Enantioselective analytical methods in chiral drug metabolism

Abstract

Abstract:

The chiral nature of biological systems enables their stereoselective interaction with chiral compounds. It has been well documented that the enantiomers of a chiral drug may show differences in drug disposition especially in metabolic behavior. As a result, it is of vital importance to separate the enantiomers of a chiral drug in metabolic studies. This paper discusses enantioselective methods (include high-performance liquid chromatography, gas chromatography, capillary electrophoresis and high-performance liquid chromatography-mass spectrometry) that applied in chiral drug metabolism, using most recent examples where possible.

Key words: Enantioselective analytical methods, Enantioselective analytical methods, Chiral drug, Chiral drug, Drug metabolism, Drug metabolism, ,

CLC Number:

R917

Supporting:

Yan-Jun Hong, Ling-Bo Gao, Su Zeng^*. Enantioselective analytical methods in chiral drug metabolism[J]. .

References

[1] Mannhold, R.; Kubinyi, H.; Folkers, G. Chirality in Drug Reasearch, Germany: Wiley-VCH, 2006, 3-4.
[2] Qian, M.R.; Zeng, S. Asian. J. Drug. Metab. Pharmacokinet. 2003, 3, 99-103.
[3] Rentsch, K.M. J. Biochem. Biophys. Methods. 2002, 54, 1-9.
[4] Eeckhaut, A.V.; Michotte, Y. Electrophoresis. 2006, 27, 2880-2895.
[5] Eichelbaum, M.; Testa, B.; Somogyi, A. Stereochemical Aspects of Drug Action and Disposition, Handbook of Experimental Pharmacology, Vol. 153, Germany: Berlin, Springer, 2003.
[6] Lu, H.; Wang, J.J.; Chan, K.K.; Philip, P.A. Xenobiotica. 2006, 36, 367-385.
[7] Gharavi, N.; Sattari, S.; Shayeganpour, A.; El-Kadi, A. O.; Brocks, D.R. Chirality. 2007, 19, 22-33.
[8] Suchanova, B.; Sispera, L.; Wsol, V. Anal. Chim. Acta. 2006, 573-574, 273-283.
[9] Wu, Y.J.; Ma, M.M.; Zeng, S. J. Zhejiang .Univ. Sci. 2004, 5, 226-229.
[10] Gerber, J.G.; Rhodes, R.J.; Gal, J.J. Chirality. 2004, 16, 36-44.
[11] Yu, L.S.; Luan, L.J.; Ni, Q.S.; Zeng, S. Biomed. Chromatogr. 2004, 18, 833-837.
[12] Kobayashi, K.; Kogo, M.; Tani, M.; Shimada, N.; Ishizaki, T.; Numazawa, S.; Yoshida, T.; Yamamoto, T.; Kuroiwa, Y.; Chiba, K. Drug Metab. Dispos. 2001, 29, 36-40. 13] Äbelö, A.; Andersson, T.B.; Antonsson, M.; Naudot, A.K.; , I.; Weidolf, L. Drug Metab. Dispos. 2000, 28, 966-972.
[14] Margolis, J.M.; O’Donnell, J.P.; Mankowski, D.C.; Ekins, S.; Obach, R.S. Drug. Metab. Dispos. 2000, 28, 1187-1191.
[15] Ekins, S.; Ring, B.J.; Grace, J. J. Pharmacol. Toxicol. Methods. 2000, 44, 313-324.
[16] Haginaka, J. J. Pharm. Biomed. Anal. 2002, 27, 357-372.
[17] Gübitz, G.; Schmid, M.G. Biopharm. Drug Dispos. 2001, 22, 291-336.
[18] Chen, J.W.; Korfmacher, W.A.; Hsieh, Y. J. Chromatogr. B. 2005, 820, 1-8.
[19] Schurig, V. J. Chromatogr. A. 2002, 965, 315-356.
[20] He, L.F.; Beesley, T.E. J. Liq .Chromatogr. Relat. Technol. 2005, 28, 1075-1114.
[21] Bhushan, R.; Gupta, D. Biomed. Chromatogr. 2005, 19, 474-478.
[22] Coe, R.A.; Rathe, J.O.; Lee, J.W. J. Pharm. Biomed. Anal. 2006, 42, 573-580.
[23] Van Eeckhaut, A.; Michotte, Y. Electrophoresis. 2006, 27, 2880-2895.
[24] Scriba, G.K. Electrophoresis. 2003, 24, 2409-2421.
[25] Pyell, U. Anal. Bioanal. Chem. 2003, 375, 20-22.
[26] Amini, A. Electrophoresis. 2001, 22, 3107-3130.
[27] Fanali, S.; Catarcini, P.; Blaschke, G.; Chankvetadze, B. Electrophoresis. 2001, 22, 3131-3151.
[28] Marzo, A.; Heftmann, E. J. Biochem. Biophys. Methods. 2002, 54, 57-70.
[29] Srinivas, N.R. Biomed. Chromatogr. 2004, 18, 207-233.
[30] Ward, T.J. Anal. Chem. 2006, 78, 3947-3956.
[31] Cardoso, C.D.; Bonato, P.S.; J. Pharm. Biomed. Anal. 2005, 37, 703-708.
[32] Heinemann, U.; Blaschke, G.; Knebel, N. J. Chromatogr. B. 2003, 793, 389-404.
[33] Ye, J.; Chen, G.; Zeng, S. J. Chromatogr. B. Analyt. Technol. Biomed. Life. Sci. 2006, 843, 289-294.
[34] Miku, P.; Kubaák, P.; Valáková, I.; Havránek, E. Talanta. 2006, 70, 840-846.
[35] Ha, P.T.T.; Sluyts, I.; Dyck, S.V.; Zhang, J.; Gilissen, R.A.H.J.; Hoogmartens, J.; Schepdael, A.V. J. Chromatogr. A. 2006, 1120, 94-101.
[36] Afshar, M.; Thormann, W. Electrophoresis. 2006, 27, 1517-1525.
[37] Afshar, M.; Thormann, W. Electrophoresis. 2006, 27, 1526-1536.
[38] Szök, Tábi, T.; Borbás, T.; Dalmadi, B.; Tihanyi, K.; Magyar, K. Electrophoresis. 2004, 25, 2866-2875.
[39] Bortocan, R.; Bonato, P.S. Electrophoresis. 2004, 25, 2848-2853.
[40] Srinivas, N.R.; Shyu, W.C.; Barbhaiya, R.H. Biomed. Chromatogr. 1995, 9, 1-9.
[41] Kunze, K.L.; Nelson, W.L.; Kharasch, E.D.; Thummel, K.E.; Isoherranen, N. Drug Metab. Dispos. 2006, 34, 583-590.
[42] Babú, Y.N.; Nemec, M.; Solich, P.; Wsól, V. Talanta. 2008, 75, 494-502.
[43] Coles, R; Kharasch, E.D. J. Chromatogr. B. 2007, 857, 67-75.
[44] Kammerer, B.; Kahlich, R.; Ufer, M. Anal. Biochem. 2005, 339, 297-309.
[45] Hadley, M.R.; Camilleri, P.; Hutt, A.J. Electrophoresis. 2000, 21, 1953-1976.

[1]	Wenzhe Li, Xia Yuan, Bo Xu, Shuxiang Song. Applications of multiplexed immunohistochemistry/immunofluorescence and multispectral imaging technology in the field of tumor immunotherapy [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(10): 734-747.
[2]	Yi Zhou, Junli Lai, Feng Qiu, Jun Zhang. Development and validation of an HPLC-UV method for routine trough plasma concentration monitoring of imatinib in Chinese patients with gastrointestinal stromal tumor [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(9): 637-648.
[3]	Qian Wang, Jing Wang, Shuxiang Song, Guiwang Zhu, Ze Cao, Zhenming Liu. Microscale thermophoresis in the investigation of biomolecular interactions [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(9): 656-665.
[4]	Wen Ma, Shuxiang Song, Jun Li. Surface-assisted laser desorption/ionization mass spectrometry for drug and metabolite analysis [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(8): 577-590.
[5]	Shaojing Liu, Bei Qin, Hongfang Han, Li Li, Lili Yu, Xiaojing Xu. Preparative separation of high-purity troxerutin and related substances from mother liquor of troxerutin by silica gel column chromatography and semi-preparative liquid chromatography [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(7): 487-493.
[6]	Jing Wang, Qian Wang, Shuxiang Song. Research progress of surface plasmon resonance technology in drug discovery [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(7): 504-513.
[7]	Jialin Du, Liangjiu Yang, Kezhao Wei, Can Gong, Jianping Gao, Xu Xu. Determination of free fatty acids in rabbit plasma by GC-MS after trimethylsilylation derivatization [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(6): 411-421.
[8]	Xuejiao Li, Jianwei Dong, Xiu Gao, Guijun Li, Junyou Shi, Yanqing Zhang. Application of a quantitative 1H NMR method for rapid extraction and determination of the content of paeonol in Cynanchum paniculatum [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(6): 422-430.
[9]	Yufang Sun, Chen Zheng, Bo Xu. Research on Moflo XDP high speed cell sorting techniques and parameter optimization [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(5): 355-363.
[10]	Xiaoting Liu, Jingna Xu, Kun Xiao, Qiangsheng Guo, Xu Xu. Determination of chlorogenic acid in traditional Chinese prescription Shuanghuanglian capsule using quantitative nuclear magnetic resonance spectroscopy in combination with solid phase extraction [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(4): 227-235.
[11]	Sufang Zhang, Cong Li, Ying Zhang, Juncheng Zou, Yinzhu Cui, Xiaomei Ling. Determination of β-amyloid peptides in vitro aggregation process by electrochemistry [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(3): 199-205.
[12]	Yue Zou, Yang Li, Nanyin Han. The granule characteristics of yam, sweet potato and tapioca starches determined by gravitational field-flow fractionation [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(2): 113-122.
[13]	Shuxiang Song. Construction and open access management of large-scale instrument platform [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(2): 130-138.
[14]	Xiwei Ji, Zisheng Kang, Yun Li, Xiping Yang, Xifeng Ma, Chongtie Shi, Yuan Lv. An established LC-MS/MS method and a developed PK model for the study of pharmacokinetic properties of benapenem in infected mice [J]. Journal of Chinese Pharmaceutical Sciences, 2019, 28(11): 802-811.
[15]	Ruiyan Li, Mingbo Zhao, Pengfei Tu, Yong Jiang. Simultaneous determination of five phenylethanoid glycosides in Cistanches Herba using quantitative analysis of multi-components by single marker [J]. Journal of Chinese Pharmaceutical Sciences, 2019, 28(8): 537-546.