Fragmentation studies of synthetic 2-acylamino-1,4-naphthoquinones by electrospray ionization mass spectrometry

Journal of Mass Spectrometry

Volumn 41, Issue 9, 2006, Pages 1219-1225

  Vessecchi, Ricardo ^a   Nascimento, Paulo G B D ^a   Lopes, José N C ^a   Lopes, Norberto P ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

1,4 naphthoquinones; Mass spectrometry; Theoretical calculations

Indexed keywords

DERIVATIVES; IONIZATION; MASS SPECTROMETRY; NITROGEN;

1,4-NAPHTHOQUINONES; FRAGMENTATION PATHWAYS; NUCLEOPHILIC ATOMIC INDICES; PROTONATION; TRIPLE-QUADRUPOLE MASS SPECTROMETERS;

ORGANIC COMPOUNDS;

1,4 NAPHTHOQUINONE DERIVATIVE; 2 ACETYLAMINO 1,4 NAPHTHOQUINONE; 2 BENZOYLAMINO 1,4 NAPHTHOQUINONE; 2 BUTYLAMINO 1,4 NAPHTHOQUINONE; 2 PROPIONYLAMINO 1,4 NAPHTHOQUINONE; 2 SUCCINYLAMINO 1,4 NAPHTHOQUINONE; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; FRAGMENTATION REACTION; PRIORITY JOURNAL; PROTON TRANSPORT; STRUCTURE ANALYSIS;

INDICATORS AND REAGENTS; NAPHTHOQUINONES; NITROGEN; PROTONS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 33749039189     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1092     Document Type: Article

References (43)

1. Monks TJ, Hanzlik RP, Cohen GM, Ross D, Graham DG. Quinones chemistry and toxicity. Toxicol. Appl. Pharmacol. 1992; 112: 2.
2. Abreu FC, Ferraz PA, Goulart MOF. Some applications of electrochemistry in biomedical chemistry: emphasis on the correlation of electrochemical and bioactive properties. J. Braz. Chem. Soc. 2002; 13: 19.
3. Goulart MOF, Zani CL, Tonholo J, Freitas LR, deAbreu FC, Oliveira AB, Raslan DS, Starling S, Chiari E. Trypanocidal activity and redox potential of heterocyclic and 2-hydroxy-naphtoquinones. Bioorg. Med. Chem. Lett. 1997; 7: 2043.
4. Thomson RH. Naturally Occurring Quinones, 2nd ed., chapter 4. Academic Press: London, 1971; 203.
5. Oeriu I, Benesch H. Relations entre la structure chimique et activite antituberculeuse de certains derives de 1 alpha-naphtoquinone, substitutes dans les positions 2 et 3 par des thiols et des amines. Bull. Soc. Chim. Biol. 1962; 44: 91.
6. Prescott B. Potential antimalarial agents. Derivatives of 2-chloro-1,4-naphthoquinone. J. Med. Chem. 1969; 12: 181.
7. Dudley KH, Miller HW. Potential naphthoquinone antimalarials - 2-acylhydrazino-1,4-naphthoquinones. J. Med. Chem. 1970; 13: 535.
8. Silver RF, Holmes HL. Synthesis of some 1,4-naphthoquinones and reactions relating to their use in study of bacterial growth inhibition. Can. J. Chem. 1968; 46: 1859.
9. Hodnett EM, Wongwiechintana C, Dunn WJ, Marrs P. Substituted 1,4-naphthoquinones vs the ascitic sarcoma-180 of mice. J. Med. Chem. 1983; 26: 570.
10. Lopes JNC, Johnson AW, Grove JF, Bulhões MS. Synthesis of 2-amino-1,4-naphtoquinone derivatives and the evaluation of their larvicidal and molluscicidal activities. Ciência & Cultura (São Paulo). 1977; 29: 1145.
11. Clark NG. The fungicidal activity of substituted 1,4-naphthoquinones. 3. Amino, anilino and acylamino derivatives. Pestic. Sci 1985; 16: 23.
12. Morton RA. Biochemistry of Quinones. Academic press: New York, 1965; 585.
13. Macias-Ruvalcaba NA, Gonzales I, Aguilar-Martinez M. Evolution from hydrogen bond to proton transfer pathways in the electroreduction of alpha-NH-quinones in acetonitrile. J. Electrochem. Soc. 2004; 151: E110.
14. Fieser LF, Berliner E, Bondhus FJ, Chang FC, Dauben WG, Ettlinger MG, Fawaz G, Fields M, Heidelberger C, Heymann H, Vaughan WR, Wilson AG, Wilson E, Wu M, Leffler M, Hamlin KE, Matson EJ, Moore EE, Moore MB, Zaugg HE. Naphthoquinone antimalarials. 4.5.6.7.8.9.10.11. Synthesis. J. Am. Chem. Soc. 1948; 70: 3174.
15. Fieser LF, Fieser M. Advanced Organic Chemistry. Chapman & Hall: New York, 1961; 845.
16. Fenn JB, Mann M, Meng CK, Wong SF, Whitehouse CM. Electrospray ionization for mass-spectrometry of large biomolecules. Science 1989; 246: 64.
17. Zhan DL, Fenn JB. Electrospray mass spectrometry of fossil fuels. Int. J. Mass Spectrom. 2000; 194: 197.
18. Maurin AJM, Iamamoto Y, Lopes NP, Lindsay-Smith JR, Bonato PS. LC-MS-MS Identification of drug metabolites obtained by metalloporphyrin mediated oxidation. J. Braz. Chem. Soc. 2003; 14: 322.
19. Crotti AEM, Fonseca T, Hong H, Staunton J, Galembeck SE, Lopes NP, Gates PJ. The fragmentation mechanism of five-membered lactones by electrospray ionisation tandem mass spectrometry. Int. J. Mass Spectrom. 2004; 232: 271.
20. 0). Anal. Chem. 2004; 76: 5223.
21. Cole RB (ed.). Electrospray Mass Spectrometry: Fundamentals, Instrumentation & Applications. John Wiley and Sons: New York, 1997; 65.
22. Mollah S, Pris AD, Johnson SK, Gwizdala AB, Houk RS. Identification of metal cations, metal complexes, and anions by electrospray mass spectrometry in the negative mode ion mode. Anal. Chem. 2000; 72: 985.
23. Xu XM, Nolan SP, Cole RB. Electrochemical oxidation and nucleophilic addition: Reactions of metallocenes in electrospray mass spectrometry. Anal. Chem. 1994; 66: 119.
24. VanBerkel GJ, Mcluckey SA, Glish G. Electrochemical origin of radical cations observed in electrospray ionization mass spectra. Anal. Chem. 1992; 64: 1586.
25. De La Mora JF, Van Berkel GJ, Enke CG, Cole RB, Martinez-Sanchez M, Fenn JB. Electrochemical processes in electrospray ionization mass spectrometry - discussion. J. Mass Spectrom. 2000; 35: 939.
26. Guaratini T, Vessecchi R, Pinto E, Colepicolo P, Lopes NP. Balance of xanthophylls molecular and protonated molecular ions in electrospray ionization. J. Mass Spectrom. 2005; 40: 963.
27. + complexation to polyciclic aromatic hydrocarbons (PAHs). Org. Biol. Chem. 2005; 3: 2319.
28. Gal JF, Maria PC, Raczynska ED. Thermochemical aspect of proton transfer in the gas phase. J. Mass Spectrom. 2001; 36: 699.
29. Amad MH, Cech NB, Jackson GS, Enke CG. Importance of gas-phase proton affinities in determining the electrospray ionization response for analytes and solvents. J. Mass Spectrom. 2000; 35: 784.
30. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann 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, Cliffords, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, 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.1. Gaussian, Inc.: Pittsburgh, PA, 1998.
31. MOPAC Program, version 6.0; Quantum Chemistry Exchange No. 455.
32. Stewart JJP. Optimization of parameters for semiempirical methods. 2. Applications. J. Comput. Chem. 1989; 10: 221.
33. Fukui K. Theory of Orientation and Stereoselection. Springer-Verlag: Berlin, 1975; 34.
34. Katritzky AR, Karelson M, Petrukhin R. Comprehensive Descriptors for Structural and Statistical Analysis (CODESSA). Semichem, Inc.: 1992; 199.
35. Binkley JS, Pople JA, Hehre WJ. Self-consistent molecular-orbital methods. 21. Small split-valence basis-sets for 1st-row elements. J. Am. Chem. Soc. 1980; 102: 939.
36. McLean AD, Chandler GS. Contracted Gaussian-basis sets for molecular calculations.1. 2nd row atoms, z = 11-18. J. Chem. Phys. 1980; 72: 5639.
37. HeadGordon M, Pople JA, Frisch MJ. MP2 energy evaluation by direct methods. Chem. Phys. Lett. 1988; 153: 503.
38. Flükiger P, Lüthi HP, Portmann S, Weber J. MOLEKEL 4.3. Win32, Swiss Center for Scientific Computing, Manno, Switzerland, 2000-2002. www.cscs.ch/molekel.
39. Solomons TWG. In Fundamentals of Organic Chemistry, 4th Edition. Wiley: New York, 1994; 1047.
40. Homer RB, Johnson CD. In The Chemistry of Amides, Patai S (ed.). John Wiley: Chichester, 1970; 188.
41. Carey FA, Sundberg RJ. Advanced Organic Chemistry Part A: Structure and Mechanisms, 4th ed. Kluwer Academic/Plenum: New York, London, 2001; 807.
42. Tu Y. Fragmentation of conjugated amides at the C-C(O) bond in electrospray mass spectrometry: a proton bound dimeric intermediate identified by the kinetic method. Rapid Commun. Mass Spectrom. 2004; 18: 1345.
43. Scudder PH. Electron Flow in Organic Chemistry. John Wiley and Sons: Canada, 1992; 123.