Use of ketoprofenate and xanthonate photocages for antiviral release

NATO Science for Peace and Security Series B: Physics and Biophysics

Volumn , Issue , 2010, Pages 95-105

  Scaiano, Juan C ^a   Blake, Jessie A ^a   Griffith, May ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

Acyclovir; Drug delivery; Herpes simplex virus; Ketoprofen; Photocages; Photodecarboxylation; Photolabile protecting groups; Phototherapy; Xanthone

Indexed keywords

SIMPLEXVIRUS;

EID: 76149137746     PISSN: 18746500     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-90-481-3634-6_6     Document Type: Conference Paper

References (27)

1. Abdullah, K.A., Kemp, T.J.: Solvatochromic effects in the fluorescence and triplet-triplet absorption spectra of xanthone, thioxanthone and N-methylacridone. J. Photochem. 32(1), 49-57 (1986)
2. Blake, J.A., Gagnon, E., Lukeman, M., Scaiano, J.C.: Photodecarboxylation of xanthone acetic acids: C-C bond heterolysis from the singlet excited state. Org. Lett. 8(6), 1057-1060 (2006)
3. Blake, J.A., Lukeman, M., Scaiano, J.C.: Photolabile protecting groups based on the singlet state photodecarboxylation of xanthone acetic acid. J. Am. Chem. Soc. 131(11), 4127-4135 (2009)
4. Bosca, F., Miranda, M.A.: Photosensitizing drugs containing the benzophenone chromophore. J. Photochem. Photobiol. B 43(1), 1-26 (1998)
5. Bosca, F., Marin, F.L., Miranda, M.A.: Photoreactivity of the nonsteroidal anti-inflammatory 2-arylpropionic acids with photosensitizing side effects. Photochem. Photobiol. 74(5), 637- 655 (2001)
6. Cleator, G.M., Klapper, P.E.: Herpes Simplex. In: Zuckerman, A.J., Banatvala, H.E., Pattison, J.R. (eds.), Principles and Practice of Clinical Virology, 4th edn. Wiley, Chichester (2000)
7. Coen, D.M., Safrin, S.: Herpes Simplex Virus and Varicella Zoster Virus. In: Richman, D.D. (ed.), Antiviral Drug Resistance. Wiley, London (1996)
8. Costanzo, L.L., De Guidi, G., Condorelli, G., Cambria, A., Fama, M.: Molecular mechanism of drug photosensitization. II. Photohemolysis sensitized by ketoprofen. Photochem. Photobiol. 50(3), 359-365 (1989)
9. Cosa, G., Martinez, L.J., Scaiano, J.C.: Influence of solvent polarity and base concentration on the photochemistry of ketoprofen: independent singlet and triplet pathways. Phys. Chem. Chem. Phys. 1(15), 3533-3537 (1999)
10. Cosa, G., Llauger, L., Scaiano, J.C., Miranda, M.A.: Absolute rate constants for water protonation of 1-(3-benzoylphenyl) alkyl carbanions. Org. Lett. 4(18), 3083-3085 (2002)
11. Goeldner, M., Givens, R.: Dynamic Studies in Biology; Wiley-VCH: Weinheim, Vol. 1. (2005)
12. Heinz, B., Schmidt, B., Root, C., Satzger, H., Milota, F., Fierz, B., Kiefhaber, T., Zinth, W., Gilch, P.: On the unusual fluorescence properties of xanthone in water. Phys. Chem. Chem. Phys. 8(29), 3432-3439 (2006)
13. Laferriere, M., Sanramé, C., Scaiano, J.C.: A remarkably long-lived benzyl carbanion. Org. Lett. 6(6), 873-875 (2004)
14. Ley, C., Morlet-Savary, F., Fouassier, J.P., Jacques, P.: The spectral shape dependence of xanthone triplet-triplet absorption on solvent polarity. J. Photochem. Photobiol. A 137(2-3), 87-92 (2000)
15. Liesegang, T.J., Melton, L.J., Daly, P.J., Ilstrup, D.M.: Epidemiology of ocular herpes simplex. Incidence in Rochester, Minn, 1950 through 1982. Arch. Ophthalmol. 107(8), 1155-1159 (1989)
16. Llauger, L., Miranda, M.A., Cosa. G., Scaiano, J.C.: Comparative study of the reactivities of substituted 3-(benzoyl) benzyl carbanions in water and in DMSO. J. Org. Chem. 69(21), 7066-7071 (2004)
17. Lukeman, M., Scaiano, J.C.: Carbanion-mediated photocages: rapid and efficient photorelease with aqueous compatibility. J. Am. Chem. Soc. 127(21), 7698-7699 (2005)
18. Martinez, L.J., Scaiano, J.C.: Transient intermediates in the laser flash photolysis of ketoprofen in aqueous solutions: unusual photochemistry for the benzophenone chromophore. J. Am. Chem. Soc. 119(45), 11066-11070 (1997)
19. Monti, S., Sortino, S., De Guidi, G., Marconi, G.: Photochemistry of 2-(3-benzoylphenyl) propionic acid (ketoprofen). Part 1. A picosecond and nanosecond time resolved study in aqueous solution. J. Chem. Soc., Faraday Trans. 93(13), 2269-2275 (1997)
20. O'Brien, J.J., Campoli-Richards, D.M.: Acyclovir: an updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs 37(3), 233-309 (1989)
21. Papageorgiou, G., Barth, A., Corrie, J. E. T.: Photochem. Photobiol. Sci. 4, 216-220 (2005)
22. Pelliciolli, A. P., Wirz, J.: Photochem. Photobiol. Sci. 1, 441-458, 74 (5), 637-655 (2002)
23. Pepose, J.S., Leib, D.A., Stuart, P.M., Easty, D.L.: Herpes simplex virus diseases: anterior segment of the eye. In: Holland, G.N., Wilhelmus, K.R. (eds.), Ocular Infection and Immunity. Mosby, St. Louis, MO, pp. 905-932 (1996)
24. Scaiano, J.C.: Solvent effects in the photochemistry of xanthone. J. Am. Chem. Soc. 102(26), 7747-7753 (1980)
25. Scaiano, J.C., Weldon, D., Pliva, C.N., Martinez, L.J.: Photochemistry and photophysics of 1-azaxanthone in organic solvents. J. Phys. Chem. A 102(35), 6898-6903 (1998)
26. Toma, H.S., Murina, A.T., Areaux, R.G. Jr., Neumann, D.M., Bhattacharjee, P.S., Foster, T.P., Kaufman, H.E., Hill, J.M.: Ocular HSV-1 latency, reactivation and recurrent disease. Semin. Ophthalmol. 23(4), 249-273 (2008)
27. Zimmerman, H.E.: J. Am. Chem. Soc. 117(35), 8988-8991 (1995)