阳离子型稳定同位素标记探针的制备及其在<i>α</i>-二羰基化合物分析中的应用

引用本文: 张世娟, 常芮, 王雪婷, 纪仲胤, 李言信, 尤进茂. 阳离子型稳定同位素标记探针的制备及其在α-二羰基化合物分析中的应用[J]. 分析化学, 2022, 50(8): 1269-1277. doi: 10.19756/j.issn.0253-3820.221172 shu

Citation: ZHANG Shi-Juan, CHANG Rui, WANG Xue-Ting, JI Zhong-Yin, LI Yan-Xin, YOU Jin-Mao. Preparation of Cationic Stable Isotope Labeling Probe and

Its Application in Analysis of α-Dicarbonyl Compounds[J]. Chinese Journal of Analytical Chemistry, 2022, 50(8): 1269-1277. doi: 10.19756/j.issn.0253-3820.221172 shu

阳离子型稳定同位素标记探针的制备及其在α-二羰基化合物分析中的应用

曲阜师范大学化学与化工学院, 曲阜 273165

通讯作者: 李言信,E-mail:liyanxin04@163.com

基金项目:
国家自然科学基金项目(Nos.31801624, 21976105)资助。

摘要: 合成了阳离子型稳定同位素标记探针4-三甲基胺基苯甲酰肼(HCTA)和氘代4-三甲基胺基苯甲酰肼(d₃-HCTA),将其用于α-二羰基化合物的质谱增敏标记和超高效液相色谱-串联质谱(UPLC-MS/MS)分析。阳离子型标记探针使得标记产物带有正电荷,提高了质谱分析灵敏度;稳定同位素标记的内标定量检测功能有效降低了基质效应,提升了方法的准确度。对α-二羰基化合物的标记反应条件和色谱、质谱参数进行了优化,方法检出限为4.1~9.2 ng/kg,回收率为90.1%~95.3%。将阳离子型稳定同位素标记探针用于食品中α-二羰基化合物的UPLC-MS/MS分析,结果令人满意。

关键词:

English

Preparation of Cationic Stable Isotope Labeling Probe and
Its Application in Analysis of α-Dicarbonyl Compounds

School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, China

Corresponding author: LI Yan-Xin, liyanxin04@163.com

Received Date: 08 April 2022
Revised Date: 17 May 2022
Fund Project:
Supported by the National Natural Science Foundation of China (Nos.31801624, 21976105).

Abstract: A pair of cationic stable isotope labelling (SIL) probes, 4-trimethylaminobenzoyl hydrazide (HCTA) and its deuterated counterpart d₃-HCTA, were designed and synthesized for labeling and ultra-high performance liquid chromatography-tandem triple quadrupole mass spectrometry (UPLC-MS/MS) analysis of α-dicarbonyl compounds. The labeled products were positively charged and thus the MS sensitivity was enhanced; the internal standard quantitative function of stable isotope labelling strategy effectively reduced the matrix effect and improved the method accuracy. The labeling conditions, chromatography and mass spectrometry parameters were optimized. The detection limits and recoveries of the method were 4.1-9.2 ng/L and 90.1%-95.3%, respectively. The cationic SIL probe was applied to the UPLC-MS/MS analysis of α-dicarbonyl compounds in food with satisfactory results.

Key words:

1. [1]
  ZHUANG Y, DONG L, WANG J P, WANG S J, WANG S. J. Sci. Food Agric., 2020, 100(5):2296-2304.ZHUANG Y, DONG L, WANG J P, WANG S J, WANG S. J. Sci. Food Agric., 2020, 100(5):2296-2304.
2. [2]
  WANG M, LIU Y, GUO B, ZHANG F, CHOU F, MA M, HUANG L, LUO Z, CHEN B, CHEN X. J. Agric. Food Chem., 2021, 69(35):10379-10393.WANG M, LIU Y, GUO B, ZHANG F, CHOU F, MA M, HUANG L, LUO Z, CHEN B, CHEN X. J. Agric. Food Chem., 2021, 69(35):10379-10393.
3. [3]
  ZHAO D, LE T T, LARSEN L B, LI L, QIN D, SU G, LI B. Food Res. Int., 2017, 102:313-322.ZHAO D, LE T T, LARSEN L B, LI L, QIN D, SU G, LI B. Food Res. Int., 2017, 102:313-322.
4. [4]
  KWON J, AHN H, LEE K G. Food Chem., 2021, 343:128525.KWON J, AHN H, LEE K G. Food Chem., 2021, 343:128525.
5. [5]
  YANG Yang, LIU Shao-Jing, JIAO Shu-Ling, ZENG Bao-Ping, WU Zhuo, QUAN Ke-Jia, HE Xiao-Wen. Chem. Bioeng., 2020, 37(10):1-6, 53.杨阳,刘少静,焦淑玲,曾宝平,毋卓,权科佳,何孝文.化学与生物工程, 2020, 37(10):1-6, 53.
6. [6]
  WANG X J, GAO F, LI L C, HUI X, LI H, GAO W Y. Microchem. J., 2018, 141:64-70.WANG X J, GAO F, LI L C, HUI X, LI H, GAO W Y. Microchem. J., 2018, 141:64-70.
7. [7]
  FENG Yan-Li, MU Cui-Cui, FU Zheng-Ru, CHEN Ying-Jun. Chin. J. Anal. Chem., 2011, 39(11):1653-1658.冯艳丽,牟翠翠,付正茹,陈颖军.分析化学, 2011, 39(11):1653-1658.
8. [8]
  KISHIKAWA N, EL-MAGHRABEY M H, KURODA N. J. Pharmaceut. Biomed., 2019, 175:112782.KISHIKAWA N, EL-MAGHRABEY M H, KURODA N. J. Pharmaceut. Biomed., 2019, 175:112782.
9. [9]
  HURTADO-SANCHEZ M D, ESPINOSA-MANSILLA A, DURAN-MERAS I. J. Chromatogr. A, 2015, 1422:117-127.HURTADO-SANCHEZ M D, ESPINOSA-MANSILLA A, DURAN-MERAS I. J. Chromatogr. A, 2015, 1422:117-127.
10. [10]
  KOCADAGLI T, GOKMEN V. J. Agric. Food Chem., 2014, 62(31):7714-7720.KOCADAGLI T, GOKMEN V. J. Agric. Food Chem., 2014, 62(31):7714-7720.
11. [11]
  MA C, ZHANG S, WU X, YOU J. J. Agric. Food Chem., 2020, 68(33):9024-9031.MA C, ZHANG S, WU X, YOU J. J. Agric. Food Chem., 2020, 68(33):9024-9031.
12. [12]
  LIU Shuan, FENG Meng-Yu, LI Xiao-Min, TANG Guang-Shi, ZHANG Qing-He, LI Xiu-Qin. Chin. J. Anal. Chem., 2021, 49(4):546-557.刘栓,冯梦雨,李晓敏,唐光诗,张庆合,李秀琴.分析化学, 2021, 49(4):546-557.
13. [13]
  LIN M, WANG Z, WANG D, CHEN X, ZHANG J L. Anal. Chem., 2019, 91(7):4504-4512.LIN M, WANG Z, WANG D, CHEN X, ZHANG J L. Anal. Chem., 2019, 91(7):4504-4512.
14. [14]
  ZHENG S J, WANG Y L, LIU P, ZHANG Z, YU L, YUAN B F, FENG Y Q. Food Chem., 2017, 237:399-407.ZHENG S J, WANG Y L, LIU P, ZHANG Z, YU L, YUAN B F, FENG Y Q. Food Chem., 2017, 237:399-407.
15. [15]
  HE Jun-Lu, LUO Yan-Bo, CHEN Huan, HOU Hong-Wei, HU Qing-Yuan. Chin. J. Anal. Chem., 2017, 45(7):1066-1077.何昀潞,罗彦波,陈欢,侯宏卫,胡清源.分析化学, 2017, 45(7):1066-1077.
16. [16]
  CHANG R, MA C, YU C, ZHANG Q, LI Y, YOU J, ZHANG S. Eur. Food Res. Technol., 2021, 247(11):2729-2738.CHANG R, MA C, YU C, ZHANG Q, LI Y, YOU J, ZHANG S. Eur. Food Res. Technol., 2021, 247(11):2729-2738.
17. [17]
  YU Y, YOU J, SUN Z, LI G, JI Z, ZHANG S, ZHOU X. Anal. Chim. Acta, 2019, 1055:44-55.YU Y, YOU J, SUN Z, LI G, JI Z, ZHANG S, ZHOU X. Anal. Chim. Acta, 2019, 1055:44-55.
18. [18]
  TIE C, HU T, JIA Z X, ZHANG J L. Anal. Chem., 2015, 87(16):8181-8185.TIE C, HU T, JIA Z X, ZHANG J L. Anal. Chem., 2015, 87(16):8181-8185.
19. [19]
  GUO N, PENG C Y, ZHU Q F, YUAN B F, FENG Y Q. Anal. Chim. Acta, 2019, 967:42-51.GUO N, PENG C Y, ZHU Q F, YUAN B F, FENG Y Q. Anal. Chim. Acta, 2019, 967:42-51.
20. [20]
  GAO S, ZHANG Z P, KARNES H T. J. Chromatogr. B, 2005, 825(2):98-110.GAO S, ZHANG Z P, KARNES H T. J. Chromatogr. B, 2005, 825(2):98-110.
21. [21]
  IWASAKI Y, NAKANO Y, MOCHIZUKI K, NOMOTO M, TAKAHASHI Y, ITO R, SAITO K, NAKAZAWA H. J. Chromatogr. B, 2011, 879(17-18):1159-1165.IWASAKI Y, NAKANO Y, MOCHIZUKI K, NOMOTO M, TAKAHASHI Y, ITO R, SAITO K, NAKAZAWA H. J. Chromatogr. B, 2011, 879(17-18):1159-1165.
22. [22]
  XIAO L, LI C, CHAI D, CHEN Y, WANG Z, XU X, WANG Y, GENG Y, DONG L. Food Sci. Nutr. 2020, 8(2):1139-1149.XIAO L, LI C, CHAI D, CHEN Y, WANG Z, XU X, WANG Y, GENG Y, DONG L. Food Sci. Nutr. 2020, 8(2):1139-1149.
23. [23]
  CAO J, JIANG X, CHEN Q, ZHANG H, SUN H, ZHANG W, LI C. LWT-Food Sci. Technol., 2020, 118:108858.CAO J, JIANG X, CHEN Q, ZHANG H, SUN H, ZHANG W, LI C. LWT-Food Sci. Technol., 2020, 118:108858.

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沈阳化工大学材料科学与工程学院沈阳 110142

阳离子型稳定同位素标记探针的制备及其在α-二羰基化合物分析中的应用

通讯作者: 李言信,E-mail:liyanxin04@163.com

English

Preparation of Cationic Stable Isotope Labeling Probe and
Its Application in Analysis of α-Dicarbonyl Compounds

Corresponding author: LI Yan-Xin, liyanxin04@163.com

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

阳离子型稳定同位素标记探针的制备及其在α-二羰基化合物分析中的应用

通讯作者: 李言信,E-mail:liyanxin04@163.com

English

Preparation of Cationic Stable Isotope Labeling Probe and Its Application in Analysis of α-Dicarbonyl Compounds

Corresponding author: LI Yan-Xin, liyanxin04@163.com

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

Preparation of Cationic Stable Isotope Labeling Probe and
Its Application in Analysis of α-Dicarbonyl Compounds

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs