Precursor Ion Scan Mode-Based Strategy for Fast Screening of Polyether lonophores by Copper-Induced Gas-Phase Radical Fragmentation Reactions

Author(s)

Crevelin, Eduardo J. ; Possato, Bruna ; Lopes, Joao L. C. ; Lopes, Norberto P. ; Crotti, Antonio E. M.

• Document type: Journal article
• Source: Analytical Chemistry; v. 89, n. 7, p. 3929-3936, APR 4 2017.
• Web of Science Citations: 3

Abstract

The potential of copper(II) to induce gas-phase fragmentation reactions in macrotetrolides, a class of polyether ionophores produced by Streptomyces species, was investigated by accurate-mass electrospray tandem mass spectrometry (ESI-MS/MS). Copper(II)/copper(I) transition directly induced production of diagnostic acylium ions with m/z 199, 185, 181, and 167 from alpha-cleavages of {[}macrotetrolides + Cu](2+). A UPLC-ESI-MS/MS methodology based on the precursor ion scan of these acylium ions was developed and successfully used to identify isodinactin (1), trinactin (2), and tetranactin (3) in a crude extract of Streptomyces sp. AMC 23 in the precursor ion scan mode. In addition, copper(II) was also used to induce radical fragmentation reactions in the carboxylic acid polyether ionophore nigericin. The resulting product ions with m/z-755 and 585 helped to identify nigericin in a crude extract of Streptomyces sp. Eucal-26 by means of precursor ion scan experiments,, demonstrating that copper-induced fragmentation reactions Can potentially identify different classes of polyether ionophores rapidly and selectively. (AU)

• FAPESP's process: 14/50265-3 - Distribution and metabolism of natural and synthetic xenobiotics: from the comprehension of reactional process to tissue imaging generation
• Grantee: Norberto Peporine Lopes
• Support Opportunities: BIOTA-FAPESP Program - Thematic Grants
• FAPESP's process: 13/20094-0 - Evaluation of the anti-parasitary and insecticidal activities of benzofuran derivatives, and study of their gas-phase fragmentation reactions using tandem mass spectrometry
• Grantee: Antônio Eduardo Miller Crotti
• Support Opportunities: Regular Research Grants