Water-soluble naphthalene derivatives as singlet oxygen (1O2, 1Δ(g)) carriers for biological media

Journal of Photochemistry and Photobiology B: Biology

Volumn 36, Issue 1, 1996, Pages 31-39

  Pierlot, C ^a   Hajjam, S ^a   Barthelemy C ^b   Aubry, J M ^a  

^a UNIV LILLE   (France)

^b Lab Pharm Galenique Biopharmacie   (France)

Author keywords

Naphthalene endoperoxides; Singlet oxygen; Singlet oxygen carriers

Indexed keywords

ENDOPEROXIDE; NAPHTHALENE DERIVATIVE; PHOTOSENSITIZING AGENT; SINGLET OXYGEN;

ARTICLE; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; DECOMPOSITION; DRUG DIFFUSION; DRUG SOLUBILITY; DRUG SYNTHESIS; HALF LIFE TIME; LIPID MEMBRANE; OXIDATION; PHOTOCHEMISTRY; PHOTOLYSIS; PRIORITY JOURNAL;

EID: 0030266005     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1011-1344(96)07324-1     Document Type: Article

References (49)

1. [1] J.-M. Aubry, New chemical sources of singlet oxygen, in C. Vigo-Pelfrey (ed.), Membrane Lipid Oxidation, Vol. 2, CRC Press, Boca Raton, FL, 1991, pp. 65-102.
2. [2] H. Wassermann and R.W. Murray (eds.), Singlet Oxygen, Academic Press, New York, 1979, pp. 115-138.
3. [3] C.S. Foote, Science, 162 (1968) 963-970.
4. [4] R.C. Straight and J.D. Spikes, Photosensitized oxidation of biomolecules, in A.A. Frimer (ed.), Singlet Oxygen, Vol. 4, CRC Press, Boca Raton, FL, 1985, pp. 91-143.
5. [5] K. Inoue, T. Matsuura and I. Saito, Bull. Chem. Soc. Jpn., 35 (1982) 2959-2964.
6. [6] J.D. Spikes and R. Livingstone, Advn. Radiat. Biol., 3 (1969) 29-121.
7. [7] P. Reusser, Int. Z. Viamin Forsch., 40 (1970) 64.
8. [8] A.W. Girotti, Photochem. Photobiol., 51 (1990) 497-509.
9. [9] T.P.A. Devasagayam, S. Steenken, M.S.W. Obendorf, W.A. Schulz and H. Sies, Biochem., 30 (1991) 6283-6589.
10. [10] J.T. Lutgerink, E. Van den Akker, I. Smeets, P. Van Dyk, J.M. Aubry, H. Joenje, M.V.H. Lafleur and J. Retel, Mutation Research, 275 (1992) 377-386.
11. [11] J. Piette, J. Photochem. Photobiol. B: Biol., 11 (1991) 241-260.
12. [12] T. Patrice, M.T. Foultier, S. Yactayo, M.C. Douet, F. Maloisel and L. Le Bodic, Photochem. Photobiol. B: Biol., 6 (1990) 157-165.
13. [13] J. North, H. Neyndorff and J.G. Levy, Photochem. Photobiol. B: Biol., 17 (1993) 99-108.
14. [14] R.W. Midden and M.L. Kaplan, J. Am. Chem. Soc., 103 (1983) 4129-4135.
15. [15] C. Moureu, C. Dufraisse and P.M. Dean, C.R. Acad. Sci., 182 (1926) 1584-1587.
16. [16] C. Moureu, C. Dufraisse and C.L. Butler, C.R. Acad. Sci., 183 (1926) 101-105.
17. [17] C. Dufraisse and N. Drisch, C.R. Acad. Sci., 194 (1932) 99-101.
18. [18] C. Dufraisse and L. Velluz, Bull. Soc. Chim. Fr., (1936) 254-265.
19. [19] J. Rigaudy, Personal communication.
20. [20] J.M. Aubry, Capture de l'oxygène singulet en solution aqueuse, Thèse de Doctorat d'Etat, Université de Paris VI, 1992.
21. [21] J.M. Aubry, J. Rigaudy and K.C. Nguyen, Photochem. Photobiol., 33 (1981) 149-158.
22. [22] I. Saito, T. Matsuura and K. Inoue, J. Am. Chem. Soc., 103 (1981) 188-190.
23. [23] I. Saito, T. Matsuura and K. Inoue, J. Am. Chem. Soc., 105 (1983) 3200-3206.
24. [24] A.W. Nieuwint, J.M. Aubry, F. Arwert, H. Kortbeek, S. Hertzberg and H. Joenje, Free Rad. Res. Commun., I (1985) 1-9.
25. [25] L.F. Fieser and M.D. Gates, J. Am. Chem. Soc., 62 (1940) 2335-2338.
26. [26] C.S. Marvel and B.D. Wilson, J. Org. Chem., 23 (1958) 1483-1486.
27. [27] R. Saint-Jean and P. Canonne, Bull. Soc. Chim. Fr., 9 (1971) 3330-3335.
28. [28] G. Lock and E. Walter, Chem. Ber., 75B (1942) 1158-1163.
29. [29] G. Lock and R. Schneider, Chem. Ber., 91 (1958) 1770-1774.
30. [30] C. Vever-Bizet, M. Dellinger, D. Brault, M. Rougée and R.V. Bensasson, Photochem. Photobiol., 5 (1989) 321-325.
31. [31] M.A.J. Rodgers and P.T. Snowden, J. Am. Chem. Soc., 104 (1982) 5541-5543.
32. [32] E.F. Kiefer, J. Med. Chem., 15 (1972) 214.
33. [33] S.V. Kessar, P. Jit, K.P. Mundra and A.K. Lumb, J. Chem. Soc., 2 (1971) 266-269.
34. [34] J.M. Aubry, J. Am. Chem. Soc., 107 (1985) 5844-5849.
35. [35] J.M. Aubry, B. Cazin and F. Duprat, J. Org. Chem., 54 (1989) 726-728.
36. [36] N.J. Turro, M.F. Chow and R. Rigaudy, J. Am. Chem. Soc., 103 (1981) 7218-7224.
37. [37] J.M. Aubry, M. Rougée and R.V. Bensasson, Communication à la Soc. Fr. Photobiol., 23-24 Nov. 1989 à Paris.
38. [38] C. Barthélémy, C. Lefèbvre and A.M. Guyot-Hermann, Il Farmaco, 41 (1986) 363-376.
39. [39] C. Barthélémy, C. Lefèbvre and A.M. Guyot-Hermann, Chimicaoggi, 11 (1987) 15-21.
40. [40] C. Barthélémy, A.M. Guyot-Hermann, J. Ringard, J.L. Parier and C. Ringard-Lefèbvre, Eur. J. Drug. Metab. Pharmacokinet., 3 (1991) 433-440.
41. [41] H.W. Dibbern and G.H. Scholz, Arzeineimittel-Forschung (Drug Research), 19 (1969) 1140-1145.
42. [42] A.A. Gorman, M.A.J. Rodgers, in J.C. Scaiano (ed.), Singlet Oxygen in Handbook of Organic Photochemistry, Vol. 2, CRC Press, Boca Raton, 1989.
43. [43] J.M. Aubry, B. Mandard-Cazin, M. Rougée and R.V. Bensasson, J. Am. Chem. Soc., 117 (1995) 9159-9164.
44. [44] B. Cazin, J.M. Aubry and J. Rigaudy, J. Chem. Soc., Chem. Commun., (1986) 951-954.
45. [45] W. Adam and M. Prein, J. Am. Chem. Soc., 115 (1993) 3766-3767.
46. [46] F. Wilkinson and J.G. Brummer, J. Phys. Chem. Ref. Data, 24 (1995) 663-1021.
47. [47] W. Drews, R. Schmidt and H.D. Brauer, J. Photochem., 6 (1976, 1977) 391-403.
48. [48] J.M. Aubry, Photochem. Photobiol., 33 (1980) 155-158.
49. [49] P.A. Shore, B.B. Brodie and C.A.M. Hogben, J. Pharm. Expt. Therap., 119 (1957) 361-373.