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Cited by 7Photodynamic Therapy Research StudiesRedox biology and oxidative stressNanoplatforms for cancer theranostics

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

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Ximenes, Valdecir F., Ximenes, Thomaz P., Morgon, Nelson H., de Souza, Aguinaldo R.·2021·Photochemistry and Photobiology
DOI 10.1111/php.13410
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Abstract

Abstract Singlet oxygen ( 1 O 2 ) is the “active principle” in photodynamic therapy. Taurine chloramine (Tau‐NHCl) and hydrogen peroxide (H 2 O 2 ) 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 H 2 O 2 acts as a slow and long‐lasting potential source of 1 O 2 . The reactions were studied by luminol‐enhanced chemiluminescence. Evidence of the formation of 1 O 2 was obtained using deuterium oxide, sodium azide and 9,10‐Anthracenediyl‐bis(methylene)dimalonic acid, a chemical trap of 1 O 2 . 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 1 O 2 . In conclusion, we propose applying these drugs combination as a potential source of 1 O 2 with applications for skin diseases treatment.

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  • HOCl-dependent formation of singlet oxygen has been documented without mechanistic involvement of photons downstream of peroxide, superoxide, or chloramine chemistry involving the chemical formation of photo-excited states ('chemiexcitation').

    “HOCl-dependent formation of highly reactive photoexcited molecular oxygen [1O2 (singlet oxygen)] has been documented without mechanistic involvement of photons downstream of peroxide (including linoleic acid hydroperoxide), superoxide, or chloramine chemistry involving the chemical formation of photo-excited states (commonly referred to as ‘chemiexcitation’) (69–71).”

    From Hypochlorous Acid: From Innate Immune Factor and Environmental Toxicant to Chemopreventive Agent Targeting Solar UV-Induced Skin Cancer (2022) · cites this paper as [70]

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Authors
Ximenes, V. F., Ximenes, T. P., Morgon, N. H., & de Souza, A. R.
Affiliations
  • Universidade Estadual Paulista (Unesp) (BR)
  • Universidade Estadual de Campinas (UNICAMP) (BR)
  • Department of Chemistry Faculty of Sciences UNESP ‐ São Paulo State University Bauru São Paulo Brazil
Corresponding author
Ximenes, Valdecir F.
ORCID
Venue
Photochemistry and Photobiology
Publisher
Wiley
Published
2021-03-11
Volume
97
Issue
5
Pages
963-970
ISSN
  • 0031-8655 (ISSN-L)
  • 1751-1097
DOI
10.1111/php.13410
OpenAlex
W3135811690
Cited by
7
References
43
Citations by year
2024: 3 · 2022: 4
FWCI
1.15
Type
journal article
Language
en
Open access
Licence
Locations
  • Photochemistry and Photobiology (publishedVersion)
  • PubMed (publishedVersion)
  • LA Referencia (Red Federada de Repositorios Institucionales de Publicaciones Científicas) (submittedVersion, other-oa)
Funders
  • Conselho Nacional de Desenvolvimento Científico e Tecnológico (303485/2019‐1, 153758/2019‐8, 302769/2018‐8, 152519/2019‐0)
  • Fundação de Amparo à Pesquisa do Estado de São Paulo (2016/20549‐5, 2019/18445‐5, 465637/2014‐0)
  • Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
Topics
  • Health Sciences › Medicine › Pulmonary and Respiratory Medicine › Photodynamic Therapy Research Studies
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
  • Physical Sciences › Engineering › Biomedical Engineering › Nanoplatforms for cancer theranostics
Keywords
singlet oxygen, taurine chloramine, hydrogen peroxide, photodynamic therapy, topical photodynamic therapy, skin diseases, chloramines, chemiluminescence, reaction mechanism, L-alanine, GABA
MeSH terms
Chloramines, Hydrogen Peroxide, Luminol, Oxygen, Taurine, Singlet Oxygen

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