手性PPCPs环境行为与效应的对映体选择性

doi:10.7536/PC151101

化学进展 ›› 2016, Vol. 28 ›› Issue (5) :744-753 DOI: 10.7536/PC151101

综述与评论

扫码查看或转发全文

手性PPCPs环境行为与效应的对映体选择性

作者信息 +

Enantioselective Environmental Behavior and Effect of Chiral PPCPs

Yin Lina^1,2, Wang Bin^1*, Ma Ruixue¹, Yuan Honglin², Yu Gang¹

Author information +

文章历史 +

摘要

新型环境有机污染物——药物和个人护理品(PPCPs)中大部分是手性物质,以外消旋体形式或单一对映体形式使用,经过一系列生物转化过程对映体组分会发生改变。复杂环境介质中手性PPCPs分离分析难度大从而限制了相关研究,手性PPCPs生物降解的立体选择性和毒理效应的立体选择性使潜在的环境行为和风险更加复杂。欧美、日本等发达国家已逐渐关注环境中手性PPCPs的立体选择性,并开展了一系列手性药物环境行为和效应的对映体选择性研究。相比之下,我国环境中手性PPCPs研究尚欠缺,亟待开展广泛深入的研究。本文综述了PPCPs的手性特征、分析方法、手性PPCP环境行为和效应选择性,分析了对映体选择性特征在污染源解析中的潜在应用,讨论了目前手性PPCPs环境行为和效应研究的局限性,并展望了研究趋势。

Abstract

Pharmaceuticals and personal care products (PPCPs) as emerging organic contaminants are mostly chiral compounds. They are usually consumed as racemic compounds or single enantiomers. Biological degradation process can lead to stereoselective enrichment of enantiomer of chiral PPCPs. Due to the difficulties in chiral separation and quantification of enantiomers in the complex environmental matrices, their environmental behavior study has been limited. Enantioselective biodegradation and ecotoxicity of chiral PPCPs tend to make their potential environmental behavior and risk more complicated. Recently, enantiomeric selectivity of chiral PPCPs in environment has gradually caused attention of environmental researchers in developed countries, such as Europe, North America and Japan. Effort has been devoted in studying enantiomeric selectivity of environmental behavior and effect about chiral PPCPs. However, in China, there are very few related studies. It is necessary to carry out more related studies. Consequently, this paper reviews chiral signature of PPCPs, analytical methods, environment behavior and effect selectivity of chiral PPCPs, as well as their potential application in pollution source apportionment. Limitation of current research on environmental behavior and effect of chiral PPCPs is also discussed. The prospect of environmental study on chiral PPCPs in the future is also proposed.

Contents
1 Introduction
2 Manufacture and use of chiral pharmaceuticals
3 Chiral signature of PPCPs
4 Analytical methods of chiral PPCPs
5 Occurrence and environment behavior of chiral PPCPs
6 Toxicological effects of chiral PPCPs
7 Application in source analysis
8 Conclusion and outlook

Graphical abstract

关键词

药物和个人护理品 / 手性 / 对映体选择性 / 生物降解 / 环境行为

Key words

pharmaceuticals and personal care products(PPCPs) / chirality / enantiomeric selectivity / biodegradation / environmental behavior

引用本文

引用格式 ▾

尹立娜, 王斌, 马瑞雪, 袁宏林, 余刚. 手性PPCPs环境行为与效应的对映体选择性[J]. 化学进展, 2016, 28(5): 744-753 DOI:10.7536/PC151101

Enantioselective Environmental Behavior and Effect of Chiral PPCPs[J]. Progress in Chemistry, 2016, 28(5): 744-753 DOI:10.7536/PC151101

登录浏览全文

4963

注册一个新账户忘记密码

参考文献

原文顺序 | 出版日期 | 本文引用

[1] Fatta-Kassinos D. Environ. Sci. Pollut. R, 2010, 17 (2): 519.
[2] Liu J L, Wong M H. Environ. Int., 2013, 59: 208.
[3] Wong C S. Anal. Bioanal. Chem., 2006, 386 (3): 544.
[4] 付长华(Fu C H), 江鸿(Jiang H), 杨大龙(Yang D L). 第六届中国药师大会(Sixth Conference of Chinese Pharmacist), 江苏(JiangSu Province), 2014.
[5] Kasprzyk-Hordern B. Chem. Soc. Rev., 2010, 39 (11): 4466.
[6] Ribeiro A R, Maia A S, Cass Q B, Tiritan M E. J. Chromatogr. B, 2014, 968: 8.
[7] Harner T, Wiberg K, Norstrom R. Environ. Sci. Technol., 2000, 34 (1): 218.
[8] Buser H R, Poiger T, Muller M D. Environ. Sci. Technol., 1999, 33 (15): 2529.
[9] Fono L, Sedlak D L. Abstracts of Papers of the American Chemical Society, 2005, 230: 1534.
[10] Ribeiro A R, Castro P M, Tiritan M E. Environ. Chem. Lett., 2012, 10 (3): 239.
[11] Nikolai L N, McClure E L, MacLeod S L, Wong C S. J. Chromatogr. A, 2006, 1131 (1): 103.
[12] Buser H R, Poiger T, Müller M D. Environ. Sci. Technol., 1999, 33 (15): 2529.
[13] Matamoros V, Hijosa M, Bayona J M. Chemosphere, 2009, 75 (2): 200.
[14] MacLeod S L, Wong C S. Water Res., 2010, 44 (2): 533.
[15] López-Serna R, Kasprzyk-Hordern B, Petrovi? M, Barceló D. Anal. Bioanal. Chem., 2013, 405 (18): 5859.
[16] MacLeod S L, Sudhir P, Wong C S. J. Chromatogr. A, 2007, 1170 (1/2): 23.
[17] Ribeiro A R, Santos L H, Maia A S, Delerue-Matos C, Castro P M, Tiritan M E. J. Chromatogr. A, 2014, 1363: 226.
[18] Morante-Zarcero S, Sierra I. Chirality, 2012, 24 (10): 860.
[19] Svan A, Hedeland M, Arvidsson T, Jasper J T, Sedlak D L, Pettersson C E. J. Chromatogr. A, 2015, 1409: 251.
[20] Wistuba D, Schurig V. J. Chromatogr. A, 2000, 875 (1): 255.
[21] Ribeiro A, Gonçalves V F, Maia A, Ribeiro C, Castro P L, Tiritan M. Environ. Chem. Lett., 2015, 13 (2): 203.
[22] Matamoros V, Uggetti E, García J, Bayona J M. J. Hazard. Mater., 2016, 301: 197.
[23] Bagnall J, Malia L, Lubben A, Kasprzyk-Hordern B. Water Res., 2013, 47 (15): 5708.
[24] Hashim N H, Khan S J. J. Chromatogr. A, 2011, 1218 (29): 4746.
[25] Baker D R, Kasprzyk-Hordern B. Sci. Total Environ., 2013, 454/455: 442.
[26] Wang L, McDonald J A, Khan S J. J. Chromatogr. A, 2013, 1303: 66.
[27] Li Z, Gomez E, Fenet H, Chiron S. Chemosphere, 2013, 90 (6): 1933.
[28] Gasser G, Pankratov I, Elhanany S, Werner P, Gun J, Gelman F, Lev O. Chemosphere, 2012, 88 (1): 98.
[29] Suzuki T, Kosugi Y, Hosaka M, Nishimura T, Nakae D. Environ. Toxicol. Chem., 2014, 33 (12): 2671.
[30] Hashim N H, Nghiem L D, Stuetz R M, Khan S J. Water Res., 2011, 45 (18): 6249.
[31] Jammer S, Voloshenko A, Gelman F, Lev O. Environ. Sci. Technol., 2014, 48 (6): 3310.
[32] Evans S E, Davies P, Lubben A, Kasprzyk-Hordern B. Anal. Chim. Acta, 2015, 882: 112.
[33] Song H, Zeng X, Yu Z, Zhang D, Cao S, Shao W, Sheng G, Fu J. Environ. Sci. Pollut. R, 2015, 22 (3): 1679.
[34] Berset J D, Kupper T, Etter R, Tarradellas J. Chemosphere, 2004, 57 (8): 987.
[35] Fono L J, Sedlak D L. Environ. Sci. Technol., 2005, 39 (23): 9244.
[36] Morante-Zarcero S, Sierra I. J. Pharmaceut. Biomed., 2012, 62: 33.
[37] Barreiro J C, Vanzolini K L, Madureira T V, Tiritan M E, Cass Q B. Talanta, 2010, 82 (1): 384.
[38] Ribeiro A R, Afonso C M, Castro P M L, Tiritan M E. Ecotoxicol. Environ. Saf., 2013, 87: 108.
[39] Ribeiro A R, Afonso C M, Castro P M, Tiritan M E. Environ. Chem. Lett., 2013, 11 (1): 83.
[40] Barclay V K H, Tyrefors N L, Johansson I M, Pettersson C E. J. Chromatogr. A, 2011, 1218 (33): 5587.
[41] Barclay V K H, Tyrefors N L, Johansson I M, Pettersson C E. J. Chromatogr. A, 2012, 1227: 105.
[42] Stanley J K, Ramirez A J, Mottaleb M, Chambliss C K, Brooks B W. Environ. Toxicol. Chem., 2006, 25 (7): 1780.
[43] Nikolai L N, McClure E L, MacLeod S L, Wong C S. J. Chromatogr. A, 2006, 1131 (1/2): 103.
[44] Kunkel U, Radke M. Water Res., 2012, 46 (17): 5551.
[45] Khan S J, Wang L L, Hashim N H, McDonald J A. Chirality, 2014, 26 (11): 739.
[46] Huang Q, Zhang K, Wang Z, Wang C, Peng X. Anal. Bioanal. Chem., 2012, 403 (6): 1751.
[47] Stanley J K, Ramirez A J, Chambliss C K, Brooks B W. Chemosphere, 2007, 69 (1): 9.
[48] De Andres F, Castaneda G, Rios A. Chirality, 2009, 21 (8): 751.
[49] Dai G, Wang B, Huang J, Dong R, Deng S, Yu G. Chemosphere, 2015, 119: 1033.
[50] Daneshvar A, Aboulfadl K, Viglino L, Broséus R, Sauvé S, Madoux-Humery A S, Weyhenmeyer G A, Prévost M. Chemosphere, 2012, 88 (1): 131.
[51] Kawashima H, Murakami M. Atmos. Environ., 2014, 89: 140.
[52] Aboul-Enein H Y, Ali I. Toxicological & Environmental Chemistry, 2004, 86 (1): 1.
[53] Li A, Jang J K, Scheff P A. Environ. Sci.Technol., 2003, 37 (13): 2958.
[54] 廖勇(Liao Y), 赵扬(Zhao Y), 潘灿平(Pan C P). 农药科学与管理(Pesticide Science and Administration), 2008, 29 (1): 47.
[55] Bidleman T F, Jantunen L M, Harner T, Wiberg K, Wideman J L, Brice K, Su K, Falconer R L, Aigner E J, Leone A D, Ridal J J, Kerman B, Finizio A, Alegria H, Parkhurst W J, Szeto S Y. Environ. Pollut., 1998, 102 (1): 43.
[56] Bidleman T F, Jantunen L M, Kurt-Karakus P B, Wong F. Atmospheric Pollution Research, 2012, 3 (4): 371.
[57] Upadhyay N, Sun Q, Allen J O, Westerhoff P, Herckes P. Water Res., 2011, 45 (3): 1071.