Literature DB >> 22290485

Using electron induced dissociation (EID) on an LC time-scale to characterize a mixture of analogous small organic molecules.

Aruna S Prakash1, Michael J P Smith, Zied Kaabia, Glenn Hurst, Ci Yan, Martin Sims, Anthony W T Bristow, Peter Stokes, David Parker, Jackie A Mosely.   

Abstract

LC ESI FTICR MS of a sample of cediranib identified this pharmaceutical target molecule plus an additional 10 compounds of interest, all of which were less than 10% total ion current (TIC) peak intensity relative to cediranib. LC FTICR tandem mass spectrometry using electron induced dissociation (EID) has been achieved and has proven to be the best way to generate useful product ion information for all of these singly protonated molecules. Cediranib [M + H](+) fragmented by EID to give 29 product ions whereas QTOF-CID generated only one very intense product ion, and linear ion trap-CID, which generated 10 product ions, but all with poor S/N. Twenty-six of the EID product ions were unique to this fragmentation technique alone. By considering the complementary LC-EID and LC-CID data together, all 10 unknown compounds were structurally characterized and proven to be analogous to cediranib. Of particular importance, EID produced unique product ion information for one of the low level cediranib analogues that enabled full characterization of the molecule such that the presence of an extra propylpyrrolidine group was discovered and proven to be located on the pyrrolidine ring of cediranib, solving an analytical problem that could not be solved by collision induced dissociation (CID). Thus, it has been demonstrated that EID is in harmony with the chromatography duty-cycle and the dynamic concentration range of synthetic compounds containing trace impurities, providing crucial analytical information that cannot be obtained by more traditional methodologies.

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Year:  2012        PMID: 22290485     DOI: 10.1007/s13361-012-0338-6

Source DB:  PubMed          Journal:  J Am Soc Mass Spectrom        ISSN: 1044-0305            Impact factor:   3.109


  26 in total

1.  Electron capture dissociation of polypeptides using a 3 Tesla Fourier transform ion cyclotron resonance mass spectrometer.

Authors:  Nicolas C Polfer; Kim F Haselmann; Roman A Zubarev; Pat R R Langridge-Smith
Journal:  Rapid Commun Mass Spectrom       Date:  2002       Impact factor: 2.419

2.  Liquid chromatography and electron-capture dissociation in Fourier transform ion cyclotron resonance mass spectrometry.

Authors:  Magnus Palmblad; Youri O Tsybin; Margareta Ramström; Jonas Bergquist; Per Håkansson
Journal:  Rapid Commun Mass Spectrom       Date:  2002       Impact factor: 2.419

3.  Tandem mass spectrometry: dissociation of ions by collisional activation

Authors: 
Journal:  J Mass Spectrom       Date:  2000-09       Impact factor: 1.982

Review 4.  The role of electron capture dissociation in biomolecular analysis.

Authors:  Helen J Cooper; Kristina Håkansson; Alan G Marshall
Journal:  Mass Spectrom Rev       Date:  2005 Mar-Apr       Impact factor: 10.946

Review 5.  Detecting and characterizing reactive metabolites by liquid chromatography/tandem mass spectrometry.

Authors:  Shuguang Ma; Raju Subramanian
Journal:  J Mass Spectrom       Date:  2006-09       Impact factor: 1.982

6.  Tandem mass spectrometry of very large molecules: serum albumin sequence information from multiply charged ions formed by electrospray ionization.

Authors:  J A Loo; C G Edmonds; R D Smith
Journal:  Anal Chem       Date:  1991-11-01       Impact factor: 6.986

7.  Electron-induced dissociation of protonated peptides yields backbone fragmentation consistent with a hydrogen-deficient radical.

Authors:  Tony Ly; Sheng Yin; Joseph A Loo; Ryan R Julian
Journal:  Rapid Commun Mass Spectrom       Date:  2009-07       Impact factor: 2.419

8.  Electron-induced dissociation of singly charged organic cations as a tool for structural characterization of pharmaceutical type molecules.

Authors:  Jackie A Mosely; Michael J P Smith; Aruna S Prakash; Martin Sims; Anthony W T Bristow
Journal:  Anal Chem       Date:  2011-04-29       Impact factor: 6.986

9.  Tandem mass spectrometry.

Authors:  F W McLafferty
Journal:  Science       Date:  1981-10-16       Impact factor: 47.728

10.  The effect of phosphorylation on the electron capture dissociation of peptide ions.

Authors:  Andrew J Creese; Helen J Cooper
Journal:  J Am Soc Mass Spectrom       Date:  2008-05-28       Impact factor: 3.109

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  4 in total

1.  Liquid Extraction Surface Analysis (LESA) Electron-Induced Dissociation and Collision-Induced Dissociation Mass Spectrometry of Small Molecule Drug Compounds.

Authors:  Andrea F Lopez-Clavijo; Rian L Griffiths; Richard J A Goodwin; Helen J Cooper
Journal:  J Am Soc Mass Spectrom       Date:  2018-08-27       Impact factor: 3.109

2.  Electron-induced dissociation of peptides in a triple quadrupole mass spectrometer retrofitted with an electromagnetostatic cell.

Authors:  Valery G Voinov; Samuel E Bennett; Douglas F Barofsky
Journal:  J Am Soc Mass Spectrom       Date:  2015-02-05       Impact factor: 3.109

3.  Electron-induced dissociation (EID) for structure characterization of glycerophosphatidylcholine: determination of double-bond positions and localization of acyl chains.

Authors:  Jace W Jones; Christopher J Thompson; Claire L Carter; Maureen A Kane
Journal:  J Mass Spectrom       Date:  2015-12       Impact factor: 1.982

4.  Characterisation of phosphorylated nucleotides by collisional and electron-based tandem mass spectrometry.

Authors:  Andrew T Ball; Aruna S Prakash; Anthony W T Bristow; Martin Sims; Jackie A Mosely
Journal:  Rapid Commun Mass Spectrom       Date:  2016-10-15       Impact factor: 2.419

  4 in total

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