某些芳香族氨基酸作探针荧光猝灭法测定安乃近及其代谢产物

doi:10.6023/A1106072

化学学报 ›› 2012, Vol. 70 ›› Issue (01): 58-64.DOI: 10.6023/A1106072 上一篇下一篇

研究论文

某些芳香族氨基酸作探针荧光猝灭法测定安乃近及其代谢产物

甘晓娟, 刘绍璞, 刘忠芳, 王亚琼, 崔志平, 胡小莉

发光与实时分析教育部重点实验室, 西南大学化学化工学院, 重庆 400715

投稿日期:2011-06-07 修回日期:2011-07-31 发布日期:2012-02-25
通讯作者: 胡小莉 E-mail:xiaolihu@swu.edu.cn
基金资助:
国家自然科学基金(No.20875078)资助项目.

Fluorescence Quenching Method for the Determination of Analgin and Metabolin with Some Aromatic Amino Acids as Probes

Gan Xiaojuan, Liu Shaopu, Liu Zhongfang, Wang Yaqiong, Cui Zhiping, Hu Xiaoli

Education Ministry Key Laboratory on Luminescence and Real-Time Analysis, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715

Received:2011-06-07 Revised:2011-07-31 Published:2012-02-25
Supported by:
Project supported by the National Natural Science Foundation of China(No.20875078).

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摘要/Abstract

在pH3.2的缓冲介质中,安乃近(ANG)及其代谢产物4-甲氨基安替比林(MAA)、4-乙酰氨基安替比林(AAA)与色氨酸(Trp)、酪氨酸(Tyr)和苯丙氨酸(Phe)等芳香族氨基酸反应并形成结合产物,引起上述氨基酸的荧光发生猝灭,最大猝灭波长分别位于352nm(ANG-Trp体系)、304nm(ANG-Tyr,MAA-Tyr和AAA-Tyr体系)和284nm(ANG-Phe体系).其荧光猝灭值(ΔF)在一定范围内与ANG,MAA和AAA成正比.荧光猝灭反应具有较高灵敏度,对于ANG,MAA和AAA的检出限为13.3ng/mL(ANG-Trp体系)、15.8ng/mL(ANG-Tyr体系)、64.5ng/mL(ANG-Phe体系)、150.0ng/mL(MAA-Tyr体系)和230.8ng/mL(AAA-Tyr体系).实验研究了荧光猝灭反应的适宜条件和影响因素,考察了共存物质的影响,表明方法具有良好的选择性,可用于ANG片剂及其代谢物尿药浓度的快速测定.从吸收光谱的变化、温度的影响以及Stern-Volmer作图,判断该反应为静态猝灭反应,氨基酸和安乃近通过静电引力和芳基堆积作用而形成1:1的复合物.

关键词: 安乃近, 氨基酸, 4-甲氨基安替比林, 4-乙酰氨基安替比林, 荧光猝灭

In pH 3.2 Britton-Robinson(BR)buffer medium,analgin(ANG)and metabolin of 4-methylaminoantipyrine(MAA)and 4-acetylaminoantipyrine(AAA)can react with some aromatic amino acids such as tryptophane(Trp),tyrosine(Tyr)and phenylalanine(Phe)to form complexes,which lead to fluorescence quenching of above amino acids,and the maximum quenching wavelength is at 352 nm (ANG-Trp system),304 nm(ANG-Tyr,MAA-Tyr and AAA-Tyr system),284 nm(ANG-Phe system),respectively.Fluorescence quenching value(ΔF)is proportional to the concentration of ANG,MAA and AAA in a certain range.Fluorescence quenching methods for the determination of ANG,MAA and AAA have high sensitivity with the detection limits of 13.3 ng/mL(Trp-ANG system),15.8 ng/mL(Tyr-ANG system), 64.5 ng/mL(Phe-ANG system),150.0 ng/mL(MAA-Tyr system)and 230.8 ng/mL(AAA-Tyr system),re- spectively.The optimum conditions of the reaction,influencing factors and the effect of coexisting sub-stances are investigated,and the results show this method has a good selectivity.This method has been successfully applied to the quick determination of ANG in tablets and its metabolin in urine samples.Judging from the change of the absorption spectra,the effect of temperature and the Stern-Volmer plots,the quenching of fluorescence of amino acids by ANG is a static quenching process.Experimental results show that a 1:1 compound of ANG and amino acid is formed by electrostatic attraction and aromatic stacking interaction.

Key words: analgin, amino acids, 4-methylaminoantipyrine, 4-acetylaminoantipyrine, fluorescence quenching

引用此文

甘晓娟, 刘绍璞, 刘忠芳, 王亚琼, 崔志平, 胡小莉. 某些芳香族氨基酸作探针荧光猝灭法测定安乃近及其代谢产物[J]. 化学学报, 2012, 70(01): 58-64.

Gan Xiaojuan, Liu Shaopu, Liu Zhongfang, Wang Yaqiong, Cui Zhiping, Hu Xiaoli. Fluorescence Quenching Method for the Determination of Analgin and Metabolin with Some Aromatic Amino Acids as Probes[J]. Acta Chimica Sinica, 2012, 70(01): 58-64.

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参考文献

1 Zheng, H. Pharmaceutical Chemistry, Chinese Medicine and Technology Publishing House, 1st ed. , 2000, p. 36(in Chinese). (郑虎, 药物化学, 中国医药科技出版社(第一版), 2000, p. 36. )

2 Jiang, Z. -J. ; Shao, M. -L. ; Li, Z. -J. The People's Republic of China Pharmacopoeia(II), Chemical Industry Press, Bei- jing, 2005, p. 210(in Chinese). (蒋作君, 邵明立, 李振吉, 中华人民共和国药典(第二部), 化学工业出版社, 北京, 2005, p. 210. )

3 Perezruiz, T. ; Martinezlozano, C. ; Tomas, V. ; Carpena, J. Microchem. J. 1993, 47(3), 296.

4 Huang, H. -Q. ; Huang, Z. -Z. Chin. J. Spectrosc. Lab. 2002, 19(6), 777(in Chinese). (王慧琴, 黄振中, 光谱实验室, 2002, 19(6), 777. )

5 Sakiara, K. -A. ; Pezza, L. ; Melios, C. -B. ; Pezza, H. -R. ; De- Moraes, M. Farmaco 1999, 54, 629.

6 Dine, E. ; Onur, F. Sci. Pharm. 1999, 67, 57.

7 Ma, W. -X. Spectrosc. Spect. Anal. 1999, 19(3), 505(in Chinese). (马卫兴, 光谱学与光谱分析, 1999, 19(3), 505. )

8 Vlasova, I. -V. ; Shilova, A. -V. ; Fokina, Y. -S. Khim. -Farm. Zh. 2008, 42(10), 49.

9 Li, Y. -G. ; Yang, S. -K. Appl. Chem. Ind. 2009, 38(10), 1521(in Chinese). (李元岗, 杨胜科, 应用化工, 2009, 38(10), 1521. )

10 Zhang, H. -G. ; Zhu, X. -H. ; He, Y. -H. Chin. J. Anal. Lab. 2005, 24(1), 5(in Chinese). (张红鸽, 祝兴华, 何云华, 分析试验室, 2005, 24(1), 5. )

11 Zhao, L. -X. ; Li, B. -X. ; Zhang, Z. -J. ; Lin, J. -M. Sens. Ac- tuators, B 2004, 97, 266.

12 Yang, F. -Z. ; Zhang, C. ; Wang, J. -N. Spectrosc. Spect. Anal. 2004, 24(2), 145(in Chinese). (杨凤珍, 张超, 王建宁, 光谱学与光谱分析, 2004, 24(2), 145. )

13 Huang, Y. -M. ; Zhang, C. ; Zhang, X. -R. ; Zhang, Z. -J. Fresenius J. Anal. Chem. 1999, 365(4), 381.

14 Song, Z. -H. ; Zhang, N. Bioorg. Med. Chem. 2002, 10(7), 2091.

15 He, Y. -H. ; Lu, J. -R. ; Zhang, H. -G. ; Du, J. -X. Chem. J. Chin. Univ. 2005, 26(4), 642(in Chinese). (何云华, 吕九如, 张红鸽, 杜建修, 高等学校化学学报, 2005, 26(4), 642. )

16 Huang, Y. -M. ; Zhang, C. ; Zhang, X. -R. ; Zhang, Z. -J. J. Pharm. Biomed. Anal. 1999, 21(4), 817.

17 Buhl, F. ; Hachula, U. ; Chwistek, M. J. Chromatogr. , A 1981, 219(1), 189.

18 Shen, J. -C. ; Pang, G. -F. ; Xie, L. -Q. Chin. J. Anal. Chem.

2007, 35(11), 1565(in Chinese). (沈金灿, 庞国芳, 谢丽琪, 分析化学, 2007, 35(11), 1565. )

19 Penney, L. ; Bergeron, C. ; Coates, B. J. AOAC Int. 2005, 88, 496.

20 Ruiz, T. -P. ; Lozano, C. -M. ; Tomás, V. J. Pharm. Biomed. Anal. 1994, 12(9), 1109.

21 Chen, G. -Z. ; Huang, X. -Z. ; Zheng, B. -Z. ; Xu, J. -G. ; Wang, Z. -B. Fluorescence Analysis, 2nd ed. , Science Press, Beijing, 1990, p. 112(in Chinese). (陈国珍, 黄贤智, 郑本梓, 许金钩, 王尊本, 荧光分析法(第二版), 科学出版社, 北京, 1990, p. 112. )

22 Lakawicz, J. -R. Principles of Fluorescence Spectroscopy, 3rd ed. , Springer-Verlag, Berlin Heidelberg, 2006, p. 64.

23 Ni, Y. -N. ; Wang, S. -S. ; Kokot, S. Anal. Chim. Acta 2010, 663(2), 139.

24 Dlab, A. -M. Die Pharmazie 1977, 32(4), 226.

25 Asmard, G. ; Jamali, F. Eur. J. Drug Metab. Pharmacokinet. 1985, 10(2), 121.

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某些芳香族氨基酸作探针荧光猝灭法测定安乃近及其代谢产物

Fluorescence Quenching Method for the Determination of Analgin and Metabolin with Some Aromatic Amino Acids as Probes

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