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

作者：Amorim Madeira Paulo J; Fernandes Sitoe Ana Raquel; Goncalves Daniel; Rodrigues Tiago; Guedes Rita C; Lopes Francisca; Moreira Rui; Rosario Bronze M

来源：Journal of the American Society for Mass Spectrometry, 2014, 25(9): 1650-1661.

DOI：10.1007/s13361-014-0940-x

• Electrospray ionization
• Triple quadrupole
• Collision induced dissociation
• Antimalarial drugs
• Liver stage
• DFT

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.

• 出版日期2014-9
• 单位河北医科大学