Quantification of 4-beta-hydroxycholesterol in human plasma using automated sample preparation and LC-ESI-MS/MS analysis

Chemical Research in Toxicology

Volumn 24, Issue 9, 2011, Pages 1575-1585

  Goodenough, Angela K ^a   Onorato, Joelle M ^a   Ouyang, Zheng ^a   Chang, Shu ^a   Rodrigues, A David ^a   Kasichayanula, Sreeneeranj ^a   Huang, Shu Pang ^a   Turley, Wesley ^a   Burrell, Richard ^a   Bifano, Marc ^a   Jemal, Mohammed ^a   Lacreta, Frank ^a   Tymiak, Adrienne ^a   Wang Iverson, David ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 BETA HYDROXYCHOLESTEROL; CHOLESTEROL DERIVATIVE; KETOCONAZOLE; RIFAMPICIN; UNCLASSIFIED DRUG;

ADULT; ARTICLE; BLOOD LEVEL; CALIBRATION; DERIVATIZATION; ELECTROSPRAY MASS SPECTROMETRY; FEMALE; HUMAN; HUMAN EXPERIMENT; LIQUID CHROMATOGRAPHY; MALE; NORMAL HUMAN; SAPONIFICATION; TANDEM MASS SPECTROMETRY;

ADULT; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; HYDROXYCHOLESTEROLS; MALE; REPRODUCIBILITY OF RESULTS; SENSITIVITY AND SPECIFICITY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY; TIME FACTORS;

EID: 80053013798     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx2001898     Document Type: Article

References (41)

1. Bodin, K., Bretillon, L., Aden, Y., Bertilsson, L., Broomé, U., Einarsson, C., and Diczfalusy, U. (2001) Antiepileptic drugs increase plasma levels of 4β-hydroxycholesterol in humans. Evidence for involvement of cytochrome P450 3A4 J. Biol. Chem. 276, 38685-38689
2. Tomalik-Scharte, D., Lütjohann, D., Doroshyenko, O., Frank, D., Jetter, A., and Fuhr, U. (2009) Plasma 4β-hydroxycholesterol: An endogenous CYP3A metric Clin. Pharmacol. Ther. 86, 147-153
3. Eichelbaum, M. and Burk, O. (2001) CYP3A genetics in drug metabolism Nat. Med. 7, 285-287 (Pubitemid 32224337)
4. Kanebratt, K. P., Diczfalusy, U., Bäckström, T., Sparve, E., Bredberg, E., Böttiger, Y., Andersson, T. B., and Bertilsson, L. (2008) Cytochrome P450 induction by rifampicin in healthy subjects: Determination using the Karolinska cocktail and the endogenous CYP3a4 marker 4β- hydroxycholesterol Clin. Pharmacol. Ther. 84, 589-594
5. Wide, K., Larsson, H., Bertilsson, L., and Diczfalusy, U. (2008) Time course of the increase in 4β-hydroxycholesterol concentration during carbamazepine treatment of paediatric patients with epilepsy Br. J. Clin. Pharmacol. 65, 708-715 (Pubitemid 351535081)
6. Diczfalusy, U., Nylén, H., Elander, P., and Bertilsson, L. (2011) 4β-Hydroxycholesterol, an endogenous marker of CYP3A4/5 activity in humans Br. J. Clin. Pharmacol. 71, 183-189
7. Josephson, F., Bertilsson, L., Böttiger, Y., Flamholc, L., Gisslén, M., Ormaasen, V., Sönnerborg, A., and Diczfalusy, U. (2008) CYP3A induction and inhibition by different antiretroviral regimens reflected by changes in plasma 4β-hydroxycholesterol levels Eur. J. Clin. Pharmacol. 64, 775-781
8. Diczfalusy, U., Kanebratt, K. P., Bredberg, E., Andersson, T. B., Böttiger, Y., and Bertilsson, L. (2008) 4β-Hydroxycholesterol as an endogenous marker for CYP3A4/5 activity. Stability and half-life of elimination after induction with rifampicin Br. J. Clin. Pharmacol. 67, 38-43
9. Diczfalusy, U., Miura, J., Roh, H. K., Mirghani, R. A., Sayi, J., Larsson, H., Bodin, K. G., Allqvist, A., Jande, M., Kim, J. W., Aklillu, E., Gustafsson, L. L., and Bertilsson, L. (2008) 4β-Hydroxycholesterol is a new endogenous CYP3A marker: Relationship to CYP3A5 genotype, quinine 3-hydroxylation and sex in Koreans, Swedes and Tanzanians Pharmacogenet. Genomics 18, 201-208 (Pubitemid 351323234)
10. Lütjohann, D., Marinova, M., Schneider, B., Oldenburg, J., von Bergmann, K., Bieber, T., Björkhem, I., and Diczfalusy, U. (2009) 4β-hydroxycholesterol as a marker of CYP3A4 inhibition in vivo: Effects of itraconazole in man Int. J. Clin. Pharmacol. Ther. 47, 709-715
11. Streetman, D. S., Bertino, J. S., and Nafziger, A. N. (2000) Phenotyping of drug-metabolizing enzymes in adults: A review of in-vivo cytochrome P450 phenotyping probes Pharmacogenetics 10, 187-216 (Pubitemid 30242736)
12. Rivory, L. P., Slaviero, K. A., Hoskins, J. M., and Clarke, S. J. (2001) The erythromycin breath test for the prediction of drug clearance Clin. Pharmacokinet. 40, 151-158 (Pubitemid 32324447)
13. Kinirons, M. T., O'Shea, D., Kim, R. B., Groopman, J. D., Thummel, K. E., Wood, A. J. J., and Wilkinson, G. R. (1999) Failure of erythromycin breath test to correlate with midazolam clearance as a probe of cytochrome P4503A Clin. Pharmacol. Ther. 66, 224-231 (Pubitemid 29451753)
14. Nylén, H., Sergel, S., Forsberg, L., Lindemalm, S., Bertilsson, L., Wide, K., and Diczfalusy, U. (2011) Cytochrome P450 3A activity in mothers and their neonates as determined by plasma 4β-hydroxycholesterol Eur. J. Clin. Pharmacol. 1-8
15. Bodin, K. and Diczfalusy, U. (2002) Analysis of cholesterol oxidation products in plasma, tissues and food Eur. J. Lipid Sci. Technol. 104, 435-439 (Pubitemid 34840195)
16. Breuer, O., Dzeletovic, S., Lund, E., and Diczfalusy, U. (1996) The oxysterols cholest-5-ene-3β,4α-diol-diol, cholest-5-ene-3β, 4β-diol and cholestane-3β,5α,6α-triol are formed during in vitro oxidation of low density lipoprotein, and are present in human atherosclerotic plaques Biochim. Biophys. Acta 1302, 145-152 (Pubitemid 26247084)
17. Galteau, M. M. and Shamsa, F. (2003) Urinary 6β-hydroxycortisol: A validated test for evaluating drug induction or drug inhibition mediated through CYP3A in humans and in animals Eur. J. Clin. Pharmacol. 59, 713-733 (Pubitemid 38041296)
18. Diczfalusy, U. (2004) Analysis of cholesterol oxidation products in biological samples J. AOAC Int. 87, 467-473
19. Dzeletovic, S., Breuer, O., Lund, E., and Diczfalusy, U. (1995) Determination of cholesterol oxidation products in human plasma by isotope dilution-mass spectrometry Anal. Biochem. 225, 73-80
20. Van de Merbel, N. C., Bronsema, K. J., van Hout, M. W. J., Nilsson, R., and Sillén, H. (2011) A validated liquid chromatography-tandem mass spectrometry method for the quantitative determination of 4β- hydroxycholesterol in human plasma J. Pharm. Biomed. Anal. 55, 1089-1095
21. Saldanha, T., Frankland Sawaya, A. C. H., Eberlin, M. N., and Bragagnolo, N. (2006) HPLC separation and determination of 12 cholesterol oxidation products in fish: Comparative study of RI, UV, and APCI-MS detectors J. Agric. Food Chem. 54, 4107-4113 (Pubitemid 44013310)
22. Shui, G., Cheong, W. F., Jappar, I. A., Hoi, A., Xue, Y., Fernandis, A. Z., Tan, B. K. H., and Wenk, M. R. (2011) Derivatization-independent cholesterol analysis in crude lipid extracts by liquid chromatography/mass spectrometry: Applications to a rabbit model for atherosclerosis J. Chromatogr., A 1218, 4357-4365
23. Burkard, I., Rentsch, K. M., and Von Eckardstein, A. (2004) Determination of 24S- and 27-hydroxycholesterol in plasma by high-performance liquid chromatography-mass spectrometry J. Lipid Res. 45, 776-781 (Pubitemid 38405686)
24. Karuna, R., von Eckardstein, A., and Rentsch, K. M. (2009) Dopant assisted-atmospheric pressure photoionization (DA-APPI) liquid chromatography-mass spectrometry for the quantification of 27-hydroxycholesterol in plasma J. Chromatogr., B 877, 261-268
25. McDonald, J. G., Thompson, B. M., McCrum, E. C., and Russell, D. W. (2007) Extraction and Analysis of Sterols in Biological Matrices by High Performance Liquid Chromatography Electrospray Ionization Mass Spectrometry, in Methods in Enzymology (Brown, H. A., Ed.) Elsevier Inc. / Academic Press: Maryland Heights, MO, Vol. 432, pp 145-170.
26. Honda, A., Yamashita, K., Hara, T., Ikegami, T., Miyazaki, T., Shirai, M., Xu, G., Numazawa, M., and Matsuzaki, Y. (2009) Highly sensitive quantification of key regulatory oxysterols in biological samples by LC-ESI-MS/MS J. Lipid Res. 50, 350-357
27. Honda, A., Yamashita, K., Miyazaki, H., Shirai, M., Ikegami, T., Xu, G., Numazawa, M., Hara, T., and Matsuzaki, Y. (2008) Highly sensitive analysis of sterol profiles in human serum by LC-ESI-MS/MS J. Lipid Res. 49, 2063-2073
28. Griffiths, W. J., Hornshaw, M., Woffendin, G., Baker, S. F., Lockhart, A., Heidelberger, S., Gustafsson, M., Sjövall, J., and Wang, Y. (2008) Discovering oxysterols in plasma: A window on the metabolome J. Proteome Res. 7, 3602-3612
29. Griffiths, W. J., Wang, Y., Alvelius, G., Liu, S., Bodin, K., and Sjövall, J. (2006) Analysis of oxysterols by electrospray tandem mass spectrometry J. Am. Soc. Mass Spectrom. 17, 341-362 (Pubitemid 43290194)
30. Karu, K., Turton, J., Wang, Y., and Griffiths, W. J. (2011) Nano-liquid chromatography-tandem mass spectrometry analysis of oxysterols in brain: monitoring of cholesterol autoxidation. Chem. Phys. Lipids., doi: 10.1016/j.chemphyslip.2011.04.011.
31. Jiang, X., Ory, D. S., and Han, X. (2007) Characterization of oxysterols by electrospray ionization tandem mass spectrometry after one-step derivatization with dimethylglycine Rapid Commun. Mass Spectrom. 21, 141-152 (Pubitemid 46095472)
32. Tang, Z. and Guengerich, F. P. (2010) Dansylation of unactivated alcohols for improved mass spectral sensitivity and application to analysis of cytochrome P450 oxidation products in tissue extracts Anal. Chem. 82, 7706-7712
33. Myant, N. B. (1982) The Biology of Cholesterol and Related Steroids, Heinemann Medical Books,: London, England.
34. Teng, J. I., McGehee, M. F., and Smith, L. L. (1981) Sterol metabolism. XLVI. Synthesis of oxidized cholesterol fatty acyl esters J. Steroid Biochem. 14, 569-573 (Pubitemid 11037813)
35. Viger, A., Marquet, A., Barton, D. H. R., Motherwell, W. B., and Zard, S. Z. (1982) Stereochemistry of the reduction of 3β-benzoyloxycholest-5-en-4- one with sodium borohydride J. Chem. Soc., Perkin Trans. 1 1, 1937-1940
36. Turley, W. A., Burrell, R. C., B., S. J., Jr, Balasubramanian, B., Goodenough, A. K., and Onorato, J. M. Synthesis of [D4- and [D7-4β- hydroxycholesterols for use in a novel drug-drug interaction assay. J. Labelled Compd. Radiopharm. 2011, in press.
37. Poza, J., Rega, M., Paz, V., Alonso, B., Rodriguez, J., Salvador, N., Rernandez, A., and Jimenez, C. (2007) Synthesis and evaluation of new 6-hydroximinosteroid analogs as cytotoxic agents Bioorg. Med. Chem. 15, 4722-4740 (Pubitemid 46850827)
38. Shinkyo, R. and Guengerich, F. P. (2011) Inhibition of human cytochrome P450 3A4 by cholesterol J. Biol. Chem. 286, 18426-18433
39. Licea-Perez, H., Wang, S., Szapacs, M. E., and Yang, E. (2008) Development of a highly sensitive and selective UPLC/MS/MS method for the simultaneous determination of testosterone and 5α-dihydrotestosterone in human serum to support testosterone replacement therapy for hypogonadism Steroids 73, 601-610
40. Yang, Z. and Rodrigues, A. D. (2010) Does the Long plasma half-life of 4β-hydroxycholesterol impact its utility as a cytochrome P450 3A (CYP3A) metric? J. Clin. Pharmacol. 50, 1330-1338
41. Gebeyehu, E., Engidawork, E., Bijnsdorp, A., Aminy, A., Diczfalusy, U., and Aklillu, E. (2011) Sex and CYP3A5 genotype influence total CYP3A activity: High CYP3A activity and a unique distribution of CYP3A5 variant alleles in Ethiopians Pharmacogenomics J. 11, 130-137