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Dissociation reactions of protonated anthracycline antibiotics following electrospray ionization-tandem mass spectrometry

DOITrouver le DOI : https://doi.org/10.1016/j.ijms.2006.02.003
AuteurRechercher : 1; Rechercher : ; Rechercher : 1
Affiliation
  1. Conseil national de recherches Canada. Institut des biosciences marines du CNRC
FormatTexte, Article
Sujetanthracycline antibiotic; doxorubicin; fragmentation mechanism; tandem mass spectrometry; computational chemistry
Résumé
Fragmentation pathways of doxorubicin, a common cancer therapy agent, and three closely related analogs (epirubicin, daunorubicin, idarubicin) were compared using electrospray ionization with tandem mass spectrometry. This class of antibiotics with anti-tumour activity has important structural features, with a tetracyclic aromatic, polyketide portion, which is glycosylated with an amino sugar in order to exhibit its biological activity. Collision-induced dissociation spectra revealed very similar product ions for each analog, however, important differences were seen in the relative abundances and the ease at which certain fragments were formed. Fragment ions observed included those from cleavage of the glycosidic bond, loss of the side chain from the aglycone moiety, water losses and loss of a methyl radical. Following cleavage of the glycosidic bond, the charge can either reside on the aglycone portion or the sugar moiety, and each of these primary fragments undergoes several secondary dissociation pathways, depending on the collision energy. By ramping the collision voltage, we were able to correlate the changes in fragmentation behavior with small alterations in the structure of the precursor ion. The detailed study of the fragmentation behavior of doxorubicin was supported by accurate mass measurements, using an electrospray-time of flight instrument, as well as MS3 data from a quadrupole-linear ion trap mass spectrometer. Computational studies were also performed to help explain the role of certain functional groups in the fragmentation reactions.
Date de publication
Conditions d’utilisation
  • Copyright © 2006 Elsevier B.V. All rights reserved.
Dans
  • International Journal of Mass Spectrometry 255-256 (7 mars 2006) : 130–138.
Langueanglais
Publications évaluées par des pairsOui
Numéro du CNRCNRCC 55860
1620
Numéro NPARC3538323
Exporter la noticeExporter en format RIS
Signaler une correctionSignaler une correction (s'ouvre dans un nouvel onglet)
Identificateur de l’enregistrementedcbf3a9-ca46-4ac8-a401-fc3e56502510
Enregistrement créé2009-03-01
Enregistrement modifié2020-04-22

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