Letter:: Fast atom bombardment, electrospray, ionspray and tandem mass spectrometry of 1 : 1 β-cyclodextrin/5-methoxytryptamine hydrochloride host-guest complex:: host protonation and fragmentation due to guest deamination

被引:11
作者
Mele, A
Panzeri, W
Selva, A
Mauri, P
机构
[1] CNR, Ctr Studio Sostanze Organ Nat, Dipartimento Chim, Politecn Milan, I-20131 Milan, Italy
[2] CNR, Ist Tecnol Biomed Avanzate, I-20090 Segrate, Italy
关键词
beta-cyclodextrin; host-guest complexes; 5-methoxytryptamine; FAB; electrospray/ionspray; tandem mass spectrometry;
D O I
10.1255/ejms.319
中图分类号
O64 [物理化学(理论化学)、化学物理学]; O56 [分子物理学、原子物理学];
学科分类号
070203 ; 070304 ; 081704 ; 1406 ;
摘要
The 1 : 1 inclusion complex of beta -cyclodextrin (beta CD) with 5-methoxytryptamine (5MTA) hydrochloride was studied by mass spectrometry (MS) and tandem-MS with fast atom bombardment (FAB), electrospray (ES) and ionspray (IS) ionisation and triple quadrupole or ion trap analysers. A protonated 1 : 1 beta CD/MTA gaseous association was always observed; the protonated species of deaminated 5MTA and of some typical beta CD fragments were obtained, in addition to the expected protonated 5MTA, as tandem-MS dissociation products. A reaction pattern starting from the deamination of protonated 5MTA, as a recently described high pressure chemical ionisation or ES process of primary amines, was suggested, which accounts for the formation of excited protonated beta CD and its fragmentation by tandem-MS, even under unimolecular conditions.
引用
收藏
页码:169 / 174
页数:6
相关论文
共 29 条
[1]  
BALZANI V, 1991, SUPRAMOLECULAR CHEM
[2]   ANALYZING THE COMPLEXATION OF AMINO-ACIDS AND PEPTIDES WITH BETA-CYCLODEXTRIN USING ELECTROSPRAY-IONIZATION MASS-SPECTROMETRY [J].
CAMILLERI, P ;
HASKINS, NJ ;
NEW, AP ;
SAUNDERS, MR .
RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 1993, 7 (10) :949-952
[3]   Study of the inclusion complexes of aromatic molecules with cyclodextrins using ionspray mass spectrometry [J].
Cescutti, P ;
Garozzo, D ;
Rizzo, R .
CARBOHYDRATE RESEARCH, 1996, 290 (02) :105-115
[4]   FALSE POSITIVES AND THE DETECTION OF CYCLODEXTRIN INCLUSION COMPLEXES BY ELECTROSPRAY MASS-SPECTROMETRY [J].
CUNNIFF, JB ;
VOUROS, P .
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 1995, 6 (05) :437-447
[5]  
Fromming KH., 1994, CYCLODEXTRINS PHARM
[6]   Cyclodextrin-piroxicam inclusion complexes: analyses by mass spectrometry and molecular modelling [J].
Gallagher, RT ;
Ball, CP ;
Gatehouse, DR ;
Gates, PJ ;
Lobell, M ;
Derrick, PJ .
INTERNATIONAL JOURNAL OF MASS SPECTROMETRY, 1997, 165 :523-531
[7]   THE COMPLEXATION AND CHIRAL SELECTIVITY OF 2-HYDROXYPROPYL-BETA-CYCLODEXTRIN WITH GUEST MOLECULES AS STUDIED BY ELECTROSPRAY MASS-SPECTROMETRY [J].
HASKINS, NJ ;
SAUNDERS, MR ;
CAMILLERI, P .
RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 1994, 8 (05) :423-426
[8]   SUPRAMOLECULAR CHEMISTRY - SCOPE AND PERSPECTIVES MOLECULES, SUPERMOLECULES, AND MOLECULAR DEVICES [J].
LEHN, JM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1988, 27 (01) :89-112
[9]   Pharmaceutical applications of cyclodextrins .1. Drug solubilization and stabilization [J].
Loftsson, T ;
Brewster, ME .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1996, 85 (10) :1017-1025
[10]   DETECTION OF 1/1 ADDUCTS OF PIROXICAM WITH BETA-CYCLODEXTRIN OR WITH MALTOHEXAOSE BY FAST-ATOM-BOMBARDMENT MASS-SPECTROMETRY [J].
MELE, A ;
SELVA, A .
JOURNAL OF MASS SPECTROMETRY, 1995, 30 (04) :645-647