scholarly journals Electrospray Ionization Mass Spectrometry as a Valuable Tool in the Characterization of Novel Primaquine Peptidomimetic Derivatives

2009 ◽  
Vol 15 (5) ◽  
pp. 627-640 ◽  
Author(s):  
Nuno Vale ◽  
Joana Matos ◽  
Rui Moreira ◽  
Paula Gomes

Novel primaquine-derived antimalarials have been extensively characterized by electrospray ionization-ion trap mass spectrometry (ESI-MS). Experiments by in-source collision-induced dissociation (CID) in the nozzle–skimmer region (NSR) or by tandem mass spectrometry (MS/MS) are shown to be most valuable tools for the physico–chemical characterization of these 8-aminoquinolinic drugs that also bear the biologically relevant imidazolidin-4-one scaffold. It was possible to find parallelism between compound stability in the NSR and its reactivity towards hydrolysis at physiological pH and T. Moreover, MS/MS fragmentation patterns were characteristic for each family, providing a means for structural distinction of isomers and allowing interesting correlations to be found between the relative abundance of particular fragments and relevant structure–activity determinants, such as the Charton steric parameter, ν. In conclusion, this work provides a solid ground for establishing ESI-MS as a key tool for the physico–chemical characterization of biopharmaceuticals bearing the 8-aminoquinoline and/or the imidazolidin-4-one moieties.

Author(s):  
Suman Lata ◽  
Sanjiv Kumar Mittal

The present work is to identify the Chemical Composition of methanolic extract from Cucumis dipsaceus Ehrenb. (Fruit) by using HPLC-UV-ESI-MS Methods. It is very proficient method with amalgamation of liquid chromatography attached to electrospray ionization mass spectrometry in tendem means with positive and negative ion recognition. This is a simple and rapid method for characterization of flavonoid glycosides by using Reversed Phase High Performance Liquid Chromatography coupled to Electrospray Ionization Quadropole Time – of – Flight Mass Spectrometry (RP-HPLC-ESI-Q-TOF-MS). The correctness of mass information generated by Q-TOF-MS jointly with the fragmentation blueprint of the complete scan sprint of MS/MS investigation has been a valuable tool to cautiously characterization of 12 flavonoid glycosides (Molecular weight: 497.04 (RT:3.586), 475.06 (RT:6.801), 393.48 (RT:12.594), 336.50 (RT:16.473), 723.00 (RT:17.774), 452.52(RT:18.253), 978.95 (RT: 25.665), 836.20 (RT: 26.889), 893.00 (RT: 27.925), 838.32 (RT: 31.592), 507.44 (RT: 31.592), 415.18, (RT:33.849) in the methanol extract of this fruit. All these flavonoid glycosides are the first time reported from fruit of Cucumis dipsaceus Ehrenb., and also highlighting the importance of this fruit as a rich source of likely flavonoid glycosides as antioxidants and hepatoprotective agent. It was concluded that these flavonoid glycosides were Myceritin -3-O- β -D-glucopyranoside (497), Apigenin 7 – O – 6’’ – O acetyl – β – D - glucopyranoside (475), 5,6 Dihydroxy 7,8 – dimethoxyapigenin - 6 – O – sulfate (393), 5-p-coumaroylquinic acid (336 or 338), 6’’ -O-(3-hydroxy-3- methylglutaroyl)-2’’ - O - pentosyl-C - hexosyl-luteolin (723), Catechin-3-O-glucoside (452), 3’,4’,5’,5,7 – Methyl derivative of quercetin 3 – O – (2” - feruloylglucosyl)(1->6) – [apiosyl1->2)] glucoside (978.859), Quercetin 3 – O – β – D -(6 – O – sinnapoyl – 2 – O - – O – β – D glucopyranosyl) glucopyranoside (833), Apigenin 7-O-(6''-dihydrogalloyl)-glucosyl-8-C-rhamnosyl-6-C-glucoside (893), precursor or isomer ion of Quercetin 3 – O – β – D -(6 – O – sinnapoyl – 2 – O - – O – β – D glucopyranosyl) glucopyranoside 838.32 , 3’,4’,7 – Methyl derivative of quercetin 3 – O – β – D - glucopyranoside (507) and 415 (Daidzein 7 – O – glucoside).


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