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Quantifying Non‐Covalent Binding Interactions between Tobacco Alkaloids and Cyclodextrin Using Mass Spectrometry and the Application in Cigarette Smoke
Author(s) -
Wu Fangling,
Yao Rujiao,
Yu Shaoning,
Tang Keqi,
Xiao Yu,
Ding ChuanFan
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202000369
Subject(s) - chemistry , electrospray ionization , dissociation constant , cyclodextrin , binding constant , mass spectrometry , nornicotine , tandem mass spectrometry , titration , electrospray , ion mobility spectrometry , stereochemistry , binding site , chromatography , organic chemistry , alkaloid , biochemistry , receptor
The host‐guest inclusion complexes between cyclodextrin (CD) and five tobacco alkaloids (TAs), namely 1‐(4‐Nitrophenyl) piperazine (NHK), nicotinamide (NAm), nornicotine (NCt), DL‐Anabasine (DL‐ABs), and nicotinic acid (NTa), were explored via electrospray ionization mass spectrometry (ESI‐MS). The MS results of these CD complexes confirmed the 1 : 1 stoichiometry of the host‐guest assemblies formed. The binding constants of the complexes were studied to quantify the interactions between TAs and CDs. The binding constants (lg K R ) of [CD‐NHK+H] + were first obtained via ESI‐MS titration as a reference; the values obtained were 4.26, 4.11, and 4.03 for [α‐, β‐, and γ‐CD+NHK+H] + , respectively. The binding constants for other CD complexes were then acquired via competitive ESI‐MS based on the reference binding constants. The gas‐phase binding affinity of the CD complexes was probed by collision‐induced dissociation, which indicated the same variation trend as their binding constants, i. e. bigger binding constant results in better kinetic stability of the complex. Finally, considering the non‐toxicity and cost‐effectiveness of β‐CD, it was applied to practical samples of mainstream cigarette smoke (MSS) and the aforementioned special m/z values were identified as the [β‐CD+TA+H] + complexes using tandem mass spectrometry. Our results reveal that β‐CD could effectively extract TAs and some other ingredients from the MSS during smoking. Therefore, applying CDs such as β‐CD in hookah or even in cigarette filter tips might be a potentially promising strategy to extract some harmful components of MSS to reduce the harm caused to the smoker.