UVA Photoirradiation of Oxygenated Benz[a]anthracene and 3-Methylcholanthene - Generation of Singlet Oxygen and Induction of Lipid Peroxidation

Bibliographic Data

ID15500433
AuthorsJun‐Jie Yin (0000-0003-0532-2116, Center for Food Safety and Applied Nutrition), Jun-Jie Yin (Center for Food Safety and Applied Nutrition), Qingsu Xia (National Center for Toxicological Research), Shu-Hui Cherng (National Center for Toxicological Research), I-Wah Tang (National Center for Toxicological Research), Peter P Fu (0000-0003-1902-1189, National Center for Toxicological Research), Ge Lin (0000-0002-4586-2603, Chinese University of Hong Kong), Hongtao Yu (0000-0002-9438-0432, Jackson State University), Diógenes Herreño Sáenz (University of Puerto Rico System, corresponding author)
Year2008
Volume5
Issue1
Pages26-31
Publication date2008-03-30
Peer ReviewedYes
Open AccessYes
TypeARTICLE
VenueInternational Journal of Environmental Research and Public Health (JOURNAL)
Journal identifiersISSN: 1661-7827 • E-ISSN: 1660-4601
PublisherMultidisciplinary Digital Publishing Institute (PUBLISHER • CH)
DOI10.3390/ijerph5010026
PMID18441402
OpenAlexW2134572160
LanguageEN
References cited29

Polycyclic aromatic hydrocarbons (PAHs) are widespread genotoxic environmental pollutants and potentially pose a health risk to humans. Although the biological and toxicological activities, including metabolism, mutagenicity, and carcinogenicity, of PAHs have been thoroughly studied, their phototoxicity and photo-induced biological activity have not been well examined. We have long been interested in phototoxicity of PAHs and their derivatives induced by irradiation with UV light. In this paper we report the photoirradiation of a series of oxygenated benz[a]anthracene (BA) and 3-methylcholanthene (3-MC) by UVA light in the presence of a lipid, methyl linoleate. The studied PAHs include 2-hydroxy-BA (2-OH-BA), 3-hydroxy-BA (3-OH-BA), 5-hydroxymethyl-BA (5- CH2OH-BA), 7-hydroxymethyl-BA (7-CH2OH-BA), 12-hydroxymethyl-BA (12-CH2OH-BA), 7-hydroxymethyl-12- methyl-BA (7-CH2OH-12-MBA), 5-formyl-BA (5-CHO-BA), BA 5,6-cis-dihydrodiol (BA 5,6-cis-diol), 1-hydroxy-3- methylcholanthene (1-OH-3-MC), 1-keto-3-methylcholanthene (1-keto-3-MC), and 3-MC 1,2-diol. The results indicate that upon photoirradiation by UVA at 7 and 21 J/cm2, respectively all these compounds induced lipid peroxidation and exhibited a relationship between the dose of the light and the level of lipid peroxidation induced. To determine whether or not photoirradiation of these compounds by UVA light produces ROS, an ESR spin-trap technique was employed to provide direct evidence. Photoirradiation of 3-keto-3-MC by UVA (at 389 nm) in the presence of 2,2,6,6-tetramethylpiperidine (TEMP), a specific probe for singlet oxygen, resulted in the formation of TEMPO, indicating that singlet oxygen was generated. These overall results suggest that UVA photoirradiation of oxygenated BA and 3-methylcholanthrene generates singlet oxygen, one of the reactive oxygen species (ROS), which induce lipid peroxidation

Anthracene · Antioxidant · Carcinogen · Diol · Hydroxymethyl · In vitro · Lipid peroxidation · Medicinal chemistry · Oxygen · Photochemistry · Phototoxicity · Singlet oxygen · Carcinogens and Genotoxicity Assessment · Chemistry · Free Radicals and Antioxidants · Toxic Organic Pollutants Impact · Biochemistry · Organic Chemistry

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