Antiplasmodial Drugs in the Gas Phase: A CID and DFT Study of Quinolon-4(1H)-Imine Derivatives

The gas-phase behavior of 12 quinolon-4( 1H )-imine derivatives with antiplasmodial activity was investigated using electrospray ionization tandem mass spectrometry together with collision induced dissociation and density functional theory (DFT) calculations. The most probable protonation site was p...

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Bibliographic Details
Published in:Journal of the American Society for Mass Spectrometry 2014-09, Vol.25 (9), p.1650-1661
Main Authors: Amorim Madeira, Paulo J., Sitoe, Ana Raquel Fernandes, Gonçalves, Daniel, Rodrigues, Tiago, Guedes, Rita C., Lopes, Francisca, Moreira, Rui, Bronze, M. Rosário
Format: Article
Language:English
Subjects:
Affinity
Analytical Chemistry
Bioinformatics
Biotechnology
Chemistry
Chemistry and Materials Science
Collision dynamics
Data acquisition
Density functional theory
Derivatives
Ionization
Ions
Mass spectrometry
Mathematical analysis
Organic Chemistry
Proteomics
Protonation
Quinoline
Research Article
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Summary:The gas-phase behavior of 12 quinolon-4( 1H )-imine derivatives with antiplasmodial activity was investigated using electrospray ionization tandem mass spectrometry together with collision induced dissociation and density functional theory (DFT) calculations. The most probable protonation site was predicted by calculating the proton affinity (PA) values for each possible protonation site and it was found to be the imine nitrogen for all compounds under study. Fragmentation pathways of the protonated molecules were proposed and the assignment of product ion structures was performed taking into account theoretical calculations. The nature of the quinoline substituent was found to influence the gas-phase behavior of the compounds under study. The data acquired allowed to bracket the proton affinity of the quinolin-4-imine scaffold, which can be a useful starting point to choose appropriate references for determining PA values of this scaffold. Figure ᅟ
ISSN:1044-0305
1879-1123
DOI:10.1007/s13361-014-0940-x