Get access

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

Authors

  • Felipe Augusto Dörr,

    1. Universidade de São Paulo, Faculdade de Ciências Farmacêuticas, Departamento de Análises Clínicas e Toxicológicas, Av Professor Lineu Prestes, 580 CEP 05508-900, São Paulo-SP, Brazil
    Search for more papers by this author
  • José Carlos Tomaz,

    1. Universidade de São Paulo, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Departamento de Química, Av do Café, s/n CEP 14040-903, Ribeirão Preto, SP, Brazil
    Search for more papers by this author
  • Norberto Peporine Lopes,

    1. Universidade de São Paulo, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Departamento de Química, Av do Café, s/n CEP 14040-903, Ribeirão Preto, SP, Brazil
    Search for more papers by this author
  • Ernani Pinto

    Corresponding author
    1. Universidade de São Paulo, Faculdade de Ciências Farmacêuticas, Departamento de Análises Clínicas e Toxicológicas, Av Professor Lineu Prestes, 580 CEP 05508-900, São Paulo-SP, Brazil
    • Departamento de Análises Clínicas e Toxicológicas, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, Av. Lineu Prestes, 580, 05508900, São Paulo, SP, Brazil.
    Search for more papers by this author

Abstract

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.

Ancillary