Approach for in vivo protein binding of 5-n-butyl-pyrazolo[1,5-a]pyrimidine bioactivated in chimeric mice with humanized liver by two-dimensional electrophoresis with accelerator mass spectrometry

Chemical Research in Toxicology

Volumn 23, Issue 1, 2010, Pages 152-158

  Yamazaki, Hiroshi ^a   Kuribayashi, Shunji ^b   Inoue, Tae ^c,d   Tateno, Chise ^c   Nishikura, Yasufumi ^c   Oofusa, Ken ^e   Harada, Daisuke ^b   Naito, Shinsaku ^b   Horie, Toru ^c   Ohta, Shigeru ^d  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

^b OTSUKA PHARMACEUTICAL CO LTD   (Japan)

^c PhoenixBio USA Corporation   (Japan)

^d HIROSHIMA UNIVERSITY   (Japan)

^e Towa Environment Science Co Ltd   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5 N BUTYL PYRAZOLO[1,5 A]PYRIMIDINE; CYTOCHROME P450 1A2; GLUTATHIONE; LIVER PROTEIN; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CHIMERA; CONJUGATE; COVALENT BOND; CYTOSOL; IN VITRO STUDY; IN VIVO STUDY; ISOTOPE LABELING; LIQUID CHROMATOGRAPHY; LIVER; LIVER MICROSOME; LIVER TOXICITY; MALE; MASS SPECTROMETRY; METABOLITE; MOUSE; NONHUMAN; PLASMA; PROTEIN BINDING; TWO DIMENSIONAL ELECTROPHORESIS;

ANALGESICS; ANIMALS; CHIMERA; CYTOCHROME P-450 CYP1A2; ELECTROPHORESIS, GEL, TWO-DIMENSIONAL; GLUTATHIONE; HUMANS; LIVER; MALE; MASS SPECTROMETRY; MICE; MICROSOMES, LIVER; PROTEIN BINDING; PYRAZOLES; PYRIMIDINES;

ANIMALIA; MUS; RATTUS;

EID: 75149137516     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx900323a     Document Type: Article

References (20)

1. Guengerich, F. P. (2008) Cytochrome P450 and chemical toxicology. Chem. Res. Toxicol. 21, 70-83.
2. James, L. P., Mayeux, P. R., and Hinson, J. A. (2003) Acetaminophen-induced hepatotoxicity. Drug Metab. Dispos. 31, 1499-1506.
3. Kassahun, K., Pearson, P. G., Tang, W., McIntosh, I., Leung, K., Elmore, C., Dean, D., Wang, R., Doss, G., and Baillie, T. A. (2001) Studies on the metabolism of troglitazone to reactive intermediates in vitro and in vivo. Evidence for novel biotransformation pathways involving quinone methide formation and thiazolidinedione ring scission. Chem. Res. Toxicol. 14, 62-70.
4. Gonzalez, F. J., and Yu, A. M. (2006) Cytochrome P450 and xenobiotic receptor humanized mice. Annu. Rev. Pharmacol. Toxicol. 46, 41-64.
5. Kuribayashi, S., Goto, K., Naito, S., Kamataki, T., and Yamazaki, H. (2009) Human cytochrome P450 1A2 involvement in the formation of reactive metabolites from a species-specific hepatotoxic pyrazolopyrimidine derivative, 5-n-butyl-7-(3,4,5-trimethoxybenzoylamino) pyrazolo[1,5-a]pyrimidine. Chem. Res. Toxicol. 22, 323-331.
6. Powley, M. W., Frederick, C. B., Sistare, F. D., and DeGeorge, J. J. (2009) Safety assessment of drug metabolites: implications of regulatory guidance and potential application of genetically engineered mouse models that express human P450s. Chem. Res. Toxicol. 22, 257-262.
7. Tateno, C., Yoshizane, Y., Saito, N., Kataoka, M., Utoh, R., Yamasaki, C., Tachibana, A., Soeno, Y., Asahina, K., Hino, H., Asahara, T., Yokoi, T., Furukawa, T., and Yoshizato, K. (2004) Near completely humanized liver in mice shows human-type metabolic responses to drugs. Am. J. Pathol. 165, 901-912.
8. Katoh, M., Tateno, C., Yoshizato, K., and Yokoi, T. (2008) Chimeric mice with humanized liver. Toxicology 246, 9-17.
9. Emoto, K., Tateno, C., Hino, H., Amano, H., Imaoka, Y., Asahina, K., Asahara, T., and Yoshizato, K. (2005) Efficient in vivo xenogeneic retroviral vector-mediated gene transduction into human hepatocytes. Hum. Gene Ther. 16, 1168-1174.
10. 3H-warfarin using chimeric mice with humanized liver. Drug Metab. Pharmacokinet. 24, 153-160.
11. Laemmli, U. K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227, 680-685.
12. Sanchez, J. C., Rouge, V., Pisteur, M., Ravier, F., Tonella, L., Moosmayer, M., Wilkins, M. R., and Hochstrasser, D. F. (1997) Improved and simplified in-gel sample application using reswelling of dry immobilized pH gradients. Electrophoresis 18, 324-327.
13. Rabilloud, T., Valette, C., and Lawrence, J. J. (1994) Sample application by in-gel rehydration improves the resolution of two-dimensional electrophoresis with immobilized pH gradients in the first dimension. Electrophoresis 15, 1552-1558.
14. Lopez, M. F., Berggren, K., Chernokalskaya, E., Lazarev, A., Robinson, M., and Patton, W. F. (2000) A comparison of silver stain and SYPRO Ruby Protein Gel Stain with respect to protein detection in two-dimensional gels and identification by peptide mass profiling. Electrophoresis 21, 3673-3683.
15. Kristensen, D. B., Imamura, K., Miyamoto, Y., and Yoshizato, K. (2000) Mass spectrometric approaches for the characterization of proteins on a hybrid quadrupole time-of-flight (Q-TOF) mass spectrometer. Electrophoresis 21, 430-439.
16. Gharahdaghi, F., Weinberg, C. R., Meagher, D. A., Imai, B. S., and Mische, S. M. (1999) Mass spectrometric identification of proteins from silver-stained polyacrylamide gel: a method for the removal of silver ions to enhance sensitivity. Electrophoresis 20, 601-605.
17. Miyaoka, T., Isono, Y., Setani, K., Sakai, K., Yamada, I., Sato, Y., Gunji, S., and Matsui, T. (2007) Bioanalysis works in the IAA AMS facility: Comparison of AMS analytical method with LSC method in human mass balance study. Nucl. Instrum. Methods Phys. Res., Sect. B 259, 779-785.
18. Park, B. K., Kitteringham, N. R., Powell, H., and Pirmohamed, M. (2000) Advances in molecular toxicology-towards understanding idiosyncratic drug toxicity. Toxicology 153, 39-60.
19. Uetrecht, J. (2003) Screening for the potential of a drug candidate to cause idiosyncratic drug reactions. Drug Discovery Today 8, 832-837.
20. Evans, D. C., Watt, A. P., Nicoll-Griffith, D. A., and Baillie, T. A. (2004) Drug-protein adducts: An industry perspective on minimizing the potential for drug bioactivation in drug discovery and development. Chem. Res. Toxicol. 17, 3-16. TX900323A