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Determination of two mercapturic acids related to crotonaldehyde in human urine: influence of smoking

ABF Analytisch-Biologisches Forschungslabor GmbH, Goethestrasse 20, 80336 Muenchen, Germany, gerhard.scherer{at}abf-lab.com

M Urban

ABF Analytisch-Biologisches Forschungslabor GmbH, Goethestrasse 20, 80336 Muenchen, Germany

H-W Hagedorn

ABF Analytisch-Biologisches Forschungslabor GmbH, Goethestrasse 20, 80336 Muenchen, Germany

S Feng

Philip Morris USA, Research Center, 4201 Commerce Road, Richmond, VA 23234, USA

R D Kinser

Philip Morris USA, Research Center, 4201 Commerce Road, Richmond, VA 23234, USA

M Sarkar

Philip Morris USA, Research Center, 4201 Commerce Road, Richmond, VA 23234, USA

Q Liang

Philip Morris USA, Research Center, 4201 Commerce Road, Richmond, VA 23234, USA

H-J Roethig

Philip Morris USA, Research Center, 4201 Commerce Road, Richmond, VA 23234, USA

Crotonaldehyde, an ß-unsaturated aldehyde, and a potent alkylating agent, is present in many foods and beverages, ambient air and tobacco smoke. A previous study indicated that two metabolites, 3-hydroxy-1- methylpropylmercapturic acid (HMPMA) and 2-carboxy1-1-methylethylmercapturic acid (CMEMA), were excreted in rat urine after subcutaneous injection of crotonaldehyde. Herein, we report the development of a method based on liquid chromatography with tandem mass spectrometry (LC-MS/MS) and deuterated analytes as internal standards, for the determination of HMPMA and CMEMA in human urine. The limits of quantification of the method were 92 and 104 ng/mL for HMPMA and CMEMA, respectively. The calibration curves for both compounds were linear up to 7500 ng/mL with R² >0.99. It was found that cigarette smokers excreted about three to five-fold more HMPMA, and only slightly elevated amounts of CMEMA, in their urine compared to non-smokers. In smokers, we also found significant correlations between the urinary excretion levels of HMPMA (but not CMEMA) and several markers of exposure for smoking, including the daily cigarette consumption, carbon monoxide in exhaled breath, salivary cotinine, and nicotine plus five of its major metabolites in urine. Smoking cessation or switching from smoking conventional cigarettes to experimental cigarettes with lower crotonaldehyde delivery led to significant reductions of urinary HMPMA excretion, but not CMEMA excretion. Alcohol consumption did not influence either urinary HMPMA or CMEMA excretion. We conclude that HMPMA is a potentially useful biomarker for smoking-related exposure to crotonaldehyde.

Key Words: biomarkers • crotonaldehyde • mercapturic acids • smoking

Human & Experimental Toxicology, Vol. 26, No. 1, 37-47 (2007)
DOI: 10.1177/0960327107073829


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