Comparative analysis of the gas-phase reactions of cylindrospermopsin and the difference in the alkali metal cation mobility

Cylindrospermopsin (CYN) belongs to a group of toxins produced by several strains of freshwater cyanobacteria. It is a compact zwitterionic molecule composed of a uracil section and a tricyclic guanidinium portion with a primarily hepatotoxic effect. Using low multi‐stage and high‐resolution mass sp...

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Bibliographic Details
Published in:Rapid communications in mass spectrometry 2008-07, Vol.22 (13), p.2015-2020
Main Authors: Dörr, Felipe Augusto, Tomaz, José Carlos, Lopes, Norberto Peporine, Pinto, Ernani
Format: Article
Language:English
Subjects:
Alkalies - chemistry
Bacterial Toxins
Cations
Cyanobacteria - isolation & purification
Cyanobacteria - metabolism
Gases - chemistry
Metals - chemistry
Phase Transition
Spectrometry, Mass, Electrospray Ionization - methods
Uracil - analogs & derivatives
Uracil - analysis
Uracil - chemistry
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Summary:Cylindrospermopsin (CYN) belongs to a group of toxins produced by several strains of freshwater cyanobacteria. It is a compact zwitterionic molecule composed of a uracil section and a tricyclic guanidinium portion with a primarily hepatotoxic effect. Using low multi‐stage and high‐resolution mass spectrometry, the gas‐phase reactions of this toxin have been investigated. Our data show that collision‐induced dissociation (CID) spectra of CYN are dominated by neutral losses, and three major initial fragmentation pathways are clearly distinguishable. Interestingly, comparative analysis of protonated and cationizated molecules showed a significant difference in the balance of the SO3 and terminal ring elimination. These data indicate that the differential ion mobility of H+, Li+, Na+ and K+ leads to different fragmentation pathways, giving rise to mass spectra with different profiles. Copyright © 2008 John Wiley & Sons, Ltd.
ISSN:0951-4198
1097-0231
DOI:10.1002/rcm.3567