Synthesis of neutral and cationic tripyridylporphyrin-d-galactose conjugates and the photoinactivation of HSV-1

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 14, 2007, Pages 4705-4713

  Tomé, João P C ^a   Silva, Eduarda M P ^a   Pereira, Ana M V M ^a   Alonso, Cristina M A ^a   Faustino, Maria A F ^a   Neves, Maria G P M S ^a   Tomé, Augusto C ^a   Cavaleiro, José A S ^a   Tavares, Sabina A P ^b   Duarte, Ricardo R ^b   Caeiro, Maria F ^c   Valdeira, Maria L ^b  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b UNIVERSITY OF LISBON   (Portugal)

^c UNIVERSITY OF LISBON   (Portugal)

Author keywords

Antiviral compounds; Cationic porphyrins; HSV 1; Sugars

Indexed keywords

5 [4 (1,2:3,4 BIS O ISOPROPYLIDENE ALPHA DEXTRO GALACTOPYRANOSYL 6 OXYCARBONYL)PHENYL] 10,15,20 TRIS(4 PYRIDYL)PORPHYRIN; 5 [4 (1,2:3,4 BIS O ISOPROPYLIDENE ALPHA DEXTRO GALACTOPYRANOSYL 6 OXYCARBONYL)PHENYL] 10,15,20 TRIS(N METHYLPYRIDINIUM 4 YL)PORPHYRIN TRIIODIDE; 5 [4 (ALPHA BETA DEXTRO GALACTOPYRANOSYL 6 OXYCARBONYL)PHENYL] 10,15,20 TRIS(4 PYRIDYL)PORPHYRIN; 5 [4 (ALPHA BETA DEXTRO GALACTOPYRANOSYL 6 OXYCARBONYL)PHENYL] 10,15,20 TRIS(N METHYLPYRIDINIUM 4 YL)PORPHYRIN TRIIODIDE; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG SCREENING; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 1; NONHUMAN; PHOTOACTIVATION; VIRUS INACTIVATION; VIRUS INFECTION; VIRUS REPLICATION;

ANIMALS; ANTIVIRAL AGENTS; CATIONS; CELL SURVIVAL; CERCOPITHECUS AETHIOPS; ELECTROSTATICS; GALACTOSE; HERPESVIRUS 1, HUMAN; MOLECULAR STRUCTURE; PHOTOSENSITIZING AGENTS; PORPHYRINS; PYRIDINES; SINGLET OXYGEN; STRUCTURE-ACTIVITY RELATIONSHIP; TIME FACTORS; VERO CELLS;

HUMAN HERPESVIRUS 1;

EID: 34249681811     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.05.005     Document Type: Article

References (38)

1. Roizman B. The Family Herpesviridae: A Brief Introduction. In: Fields B.N., and Knipe D.M. (Eds). Virology. Second ed. (1990), Raven, New York 1787-1794
2. Pinna A.D., Rakela J., Demetris A.J., and Fung J.J. Dig. Dis. Sci. 47 (2002) 750
3. Rand K.H., Rasmussen L.E., Pollard R.B., Arvin A., and Merigen T.C. New Engl. J. Med. 296 (1997) 1372
4. Kleymann G. Expert Opin. Invest. Drugs 12 (2003) 165
5. Kleymann G., Fischer R., Betz U.A.K., Hendrix M., Bender W., Schneider U., Handke G., Eckenberg P., Hewlett G., Pevzner V., Baumeister J., Weber O., Henninger K., Keldenich J., Jensen A., Kolb J., Bach U., Popp A., Maben J., Frappa I., Haebich D., Lockhoff O., and Rubsamen-Waigmann H. Nat. Med. 8 (2002) 392
6. De Clercq E. J. Clin. Virol. 30 (2004) 115
7. Corey L. J. Infect. Dis. 186 (2002) S29
8. In: Bock G., and Harnett S. (Eds). Photosensitizing Compounds: Their Chemistry, Biology and Clinical Use (1989), Wiley, Chichester
9. Matthews J.L., Sogandares-Bernal F., Judy M., Gulliya K., Newman J., Chanh T., and Marengo-Rowe A. Blood Cells 1 (1992) 75
10. Legrand-Poels S., Hoebeke M., Vaira D., Rentier B., and Piette J. J. Photochem. Photobiol. B: Biol. 17 (1993) 229
11. Smetana Z., Mendelson E., Manor J., Van Lier J.E., Ben-Hur E., Salzberg S., and Malik Z. J. Photochem. Photobiol. B: Biol. 22 (1994) 37
12. Smetana Z., Ben-Hur E., Mendelson E., Salzberg S., Wagner P., and Malik Z. J. Photochem. Photobiol. B: Biol. 44 (1998) 77
13. Lim D.-S., Ko S.-H., Kim S.-J., Park Y.-J., Park J.-H., and Lee W.-Y. J. Photochem. Photobiol. B: Biol. 67 (2002) 149
14. Bonnett R. Chemical Aspects of Photodynamic Therapy (2000), Gordon and Breach Science, London
15. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook-Applications: Past, Present and Future Vol. 6 (2000), Academic Press, New York
16. Trannoy L.L., Lagerberg J.W.M., Dubbelman T.M.A.R., Schuitmaker H.J., and Anneke B. Transfusion 44 (2004) 1186
17. Tomé, J. P. C.; Mendonça, A. F.; Neves, M. G. P. M. S.; Tomé, A. C.; Valdeira, M. L.; Cavaleiro, J. A. S. PT Patent 102,572, 2001.
18. Dixon, D. W.; Atlanta, G. A.; Schinazi, R. F.; Decatur, G. A.; Marzilli, L. G.; Atlanta, G. A. U.S. Patent 5,281,616, 1994.
19. Sternberg E.D., Dolphin D., and Bruckner C. Tetrahedron 54 (1998) 4151
20. Sylvain I., Zerrouki R., Granet R., Huang Y.M., Lagorce J.-F., Guilloton M., Blais J.-C., and Krausz P. Bioorg. Med. Chem. 10 (2002) 57
21. Laville I., Figueiredo T., Loock B., Pigaglio S., Maillard Ph., Grierson D.S., Carrez D., Croisy D., and Blais J. Bioorg. Med. Chem. 11 (2003) 1643
22. Embleton M.L., Nair S.P., Heywood W., Menon D.C., Cookson B.D., and Wilson M. Antimicrob. Agents Chemother. 49 (2005) 3690
23. Tomé J.P.C., Neves M.G.P.M.S., Tomé A.C., Cavaleiro J.A.S., Soncin M., Magaraggia M., Ferro S., and Jori G. J. Med. Chem. 47 (2004) 6649
24. Liu J., Shi S., Ji L.-N., and Mei W.-J. Transition Metal Chem. 30 (2005) 684
25. Tomé J.P.C., Neves M.G.P.M.S., Tomé A.C., Cavaleiro J.A.S., Mendonça A.F., Pegado I.N., Duarte R., and Valdeira M.L. Bioorg. Med. Chem. 13 (2005) 3878
26. Silva E.M.P., Giuntini F., Faustino M.A.F., Tomé J.P.C., Neves M.G.P.M.S., Tomé A.C., Silva A.M.S., Santana-Marques M.G., Ferrer-Correia A.J., Cavaleiro J.A.S., Caeiro M.F., Duarte R.R., Tavares S.A.P., Pegado I.N., d'Almeida B., Matos A.P.A., and Valdeira M.L. Bioorg. Med. Chem. Lett. 15 (2005) 3333
27. Egyeki M., Tukóczy G., Majer Zs., Tóth K., Fekete A., Maillard Ph., and Csik G. Biochim. Biophys. Acta 1624 (2003) 115
28. Powell L.D., and Varki A. J. Biol. Chem. 269 (1994) 10628
29. Nicolaou K.C., and Mitchell H.J. Angew. Chem., Int. Ed. 40 (2001) 1576
30. Dwek R.A. Chem. Rev. 96 (1996) 683
31. Recent review on the synthesis of glycoporphyrins. Aksenova A.A., Sebyakin Y.L., and Mironov A.F. Russ. J. Bioorg. Chem. 3 (2003) 201
32. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook-Synthesis and Organic Chemistry Vol. 1 (2000), Academic Press, New York
33. Mitzel F., Fitzgerald S., Beeby A., and Faust R. Eur. J. Org. Chem. (2004) 1136
34. Mitzel F., Fitzgerald S., Beeby A., and Faust R. Chem. Commun. (2001) 2596
35. Oda K., Ogura S., and Osekura I. J. Photochem. Photobiol. B 59 (2000) 20
36. Michelsen U., Kliesch H., Schnurpfeil G., Sobbi A.K., and Wöhrle D. Photochem. Photobiol. 64 (1996) 694
37. Mossman T.J. Immunol. Methods 65 (1983) 55
38. Valdeira M.L., Duque-Magalhães M.C., and Geraldes A. Arch. Virol. 113 (1990) 125