Gas-phase reactivity of 2-hydroxy-1,4-naphthoquinones: A computational and mass spectrometry study of lapachol congeners

Journal of Mass Spectrometry

Volumn 47, Issue 12, 2012, Pages 1648-1659

  Vessecchi, Ricardo ^a   Emery, Flávio S ^a   Galembeck, Sérgio E ^a   Lopes, Norberto P ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

even electron rule; fragmentation studies; gas phase ion chemistry; proton affinity; quinone; theoretical calculations

Indexed keywords

EVEN-ELECTRON RULE; FRAGMENTATION STUDIES; GAS PHASE ION CHEMISTRY; PROTON AFFINITY; QUINONE; THEORETICAL CALCULATIONS;

ACIDITY; ALKALINITY; ELECTRON AFFINITY; ELECTROSPRAY IONIZATION; HYDROGEN BONDS; IODINE; MASS SPECTROMETRY; MOLECULES; PROTONATION; PROTONS; QUANTUM CHEMISTRY;

KETONES;

LAPACHOL; LAWSONE;

ARTICLE; ELECTROSPRAY MASS SPECTROMETRY; GAS; MASS SPECTROMETRY; MOLECULAR INTERACTION; PRIORITY JOURNAL; QUANTUM CHEMISTRY; TANDEM MASS SPECTROMETRY;

COMPUTER SIMULATION; IONS; MODELS, MOLECULAR; NAPHTHOQUINONES; PROTONS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY; THERMODYNAMICS;

EID: 84871833964     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.3101     Document Type: Article

References (58)

1. T. J. Monks, P. Hanzlik, G. M. Cohen, D. Ross, D. G. Graham,. Quinones chemistry and toxicity. Toxicol. Appl. Pharmacol. 1992, 112, 2.
2. J. W. Lockman, A. D. Hamilton,. Recent developments in the identification of chemotherapeutics for chagas disease. Curr. Med. Chem. 2005, 12, 945.
3. P. J. O'Brien,. Molecular mechanisms of quinone cytotoxicity. Chem. Biol. Interact. 1991, 80, 1.
4. M. O. F. Goulart, L. R. Freitas, J. Tonholo, F. C. de Abreu, D. S. Raslan, S. Starling, C. L. Zani, A. B. Oliveira, E. Chiari,. Trypanocidal activity and redox potential of heterocyclic- and 2-hydroxy-naphthoquinones. Bioorg. Med. Chem. Lett., 1997, 7, 2043.
5. L. Sagrero-Nieves,. Isolation of lapachol from diphysa robinoides. J. Nat. Prod. 1986, 49, 547.
6. R. H. Thomson,. Naturally Occurring Quinones III. Recent Advances, Chapman and Hall: London, 1987.
7. K. V. Rao, T. J. McBride, J. J. Oleson,. Recognation and evaluation of lapachol as a antitumor agent. Cancer Res. 1968, 28, 1952.
8. C. Neves-Pinto, A. P. Dantas, K. C. G. Moura, F. S. Emery, P. F. Polequevitch, M. C. F. R. Pinto, S. L. de Castro, A. V. Pinto,. Chemical reactivity studies with naphthoquinones from Tabebuia with anti-trypanosomal efficacy. ArzneimForsch/DrugRes. 2000, 50, 1120.
9. E. Pérez-Sacau, R. G. Díaz-Peñate, A. Estévez-Braun, A. G. Ravelo, J. M. Garcia-Castellano, L. Pardo, M. Campillo,. Synthesis and pharmacophore modeling of naphthoquinone derivatives with cytotoxic activity in human promyelocytic leukemia HL-60 cell line. J. Med. Chem. 2007, 50, 696.
10. E. N. da Silva, M. A. B. F. de Moura, A. V. Pinto, M. D. F. R. Pinto, M. C. B. V. de Souza, A. J. Araujo, C. Pessoa, L. V. Costa-Lotufo, R. C. Montenegro, M. O. de Moraes, V. F. Ferreira, M. O. F. Goulart,. Cytotoxic, trypanocidal activities and physicochemical parameters of nor-beta-lapachone- based 1,2,3-triazoles. J. Braz. Chem. Soc. 2009, 20, 635.
11. E. A. Hillard, F. C. de Abreu, D. C. M. Ferreira, G. Jaouen, M. O. F. Goulart, C. Amatore,. Electrochemical parameters and techniques in drug development, with an emphasis on quinones and related compounds. Chem. Commun. 2008, 23, 2612.
12. T. Ossowski, P. Pipka, A. Liwo, D. Jeziorek,. Electrochemical and UV-spectrophotometric study of oxygen and superoxide anion radical interaction with anthraquinone derivatives and their radical anions Electrochim. Acta. 2000, 45, 3581.
13. J. H. Lee, J. H. Cheong, Y. M. Park, Y. H. Choi,. Down-regulation of cyclooxygenase-2 and telomerase activity by beta-lapachone in human prostate carcinoma cells. Pharmacolog. Res. 2005, 51, 553.
14. E. B. Skibo, C. Xing, R. T. Dorr,. Aziridinyl quinone antitumor agents based on indoles and cyclopent[b]indoles: Structure-activity relationships for cytotoxicity and antitumor activity. J. Med. Chem. 2001, 44, 3545.
15. V. F. Ferreira, A. Jorqueira, A. M. T. Souza, M. N. Da Silva, M. C. B. V. De Souza, R. M. Gouvêa, C. R. Rodrigues, A. V. Pinto, H. C. Castro, D. O. Santos, H. P. Araújo, S. C. Bourguignon,. Trypanocidal agents with low cytotoxicity to mammalian cell line: A comparison of the theoretical and biological features of lapachone derivatives. Bioorg. Med. Chem. 2006, 14, 5459.
16. F. C. da Silva, S. B. Ferreira, C. R. Kaiser, A. C. Pinto, V. F. Ferreira,. Synthesis of α- and β-lapachone derivatives from hetero diels-alder trapping of alkyl and aryl o-quinone methides. J Braz. Chem. Soc. 2009, 8, 1478.
17. R. Vessecchi, F. S. Emery, S. E. Galembeck, N. P. Lopes,. Fragmentation studies and electrospray ionization mass spectrometry of lapachol: protonated, deprotonated and cationized species. Rapid Comm. Mass Spectrum. 2010, 24, 2101.
18. M. N. Eberlin,. Electrospray ionization mass spectrometry: a major tool to investigate reaction mechanisms in both solution and gas-phase. Eur. J. Mass Spectrom. 2007, 13, 19.
19. J. Roithová,. Characterization of reaction intermediates by ion spectroscopy. Chem. Soc. Rev., 2012, 41, 547.
20. A. E. M. Crotti, E. S. Bronze-Uhle, P. G. B. D. Nascimento, P. M. Donate, S. E. Galembeck, R. Vessecchi, N. P. Lopes,. Gas-phase fragmentation of gamma-lactone derivatives by electrospray ionization tandem mass spectrometry. J. Mass Spectrom. 2009, 44, 1733.
21. R. Vessecchi, S. E. Galembeck, N. P. Lopes, P. G. B. D. Nascimento, A. E. M. Crotti,. Application of computational quantum chemistry to chemical processes involved in mass spectrometry. Quim. Nova, 2008, 31, 840.
22. a) A. D. Becke,. Density-functional thermochemistry.3. The role of exact exchange. J. Chem. Phys. 1993, 98, 5648
23. b) C. Lee, W. Yang, R. G. Parr,. Development of the colle-salvetti correlation-energy formula into a functional of the electron-density. Phys. Rev. B. 1988, 37, 785.
24. R. Ditchfield, W. J. Hehre, J. A. Pople,. Self-Consistent Molecular Orbital Methods. 9. Extended Gaussian-type basis for molecular-orbital studies of organic molecules. J. Chem. Phys. 1971, 54, 724.
25. A. G. Harrison,. Energy-resolved mass spectrometry: A comparison of quadrupole cell and cone-voltage collision-induced dissociation. Rapid Comm. Mass Spectrom. 1999, 13, 1663.
26. K. C. Nicolaou, D. L. F. Gray, Total synthesis of hybocarpone and analogues thereof. A facile dimerization of naphthazarins to pentacyclic systems. J. Am. Chem. Soc. 2004, 126, 607.
27. S. C. Hooker,. Condensation of aldehydes with beta-hydroxy-alpha- naphthoquinone, synthesis of hydrolapachol. J. Am. Chem. Soc. 1936, 58, 1163.
28. B. A. Oliveira, D. S. Raslan, F. Khuong-Huu,. Selenium reagent in the synthesis of naphtho[2,3-b]furan-4,9-diones. Tetrahedron Lett. 1990, 31, 6873.
29. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, N. Takajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople,. Gaussian 03, Revision D.01, Gaussian, Inc.: Wallingford CT, 2004.
30. K. E. Wise, A. K. Grafton, R. A. Wheeler,. Trimethyl-p-benzoquinone provides excellent structural, spectroscopic, and thermochemical models for plastoquinone-1 and its radical anion. J. Phys. Chem. A 1997, 101, 1160
31. J. Bernstein, M. D. Cohen, L. Leiserowitz,. in The chemistry of the quinonoid compound. Part 1, S. Patai, (Ed). John Wiley & Sons: London, 1974, 37-110.
32. R. Vessecchi, S. E. Galembeck,. Evaluation of the enthalpy of formation, proton affinity, and gas-phase basicity of gamma-butyrolactone and 2-pyrrolidinone by isodesmic reactions. J. Phys. Chem. A 2008, 112, 4060.
33. R. Vessecchi, Z. Naal, J. N. C. Lopes, S. E. Galembeck, N. P. Lopes,. Generation of naphthoquinone radical anions by electrospray ionization: solution, gas-Phase, and computational chemistry studies. J. Phys. Chem. A 2011, 115, 5453.
34. U. Varetto,. < MOLEKEL 5.4 >, Swiss National Supercomputing Centre: Manno (Switzerland).
35. Jmol: an open-source Java viewer for chemical structures in 3D. http://www.jmol.org/
36. NBO 5.0., E. D. Glendening, J. K. Badenhoop, A. E. Reed, J. E. Carpenter, J. A. Bohmann, C. M. Morales, F. Weinhold,. Theoretical Chemistry Institute, University of Winsconsin, Madison, 2001.
37. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ã. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox,. Gaussian 09, Revision A.1, Gaussian, Inc.: Wallingford CT, 2009.
38. C. A. Deakyne,. Proton affinities and gas-phase basicities: theoretical methods and structural effects. Int. J. Mass Spectrom. 2003, 227, 601.
39. D. McQuarrie,. Statistical Mechanics. HarperCollins, New York, 1976.
40. R. F. W. Bader,. Definition of molecular structure: by choice or by appeal to observation? J. Phys. Chem. A 2010, 114, 7431
41. R. F. W. Bader,. A quantum theory of molecular structure and its applicatlons. J. Phys. Chem. A 1991, 91, 893.
42. R. Vessecchi, J. N. C. Lopes, N. P. Lopes, S. E. Galembeck,. Application of the atoms in molecules theory and computational chemistry in mass spectrometry analysis of 1,4-naphthoquinone derivatives. J. Phys. Chem. A 2011, 115, 12780.
43. AIM 2000, Version 2.0, Copyright 2002. AIM2000 Home Page. http://www.aim2000.de
44. F. Biegler-König, J. Schönbohm,. Update of the AIM2000-program for atoms in molecules, J. Comp. Chem. 2002, 23, 1489.
45. C. Peng, B. H. Schlegel,. Combining synchronous transit and quasi-newton methods for finding transition states Israeli J. Chem. 1994, 33, 449.
46. A. Dupont, J.-P. Gisselbrecht, E. Leize, L. Wagner, A. Van Dorsselaer,. Electrospray mass spectrometry of electrochemically ionized molecules: application to the study of fullerenes. Tetrahedron Lett. 1994, 35, 6083
47. V. Kertesz, G. J. Van Berkel,. Monitoring ionic adducts to elucidate reaction mechanisms: reduction of tetracyanoquinodimethane and oxidation of triphenylamine investigated using on-line electrochemistry/electrospray mass spectrometry. J. Solid State Electrochem. 2005, 9, 390.
48. G. Lamoureux, A. L. Perez, M. Araya, C. Agüero,. Reactivity and structure of derivatives of 2-hydroxy-1,4-naphthoquinone (lawsone). J. Phys. Org. Chem. 2008, 21, 1022.
49. U. Koch, P. L. A. Popelier,. Characterization of C-H-O hydrogen bonds on the basis of the charge density. J. Phys. Chem. 1995, 99, 9747.
50. W. Nakanishi, S. Hayashi, K. Narahara,. Atoms-in-molecules dual parameter analysis of weak to strong interactions: behaviors of electronic energy densities versus laplacian of electron densities at bond critical points. J. Phys. Chem. A 2008, 112, 13595.
51. A. E. Reed, L. A. Curtiss, F. Weinhold,. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem. Rev. 1988, 88, 899.
52. NIST-National Institute of Standards and Technology-webbook.nist.gov/ chemistry
53. S. A. McLuckey,. Principles of collisional activation in analytical mass spectrometry. J. Am. Soc. Mass Spectrom. 1992, 3, 599.
54. C. A. Grob, W. Baumann,. Die 1,4-Eliminierung unter fragmentierung. Helv. Chim. Acta 1955, 38, 594.
55. R. Vessecchi, G. J. Zocolo, D. R. Gouvea, F. Hubner, B. Cramer, M. R. R. de Marchi, H. U. Humpf, N. P. Lopes,. Re-examination of the anion derivatives of isoflavones by radical fragmentation in negative electrospray ionization tandem mass spectrometry: experimental and computational studies. Rapid Comm. Mass Spectrom. 2011, 25, 2020.
56. K. Levsen, H. M. Schiebel, J. K. Terlouw, K. J. Jobst, M. Elend, A. Preiss, H. Thiele, A. Ingendoh,. Even-electron ions: a systematic study of the neutral species lost in the dissociation of quasi-molecular ions. J. Mass Spectrom. 2007, 42, 1024.
57. M. Karni, A. Mandelbaum,. The even-electron rule. Org. Mass Spectrom. 1980, 15, 53.
58. R. Vessecchi, C. A. Carollo, J. N. C. Lopes, A. E. M. Crotti, N. P. Lopes, S. E. Galembeck,. Gas-phase dissociation of 1,4-naphthoquinone derivative anions by electrospray ionization tandem mass spectrometry. J. Mass Spectrom. 2009, 44, 1224.