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Characterization of the lowest singlet and triplet states of S-Flurbiprofen

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Characterization of the lowest singlet and triplet states of S-Flurbiprofen

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dc.contributor.author Jiménez Molero, María Consuelo es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.contributor.author Tormos Faus, Rosa Esperanza es_ES
dc.contributor.author Vayá Pérez, Ignacio es_ES
dc.date.accessioned 2020-09-18T03:35:33Z
dc.date.available 2020-09-18T03:35:33Z
dc.date.issued 2004 es_ES
dc.identifier.issn 1474-905X es_ES
dc.identifier.uri http://hdl.handle.net/10251/150337
dc.description.abstract [EN] The photophysical properties of S-flurbiprofen [S-2-fluoro-alpha-methyl-4-biphenylacetic acid], a nonsteroidal anti-inflammatory drug, have been examined using steady-state and time-resolved spectroscopic techniques. The energy of its first singlet excited state is 99 kcal mol(-1). The fluorescence quantum yields and lifetimes (at 300 nm) have been determined in acetonitrile, methanol, hexane and PBS; they are in the range 0.15 < &phi;(F) < 0.33 and 0.7 < &tau;(F) < 2.0 ns. The intersystem crossing quantum yields are between 0.45 and 0.71; the lambda(max) of the T-T absorption is 360 nm, and the triplets live from 15 to 106 mus. Steady state photolysis in aqueous medium leads to S-2-hydroxy-alpha-methyl-4-biphenylacetic acid via photonucleophilic aromatic substitution, in addition to the photodecarboxylation products observed in organic solvents. es_ES
dc.description.sponsorship Financial support from the MCYT (BQU2001-2725), the Generalitat Valenciana (Grupos03/82 and GV04B/468) and the U.P.V. (Project 2003-0522) is gratefully acknowledged. I. V. thanks Fundación José y Ana Royo for a fellowship. es_ES
dc.language Inglés es_ES
dc.publisher The Royal Society of Chemistry es_ES
dc.relation.ispartof Photochemical & Photobiological Sciences es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Characterization of the lowest singlet and triplet states of S-Flurbiprofen es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1039/b408530b es_ES
dc.relation.projectID info:eu-repo/grantAgreement/UPV//PI 2003-0522/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GVA//GV04B%2F468/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MICYT//BQU2001-2725/ es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Jiménez Molero, MC.; Miranda Alonso, MÁ.; Tormos Faus, RE.; Vayá Pérez, I. (2004). Characterization of the lowest singlet and triplet states of S-Flurbiprofen. Photochemical & Photobiological Sciences. 3(11-12):1038-1041. https://doi.org/10.1039/b408530b es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1039/b408530b es_ES
dc.description.upvformatpinicio 1038 es_ES
dc.description.upvformatpfin 1041 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 3 es_ES
dc.description.issue 11-12 es_ES
dc.relation.pasarela S\25380 es_ES
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder Ministerio de Ciencia y Tecnología es_ES
dc.contributor.funder Universitat Politècnica de València es_ES
dc.description.references Kean, W. F., Antal, E. J., Grace, E. M., Cauvier, H., Rischke, J., & Buchanan, W. W. (1992). The Pharmacokinetics of Flurbiprofen in Younger and Elderly Patients with Rheumatoid Arthritis. The Journal of Clinical Pharmacology, 32(1), 41-48. doi:10.1002/j.1552-4604.1992.tb03786.x es_ES
dc.description.references Preston, S., Arnold, M., Beller, E., Brooks, P., & Buchanan, W. (1988). Variability in response to nonsteroidal anti-inflammatory analgesics: evidence from controlled clinical therapeutic trial of flurbiprofen in rheumatoid arthritis. British Journal of Clinical Pharmacology, 26(6), 759-764. doi:10.1111/j.1365-2125.1988.tb05316.x es_ES
dc.description.references Moore, R. A., Tramer, M. R., Carroll, D., Wiffen, P. J., & McQuay, H. J. (1998). Quantitive systematic review of topically applied non-steroidal anti-inflammatory drugs. BMJ, 316(7128), 333-338. doi:10.1136/bmj.316.7128.333 es_ES
dc.description.references Muckle, D. S. (1986). Flurbiprofen for the treatment of soft tissue trauma. The American Journal of Medicine, 80(3), 76-80. doi:10.1016/0002-9343(86)90116-6 es_ES
dc.description.references Muckle, D. S. (1976). A comparative study of flurbiprofen and aspirin in soft tissue trauma. British Journal of Sports Medicine, 10(1), 11-13. doi:10.1136/bjsm.10.1.11 es_ES
dc.description.references Mena, H. R., Lomen, P. L., Turner, L. F., Lamborn, K. R., & Brinn, E. L. (1986). Treatment of acute shoulder syndrome with flurbiprofen. The American Journal of Medicine, 80(3), 141-144. doi:10.1016/0002-9343(86)90133-6 es_ES
dc.description.references Solomon, G. D., & Kunkel, R. S. (1993). Flurbiprofen in the prophylaxis of migraine. Cleveland Clinic Journal of Medicine, 60(1), 43-48. doi:10.3949/ccjm.60.1.43 es_ES
dc.description.references A. Sunshine and E. M.Laska, Prevention or treatment of sunburn using S(+)-flurbiprofen, PCT Int. Appl., 1991, 46 pp., CODEN: PIXXD2 WO 9117740 A1 19911128 CAN 116:46072 AN 1992:46072 es_ES
dc.description.references Lomen, P. L., Turner, L. F., Lamborn, K. R., Winblad, M. A., Sack, R. L., & Brinn, E. L. (1986). Flurbiprofen in the treatment of acute gout: A comparison with indomethacin. The American Journal of Medicine, 80(3), 134-139. doi:10.1016/0002-9343(86)90131-2 es_ES
dc.description.references Butler, R., Goddard, D., Higgens, C., Hollingworth, P., Pease, C., Stodell, M., & Scott, J. (1985). Double-blind trial of flurbiprofen and phenylbutazone in acute gouty arthritis. British Journal of Clinical Pharmacology, 20(5), 511-513. doi:10.1111/j.1365-2125.1985.tb05110.x es_ES
dc.description.references Vetrugno, M., Maino, A., Quaranta, G. M., & Cardia, L. (2000). A randomized, double-masked, clinical study of the efficacy of four nonsteroidal anti-inflammatory drugs in pain control after excimer laser photorefractive keratectomy. Clinical Therapeutics, 22(6), 719-731. doi:10.1016/s0149-2918(00)90006-7 es_ES
dc.description.references Appiotti, A., Gualdi, L., Alberti, M., & Gualdi, M. (1998). Comparative study of the analgesic efficacy of flurbiprofen and diclofenac in patients following excimer laser photorefractive keratectomy. Clinical Therapeutics, 20(5), 913-920. doi:10.1016/s0149-2918(98)80073-8 es_ES
dc.description.references Bayly, C. I., Black, W. C., Léger, S., Ouimet, N., Ouellet, M., & Percival, M. D. (1999). Structure-based design of COX-2 selectivity into flurbiprofen. Bioorganic & Medicinal Chemistry Letters, 9(3), 307-312. doi:10.1016/s0960-894x(98)00717-3 es_ES
dc.description.references Smith, T., McCracken, J., Shin, Y.-K., & DeWitt, D. (2000). Arachidonic Acid and Nonsteroidal Anti-inflammatory Drugs Induce Conformational Changes in the Human Prostaglandin Endoperoxide H2Synthase-2 (Cyclooxygenase-2). Journal of Biological Chemistry, 275(51), 40407-40415. doi:10.1074/jbc.m005563200 es_ES
dc.description.references Kiefer, J. R., Pawlitz, J. L., Moreland, K. T., Stegeman, R. A., Hood, W. F., Gierse, J. K., … Kurumbail, R. G. (2000). Structural insights into the stereochemistry of the cyclooxygenase reaction. Nature, 405(6782), 97-101. doi:10.1038/35011103 es_ES
dc.description.references Kurumbail, R. G., Stevens, A. M., Gierse, J. K., McDonald, J. J., Stegeman, R. A., Pak, J. Y., … Stallings, W. C. (1996). Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature, 384(6610), 644-648. doi:10.1038/384644a0 es_ES
dc.description.references Timofeevski, S. L., Prusakiewicz, J. J., Rouzer, C. A., & Marnett, L. J. (2002). Isoform-Selective Interaction of Cyclooxygenase-2 with Indomethacin Amides Studied by Real-Time Fluorescence, Inhibition Kinetics, and Site-Directed Mutagenesis†. Biochemistry, 41(30), 9654-9662. doi:10.1021/bi0203637 es_ES
dc.description.references Lanzo, C. A., Sutin, J., Rowlinson, S., Talley, J., & Marnett, L. J. (2000). Fluorescence Quenching Analysis of the Association and Dissociation of a Diarylheterocycle to Cyclooxygenase-1 and Cyclooxygenase-2:  Dynamic Basis of Cyclooxygenase-2 Selectivity†. Biochemistry, 39(20), 6228-6234. doi:10.1021/bi992761o es_ES
dc.description.references Lanzo, C. A., Beechem, J. M., Talley, J., & Marnett, L. J. (1998). Investigation of the Binding of Isoform-Selective Inhibitors to Prostaglandin Endoperoxide Synthases Using Fluorescence Spectroscopy†. Biochemistry, 37(1), 217-226. doi:10.1021/bi971691n es_ES
dc.description.references RAHMAN, M. H., YAMASAKI, K., SHIN, Y.-H., LIN, C. C., & OTAGIRI, M. (1993). Characterization of High Affinity Binding Sites of Non-steroidal Anti-inflammatory Drugs with Respect to Site-Specific Probes on Human Serum Albumin. Biological & Pharmaceutical Bulletin, 16(11), 1169-1174. doi:10.1248/bpb.16.1169 es_ES
dc.description.references Takla, P. G., Schulman, S. G., & Perrin, J. H. (1985). Measurement of flurbiprofen—human serum albumin interaction by fluorimetry. Journal of Pharmaceutical and Biomedical Analysis, 3(1), 41-50. doi:10.1016/0731-7085(85)80005-4 es_ES
dc.description.references Boscá, F., Marín, M. L., & Miranda, M. A. (2001). Photoreactivity of the Nonsteroidal Anti-inflammatory 2-Arylpropionic Acids with Photosensitizing Side Effects¶. Photochemistry and Photobiology, 74(5), 637. doi:10.1562/0031-8655(2001)074<0637:potnai>2.0.co;2 es_ES
dc.description.references Castell, J. V., Gómez-Lechón, M. J., Miranda, M. A., & Morera, I. M. (1992). Phototoxicity of non-steroidal anti-inflammatory drugs: in vitro testing of the photoproducts of Butibufen and Flurbiprofen. Journal of Photochemistry and Photobiology B: Biology, 13(1), 71-81. doi:10.1016/1011-1344(92)80041-s es_ES
dc.description.references Lewis, F. D., Bassani, D. M., Caldwell, R. A., & Unett, D. J. (1994). Singlet State Cis,Trans Photoisomerization and Intersystem Crossing of 1-Arylpropenes. Journal of the American Chemical Society, 116(23), 10477-10485. doi:10.1021/ja00102a014 es_ES
dc.description.references Wintgens, V., Johnston, L. J., & Scaiano, J. C. (1988). Use of a photoreversible fulgide as an actinometer in one- and two-laser experiments. Journal of the American Chemical Society, 110(2), 511-517. doi:10.1021/ja00210a034 es_ES
dc.description.references S. L. Murov , I.Carmichael and G. L.Hug, Handbook of Photochemistry, Marcel Dekker, Inc., New York, 2nd edn., 1993 es_ES
dc.description.references S. S. Adams , B. J.Armitage and J. S.Nicholson, Hydroxybiphenyl compounds, Ger. Offen., 1974, 54 pp., CODEN: GWXXBX DE 2329125 19740103 CAN 82:16565 AN 1975:16565 es_ES
dc.description.references Fasani, E., Barberis Negra, F. F., Mella, M., Monti, S., & Albini, A. (1999). Photoinduced C−F Bond Cleavage in Some Fluorinated 7-Amino-4-quinolone-3-carboxylic Acids. The Journal of Organic Chemistry, 64(15), 5388-5395. doi:10.1021/jo982456t es_ES
dc.description.references Albini, A., & Monti, S. (2003). Photophysics and photochemistry of fluoroquinolones. Chemical Society Reviews, 32(4), 238. doi:10.1039/b209220b es_ES


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