Guest-to-host proton transfer in melatonin-β-cyclodextrin inclusion complex by ionspray, fast atom bombardment and tandem mass spectrometry

被引:15
作者
Bongiorno, D
Ceraulo, L
Mele, A
Panzeri, W
Selva, A
Liveri, VT
机构
[1] Politecn Milan, CNR, Dipartimento Chim, Ctr Studio Sostanze Organ Nat, I-20131 Milan, Italy
[2] CNR, Dipartimento Chim & Tecnol Farmaceut, I-90123 Palermo, Italy
[3] Dipartimento Chim Fis, I-90128 Palermo, Italy
来源
JOURNAL OF MASS SPECTROMETRY | 2001年 / 36卷 / 11期
关键词
beta-cyclodextrin host-guest complexes; melatonin; fast atom bombardment; electrospray; ionspray; tandem mass speetrometry; endothermic guest-to-host proton transfer;
D O I
10.1002/jms.226
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Ionspray (IS) and fast atom bombardment (FAB) positive ionisation mass spectrometry (MS) of 1:1 beta -cyclodextrin (beta -CD)-melatonin (MLT) host-guest complex allowed the detection of gaseous protonated 1:1 beta -CD-MLT. Tandem MS collision-induced dissociation (CID} of such protonated 1:1 beta -CD-MLT species showed the proton (charge} to be retained to a significant extent by the host and by its cage fragmentation products, in spite of the higher proton affinity of MLT with respect to that of beta -CD. This requires an endothermic guest-to-host proton transfer to occur within the gaseous association. Collisional activation could be accounted for by the promotion of such an endothermic process; however, the proton affinity decrease of the guest determined by the loss of the elements of acetamide, which is a dominant MS dissociation reaction of pure protonated MLT, could also provide a rationale for such an endothermic guest-to-host proton transfer. This proposal parallels the reaction scheme we had previously formulated for the analogous MS and tandem MS behaviour of 1:1 beta -CD-5-methoxytryptamine inclusion complex with the protonated 5-methoxytryptamine guest undergoing deamination. Copyright (C) 2001 John Wiley & Sons, Ltd.
引用
收藏
页码:1189 / 1194
页数:6
相关论文
共 29 条
[1]  
Fromming KH., 1994, CYCLODEXTRINS PHARM
[2]   H-1 NMR and molecular modeling study on the inclusion complex beta-cyclodextrin indomethacin [J].
Fronza, G ;
Mele, A ;
Redenti, E ;
Ventura, P .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03) :909-914
[3]  
HATTORI A, 1995, BIOCHEM MOL BIOL INT, V35, P627
[4]   Evidence for an intermolecular proton-transfer reaction induced by collision in gas-phase noncovalently bound complexes [J].
He, F ;
Ramirez, J ;
Lebrilla, CB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (19) :4726-4727
[5]   Gas-phase basicity of simple amides toward proton and lithium cation: an experimental and theoretical study [J].
Herreros, M ;
Gal, JF ;
Maria, PC ;
Decouzon, M .
EUROPEAN MASS SPECTROMETRY, 1999, 5 (04) :259-265
[6]   ENANTIOSELECTIVE BINDING OF TRYPTOPHAN BY ALPHA-CYCLODEXTRIN [J].
LIPKOWITZ, KB ;
RAGHOTHAMA, S ;
YANG, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1554-1562
[7]  
Manchester LC, 1995, CELL MOL BIOL RES, V41, P391
[8]   Fast-atom bombardment mass spectrometric and tandem mass spectrometric study of (-)-menthol-β-(D)-glucopyranoside, neohesperidin dihydrochalcone and their non-covalent association with β-cyclodextrin.: Two examples of interaction of a carbohydrate host with glycoconjugate guests [J].
Mele, A ;
Panzeri, W ;
Selva, A .
EUROPEAN MASS SPECTROMETRY, 1997, 3 (05) :347-354
[9]   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 [J].
Mele, A ;
Panzeri, W ;
Selva, A ;
Mauri, P .
EUROPEAN JOURNAL OF MASS SPECTROMETRY, 2000, 6 (02) :169-174
[10]   Non-covalent associations of cyclomaltooligosaccharides (cyclodextrins) with trans-β-carotene in water:: evidence for the formation of large aggregates by light scattering and NMR spectroscopy [J].
Mele, A ;
Mendichi, R ;
Selva, A .
CARBOHYDRATE RESEARCH, 1998, 310 (04) :261-267