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Quantitation of a minor enantiomer of phenanthrene tetraol in human urine: correlations with levels of overall phenanthrene tetraol, benzo[a]pyrene tetraol, and 1-hydroxypyrene


, : Quantitation of a minor enantiomer of phenanthrene tetraol in human urine: correlations with levels of overall phenanthrene tetraol, benzo[a]pyrene tetraol, and 1-hydroxypyrene. Chemical Research in Toxicology 24(2): 262-268

Polycyclic aromatic hydrocarbons (PAH) are well established carcinogens that are likely to play a role in causing some human cancers. One accepted pathway of PAH metabolic activation is the formation of bay region diol epoxides. Some individuals may be particularly susceptible to PAH carcinogenesis because they metabolically activate PAH more effectively than others. We have used the measurement of urinary phenanthrene tetraols (Phe-tetraols) as a biomarker of PAH exposure plus metabolic activation since bay region diol epoxides are hydrolyzed to tetraols. Because of stereoselectivity in Phe metabolism, Phe-(1R,2S,3R,4S)-tetraol (4) results mainly from the bay region diol epoxide pathway, and Phe-(1S,2R,3S,4R)-tetraol (7) is formed mainly from the reverse diol epoxide pathway, not generally associated with carcinogenicity. The latter pathway accounts for more than 95% of human urinary Phe-tetraol. In most previous studies, Phe-tetraol was quantified without enantiomeric resolution, using a relatively rapid and practical method, applicable to large studies. It was not clear, however, whether measurement of overall unresolved Phe-tetraol would accurately represent the bay region diol epoxide metabolic activation pathway. Therefore, in this study we specifically quantified Phe-(1R,2S,3R,4S)-tetraol (4) by supplementing our usual analysis with chiral HPLC separations and using [(13)C(6)]Phe-(1R,2S,3R,4S)-tetraol as internal standard. We then investigated the relationship of urinary levels of 4 to those of Phe-tetraols (4 + 7), quantified without enantiomeric resolution. We applied these methods to urine samples from cigarette smokers and highly PAH-exposed creosote workers. The results were also compared to levels of benzo[a]pyrene-7,8,9,10-tetraol and 1-hydroxypyrene in the same samples. Levels of 4 were highly correlated with those of 4 + 7 (r > 0.9, P < 0.0001) in both types of urine samples. Strong correlations of 4 and 4 + 7 with benzo[a]pyrene-7,8,9,10-tetraol and 1-hydroxypyrene were also observed. The results of this study demonstrate therefore that practical and convenient measurement of overall Phe-tetraols (4 + 7) in human urine, without enantiomeric resolution, is an excellent indicator of PAH exposure and metabolism by the bay region diol epoxide metabolic activation pathway.

US$19.90

PMID: 21229973

DOI: 10.1021/tx100391z


Other references

Varma, A.K.; Sahai, B.N.; Singh, S.P.; Lakra, P.; Shrivastava, V.K., 1971: On Setaria digitata, its specific characters, incidence and development in Aedes vittatus and Armigeres obturbans in India with a note on its ectopic occurrence. Fifteen Setaria cervi and 514 S. digitata were recovered from 63 of 136 Bos indices in Bihar, India. 109 S. cervi and 14 S. digitata were recovered from 27 of 58 Bubalus bubalis from the same area. The morphology of the 2 species is described. Adu...

Borten M.; Friedman E.A., 1985: Early pregnancy interruption with a single prostaglandin f 2 alpha 15 methyl analog vaginal suppository. Pregnancy was interrupted successfully in 70% of 20 early pregnancies, 35-49 days in duration as dated from the first day of the last menstrual period, by administration of a single intravaginal suppository containing 3 mg of (15S)-15-methyl prost...

Yu, J.S.; Chin, L.; Oh, J.; Farias, J., 2017: Performance-Based Risk-Sharing Arrangements for Pharmaceutical Products in the United States: A Systematic Review. Value for money is a growing necessity in today's U.S. health care system in which drug spending is expected to increase by an average rate of 6.7% yearly through 2025. In response to uncertainty about real-world clinical and economic outcome...

Montag, R.; Gängler, P., 1984: Demonstration of the effectiveness of plaque inhibition using a chlorhexidine mouthwash. A clinically controlled study. Stomatologie der Ddr 34(6): 348-354

Jones, A.P.; van Sluijs, E.M.F.; Ness, A.R.; Haynes, R.; Riddoch, C.J., 2010: Physical activity in children: does how we define neighbourhood matter?. Physical activity levels in children are low and factors in the neighbourhood are believed to be influential. However, uncertainty remains about how best to define the neighbourhood. We therefore sought to study the role of area definition on neig...

McLaren, I., 1992: Cystostomy in a cat with urethral trauma. A 6-year-old castrated male cat which had undergone perineal surgery to relieve urethral obstruction on 3 occasions was referred with urethral obstruction; no urethral opening was visible and it was not possible to introduce a catheter. A prepubic...

Matsumoto, K.; Toh-e, A.; Oshima, Y., 1978: Genetic control of galactokinase synthesis in Saccharomyces cerevisiae: evidence for constitutive expression of the positive regulatory gene gal4. Temperature-sensitive (ts) mutants for the gal80 and gal4 genes of Saccharomyces cerevisiae were isolated and characterized. These mutants were classified into two categories; one showed thermolability (TL) and the other showed temperature-sensiti...

Spiller, M.; Brown, R.D.; Koenig, S.H.; Wolf, G.L., 1988: Longitudinal proton relaxation rates in rabbit tissues after intravenous injection of free and chelated Mn2+. The factors that determine the field-dependent increase in 1/T1 of tissue water protons were investigated for MnCl2 and Mn2+ (PDTA) (1,3-propylenediamine-N,N',N'',N'''-tetraacetic acid) introduced intravenously into r...

Pietra, Dominici, 1928: Influence of liver on water metabolism. Gior Accad Med Torino 90(7): 371

Lamb, T.D.; Pugh, E.N., 1992: G-protein cascades: gain and kinetics. G-protein cascades provide amplification in a wide variety of biological signal transducers--from hormonal and synaptic systems to the receptor cells of vision and olfaction. Through recent understanding of the molecular mechanisms involved, it is...