Please use this identifier to cite or link to this item:
http://hdl.handle.net/10397/92369
Title: | Self-assembled binuclear Cu(II)−histidine complex for absolute configuration and enantiomeric excess determination of naproxen by tandem mass spectrometry | Authors: | Yu, X Chau, MC Tang, WK Siu, CK Yao, ZP |
Issue Date: | 20-Mar-2018 | Source: | Analytical chemistry, 20 Mar. 2018, v. 90, no. 6, p. 4089-4097 | Abstract: | Naproxen is one of the most consumed nonsteroidal anti-inflammatory drugs and marketed as S-naproxen since R-naproxen is hepatotoxic. In this study, chiral recognition of naproxen has been investigated by tandem mass spectrometry (MS/MS). Among all diastereomeric complexes formed between naproxen and the examined chiral selectors, including cyclodextrins (α/β/γ-CD), modified phenylalanines (N-acetyl-phenylalanine, N-t-butoxycarbonyl-phenylalanine, N-9-fluorenylmethyloxycarbonyl-phenylalanine), amino acids (Trp, Phe, Tyr, His), glucose, tartaric acid, and vancomycin, a novel binuclear metal bound diastereomeric complexes [(M(II))2(S/R-naproxen)(l-His)2-3H]+ (M = Cu, Ni, or Co with Cu being the best) could allow effective identification of the absolute configuration of naproxen and determination of its enantiomeric excess (ee) through MS/MS analysis. The key candidate structure of [(Cu(II))2(S/R-naproxen)(l-His)2-3H]+ has been revealed by means of collision-induced dissociation, ion mobility mass spectrometry and density functional theory calculations, indicating an interesting and unusual self-assembled compact geometry with the two Cu(II) ions bridged closely together (Cu-Cu distance is 3.04 Å) by the carboxylate groups of the two histidines. It was shown that the difference in dissociation efficiency between the two diastereomers was attributed to the interaction between the NH2 bond of the amino group of one histidine and the naphthyl ring of naproxen. The present report is the first to observe and characterize the complex of (Cu(II))2(His)2 with aromatic acid, which could contribute to the chiral recognition of other chiral aromatic acids, design of catalysts based on binuclear copper bound complex, as well as the better understanding of metal ion complexation by His or His-containing ligands. | Publisher: | American Chemical Society | Journal: | Analytical chemistry | ISSN: | 0003-2700 | EISSN: | 1520-6882 | DOI: | 10.1021/acs.analchem.7b05407 | Rights: | © 2018 American Chemical Society This document is the Accepted Manuscript version of a Published Work that appeared in final form in Analytical Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.analchem.7b05407 |
Appears in Collections: | Journal/Magazine Article |
Files in This Item:
File | Description | Size | Format | |
---|---|---|---|---|
Yu_Self-Assembled_Binuclear_Complex.pdf | Pre-Published version | 914.04 kB | Adobe PDF | View/Open |
Page views
69
Last Week
0
0
Last month
Citations as of Apr 28, 2024
Downloads
104
Citations as of Apr 28, 2024
SCOPUSTM
Citations
16
Citations as of May 3, 2024
WEB OF SCIENCETM
Citations
16
Citations as of May 2, 2024
Google ScholarTM
Check
Altmetric
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.