4.8 Article

Photo-induced oxidative damage to dissolved free amino acids by the photosensitizer polycyclic musk tonalide: Transformation kinetics and mechanisms

Journal

WATER RESEARCH
Volume 115, Issue -, Pages 339-346

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.watres.2017.03.006

Keywords

Polycyclic musks; Amino acids; Oxidative damage; Health effects; Transformation mechanism; Photosensitization damage

Funding

  1. National Natural Science Funds for Distinguished Young Scholars [41425015]
  2. NSFC [41573086, 41603115]

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Residue from the polycyclic musks (PCMs) in household and personal care products may harm human beings through skin exposure. To understand the health effects of PCMs when exposed to sunlight at molecular level, both experimental and computational methods were employed to investigate the photosensitized oxidation performance of 19 natural amino acids, the most basic unit of life. Results showed that a typical PCM, tonalide, acts as a photosensitizer to significantly increase photo-induced oxidative damage to amino acids. Both common and exceptional transformation pathways occurred during the photosensitization damage of amino acids. Experimental tests further identified the different mechanisms involved. The common transformation pathway occurred through the electron transfer from alpha amino-group of amino acids, accompanying with the formation of O-2(center dot-). This pathway was controlled by the electronic density of N atom in alpha amino-group. The exceptional transformation pathway was identified only for five amino acids, mainly due to the reactions with reactive oxygen species, e.g. O-1(2) and excited triplet state molecules. Additionally, tonalide photo-induced transformation products could further accelerate the photosensitization of all amino acids with the common pathway. This study may support the protection of human health, and suggests the possible need to further restrict polycyclic musks use. (C) 2017 Elsevier Ltd. All rights reserved.

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