized, and a mechanism was proposed, including theoretical calculations at B3LYP/6‐311++G(3df,2p) level of theory, adding D3Bj empirical dispersion and SMD (Water) solvent effects. Chloramines produced by the reactions between HOCl and L‐alanine, 3‐amino‐1‐propanesulfonic acid and gamma‐aminobutyric acid were also prepared, and their reactivity and stability were compared with Tau‐NHCl. We found that Tau‐NHCl is more stable and adequate for the production of 1O2. In conclusion, we propose applying these drugs combination as a potential source of 1O2 with applications for skin diseases treatment. A diluted aqueous solution of taurine chloramine and hydrogen peroxide acts as a slow source of singlet oxygen. As these compounds have well‐established tolerability, this simple technique opens new possibilities of nonphotochemical production and topical singlet oxygen applications.
ISSN:0031-8655
1751-1097
DOI:10.1111/php.13410