Electron attachment to antipyretics: Possible implications of their metabolic pathways

Journal of Chemical Physics

Volumn 136, Issue 23, 2012, Pages

  Pshenichnyuk, Stanislav A ^a   Modelli, Alberto ^b  

^a INSTITUTE OF PHYSICS OF MOLECULES AND CRYSTALS   (Russian Federation)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE AGENTS; ANTIPYRETIC AGENT; CYTOCHROME P450; DECAY CHANNELS; DENSITY FUNCTIONAL THEORY CALCULATIONS; DISSOCIATIVE ELECTRON ATTACHMENT; ELECTRON ATTACHMENT; ELECTRON TRANSMISSION; ELECTRON-ACCEPTING; FREE-RADICAL MODEL; GASPHASE; HUMAN ORGANISMS; IN-VIVO; INCIDENT ELECTRONS; LOW ENERGIES; METABOLIC PATHWAYS; NEUTRAL FRAGMENTS; NON-STEROIDAL ANTI-INFLAMMATORY DRUGS; PARACETAMOL; SIDE EFFECT; TOXIC ACTION;

CARBON TETRACHLORIDE; DENSITY FUNCTIONAL THEORY; DRUG INTERACTIONS; DRUG PRODUCTS; ELECTRON ENERGY ANALYZERS; FREE RADICALS; METABOLISM; MOLECULAR ORBITALS; NEGATIVE IONS;

PHOTODISSOCIATION;

ACETYLSALICYLIC ACID; ANTIPYRETIC AGENT; IBUPROFEN; ION; NONSTEROID ANTIINFLAMMATORY AGENT; PARACETAMOL; PHENACETIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON; HUMAN; METABOLISM; QUANTUM THEORY;

ACETAMINOPHEN; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTIPYRETICS; ASPIRIN; ELECTRONS; HUMANS; IBUPROFEN; IONS; METABOLIC NETWORKS AND PATHWAYS; MODELS, MOLECULAR; PHENACETIN; QUANTUM THEORY;

EID: 84863738768     PISSN: 00219606     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.4727854     Document Type: Article

References (108)

1. R. B. Silverman, The Organic Chemistry of Drug Design and Drug Action, 2nd ed. (Elsevier Academic, 2004).
2. G. G. Gibson and P. Skett, Introduction to Drug Metabolism, 3rd ed. (Nelson Thornes, 2001).
3. I. Zamora, L. Afzelius, and G. Cruciani, J. Med. Chem. 46, 2313 (2003). 10.1021/jm021104i
4. A. Rostami-Hodjegan and G. T. Tucker, Nat. Rev. Drug Discovery 6, 140 (2007). 10.1038/nrd2173
5. Y. Low, T. Uehara, Y. Minowa, H. Yamada, Y. Ohno, T. Urushidani, A. Sedykh, E. Muratov, V. Kuz'min, D. Fourches, H. Zhu, I. Rusyn, and A. Tropsha, Chem. Res. Toxicol. 24, 1251 (2011). 10.1021/tx200148a
6. A. Bugrima, T. Nikolskaya, and Y. Nikolsky, Drug Discovery Today 9, 127 (2004). 10.1016/S1359-6446(03)02971-4
7. C. H. Johnson, A. D. Patterson, J. R. Idle, and F. J. Gonzalez, Annu. Rev. Pharmacol. Toxicol. 52, 37 (2012). 10.1146/annurev-pharmtox-010611-134748
8. H. Kitano, Science 295, 1662 (2002). 10.1126/science.1069492
9. W. Weckwerth, Annu. Rev. Plant Biol. 54, 669 (2003). 10.1146/annurev. arplant.54.031902.135014
10. K. Dettmer, P. A. Aronov, and B. D. Hammock, Mass Spectrom. Rev. 26, 51 (2007). 10.1002/mas.20108
11. J. G. Bundy, M. P Davey, and M. R. Viant, Metabolomics 5, 3 (2009). 10.1007/s11306-008-0152-0
12. N. L. Gregory, Nature (London) 212, 1460 (1966). 10.1038/2121460a0
13. J. R. Vane and R. M. Botting, Am. J. Med. 104, 2S (1998). 10.1016/S0002-9343(97)00203-9
14. I. G. Denisov, T. M. Makris, S. G. Sligar, and I. Schlichting, Chem. Rev. 105, 2253 (2005). 10.1021/cr0307143
15. J. Rittle, M. T. Green, Science 330, 933 (2010). 10.1126/science.1193478
16. J. O. Miners and D. J. Birkett, Br. J. Clin. Pharmacol. 45, 525 (1998). 10.1046/j.1365-2125.1998.00721.x
17. I. C. Gunsalus, T. C. Pederson, and S. G. Sligar, Annu. Rev. Biochem. 44, 377 (1975). 10.1146/annurev.bi.44.070175.002113
18. J. T. Groves, Proc. Natl. Acad. Sci. U.S.A. 100, 3569 (2003). 10.1073/pnas.0830019100
19. P. R. Ortiz de Montellano, Chem. Rev. 110, 932 (2010). 10.1021/cr9002193
20. B. Meunier, S. P. de Visser, and S. Shaik, Chem. Rev. 104, 3947 (2004). 10.1021/cr020443g
21. R. Bernhardt, Encyclopedia Biol. Chem. 1, 544 (2004). 10.1016/B0-12-443710-9/00143-5
22. J. M. Saveant, Acc. Chem. Res. 26, 455 (1993). 10.1021/ar00033a001
23. F. Maran and M. S. Workentin, Electrochem. Soc. Interface 11, 44 (2002).
24. S. Antonello and F. Maran, Chem. Soc. Rev. 34, 418 (2005). 10.1039/b300085k
25. L. Sanche and G. J. Schulz, Phys. Rev. A 5, 1672 (1972). 10.1103/PhysRevA.5.1672
26. G. J. Schulz, Rev. Mod. Phys. 45, 378, 423 (1973). 10.1103/RevModPhys.45. 423
27. E. Illenberger and J. Momigny, Gaseous Molecular Ions. An Introduction to Elementary Processes Induced by Ionization (Steinkopff Verlag/Springer-Verlag, Darmstadt/New York, 1992).
28. P. Kovacic and R. Somanathan, Rev. Environ. Contam. Toxicol. 203, 119 (2010). 10.1007/978-1-4419-1352-4-4
29. P. Kovacic and R. Somanathan, Rev. Environ. Contam. Toxicol. 201, 41 (2009). 10.1007/978-1-4419-0032-6-2
30. P. Kovacic and L. E. Becvar, Curr. Pharm. Des. 6, 143 (2000). 10.2174/1381612003401046
31. P. Kovacic, Curr. Med. Chem. 10, 2705 (2003). 10.2174/0929867033456314
32. P. Kovacic and A. L. Cooksy, Med. Hypotheses 64, 357 (2005). 10.1016/j.mehy.2004.07.021
33. J. E. Biaglow, Radiat. Res. 86, 212 (1981). 10.2307/3575502
34. K. M. Ervin, I. Anusiewicz, P. Skurski, J. Simons, and W. C. Lineberger, J. Phys. Chem. A 107, 8521 (2003). 10.1021/jp0357323
35. R. O. Recknagel, E. A. Glende Jr., J. A. Dolak, and R. L. Waller, Pharmacol. Ther. 43, 139 (1989). 10.1016/0163-7258(89)90050-8
36. W. J. Brattin, E. A. Glende Jr., and R. O. Recknagel, J. Free Radic. Biol. Med. 1, 27 (1985). 10.1016/0748-5514(85)90026-1
37. M. K. Manibusan, M. Odin, and D. A. Eastmond, J. Environ. Sci. Health [C] 25, 185 (2007). 10.1080/10590500701569398
38. T. F. Slater, K. H. Cheeseman, K. U. Ingold, C. Rice-Evans, and H. Sies, Philos. Trans. R. Soc. London, Ser. B 311, 633 (1985). 10.1098/rstb.1985.0169
39. A. Bauer, A. Schumann, M. Gilbert, C. Wilhelm, J. G. Hengstler, J. Schiller, and B. Fuchs, Chem. Phys. Lipids 159, 21 (2009). 10.1016/j. chemphyslip.2009.02.006
40. M. Boll, L. W. Weber, E. Becker, and A. Stampfl, Z Naturforsch. C 56, 111 (2001).
41. G. Poli, E. Albano, and M. U. Dianzani, Chem. Phys. Lipids 45, 117 (1987). 10.1016/0009-3084(87)90063-6
42. K. D. Rainsford, Am. J. Med. 107, 27 (1999). 10.1016/S0002-9343(99)00365- 4
43. S. M. Hall, J. R. Soc. Med. 79, 596 (1986).
44. J. F. T. Glasgow and B. Middleton, Arch. Dis. Child 85, 351 (2001). 10.1136/adc.85.5.351
45. C. L. Sheen, J. F. Dillon, D. N. Bateman, K. J. Simpson, and T. M. Macdonald, Q. J. Med. 95, 609 (2002). 10.1093/qjmed/95.9.609
46. L. P. James, P. R. Mayeux, and J. A. Hinson, Drug Metab. Dispos. 31, 1499 (2003). 10.1124/dmd.31.12.1499
47. E. M. Boyd, Toxicol. Appl. Pharmacol. 1, 240 (1959). 10.1016/0041- 008X(59)90108-5
48. S. Johansson and L. Angervall, Science 204, 130 (1979). 10.1126/science.204.4389.130
49. J. M. Peters, H. Morishima, J. M. Ward, C. J. Coakley, S. Kimura, and F. J. Gonzalez, Toxicol. Sci. 50, 82 (1999). 10.1093/toxsci/50.1.82
50. L. F. Prescott, Br. J. Clin. Pharmacol. 10, 291S (1980).
51. G. J. Mulder, F. F. Kadlubar, J. B. Mays, and J. A. Hinson, Mol. Pharmacol. 26, 342 (1984).
52. D. Casper, U. Yaparpalvi, N. Rempel, and P. Werner, Neurosci. Lett. 289, 201 (2000). 10.1016/S0304-3940(00)01294-5
53. E. E. Öker, L. Hermann, C. R. Baum, K. M. Fentzke, T. Sigg, and J. B. Leikin, Acad. Emerg. Med. 7, 821 (2000). 10.1111/j.1553-2712.2000.tb02278.x
54. K. A. K. Musa and L. A. Eriksson, J. Phys. Chem. B 111, 13345 (2007). 10.1021/jp076553e
55. R. Bernhardt, Rev. Physiol. Biochem. Pharmacol. 127, 137 (1996). 10.1007/BFb0048262
56. P. R. Ortiz de Montellano, and M. A. Correia, Annu. Rev. Pharmacol. Toxicol. 23, 481 (1983). 10.1146/annurev.pa.23.040183.002405
57. A. Modelli, D. Jones, and G. Distefano, Chem. Phys. Lett. 86, 434 (1982). 10.1016/0009-2614(82)83539-2
58. A. Modelli, A. Foffani, F. Scagnolari, and D. Jones, Chem. Phys. Lett. 163, 269 (1989). 10.1016/0009-2614(89)80048-X
59. V. I. Khvostenko, Negative Ion Mass Spectrometry in Organic Chemistry (Nauka, Moscow, 1981) (in Russian).
60. S. A. Pshenichnyuk and N. L. Asfandiarov, Eur. J. Mass Spectrom. 10, 477 (2004). 10.1255/ejms.650
61. M. J. Frisch, G. W. Trucks, H. B. Schlegel, GAUSSIAN 09, Revision A.02, Gaussian, Inc., Wallingford, CT, 2009.
62. A. D. Becke, J. Chem. Phys. 98, 5648 (1993). 10.1063/1.464913
63. T. Koopmans, Physica 1, 104 (1934). 10.1016/S0031-8914(34)90011-2
64. J. Simons and K. D. Jordan, Chem. Rev. 87, 535 (1987). 10.1021/cr00079a004
65. S. W. Staley and J. T. Strnad, J. Phys. Chem. 98, 116 (1994). 10.1021/j100052a020
66. D. A. Chen and G. A. Gallup, J. Chem. Phys. 93, 8893 (1990). 10.1063/1.459228
67. A. Modelli, Phys. Chem. Chem. Phys. 5, 2923 (2003). 10.1039/b304083f
68. A. M. Scheer and P. D. Burrow, J. Phys. Chem. B 110, 17751 (2006). 10.1021/jp0628784
69. J. M. Beames and A. J. Hudson, Phys. Chem. Chem. Phys. 12, 4157 (2010). 10.1039/b923202h
70. Y. Danten, T. Tassaing, and M. Besnard, J. Phys. Chem. A 100, 8986 (2006). 10.1021/jp061845l
71. R. Glaser, J. Org. Chem. 66, 771 (2001). 10.1021/jo001241s
72. A. Choudhary, K. J. Kamer, and R. T. Raines, J. Org. Chem. 76, 7933 (2011). 10.1021/jo201389d
73. A. Modelli, Trends Chem. Phys. 6, 57 (1997).
74. S. A. Pshenichnyuk, A. S. Vorob'ev, and A. Modelli, J. Chem. Phys. 135, 1843011 (2011). 10.1063/1.3658372
75. S. A. Pshenichnyuk and A. Modelli, Int. J. Mass Spectrom. 294, 93 (2010). 10.1016/j.ijms.2010.05.025
76. See supplementary material at http://dx.doi.org/10.1063/1.4727854 E-JCPSA6-136-039223 for currents of mass-selected negative ions formed by DEA to I and II with low relative intensity as well as metastable ions detected in I.
77. C. C. Moser, J. M. Keske, K. Warncke, R. S. Farid, and P. L. Dutton, Nature (London) 355, 796 (1992). 10.1038/355796a0
78. P. Kebarle, S. Chowdhury, Chem. Rev. 87, 513 (1987). 10.1021/cr00079a003
79. P. F. Barbara, T. J. Meyer, and M. A. Rather, J. Phys. Chem. 100, 13148 (1996). 10.1021/jp9605663
80. L. G. Christophorou and D. Hadjiantoniou, Chem. Phys. Lett. 419, 405 (2006). 10.1016/j.cplett.2005.11.095
81. S. A. Pshenichnyuk and A. S. Komolov, J. Phys. Chem. A 116, 761 (2012). 10.1021/jp210224j
82. K. Aflatooni and P. D. Burrow, J. Chem. Phys. 113, 1455 (2000). 10.1063/1.481963
83. A. J. Hutt, J. Caldwell, and R. L. Smith, Xenobiotica 16, 239 (1986). 10.3109/00498258609043527
84. J. R. Vane and R. M. Botting, Thromb. Res. 110, 255 (2003). 10.1016/S0049-3848(03)00379-7
85. M. Grootveld and B. Halliwell, Biochem. Pharmacol. 37, 271 (1988). 10.1016/0006-2952(88)90729-0
86. H. M. Girvan, D. J. Heyes, N. S. Scrutton, and A. W. Munro, J. Am. Chem. Soc. 129, 6647 (2007). 10.1021/ja071355m
87. M. E. Ener, Y.-T. Lee, J. R. Winkler, H. B. Gray, and L. Cheruzel, Proc. Natl. Acad. Sci. U.S.A. 107, 18783 (2010). 10.1073/pnas.1012381107
88. D. R. Green and G. Kroemer, Science 305, 626 (2004). 10.1126/science. 1099320
89. L. C. Trost and J. J. Lemasters, J. Pharmacol. Exp. Ther. 278, 1000 (1996).
90. S. Somasundaram, G. Sigthorsson, R. J. Simpson, J. Watts, M. Jacob, I. A. Tavares, S. Rafi, A. Roseth, R. Foster, A. B. Price, J. M. Wrigglesworth, and I. Bjarnason, Aliment. Pharmacol. Ther. 14, 639 (2000). 10.1046/j.1365-2036. 2000.00723.x
91. I. Hanukoglu, R. Rapoport, L. Weiner, and D. Sklan, Arch. Biochem. Biophys. 305, 489 (1993). 10.1006/abbi.1993.1452
92. C.-S. Chen, W.-R. Shieh, P.-H. Lu, S. Harriman, and C.-Yu. Chen, Biochim. Biophys. Acta 1078, 411 (1991). 10.1016/0167-4838(91)90164-U
93. K. E. Bizovi, " Acetaminophen.," in Goldfrank's Manual of Toxicologic Emergencies, edited by, R. S. Hoffman, L. S. Nelson, M. A. Howland, N. A. Lewin, N. E. Flomenbaum, and, L. R. Goldfrank, (McGraw-Hill, 2007), Chap. 34.
94. E. D. Högestätt, B. A. G. Jönsson, A. Ermund, D. A. Andersson, H. Björk, J. P. Alexander, B. F. Cravatt, A. I. Basbaum, and P. M. Zygmunt, J. Biol. Chem. 280, 31405 (2005). 10.1074/jbc.M501489200
95. B. Hinz and K. Brune, Ann. Rheum. Dis. 71, 20 (2012). 10.1136/ard.2011.200087
96. G. G. Graham and K. F. Scott, Am. J. Ther. 12, 46 (2005). 10.1097/00045391-200501000-00008
97. D. A. Andersson, C. Gentry, L. Alenmyr, D. Killander, S. E. Lewis, A. Andersson, B. Bucher, J.-L. Galzi, O. Sterner, S. Bevan, E. D. Högestätt, and P. M. Zygmunt, Nature Commun. 2, 551 (2011). 10.1038/ncomms1559
98. H. Dong, R. L. Haining, K. E. Thummel, A. E. Rettie, and S. D. Nelson, Drug Metab. Dispos. 28, 1397 (2000).
99. D. C. Dahlin, G. T. Miwa, A. Y. Lu, and S. D. Nelson, Proc. Natl. Acad. Sci. U.S.A. 81, 1327 (1984). 10.1073/pnas.81.5.1327
100. M. Weis, G. E. N. Kass, S. Orrenius, and P. Moldeus, J. Biol. Chem. 267, 804 (1992).
101. J. A. Hinson, Environ. Health Perspect. 49, 71 (1983). 10.1289/ehp.834971
102. N. K. Hayward and M. F. Lavin, Xenobiotica 17, 115 (1987). 10.3109/00498258709047181
103. D. Djukovic, E. Appiah-Amponsah, N. Shanaiah, G. A. N. Gowda, I. Henry, M. Everly, B. Tobias, and D. Raftery, J. Pharm. Biomed. Anal. 47, 328 (2008). 10.1016/j.jpba.2007.12.035
104. M. A. Hamman, G. A. Thompson, and S. D. Hall, Biochem. Pharmacol. 54, 33 (1997). 10.1016/S0006-2952(97)00143-3
105. T. Bergner and B. Przybilla, J. Am. Acad. Dermatol. 26, 114 (1992). 10.1016/0190-9622(92)70018-B
106. Y. Liu, G. Fiskum, and D. Schubert, J. Neurochem. 80, 780 (2002). 10.1046/j.0022-3042.2002.00744.x
107. M. Reth, Nat. Immunol. 3, 1129 (2002). 10.1038/ni1202-1129
108. M. D. Maines, Annu. Rev. Pharmacol. Toxicol. 37, 517 (1997). 10.1146/annurev.pharmtox.37.1.517