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

Leopoldo Ceraulo, David Bongiorno, David Bongiorno, Vincenzo Turco Liveri, Leopoldo Ceraulo, Walter Panzeri, Antonio Selva, Andrea Mele

Risultato della ricerca: Article

17 Citazioni (Scopus)

Abstract

Ionspray (IS) and fast atom bombardment (FAB) positive ionization mass spectrometry (MS) of 1:1 β-cyclodextrin (β-CD)-melatonin (MLT) host-guest complex allowed the detection of gaseous protonated 1:1 β-CD-MLT. Tandem MS collision-induced dissociation (CID) of such protonated 1:1 β-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 β-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 β-CD-5-methoxytryptamine inclusion complex with the protonated 5-methoxytryptamine guest undergoing deamination. Copyright © 2001 John Wiley & Sons, Ltd.
Lingua originaleEnglish
pagine (da-a)1189-1194
Numero di pagine6
RivistaJournal of Mass Spectrometry
Volume36
Stato di pubblicazionePublished - 2001

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Proton transfer
Melatonin
Mass spectrometry
Atoms
5-Methoxytryptamine
Protons
Cyclodextrins
Ionization
Chemical activation
caloreen
Association reactions

All Science Journal Classification (ASJC) codes

  • Spectroscopy

Cita questo

Guest‐to‐host proton transfer in melatonin–β‐cyclodextrin inclusion complex by ionspray, fast atom bombardment and tandem mass spectrometry. / Ceraulo, Leopoldo; Bongiorno, David; Bongiorno, David; Liveri, Vincenzo Turco; Ceraulo, Leopoldo; Panzeri, Walter; Selva, Antonio; Mele, Andrea.

In: Journal of Mass Spectrometry, Vol. 36, 2001, pag. 1189-1194.

Risultato della ricerca: Article

Ceraulo, Leopoldo ; Bongiorno, David ; Bongiorno, David ; Liveri, Vincenzo Turco ; Ceraulo, Leopoldo ; Panzeri, Walter ; Selva, Antonio ; Mele, Andrea. / Guest‐to‐host proton transfer in melatonin–β‐cyclodextrin inclusion complex by ionspray, fast atom bombardment and tandem mass spectrometry. In: Journal of Mass Spectrometry. 2001 ; Vol. 36. pagg. 1189-1194.
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title = "Guest‐to‐host proton transfer in melatonin–β‐cyclodextrin inclusion complex by ionspray, fast atom bombardment and tandem mass spectrometry",
abstract = "Ionspray (IS) and fast atom bombardment (FAB) positive ionization mass spectrometry (MS) of 1:1 {\^I}²-cyclodextrin ({\^I}²-CD)-melatonin (MLT) host-guest complex allowed the detection of gaseous protonated 1:1 {\^I}²-CD-MLT. Tandem MS collision-induced dissociation (CID) of such protonated 1:1 {\^I}²-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 {\^I}²-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 {\^I}²-CD-5-methoxytryptamine inclusion complex with the protonated 5-methoxytryptamine guest undergoing deamination. Copyright {\^A}{\circledC} 2001 John Wiley & Sons, Ltd.",
author = "Leopoldo Ceraulo and David Bongiorno and David Bongiorno and Liveri, {Vincenzo Turco} and Leopoldo Ceraulo and Walter Panzeri and Antonio Selva and Andrea Mele",
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T1 - Guest‐to‐host proton transfer in melatonin–β‐cyclodextrin inclusion complex by ionspray, fast atom bombardment and tandem mass spectrometry

AU - Ceraulo, Leopoldo

AU - Bongiorno, David

AU - Bongiorno, David

AU - Liveri, Vincenzo Turco

AU - Ceraulo, Leopoldo

AU - Panzeri, Walter

AU - Selva, Antonio

AU - Mele, Andrea

PY - 2001

Y1 - 2001

N2 - Ionspray (IS) and fast atom bombardment (FAB) positive ionization mass spectrometry (MS) of 1:1 β-cyclodextrin (β-CD)-melatonin (MLT) host-guest complex allowed the detection of gaseous protonated 1:1 β-CD-MLT. Tandem MS collision-induced dissociation (CID) of such protonated 1:1 β-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 β-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 β-CD-5-methoxytryptamine inclusion complex with the protonated 5-methoxytryptamine guest undergoing deamination. Copyright © 2001 John Wiley & Sons, Ltd.

AB - Ionspray (IS) and fast atom bombardment (FAB) positive ionization mass spectrometry (MS) of 1:1 β-cyclodextrin (β-CD)-melatonin (MLT) host-guest complex allowed the detection of gaseous protonated 1:1 β-CD-MLT. Tandem MS collision-induced dissociation (CID) of such protonated 1:1 β-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 β-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 β-CD-5-methoxytryptamine inclusion complex with the protonated 5-methoxytryptamine guest undergoing deamination. Copyright © 2001 John Wiley & Sons, Ltd.

UR - http://hdl.handle.net/10447/243606

M3 - Article

VL - 36

SP - 1189

EP - 1194

JO - Journal of Mass Spectrometry

JF - Journal of Mass Spectrometry

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