Quantifying Non‐Covalent Binding Interactions between Tobacco Alkaloids and Cyclodextrin Using Mass Spectrometry and the Application in Cigarette Smoke. Issue 22 (9th June 2020)

• Record Type: Journal Article
• Authors: Wu, Fangling; Yao, Rujiao; Yu, Shaoning; Tang, Keqi; Xiao, Yu; Ding, Chuan‐Fan
• Is Part Of: ChemistrySelect. Volume 5:Issue 22(2020)
• Page Start: 6658
• Page End: 6665
• Publication Date: 2020-06-09
• Subjects: Cyclodextrin -- Cigarette smoke -- Electrospray ionization mass spectrometry -- Host-guest complexes -- Tobacco alkaloids; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202000369
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: 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 KR ) 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. Abstract : Non‐covalent interactions between cyclodextrin (CD) and tobacco alkaloids (TAs), including 1‐(4‐Nitrophenyl) piperazine (NHK), nicotinamide (NAm), nornicotine (NCt), DL‐Anabasine (DL‐ABs), and nicotinic acid (NTa) were studied via ESI‐MS. The results demonstrated that β‐CD can effectively complex with some small molecules in the cigarette smoke and remove them during cigarette smoking.