DNA photocleavage by porphyrin-polyamine conjugates

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 2, 2009, Pages 767-776

  Garcia, Guillaume ^a   Sarrazy, Vincent ^a   Sol, Vincent ^a   Morvan, Caroline Le ^a   Granet, Robert ^a   Alves, Sandra ^b   Krausz, Pierre ^a  

^a UNIVERSITÉ DE LIMOGES   (France)

^b SORBONNE UNIVERSITÉ   (France)

Author keywords

DNA photocleavage; Polyamines; Porphyrin; Singlet oxygen

Indexed keywords

HYDROXYL RADICAL; MANNITOL; PLASMID DNA; POLYAMINE; PORPHYRIN; PORPHYRIN POLYAMINE CONJUGATE; SINGLET OXYGEN; SPERMIDINE; SPERMINE; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATION; DNA BINDING; MASS SPECTROMETRY; NONHUMAN; PARTITION COEFFICIENT; PHOTOSENSITIZATION; PHOTOTHERAPY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROSCOPY;

ANIMALS; DNA; DNA CLEAVAGE; PHOTOCHEMISTRY; PHOTOTHERAPY; POLYAMINES; PORPHYRINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 58549090878     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.11.047     Document Type: Article

References (57)

1. Dougherty T.J., Gomer C.J., Henderson B.W., Jori G., Kessel D., Korbelik M., Moan J., and Peng Q. J. Natl. Cancer Inst. 90 (1998) 889-905
2. Sternberg E.D., Dolphin D., and Brückner C. Tetrahedron 54 (1998) 4151-4202
3. MacDonald I.J., and Dougherty T.J. J. Porphyrins Phthalocyanines 5 (2001) 105-129
4. Moan J., and Peng Q. Anticancer Res. 23 (2003) 3591-3600
5. Kessel D. Photodiag. Photodyn. Ther. 1 (2004) 3-7
6. Ochsner M. J. Photochem. Photobiol., B 39 (1997) 1-18
7. DeRosa M.C., and Crutchley R.J. Coord. Chem. Rev. 233-234 (2002) 351-371
8. Momenteau M., De Belinay M.-A., Maillard P., Carrez D., and Croisy A. J. Biomed. Opt. 4 (1999) 298-318
9. Schell C., and Hombrecher H.K. Chem. Eur. J. (1999) 587-597
10. Zheng G., Graham A., Shibata M., Missert J.R., Oseroff A.R., Dougherty T.J., and Pandey R.K. J. Org. Chem. 66 (2001) 8709-8716
11. Milanesio M.E., Morán F.S., Yslas E.I., Alvarez M.G., Rivarola V., and Durantini E.N. Bioorg. Med. Chem. (2001) 1943-1949
12. Chen X., Hui L., Foster D.A., and Drain C.M. Biochemistry 43 (2004) 10918-10929
13. Tomé J.P.C., Neves M.G.P.M.S., Tomé A.C., Cavaleiro J.A.S., Mendonça A.F., Pedago I.N., Duarte R., and Valdeira M.L. Bioorg. Med. Chem. 13 (2005) 3878-3888
14. Laville I., Pigaglio S., Blais J.C., Doz F., Loock B., Maillard P., Grierson D.S., and Blais J. J. Med. Chem. 49 (2006) 2558-2567
15. Borbas K.E., Mroz P., Hamblin M.R., and Lindsey J.S. Bioconjug. Chem. 17 (2006) 638-653
16. Frochot C., Di Stasio B., Vanderesse R., Belgy M.J., Dodeller M., Guillemin F., Viriot M.L., and Barberi-Heyob M. Bioorg. Chem. 35 (2007) 205-220
17. Casero Jr. R.A., and Woster P.M. J. Med. Chem. 44 (2001) 1-26 and references cited therein
18. Cullis P.M., Green R.E., Merson-Davies L., and Travis N. Chem. Biol. 6 (1999) 717-729
19. Carlisle D.L., Devereux W.L., Hacker A., Woster P.M., and Casero Jr. R.A. Clin. Cancer Res. 8 (2002) 2684-2689
20. Wang C., Delcros J.-G., Biggerstaff J., and Phanstiel IV O. J. Med. Chem. 46 (2003) 2663-2671
21. Wang C., Delcros J.-G., Biggerstaff J., and Phanstiel IV O. J. Med. Chem. 46 (2003) 2672-2682
22. Sol V., Blais J.C., Carré V., Granet R., Guilloton M., Spiro M., and Krausz P. Tetrahedron Lett. 38 (1997) 6391-6394
23. Sol V., Blais J.C., Carré V., Granet R., Guilloton M., Spiro M., and Krausz P. J. Org. Chem. 64 (1998) 4431-4444
24. Chaleix V., Sol V., Guilloton M., Granet R., and Krausz P. Tetrahedron Lett. 45 (2004) 5295-5299
25. Lucas R., Granet R., Sol V., Lemorvan C., Policar C., Rivière E., and Krausz P. e-Polymers 89 (2007)
26. Sol V., Lamarche F., Enache M., Garcia G., Granet R., Guilloton M., Blais J.C., and Krausz P. Bioorg. Med. Chem. 14 (2006) 1364-1377
27. Uno T., Hamasaki K., Tanigawa M., and Shimabayashi S. Inorg. Chem. 36 (1997) 1676-1683
28. He H., Zhou Y., Liang F., Li D., Wu J., Yang L., Zhou X., Zhang X., and Cao X. Bioorg. Med. Chem. 14 (2005) 1068-1077
29. Wu S., Li Z., Ren L., Chen B., Liang F., Zhou X., Jia T., and Cao X. Bioorg. Med. Chem. 14 (2006) 2956-2965
30. Ishikawa Y., Yamakawa N., and Uno T. Bioorg. Med. Chem. 15 (2007) 5230-5238
31. Garcia G., Sol V., Lamarche F., Granet R., Guilloton M., Champavier Y., and Krausz P. Bioorg. Med. Chem. Lett. 16 (2006) 3188-3192
32. Little R.G., Anton J.A., Loach P.A., and Ibers J.A. J. Heterocycl. Chem. 12 (1975) 343-349
33. Sakai N., and Ohfune Y. J. Am. Chem. Soc. 114 (1992) 998-1010
34. Barber D.C., Freitag-Beeston R.A., and Whitten D.G. J. Phys. Chem. 95 (1991) 4074-4086
35. Fuhrhop J.H., Demoulin C., Boettcher C., Koening J., and Siggel U. J. Am. Chem. Soc. 114 (1992) 4159-4165
36. Tomé J.P.C., Silva E.M.P., Pereira A.M.V.M., Alonso C.M.A., Faustino M.A.F., Neves M.G.P.M.S., Tomé A.C., Cavaleiro J.A.S., Tavares S.A.P., Duarte R.R., Caeiro M.F., and Valdeira M.L. Bioorg. Med. Chem. 15 (2007) 4705-4713
37. Michelsen U., Kliesch H., Schnurpfeil G., Sobbi A.K., and Wöhrle D. Photochem. Photobiol. 64 (1996) 694-701
38. Oda K., Ogura S., and Okura I. J. Photochem. Photobiol., B 59 (2000) 20-25
39. Ishikawa Y., Yamakawa N., and Uno T. Bioorg. Med. Chem. 14 (2007) 5230-5238
40. Indig G.L., Anderson G.S., Nichols M.G., Bartlett J.A., Mellon W.S., and Sieber F. J. Pharm. Sci. 89 (2000) 88-89
41. Scalise I., and Durantini E.N. J. Photochem. Photobiol., A 162 (2004) 105-113
42. Pasternack R.F., Gibbs E.J., and Villafranca J.J. Biochemistry 22 (1983) 2406-2414
43. Robic N., Bied-Charreton C., Perrée-Fauvet M., Verchère-Béaur C., Salmon L., Gaudemer A., and Pasternack R.F. Tetrahedron Lett. 31 (1990) 4739-4742
44. Kubát P., Lang K., Anzenbacher P.Jr., Jursiková K., Král V., and Ehrenberg B. J. Chem. Soc., Perkin. 1 6 (2000) 933-941
45. Kubát P., Lang K., Král V., and Anzenbacher Jr. P. J. Phys. Chem. B 106 (2002) 6784-6792
46. Chen B., Wu S., Li A., Lian F., Zhou X., Cao X., and He Z. Tetrahedron 62 (2006) 5487-5497
47. Momenteau M., Maillard P., De Bélinay M.-A., Carrez D., and Croisy A. J. Biomed. Opt. 4 (1999) 298-318
48. Li G., Graham A., Potter W., Grossman Z.D., Oseroff A., Dougherty T.J., and Pandey R.K. J. Org. Chem. 66 (2001) 1316-1325
49. Anderson M.E., Barrett A.G.M., and Hoffman B.M. Inorg. Chem. (1999) 6143-6151
50. Foote C.S., Chang T.T., and Fujimoto Y.C. Tetrahedron Lett. (1992) 45-48
51. Yamakawa N., Ishikawa Y., and Uno T. Chem. Pharm. Bull. 49 (2001) 1531-1540
52. Vileno B., Lekka M., Sienkiewicz A., Marcoux P., Kulik A.J., Kasas S., Catsicas S., Graczyk A., and Forró L. J. Phys.: Condens. Matter 17 (2005) S1471-S1482
53. Banfi S., Caruso E., Caprioli S., Mazzagatti L., Canti G., Ravizza R., Gariboldi M., and Monti E. Bioorg. Med. Chem. 12 (2004) 4853-4860
54. Scalise I., and Durantini E.N. J. Photochem. Photobiol., A 162 (2004) 105-113
55. Chen B., Qin W., Wang P., Tian T., Ma H., Cao X., Wu X., Zhou X., Zhang X.-L., Liu F., Zheng F., and Li X. Bioorg. Med. Chem. Lett. 13 (2003) 3731-3733
56. He H., Tian T., Wang P., Wu L., Xu J., Zhou X., Zhang X., Cao X., and Wu X. Bioorg. Med. Chem. Lett. 14 (2004) 3013-3016
57. Mettath S., Munson B.R., and Pandey R.K. Bioconjugate Chem. 10 (1999) 94-102