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

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: 8 April 2022
Revised Date: 17 May 2022

Fund Project: Supported by the National Natural Science Foundation of China (Nos.31801624, 21976105).

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.
1. [1]
  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.
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.
4. [4]
  KWON J, AHN H, LEE K G. Food Chem., 2021, 343:128525.
5. [5]
6. [6]
  WANG X J, GAO F, LI L C, HUI X, LI H, GAO W Y. Microchem. J., 2018, 141:64-70.
7. [7]
8. [8]
  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.
10. [10]
  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.
12. [12]
13. [13]
  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.
15. [15]
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.
17. [17]
  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.
19. [19]
  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.
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.
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.
23. [23]
  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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