Understanding the fragmentation mechanisms of methoxy-, mesyl-, and tosyl-lapachol derivatives by computational chemistry and mass spectrometry analysis

[1]  Daniel P Demarque,et al.  Fragmentation reactions using electrospray ionization mass spectrometry: an important tool for the structural elucidation and characterization of synthetic and natural products. , 2016, Natural product reports.

[2]  N. Lopes,et al.  In vitro metabolism of the alkaloid piplartine by rat liver microsomes. , 2014, Journal of pharmaceutical and biomedical analysis.

[3]  H. Humpf,et al.  A systematic investigation of the fragmentation pattern of two furanoheliangolide C-8 stereoisomers using electrospray ionization mass spectrometry. , 2014, Rapid communications in mass spectrometry : RCM.

[4]  R. Cole,et al.  Clarification of the 30 Da releases from the [M-H]⁻ and M⁻˙ ions of trinitrotoluene by electrospray high resolution mass spectrometry. , 2014, Journal of mass spectrometry : JMS.

[5]  A. Alex,et al.  Understanding collision-induced dissociation of dofetilide: a case study in the application of density functional theory as an aid to mass spectral interpretation. , 2013, The Analyst.

[6]  N. Lopes,et al.  Electronic structure and gas-phase chemistry of protonated α- and β-quinonoid compounds: a mass spectrometry and computational study. , 2013, Rapid communications in mass spectrometry : RCM.

[7]  G. Bouchoux.  From the mobile proton to wandering hydride ion: mechanistic aspects of gas-phase ion chemistry. , 2013, Journal of mass spectrometry : JMS.

[8]  N. Lopes,et al.  Gas-phase reactivity of 2-hydroxy-1,4-naphthoquinones: a computational and mass spectrometry study of lapachol congeners. , 2012, Journal of mass spectrometry : JMS.

[9]  Paolo Carloni,et al.  A Computational Model for Protein Ionization by Electrospray Based on Gas-Phase Basicity , 2012, Journal of The American Society for Mass Spectrometry.

[10]  D. Schröder,et al.  Deprotonation of p-hydroxybenzoic acid: does electrospray ionization sample solution or gas-phase structures? , 2012, Journal of the American Chemical Society.

[11]  N. Lopes,et al.  Biomimetic in vitro oxidation of lapachol: a model to predict and analyse the in vivo phase I metabolism of bioactive compounds. , 2012, European journal of medicinal chemistry.

[12]  M. Eberlin,et al.  Protomers: formation, separation and characterization via travelling wave ion mobility mass spectrometry. , 2012, Journal of mass spectrometry : JMS.

[13]  Tian Lu,et al.  Multiwfn: A multifunctional wavefunction analyzer , 2012, J. Comput. Chem..

[14]  J. Lopes,et al.  Application of the atoms in molecules theory and computational chemistry in mass spectrometry analysis of 1,4-naphthoquinone derivatives. , 2011, The journal of physical chemistry. A.

[15]  J. Lopes,et al.  Generation of naphthoquinone radical anions by electrospray ionization: solution, gas-phase, and computational chemistry studies. , 2011, The journal of physical chemistry. A.

[16]  Zhongjun Ma,et al.  A deuterium-labelling mass spectrometry–tandem diode-array detector screening method for rapid discovery of naturally occurring electrophiles , 2011, Analytical and bioanalytical chemistry.

[17]  T. Frankcombe,et al.  Potential energy surfaces for gas-surface reactions. , 2011, Physical chemistry chemical physics : PCCP.

[18]  J. Riveros,et al.  Gas-phase nucleophilic and elimination reactions in simple alkyl nitrates. , 2010, The journal of physical chemistry. A.

[19]  N. Lopes,et al.  Fragmentation studies and electrospray ionization mass spectrometry of lapachol: protonated, deprotonated and cationized species. , 2010, Rapid communications in mass spectrometry : RCM.

[20]  A Ruth Godfrey,et al.  Accurate mass measurement: Terminology and treatment of data , 2010, Journal of the American Society for Mass Spectrometry.

[21]  R. Bader.  The density in density functional theory , 2010 .

[22]  R. Cole,et al.  Characterization of an exception to the 'even-electron rule' upon low-energy collision induced decomposition in negative ion electrospray tandem mass spectrometry. , 2010, Journal of mass spectrometry : JMS.

[23]  N. Lopes,et al.  Gas-phase dissociation of 1,4-naphthoquinone derivative anions by electrospray ionization tandem mass spectrometry. , 2009, Journal of mass spectrometry : JMS.

[24]  M. Eckert-Maksić,et al.  Generation and dissociation pathways of singly and doubly protonated bisguanidines in the gas phase. , 2008, The journal of physical chemistry. A.

[25]  P. Gates,et al.  A theoretical and mass spectrometry study of the fragmentation of mycosporine-like amino acids , 2008 .

[26]  J. Supko,et al.  Identification of the in Vitro Metabolites of 3,4-Dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-dione (ARQ 501; β-Lapachone) in Whole Blood , 2008, Drug Metabolism and Disposition.

[27]  G. Orlova,et al.  Fragmentations and proton-transfer mechanisms of gaseous radical-cationic tryptophan: A theoretical study , 2007 .

[28]  H. Hussain,et al.  Lapachol: An overview , 2007 .

[29]  M. Eberlin.  Electrospray Ionization Mass Spectrometry: A Major Tool to Investigate Reaction Mechanisms in Both Solution and the Gas Phase , 2007, European journal of mass spectrometry.

[30]  E. Uggerud.  Theory and Experiment in Mass Spectrometry: A Perspective on the Relationship between Computational Modelling and Experiment in Gas-Phase Ion Chemistry , 2007, European journal of mass spectrometry.

[31]  J. Kochi,et al.  The question of aromaticity in open-shell cations and anions as ion-radical offsprings of polycyclic aromatic and antiaromatic hydrocarbons. , 2006, The Journal of organic chemistry.

[32]  J. Lopes,et al.  Fragmentation studies of synthetic 2-acylamino-1,4-naphthoquinones by electrospray ionization mass spectrometry. , 2006, Journal of mass spectrometry : JMS.

[33]  R. Mosquera,et al.  QTAIM interpretation of the basicity of substituted anilines , 2005 .

[34]  I. Alkorta,et al.  Influence of protonation on the properties derived from electron density , 2005 .

[35]  M. Eberlin.  Gas-phase polar cycloadditions , 2004 .

[36]  Vincenzo Barone,et al.  Vibrational zero-point energies and thermodynamic functions beyond the harmonic approximation. , 2004, The Journal of chemical physics.

[37]  C. Deakyne.  Proton Affinities and Gas-Phase Basicities: Theoretical Methods and Structural Effects , 2003 .

[38]  J. R. Pliego,et al.  Theoretical Calculation of pKa Using the Cluster−Continuum Model , 2002 .

[39]  Hui Hong,et al.  Fragmentation studies on monensin A and B by accurate-mass electrospray tandem mass spectrometry. , 2002, Rapid communications in mass spectrometry : RCM.

[40]  J. Gal,et al.  Thermochemical aspects of proton transfer in the gas phase. , 2001, Journal of mass spectrometry : JMS.

[41]  S. A. McLuckey,et al.  Mass analysis at the advent of the 21st century. , 2001, Chemical reviews.

[42]  B. Balta,et al.  Structures and reactivity of gaseous glycine and its derivatives , 2000 .

[43]  Michelle L. Reyzer,et al.  Gas-phase basicities of polyamines , 1998 .

[44]  S. A. McLuckey.  Principles of collisional activation in analytical mass spectrometry , 1992, Journal of the American Society for Mass Spectrometry.

[45]  R. Bader,et al.  A quantum theory of molecular structure and its applications , 1991 .

[46]  M. Mann,et al.  Electrospray ionization for mass spectrometry of large biomolecules. , 1989, Science.

[47]  V. Ferreira,et al.  Cytotoxic, Trypanocidal Activities and Physicochemical Parameters of nor-β-Lapachone-based 1,2,3-Triazoles , 2009 .

[48]  Norberto Lopes,et al.  Aplicação da química quântica computacional no estudo de processos químicos envolvidos em espectrometria de massas , 2008 .

[49]  V. F. Ferreira,et al.  Um panorama atual da química e da farmacologia de naftoquinonas, com ênfase na beta-lapachona e derivados , 2003 .

[50]  C. Enke,et al.  Practical implications of some recent studies in electrospray ionization fundamentals. , 2001, Mass spectrometry reviews.

[51]  M. Alcamí,et al.  Computational chemistry: a useful (sometimes mandatory) tool in mass spectrometry studies. , 2001, Mass spectrometry reviews.