Fragmentation studies and electrospray ionization mass spectrometry of lapachol: Protonated, deprotonated and cationized species

Rapid Communications in Mass Spectrometry

Volumn 24, Issue 14, 2010, Pages 2101-2108

  Vessecchi, Ricardo ^a   Emery, Flavio S ^a   Galembeck, Sergio E ^a   Lopes, Norberto P ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

LAPACHOL; NAPHTHOQUINONE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; METHODOLOGY; PHASE TRANSITION; PROCEDURES;

MODELS, CHEMICAL; NAPHTHOQUINONES; PHASE TRANSITION; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 77954466059     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.4625     Document Type: Article

References (50)

1. Fonseca SGC, Braga RMC, Santana DP. Rev. Bras. Farm. 2003; 84: 9.
2. Hussain H, Krohn K, Ahmad VU, Miana GA, Grenn IR. ARKIVOC 2007; (ii): 145.
3. Santos AF, Ferraz PA, Abreu FC, Chiari E, Goulart MOF, Sant'Ana AE. Planta Med. 2001; 67: 92; Santos AF, Ferraz PAL, Pinto AV, Pinto MCFR, Goulart MOF, Sant'Ana AEG, Int. J. Parasitol. 2000; 30: 1199.
4. Boveris A, Stoppani AOM, Docampo R, Cruz FS. Comp. Biochem. Physiol. 1978; 61C: 327.
5. Monks TJ, Hanzlik RP, Cohen GM, Ross D, Graham DG. Toxicol. Appl. Pharmacol. 1992; 112: 2.
6. Bolton JL, Trush MA, Penning TM, Dryhurst G, Monks TJ, Monks TJ. Chem. Res. Toxicol. 2000; 13: 135.
7. Abreu FC, Ferraz PAL, Goulart MOF. J. Braz. Chem. Soc. 2002; 13: 19.
8. Hillard EA, Abreu FC, Ferreira DCM, Jaouen G, Goulart MOF, Amatore C. Chem. Comm. 2008; v: 2612. Rapid Commun. Mass Spectrom. 2010; 24: 2101-2108
9. Goulart MOF, Falkowski P, Ossowski T, Liwo A. Biochemistry 2003; 59: 85.
10. Silva-Junior EN, Deus CF, Cavalcanti BC, Pessoa C, Costa-Lotufo LV, Montenegro RC, de Moraes MO, Pinto MCFR, De Simone CA, Ferreira VF, Goulart MOF, Andrade CKZ, Pinto AV. J. Med. Chem. 2010; 53: 504.
11. Silva TMS, Camara CA, Barbosa TP, Soares AZ, Cunha LC, Pinto AC, Vargas MD. Bioorg. Med. Chem. 2005; 13: 193.
12. Eberlin MN. Eur. J. Mass Spectrom. 2007; 13: 19.
13. Crotti AEM, Vessecchi R, Lopes JLC, Lopes NP. Quim. Nova 2006; 29: 287.
14. Kerbale P, Verkerk UH. Mass Spectrom. Rev. 2009; 28: 898.
15. O'Hair RAJ. Chem. Commun. 2006; 1469.
16. Chen P. Angew. Chem. Int. Ed. 2003; 42: 2832.
17. Levsen K, Schwarz H. Mass Spectrom. Rev. 1983; 2: 77.
18. Uggerud E. Eur. J. Mass Spectrom. 2007; 13: 97.
19. Vessecchi R, Nascimento PGBD, Lopes JNC, Lopes NP. J. Mass Spectrom. 2006; 41: 1219.
20. Furtado NAJC, Vessecchi R, Tomaz JC, Bastos JK, Lopes NP, Crotti AEM. J. Mass Spectrom. 2007; 42: 1279.
21. Cardoso KHM, Vessecchi R, Carvalho VM, Pinto E, Gates PJ, Colepicolo P, Galembeck SE, Lopes NP. Int. J. Mass Spectrom. 2008; 273: 11.
22. NIST. Avaiable: webbook.nist.gov/chemistry.
23. McLuckey SA. J. Am. Soc. Mass Spectrom. 1992; 3: 599.
24. Vessecchi R, Galembeck SE, Lopes NP, Nascimento PGBD, Crotti AEM. Quim. Nova 2008; 31: 840.
25. Alcami M, Mó O, Yan ̃ez M. Mass Spectrom. Rev. 2001; 20: 195-245. Mercero JM, Matixain JM, Lopez X, York DM, Largo A, Eriksson LA, Ugalde JM, Int. J. Mass Spectrom. 2005; 240: 37.
26. Paternó E. Gazz. Chem. Ital. 1882; 12: 337.
27. Becke AD. J. Chem. Phys. 1993; 98: 5648.
28. Lee C, Yang W, Parr RG. Phys. Rev. B 1988; 37: 785.
29. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakr-zewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03, Revision D.01, Gaussian, Inc.: Wallingford CT, 2004.
30. Reed AE, Curtiss LA, Weinhold F. Chem. Rev. 1988; 88: 905.
31. Glendening ED, Badenhoop JK, Reed AE, Carpenter JE, Bohmann JA, Morales CM, Weinhold F. NBO 5.0 Program Manual. Theoretical Chemistry Institute: Madison, WI, 2001.
32. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Strat-mann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson BG, Chen W, Wong MW, Andres JL, Head-Gordon M, Replogle ES, Pople JA. Gaussian 98, Revision A.x, Gaussian, Inc.: Pittsburgh PA, 1998.
33. Flukiger P, Luthi HP, Portmann S, Weber J. MOLEKEL 4.3. 2002.
34. M. Torrent-Sucarrat M, De Proft F, Ayers PW, Geerlings P. Phys. Chem. Chem. Phys. 2010; 12: 1072.
35. Range K, Riccardi D, Cui Q, Elstner M, York DM. Phys. Chem. Chem. Phys. 2005; 7: 3070.
36. Boys SF, Bernardi R. Mol. Phys. 1970; 19: 553.
37. van Duijneveldt FB, van Duijneveldt-van de Rijdt JGCM, van Lenthe JH. Chem. Rev. 1994; 94: 1873.
38. Armentrout PB, Rodgers MT. J. Phys. Chem. A 2000; 104: 2238.
39. Wong CHS, Siu FM, Ma NL, Tsang CW. THEOCHEM 2002; 588: 9.
40. Ye SJ, Clark AA, Armentrout PB. J. Phys. Chem. B 2008; 112: 10291.
41. Peng C, Schlegel BH. Israeli J. Chem. 1994; 33: 449.
42. Gonzalez C, Schlegel BH. J. Chem. Phys. 1989; 90: 2154.
43. Bader RFW. Chem. Rev. 1991; 91: 893; Bader RFW, J Phys. Chem. A 1998; 102: 7314.
44. th edn). Longman Scientific and Technical: New York, 1985.
45. Lamoureaux G, Perez AL, Araya M, Aguero C. J. Phys. Org. Chem. 2008; 21: 1022.
46. Vessecchi R, Carollo CA, Lopes JNC, Crotti AEM, Lopes NP, Galembeck SE. J. Mass Spectrom. 2009; 44: 1224.
47. Karni M, Mandelbaum A. Org. Mass Spectrom. 1980; 15: 53.
48. Wagner W, Heimback H, Levsen K. Int. J. Mass Spectrom. 1980; 36: 125.
49. Gabelica V, Schulz E, Karas MJ. Mass Spectrom. Rev. 2004; 39: 579.
50. Ossowski T, Goulart MOF, Abreu FC, Santana AEG, Miranda PRB, Costa CO, Liwo A, Falkowski P, Zarzeczanska D. J. Braz. Chem. Soc. 2008; 19: 175.