Photosensitized generation of hydroxyl radical by eight new sulfur and selenium analogs of psoralen

Journal of Photochemistry and Photobiology B: Biology

Volumn 35, Issue 3, 1996, Pages 221-231

  Collet, M ^a   Hoebeke, M ^a   Piette, J ^a   Jakobs, A ^a   Lindqvist, L ^b   Van De Vorst, A ^a  

^a UNIVERSITY OF LIÈGE   (Belgium)

^b CNRS   (France)

Author keywords

ESR spin trapping; Free radical photogeneration; Furocoumarin analogs

Indexed keywords

2H SELENOLO[3,2 G][1]BENZOPYRAN 2 ONE; 2H SELENOLO[3,2 G][1]BENZOTHIOPYRAN 2 ONE; 2H THIENO[3,2 G][1]BENZOPYRAN 2 ONE; 5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; 7H SELENOLO[3,2 G][1]BENZOSELENOPYRAN 7 ONE; 7H SELENOPYRANO[3,2 F][1]BENZOFURAN 7 ONE; 7H SELENOPYRANO[3,2 F][1]BENZOTHIOPHEN 7 ONE; 7H THIENO[3,2 G][1]BENZOTHIOPYRAN 7 ONE; 7H THIOPYRANO[3,2 F][1]BENZOFURAN 7 ONE; BENZOIC ACID; CYTOCHROME C; FORMIC ACID; HYDROXYL RADICAL; METHOXSALEN; PSORALEN DERIVATIVE; SUPEROXIDE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CONTROLLED STUDY; ELECTRON SPIN RESONANCE; PHOTOCHEMOTHERAPY; PHOTOLYSIS; PHOTOSENSITIZATION; PRIORITY JOURNAL; PUVA; SPECTROPHOTOMETRY;

EID: 0030249490     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1011-1344(96)07298-3     Document Type: Article

References (66)

1. [1] L. Musajo and G. Rodighiero, Mode of photosensitizing action of furocoumarins, in A.C. Giese (ed.), Photophysiology, Vol. VII, Academic Press, New York, 1972, pp. 115-147.
2. [2] J.A. Parrish, R.S. Stern, M.A. Pathak and T.B. Fitzpatrick, Photochemotherapy of skin diseases, in J.D. Regan and J.A. Parrish (eds.), The Science of Photomedicine, Plenum Press, New York, 1982, pp. 595-624.
3. [3] D. Averbeck, Photochem. Photobiol., 50 (1989) 859-882.
4. [4] M.A. Pathak and T.B. Fitzpatrick, J. Photochem. Photobiol. B: Biol., 14 (1992) 3-22.
5. [5] K. Makino, T. Hagiwara and A. Murakami, Int. J. Radiat. Appl. Instrum., Part C, Radiat. Phys. Chem., 37 (1991) 657-665.
6. [6] P.C. Joshi and M.A. Pathak, Biochem. Biophys. Res. Commun., 112 (1983) 638-646.
7. [7] A.Ya. Potapenko, J. Photochem. Photobiol. B: Biol., 9 (1991) 1-33.
8. [8] P. Mullen, M.A. Pathak, J.D. West, T.J. Harrist and F. Dall'Acqua, Natl. Cancer Inst. Monogr., 66 (1984) 205-210.
9. [9] L. Dubertret, D. Averbeck, E. Bisagni, J. Moron, E. Moustacchi, C. Billardon, D. Papadopoulo, S. Nocentini, P. Vigny, J. Blais, R.V. Bensasson, J.C. Ronfard-Haret, E.J. Land, F. Zajdela and R. Latarjet, Biochimie, 67 (1985) 417-422.
10. [10] F. Carlassare, F. Baccichetti, A. Guiotto, P. Rodighiero, O. Gia, A. Capozzi, G. Pastorini and F. Bordin, J. Photochem. Photobiol. B: Biol., 5 (1990) 25-39.
11. [11] E. Sage, L. Trabalzini, A. Capozzi, M.T. Conconi, G. Pastorini, M. Tamaro and F. Bordin, J. Photochem. Photobiol. B: Biol., 9 (1991) 43-59.
12. [12] D. Vedaldi, F. Dall'Acqua, S. Caffieri, F. Baccichetti, F. Carlassare, F. Bordin, A. Chilin and A. Guiotto, Photochem. Photobiol., 53 (1991) 143-148.
13. [13] A. Jakobs, L. Christiaens and M. Renson, Heterocycles, 34 (1992) 1119-1132.
14. [14] A. Jakobs and J. Piette, J. Photochem. Photobiol. B: Biol., 22 (1994) 9-15.
15. [15] A. Seret, J. Piette, A. Jakobs and A. Van de Vorst, Photochem. Photobiol., 56 (1992) 409-412.
16. [16] B. Halliwell and J.M.C. Gutteridge (eds.), Free Radicals in Biology and Medicine (Second Edition), Oxford University Press (Clarendon), Oxford, 1989.
17. [17] K. Reszka, P. Bilski, R.H. Sik and C.F. Chignell, Free Rad. Res. Commun., 19 (1993) S33-S44.
18. [18] G.R. Buettner, in L.W. Oberley (ed.), Superoxide Dismutase, Vol. II, CRC Press, Boca Raton, FL, 1982, pp. 63-81.
19. [19] I. Fridovich, in R.A. Greenwald (ed.), CRC Handbook of Methods for Oxygen Radical Research, CRC Press, Boca Raton, FL, 1986, pp. 121-122.
20. [20] Y. Lion, J. Decuyper, J. Piette and A. Van de Vorst, J. Photochem., 20 (1982) 169-174.
21. [21] S.P. Sanders, S.J. Harrison, P. Kuppusamy, J.T. Sylvester and J.L. Zweier, Free Radic. Biol. Med., 16 (1994) 753-761.
22. [22] M.G. Simic, I.A. Taub, J. Tocci and P.A. Hurwitz, Biochem. Biophys. Res. Commun., 62 (1975) 161-167.
23. [23] J. Butler, W.H. Koppenol and E. Margoliash, J. Biol. Chem., 257 (1982) 10747-10750.
24. [24] W.H. Koppenol, K.J.H. van Buuren, J. Butler and R. Braams, Biochim. Biophys. Acta, 449 (1976) 157-168.
25. [25] J.M. McCord, J.D. Crapo and I. Fridovich, in A.M. Michelson, J.M. McCord and I. Fridovich (eds.), Superoxide and Superoxide Dismutases, Academic Press, New York, 1977, pp. 11-17.
26. [26] M. Sasaki, T. Sakata and M. Sukigara, Chem. Lett., (1977) 701-704.
27. [27] P. Vigny, F. Gaboriau, M. Duquesne, E. Bisagni and D. Averbeck, Photochem. Photobiol., 30 (1979) 557-564.
28. [28] R.V. Bensasson, in R.V. Bensasson, G. Jori, E.J. Land and T.G. Truscott (eds.), Primary Photo-Processes in Biology and Medicine, Plenum Press, New York, 1985, pp. 241-254.
29. [29] K. Makino, M.M. Mossoba and P. Riesz, J. Am. Chem. Soc., 104 (1982) 3537-3539.
30. [30] K. Makino, M.M. Mossoba and P. Riesz, Radiat. Res., 96 (1983) 416-421.
31. [31] K. Makino, M.M. Mossoba and P. Riesz, J. Phys. Chem., 87 (1983) 1369-1377.
32. [32] G.R. Buettner, Free Radic. Biol. Med., 3 (1987) 259-303.
33. [33] E. Finkelstein, G.M. Rosen and E.J. Rauckman, Arch. Biochem. Biophys., 200 (1980) 1-16.
34. [34] J.A. Fee and J.S. Valentine, in A.M. Michelson, J.M. McCord and I. Fridovich (eds.), Superoxide and Superoxide Dismutases, Academic Press, New York, 1977, pp. 19-60.
35. [35] B. Halliwell and J.M.C. Gutteridge, in L. Packer and A.N. Glazer (eds.), Methods in Enzymology, Vol. 186, Academic Press, New York, 1990, pp. 1-85.
36. [36] J.C. Barreto, G.S. Smith, N.H.P. Strobel, P.A. McQuillin and Th.A. Miller, Life Sciences, 56 (1995) 89-96.
37. [37] J. Piette, J. Decuyper, R. Machiroux, C.M. Calberg-Bacq, A. Van de Vorst and Y. Lion, Int. J. Radiat. Biol., 42 (1982) 151-161.
38. [38] I. Kraljic and V.A. Sharpatyi, Photochem. Photobiol., 28 (1978) 583-586.
39. [39] J.B. Feix and B. Kalyanaraman, Arch. Biochem. Biophys., 291 (1991) 43-51.
40. [40] G.R. Buettner and L.W. Oberley, FEBS Lett., 121 (1980) 161-164.
41. [41] W. Kremers and A. Singh, Can. J. Chem., 58 (1980) 1592-1595.
42. [42] I.N. Rodenko, A.N. Osipov, E.P. Lysenko and A.Ya. Potapenko, J. Photochem. Photobiol. B: Biol., 19 (1993) 39-48.
43. [43] C. Ferradini, Biochimie, 68 (1986) 779-785.
44. [44] S. Cannistraro and A. Van de Vorst, Biochim. Biophys. Acta, 476 (1977) 166-177.
45. [45] J. Decuyper, J. Piette and A. Van de Vorst, Arch. Int. Physiol. Biochim., 91 (1983) 471-476.
46. [46] C.N. Knox, E.J. Land and T.G. Truscott, Photochem. Photobiol., 43 (1986) 359-363.
47. [47] E. Finkelstein, G.M. Rosen and E.J. Rauckman, J. Am. Chem. Soc., 102 (1980) 4994-4999.
48. [48] G.R. Buettner and R.P. Mason, in L. Packer and A.N. Glazer (eds.), Methods in Enzymology, Vol. 186, Academic Press, New York, 1990, pp. 127-133.
49. [49] M. Faraggi, A. Carmichael and P. Riesz, Int. J. Radiat. Biol., 46 (1984) 703-713.
50. [50] Farhataziz and A.B. Ross, Natl. Stand. Ref. Data Ser., Natl. Bur. Stand. (US), 59 (1977).
51. [51] L.M. Dorfman and G.E. Adams, Natl. Stand. Ref. Data Ser., Natl. Bur. Stand. (US), 46 (1973).
52. [52] G.R. Buettner and L.W. Oberley, Biochem. Biophys. Res. Commun., 55 (1978) 69-74.
53. [53] S.I. Liochev and I. Fridovich, Free Radic., Biol. Med., 16 (1994) 29-33.
54. [54] W.H. Koppenol, J. Butler and J.W. van Leeuwen, Photochem. Photobiol., 28 (1978) 655-660.
55. [55] G. Czapski and Y.A. Ilan, Photochem. Photobiol., 28 (1978) 651-653.
56. [56] J.D. Spikes and H.M. Swartz, Photochem. Photobiol., 28 (1978) 921-933.
57. [57] J.M.C. Gutteridge, FEBS Lett., (1985) 19-23.
58. [58] R.W. Sloper, T.G. Truscott and E.J. Land, Biochem. Biophys., 29 (1979) 1025-1029.
59. [59] M. Anbar, M. Bambenek and A.B. Ross, Natl. Stand. Ref. Data Ser., Natl. Bur. Stand. (US), 43 (1973).
60. [60] M.G. Simic, in L. Packer and A.N. Glazer (eds.), Methods in Enzymology, Vol. 186, Academic Press, New York, 1990, pp. 89-100.
61. [61] A.B. Ross, Natl. Stand. Ref. Data Ser., Natl. Bur. Stand. (US), 43 suppl. (1975).
62. [62] V. Kasche and L. Lindqvist, Photochem. Photobiol., 4 (1965) 923-933.
63. [63] R.V. Bensasson, O. Chalvet, E.J. Land and J.C. Ronfard-Haret, Photochem. Photobiol., 39 (1984) 287-291.
64. [64] J.C. Ronfard-Haret, D. Averbeck, R.V. Bensasson, E. Bisagni and E.J. Land, Photochem. Photobiol., 35 (1982) 479-489.
65. [65] M.T. Sa E Melo, D. Averbeck, R.V. Bensasson, E.J. Land and C. Salet, Photochem. Photobiol., 30 (1979) 645-651.
66. [66] M. Craw, R.V. Bensasson, J.C. Ronfard-Haret, M.T. Sa E Melo and T.G. Truscott, Photochem. Photobiol., 37 (1983) 611-615.