Towards a molecular-level understanding of the reactivity differences for radical anions of juglone and plumbagin: An electrochemical and spectroelectrochemical approach

Organic and Biomolecular Chemistry

Volumn 7, Issue 9, 2009, Pages 1896-1903

  Hernández Muñoz, Lindsay S ^a   Gómez, Martín ^b   González, Felipe J ^a   González, Ignacio ^c   Frontana, Carlos ^a,d  

^a DEPARTAMENTO DE FÍSICA   (Mexico)

^b DEPARTAMENTO DE SISTEMAS BIOLÓGICOS   (Mexico)

^c DEPARTAMENTO DE QUÍMICA   (Mexico)

^d CENTRO DE INVESTIGACIÓN Y DESARROLLO TECNOLÓGICO EN ELECTROQUÍMICA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIC; ELECTRON SPIN RESONANCE MEASUREMENTS; IN-SITU; JUGLONE; MOLECULAR LEVELS; NAPHTHOQUINONE; OH GROUPS; PLUMBAGIN; RADICAL ANIONS; SEMIQUINONE; SEMIQUINONE SPECIES; SPECTROELECTROCHEMICAL; STABLE RADICALS;

DIMETHYL SULFOXIDE; FREE RADICAL REACTIONS; KETONES; NEGATIVE IONS; PROTONATION; SPECTROELECTROCHEMISTRY; SPIN DYNAMICS;

CYCLIC VOLTAMMETRY;

ANION; DIMETHYL SULFOXIDE; FREE RADICAL; JUGLONE; NAPHTHOQUINONE; PLUMBAGIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMICAL ANALYSIS; ELECTRON SPIN RESONANCE; OXIDATION REDUCTION REACTION;

ANIONS; DIMETHYL SULFOXIDE; ELECTROCHEMICAL TECHNIQUES; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; MOLECULAR STRUCTURE; NAPHTHOQUINONES; OXIDATION-REDUCTION;

EID: 64549122372     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b822684a     Document Type: Article

References (68)

1. G. L. McNew Bull. Torrey Bot. Club. 1950 77 294 297
2. T. J. Monks D. C. Jones Curr. Drug. Metab. 2002 3 425 438
3. Z. F. Plyta T. Li V. P. Papageorgiou A. S. Mellidis A. S. A. N. Assimopoulou E. N. Pitsinos E. A. Couladouros Bioorg. Med. Chem. Lett. 1998 8 3385 3390
4. V. P. Papageorgiou A. N. Assimopoulou E. A. Couladouros D. Hepworth K. C. Nicolaou Angew. Chem., Int. Ed. 1999 38 271 300
5. J. Grolig and R. Wagner, Naphthoquinones, in: Ullmann's Encyclopedia of Industrial Chemistry, Germany, Wiley-VCH Verlag GmbH & Co, 2005, vol. 22, pp. 471, 10.1002/14356007.a17-067
6. M. Shi E. Gozal H. A. Choy H. J. Forman Free Radic. Biol. Med. 1993 15 57 67
7. H. S. Schwartz P. M. Kanter Cancer Treatment Reports 1979 63 821 825
8. F. Arcamone Cancer Research 1985 45 5995 5999
9. P. F. Conte Bull. Cancer 1993 80 152 155
10. R. S. Teixeira C. J. Valduga L. A. Benvenutti S. Schreier R. C. Maranhao J. Pharm. Pharmacol. 2008 60 1287 1295
11. P. Tardi S. Johnstone N. Harasym S. Xie T. Harasym N. Zisman P. Harvie D. Bermudes L. Mayer Leukemia Res. 2009 33 129 139
12. E. M. Perchellet M. J. Magill X. Huang D. M. Dalke D. H. Hua J. P. Perchellet Anti-Cancer Drugs 2000 11 339 352
13. T. Fukushima Y. Kawai T. Nakayama T. Yamauchi A. Yoshida Y. Urasaki S. Imamura K.-I. Kamiya H. Tsutani T. Ueda T. Nakamura Oncol. Res. 1996 8 95 100
14. S. H. Kim and H. J. Lee, Repub. Korean Kongkae Taeho Kongbo 2006, CODEN: KRXXA7 KR 2006007967 A 20060126 CAN 145:403976 AN 2006:1034723
15. Y. Chung Y.-K. Shin C.-G. Zhan S. Lee H. Cho Arch. Pharmac. Res. 2004 27 893 900
16. O. Moullet J. L. Dreyer Biochem. J. 1994 300 99 106
17. N. Gokhale S. Padhye C. Newton R. Pritchard Metal-Based Drugs 2000 7 121 128
18. A. Chichirau M. Flueraru L. L. Chepelev J. S. Wright W. G. Willmore T. Durst H. H. Hussain M. Charron Free Radic. Biol. Med. 2005 38 344 355
19. H. Babich A. Stern J. Appl. Toxicol. 1993 13 353 358
20. K. Ollinger A. Brunmark J. Biol. Chem. 1991 266 21496 21503
21. M. Y. Lim J. H. Jeon E. Y. Jeong C. H. Lee H. S. Lee Food Chem. 2006 100 1254 1258
22. T. W. Schultz A. P. Bearden Bull. Environ. Contam. Toxicol. 1998 61 405 410
23. P. J. O'Brien Chem.-Biol. Interact. 1991 80 1 41
24. J. J. Inbaraj C. F. Chignell Chem. Res. Toxicol. 2004 17 55 62
25. G. Tudor P. Gutierrez A. Aguilera-Gutierrez E. A. Sausville Biochem. Pharmacol. 2003 65 1061 1075
26. M. Aguilar-Martinez J. A. Bautista-Martinez N. Macias-Ruvalcaba I. Gonzalez E. Tovar T. Marin, del Alizal O. Collera G. Cuevas J. Org. Chem. 2001 66 8349 8363
27. M. Gómez F. J. González I. González J. Electrochem. Soc. 2003 150 E527 E534
28. M. Aguilar-Martínez N. A. Macías-Ruvalcaba J. A. Bautista-Martínez M. Gómez F. J. González I. González Curr. Org. Chem. 2004 8 1721 1738
29. M. Gómez F. J. González I. González J. Electroanal. Chem. 2005 578 193 202
30. C. Frontana I. González J. Braz. Chem. Soc. 2005 16 299 307
31. P. D. Astudillo J. Tiburcio F. J. Gonzalez J. Electroanal. Chem. 2007 604 57 64
32. C. Frontana I. González J. Electroanal. Chem. 2007 603 155 165
33. C. F. Chignell R. H. Sik Free Radic. Biol. Med. 2003 34 1029 1034
34. E. de Castro S. H. de Castro T. E. Johnson Free Radic. Biol. Med. 2004 37 139 145
35. R. V. Satyanarayana Rao G. T. Gujar Entomol. Exp. Appl. 1995 77 189 192
36. R. Munday C. M. Munday Planta Medica. 2000 66 399 402
37. L. Miseviciene Z. Anusevicius J. Sarlauskas R. J. Harris N. S. Scrutton N. Cenas Acta Biochim. Pol. 2007 54 379 385
38. D. A. Wright R. Dawson S. J. Cutler H. G. Cutler C. E. Orano-Dawson E. Graneli Water Res. 2007 41 1294 1302
39. D. M. Hernandez M. A. B. F. de Moura D. P. Valencia F. J. Gonzalez I. Gonzalez F. C. de Abreu E. N. da Silva Junior V. F. Ferreira A. Ventura, Pinto M. O. F. Goulart C. Frontana Org. Biomol. Chem. 2008 6 3414 3420
40. J. A. Morales-Morales C. Frontana M. Aguilar-Martínez J. A. Bautista-Martínez F. J. Gonzalez I. Gonzalez J. Phys. Chem. A. 2007 111 8993 9002
41. J. M. Savéant, Elements, of Molecular and Biomolecular Electrochemistry: An Electrochemical Approach to Electron Transfer Chemistry, New Jersey, Wiley Interscience, 2006
42. G. Gritzner J. Küta Pure Appl. Chem. 1984 4 461 466
43. J. D. Head M. C. Zerner Chem. Phys Lett. 1985 122 264 270
44. J. D. Head M. C. Zerner Chem. Phys. Lett. 1986 131 359 366
45. M. S. Khan Z. H. Khan Spectrochim. Acta A 2005 61 777 790
46. A. Capon R. J. Parsons J. Electroanal. Chem. 1973 46 215 222
47. J. Q. Chambers, Electrochemistry of quinones, in The Chemistry of Quinonoid Compounds, part 2, ed., S. Patai, John Wiley & Sons, London, 1974, pp. 737-791
48. L. P. Hammett J. Am. Chem. Soc. 1937 59 96 103
49. C. Hansch A. Leo R. W. Taft Chem. Rev. 1991 91 165 195
50. P. Zuman, Substituent, Effects in Organic Polarography, Plenum Press, New York, 1967
51. H. M. McConnell J. Chem. Phys. 1956 24 764 766
52. H. M. McConnell D. B. Chesnut J. Chem. Phys. 1958 28 107 117
53. J. A. Weil, J. R. Bolton, Electron Paramagnetic Resonance: Elementary Theory and Practical Applications, Wiley-Interscience, New Jersey, 2007
54. F. J. González J. M. Aceves R. Miranda I. González J. Electroanal. Chem. 1991 310 293 303
55. C. Amatore G. Capobianco G. Farnia G. Sandoná J. M. Saveánt M. G. Severin E. Vianello J. Am. Chem. Soc. 1985 107 1815 1824
56. B. Speiser A. Rieker J. Chem. Res. 1977 314 315
57. B. Speiser A. Rieker J. Electroanal. Chem. 1979 102 373 395
58. B. Speiser A. Rieker J. Electroanal. Chem. 1980 110 231 246
59. J. A. Richards D. H. Evans J. Electroanal. Chem. 1977 81 171 187
60. J. Mukherhee Radiat. Phys. Chem. 1987 29 455 462
61. M. Rudolph J. Electroanal. Chem. 2003 543 23 39
62. M. Rudolph J. Electroanal. Chem. 2004 571 289 307
63. M. Rudolph J. Electroanal. Chem. 2003 558 171 176
64. M. Rudolph J. Comp. Chem. 2005 26 619 632
65. M. Rudolph J. Comp. Chem. 2005 26 633 641
66. M. Rudolph J. Comp. Chem. 2005 26 1193 1204
67. D. F. Evans G. Pye R. Bramley A. G. Clark T. J. Dyson J. D. Hardcastle Gut. 1988 29 1035 1041
68. J. Fallingborg L. A. Christensen M. Ingeman-Nielsen B. A. Jacobsen K. Abildgaard H. H. Rasmussen S. N. Rasmussen J. Pediatr. Gastroenterol. Nutr. 1990 11 211 214