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

Jun-Jie Yin, Qingsu Xia, Shu-Hui Cherng, I-Wah Tang, Peter P. Fu, Ge Lin, Hongtao Yu and Diógenes Herreño Sáenz
Additional contact information
Jun-Jie Yin: Center for Food Safety and Applied Nutrition, U.S. Food and Drug Administration, College Park, MD 20740, USA
Qingsu Xia: National Center for Toxicological Research, Jefferson, AR 72079, USA
Shu-Hui Cherng: National Center for Toxicological Research, Jefferson, AR 72079, USA
I-Wah Tang: National Center for Toxicological Research, Jefferson, AR 72079, USA
Peter P. Fu: National Center for Toxicological Research, Jefferson, AR 72079, USA
Ge Lin: Department of Pharmacology, The Chinese University of Hong Kong, Shatin, Hong Kong, SAR
Hongtao Yu: Department of Chemistry, Jackson State University, Jackson, MS 39217, USA
Diógenes Herreño Sáenz: Department of Pharmacology and Toxicology, School of Medicine, University of Puerto Rico, P.O. Box 365067, San Juan, Puerto Rico

IJERPH, 2008, vol. 5, issue 1, 1-6

Abstract: 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-CH 2 OH-BA), 7-hydroxymethyl-BA (7-CH 2 OH-BA), 12-hydroxymethyl-BA (12-CH 2 OH-BA), 7-hydroxymethyl-12-methyl-BA (7-CH 2 OH-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.

Keywords: n/a (search for similar items in EconPapers)
JEL-codes: I I1 I3 Q Q5 (search for similar items in EconPapers)
Date: 2008
References: View references in EconPapers View complete reference list from CitEc
Citations:

Downloads: (external link)
https://www.mdpi.com/1660-4601/5/1/26/pdf (application/pdf)
https://www.mdpi.com/1660-4601/5/1/26/ (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:gam:jijerp:v:5:y:2008:i:1:p:26-31:d:2291

Access Statistics for this article

IJERPH is currently edited by Ms. Jenna Liu

More articles in IJERPH from MDPI
Bibliographic data for series maintained by MDPI Indexing Manager ().