Citation: GU Lian-Cheng, ZHOU Ai-Nan, CHEN Xin, WU Fang-Ling, LI Jian-Qi, YU Shao-Ning, ZHOU Ming-Fei, DING Chuan-Fan. Chiral Analysis of Ibuprofen through Non-covalent Complexes[J]. Chinese Journal of Analytical Chemistry, ;2021, 49(1): 95-102. doi: 10.19756/j.issn.0253-3820.201477 shu

Chiral Analysis of Ibuprofen through Non-covalent Complexes

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Department of Chemistry, Fudan University, Shanghai 200433, China;
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Shanghai Institute of Pharmaceutical Industry, Shanghai 200240, China;
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School of Material Science and Chemical Engineering, Institute of Mass Spectrometry, Ningbo University, Ningbo 315211, China

Corresponding author: LI Jian-Qi, DING Chuan-Fan,
Received Date: 7 August 2020
Revised Date: 13 November 2020

Fund Project: Supported by the National Natural Science Foundation of China (Nos.21773035, 21803013).

The recognition and discrimination of chirality is of great significance for further understanding the pharmaceutical mechanism of chiral drugs. Ibuprofen is a well-popular clinically used anti-inflammatory drug in the world. However, in R-ibuprofen and S-ibuprofen enantiomers, only S-ibuprofen is responsible for the anti-inflammatory effects. In this work, a novel discrimination method for chiral ibuprofen was investigated. A stoichiometric R- and S-Ibuprofen were mixed with γ-cyclodextrin and barium chloride to obtain the noncovalent complexes in methanol aqueous solution, and the ion mobility of the complexes was measured by trapped ion mobility spectrometry-time-of-flight mass spectrometry (TIMS-TOF-MS). The formed diastereomeric ions of[γ-CD+R-ibuprofen+Ba(BaCl)-H]²⁺ and[γ-CD+S-ibuprofen+Ba(BaCl)-H]²⁺ were successfully separated in ion mobility spectra and the collision cross section difference (ΔCCS) reached 0.07 nm².Additionally, the experimental data indicated that the fractions of mobility peak intensities for[γ-CD+S-ibuprofen+Ba(BaCl)-H]²⁺ and their molar fractions exhibited a great linear relationship. Due to that no complicate pre-treatment or chemical derivation was needed, this method could discriminate chiral molecules rapidly and efficiently.
- Ibuprofen,
- γ-Cyclodextrins,
- Barium chloride,
- Non-covalent complex,
- Chiral analysis,
- Trapped ion mobility spectrometry-time-of-flight mass spectrometry
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