Studies initiated in the 1990s in order to understand the photodegradation of NSAIDs (Nonsteroidal Anti-inflammatory Drugs) have triggered research leading to the intimate understanding of the reaction dynamics for car-banions in solution, including rate constants for protonation, S 2 and elimination Nreactions; the results provide excellent exemplars of the patterns of reactivity that today are part of all introductory curricula in organic chemistry and the fundamentals of the paradigms of nucleophilic substitution. These studies have also led to the exploitation of decarboxylation reactions through the invention of ketopro-fenate photocages (or photoremovable/photolabile protecting groups) that hold promise for applications in biochemistry and the health sciences, particularly in the area of photoactivated release of antiviral drugs.
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References
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)
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)
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)
Bosca, F., Miranda, M.A.: Photosensitizing drugs containing the benzophenone chromophore. J. Photochem. Photobiol. B 43(1), 1–26 (1998)
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)
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)
Coen, D.M., Safrin, S.: Herpes Simplex Virus and Varicella Zoster Virus. In: Richman, D.D. (ed.), Antiviral Drug Resistance. Wiley, London (1996)
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)
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)
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)
Goeldner, M., Givens, R.: Dynamic Studies in Biology; Wiley-VCH: Weinheim, Vol. 1. (2005)
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)
Laferriere, M., Sanramé, C., Scaiano, J.C.: A remarkably long-lived benzyl carbanion. Org. Lett. 6(6), 873–875 (2004)
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)
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)
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)
Lukeman, M., Scaiano, J.C.: Carbanion-mediated photocages: rapid and efficient photorelease with aqueous compatibility. J. Am. Chem. Soc. 127(21), 7698–7699 (2005)
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)
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)
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)
Papageorgiou, G., Barth, A., Corrie, J. E. T.: Photochem. Photobiol. Sci. 4, 216–220 (2005)
Pelliciolli, A. P., Wirz, J.: Photochem. Photobiol. Sci. 1, 441–458, 74(5), 637–655 (2002)
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)
Scaiano, J.C.: Solvent effects in the photochemistry of xanthone. J. Am. Chem. Soc. 102(26), 7747–7753 (1980)
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)
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)
Zimmerman, H.E.: J. Am. Chem. Soc. 117(35), 8988–8991 (1995)
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Scaiano, J.C., Blake, J.A., Griffith, M. (2010). Use of Ketoprofenate and Xanthonate Photocages for Antiviral Release. In: Hall, T.J., Gaponenko, S.V., Paredes, S.A. (eds) Extreme Photonics & Applications. NATO Science for Peace and Security Series B: Physics and Biophysics. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-3634-6_6
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