Artigo Acesso aberto Revisado por pares

Urocanic Acid Photochemistry and Photobiology

1999; Wiley; Volume: 69; Issue: 2 Linguagem: Inglês

10.1111/j.1751-1097.1999.tb03264.x

ISSN

1751-1097

Autores

Taj Mohammad, Harry Morrison, Harm HogenEsch,

Tópico(s)

Skin Protection and Aging

Resumo

Photochemistry and PhotobiologyVolume 69, Issue 2 p. 115-135 Free Access Urocanic Acid Photochemistry and Photobiology Taj Mohammad, Corresponding Author Taj Mohammad Departments of Chemistry Purdue, University, West Lafayette, IN, USA*Department of Chemistry, Purdue University, West Lafayette, IN 47907, USA. Fax: 765–494–0239 or 765–494–1736; e-mail: [email protected] or [email protected]Search for more papers by this authorHarry Morrison, Corresponding Author Harry Morrison Departments of Chemistry Purdue, University, West Lafayette, IN, USA*Department of Chemistry, Purdue University, West Lafayette, IN 47907, USA. Fax: 765–494–0239 or 765–494–1736; e-mail: [email protected] or [email protected]Search for more papers by this authorHarm HogenEsch, Harm HogenEsch Veterinary Pathobiology, Purdue University, West Lafayette, IN, USASearch for more papers by this author Taj Mohammad, Corresponding Author Taj Mohammad Departments of Chemistry Purdue, University, West Lafayette, IN, USA*Department of Chemistry, Purdue University, West Lafayette, IN 47907, USA. Fax: 765–494–0239 or 765–494–1736; e-mail: [email protected] or [email protected]Search for more papers by this authorHarry Morrison, Corresponding Author Harry Morrison Departments of Chemistry Purdue, University, West Lafayette, IN, USA*Department of Chemistry, Purdue University, West Lafayette, IN 47907, USA. Fax: 765–494–0239 or 765–494–1736; e-mail: [email protected] or [email protected]Search for more papers by this authorHarm HogenEsch, Harm HogenEsch Veterinary Pathobiology, Purdue University, West Lafayette, IN, USASearch for more papers by this author First published: 02 January 2008 https://doi.org/10.1111/j.1751-1097.1999.tb03264.xCitations: 84AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL References 1 Jaffé, M. (1874) Concerning a new constituent in the urine of dogs. Ber. Deut. Chem. Ges. 7, 1669– 1673. 2 Parrish, J. A. (1982) Therapeutic in vivo photochemistry: photochemical toxicity studies in humans. J. Natl. Cancer Inst. 69, 273– 278. 3 De Fabo, E. C. and F. P. Noonan (1983) Mechanism of immune suppression by ultraviolet irradiation in vivo. I. Evidence for the existence of a unique photoreceptor in skin and its role in photoimmunology. J. Exp. Med. 158, 84– 98. 4 Norval, M., T. J. Simpson and J. A. Ross (1989) Urocanic acid and immunosuppression. Photochem. Photobiol. 50, 267– 275. 5 Noonan, F. P. and E. C. De Fabo (1992) Immunosuppression by ultraviolet B radiation: initiation by urocanic acid. Immunol. Today, 13, 250– 254. 6 Noonan, F. P. and E. C. De Fabo (1993) UV-induced immunosuppression: relationships between changes in solar UV spectra and immunologic responses. In Environmental UV Photobiology (Edited by A. R. Young, L. O. Björm, J. Moan and W. Nultsch), pp. 113– 148. Plenum Press, New York . 7 Norval, M., N. K. Gibbs and J. Gilmour (1995) The role of urocanic acid in UV-induced immunosuppression: recent advances (1992–1994). Photochem. Photobiol. 62, 209– 217. 8 Norval, M. (1996) Chromophore for UV-induced immunosuppression: urocanic acid. Photochem. Photobiol. 63, 386– 390. 9 Morrison, H. (1985) Photochemistry and photobiology of urocanic acid. Photodermatology 2, 158– 165. 10 Morrison, H. and R. M. Deibel (1986) Photochemistry and photobiology of urocanic acid. Photochem. Photobiol. 43, 663– 665. 11 Mehler, A. H. and H. Tabor (1953) Deamination of histidine to form urocanic acid in liver. J. Biol. Chem. 201, 775– 784. 12 Furuta, T., H. Takahashi and Y. Kasuya (1990) Evidence for a carbanion intermediate in the elimination of ammonia from L.-histidine catalyzed by histidine ammonia-lyase. J. Am. Chem. Soc. 112, 3633– 3636. 13 Tabachnick, J. (1957) Urocanic acid, the major acid soluble. UV-absorbing compound in guinea pig epidermis. Arch. Biochem. Biophys. 70, 295– 298. 14 Hug, D. H. and R. C. Venema (1985) Photoinactivation of urocanase in Pseudomonas putida. Activation by a biochemically generated excited state. Ann. N. Y. Acad. Sci. 453, 388– 389. 15 Zenisek, A. and J. A. Kral (1953) The occurrence of urocanic acid in sweat. Biochim. Biophys. Acta 12, 479– 480. 16 Webber, L. J., E. Whang and E. C. De Fabo (1997) The effects of UVA-I (340–400 nm), UV-II (320–340 nm) and UVA-I + II on the photoisomerization of urocanic acid in vivo. Photochem. Photobiol. 66, 484– 492. 17 Yarosh, D. B., S. D. Gettings, L. G. Alas, J. T. Kibitel, R. H. C. San, V. O. Wagner, III and G. N. McEwen, Jr. (1992) The biological interaction of cis and trans-urocanic acid with DNA. Photodermatol. Photoimmunol. Photomed 9, 121– 126. 18 Shibata, K., Y. Nishioka, T. Kawada, T. Fushiki and E. Sugimoto (1997) High-performance liquid chromatographic measurement of urocanic acid isomers and their ratios in naturally light-exposed skin and naturally shielded skin. J. Chromatogr. B 695, 434– 438. 19 Hanson, K. M., B. Li and J. D. Simon (1997) A spectroscopic study of the epidermal ultraviolet chromophore trans-urocanic acid. J. Am. Chem. Soc. 119, 2715– 2721. 20 Mohammad, T. and H. Morrison (1991) A general approach to the synthesis of 14C-labeled photoactive acrylic acids. J. Labelled Compd. & Radiopharm. 29, 1019– 1026. 21 Edlbacher, S. and F. Hertz (1943) Urocanic acid. Z. Physiol. Chem. 279, 63– 65. 22 Kavanagh, G., J. Crosby and M. Norval (1995) Urocanic acid isomers in human skin—analysis of site variation. Br. J. Dermatol. 133, 728– 731. 23 Stab, F., U. Hoppe and G. Sauermann (1994) Urocanic acid and its function in endogenous antioxidant defense and UV-protection in human skin. J. Invest. Dermatol. 102, 666. [Abstract]. 24 Roberts, J. D., C. Yu. C. Flanagan and T. R. Birdseye (1982) A nitrogen-15 nuclear magnetic resonance study of the acid-base and tautomeric equilibria of 4-substituted imidazoles and its relevance to the catalytic mechanism of α-lytic protease. J. Am. Chem. Soc. 104, 3945– 3949. 25 Öhman, H. and A. Vahlquist (1994) In vivo studies concerning a pH gradient in human stratum corneum and upper epidermis. Acta Dermato-Venereol. (Stockh.) 74, 375– 379. 26 Lahti, A., M. Hotokka, K. Neuvonen and P. Äyräs (1997) Quantum-chemical gas-phase calculations on the protonation forms of trans-and cis-urocanic acid. Struct. Chem. 8, 331– 342. 27 Laihia, J. K., H. Lemmetyinen, P. Pasanen and C. T. Jansén (1996) Establishment of a kinetic model for urocanic acid photoisomerization. J. Photochem. Photobiol. B Biol. 33, 211– 217. 28 Hug, D. H. and J. K. Hunter (1994) Adventitious interconversion of cis-and trans-urocanic acid by laboratory light. Photochem. Photobiol. 59, 303– 308. 29 Lewis, F. D., D. K. Howard, J. D. Oxman, A. L. Upthagrove and S. L. Quillen (1986) Lewis acid catalysis of photochemical reactions. 6. Selective isomerization of β-furylacrylic and urocanic esters. J. Am. Chem. Soc. 108, 5964– 5968. 30 Furuta, T., M. Katayama, H. Shibasaki and Y. Kasuya (1992) Simultaneous determination of stable isotopically labelled L-histidine and urocanic acid in human plasma by stable isotope dilution mass spectrometry. J. Chromatogr. B 576, 213– 219. 31 Mohammad, T., A. Kasper and H. Morrison (1994) Urocanic acid photobiology. Purine-assisted photooxidation to IH-imidazole-4(5)-carboxaldehyde. Tetrahedron Lett. 35, 4903– 4906. 32 Farrow, S. J., T. Mohammad, W. Baird and H. Morrison (1990) Photochemical covalent binding of urocanic acid to polynucleic acids. Chem.-Biol. Interact. 75, 105– 118. 33 Farrow, S. J., C. R. Jones, D. L. Severance, R. M. Deibel, W. M. Baird and H. Morrison (1990) Urocanic acid photobiology. Identification and characterization of the major photoadducts formed between urocanic acid and thymidine. J. Org. Chem. 55, 275– 282. 34 Krien, P. M. and D. Moyal (1994) Sunscreens with broad-spectrum absorption decrease the trans to cis photoisomerization of urocanic acid in the human stratum corneum after multiple UV light exposures. Photochem. Photobiol. 60, 280– 287. 35 Hemelaar, P. J. and G. M. J. Beijersbergen van Henegouwen (1996) The protective effect of N-acetylcysteine on UVB-induced immunosuppression by inhibition of the action of cis-urocanic acid. Photochem. Photobiol. 63, 322– 327. 36 Jones, C. D., A. K. Barton, J. Crosby, M. Norval and N. K. Gibbs (1996) Investigating the red shift between in vitro and in vivo urocanic acid photoisomerization action spectra. Photochem. Photobiol. 63, 302– 305. 37 Gruner, S., W. Diezel, H. Stoppe, H. Oesterwitz and W. Henke (1992) Inhibition of skin allograft rejection and acute graft-host disease by cis-urocanic acid. J. Invest. Dermatol. 98, 459– 462. 38 Morrison, H., D. Avnir and T. Zarrella (1980) Analysis of Z and E isomers of urocanic acid by high-performance liquid chromatography. J. Chromatogr. 183, 83– 86. 39 De Orsi, D., L. Gagliardi, F. Chimenti and D. Tonelli (1995) High-performance liquid chromatographic determination of urocanic acid isomers in cosmetic products. Chromatographic 41, 370– 372. 40 Takahashi, M. and T. Tezuka (1997) Quantitative analysis of histidine and cis and trans isomers of urocanic acid by high-performance liquid chromatography: a new assay method and its application. J. Chromatogr. B 688, 197– 203. 41 Kammeyer, A., S. Pavel, S. S. Asghar, J. D. Bos and M. B. M. Teunissen (1997) Prolonged increase of cis-urocanic acid levels in human skin and urine after single total-body ultraviolet exposures. Photochem. Photobiol. 65, 593– 598. 42 Simmonds, S. W. (1987) Studies of the photochemical inactivation of double stranded-viral DNA in the presence of urocanic acid. M.S. Dissertation, Purdue University, West Lafayette , IN . 43 Pinkerton, T. C., T. D. Miller, S. E. Cook, J. A. Perry, J. D. Rateike and T. J. Szczerba (1986) The nature and use of internal surface reversed-phase columns: a new concept in high performance liquid chromatography. Biochromatography 1, 96– 105. 44 Mohammad, T. and H. Morrison (1990) Rapid analysis of small molecules in the presence of DNA by high-performance liquid chromatography using internal surface reversed-phase silica. J. Chromatogr. B 533, 195– 200. 45 Mohammad, T. and H. Morrison (1997) Simultaneous determination of methylene violet, halogenated methylene violet and their photoproducts in the presence of DNA by high-performance liquid chromatography using an internal surface reversed-phase column. J. Chromatogr. B 704, 265– 275. 46 Moodycliffe, A. M., M. Norval, I. Kimber and T. J. Simpson (1993) Characterization of a monoclonal antibody to cis-urocanic acid: detection of cis-urocanic acid in the serum of irradiated mice by immunoassay. Immunology 79, 667– 672. 47 Hasegawa, H. (1960) Photolysis of urocanic acid. Nagaski Igakkai Zasshi 35, 1669– 1676. Of. Chem. Abstr. 1961, 55, 9519h. 48 Farrow, S. J. (1988) The photochemistry and photobiology of urocanic acid and indoleacrylic acid. Ph.D. Dissertation, Purdue University, West Lafayette , IN . 49 Morrison, H. and R. M. Deibel (1988) Urocanic acid photobiology. Photooxidation and superoxide formation. Photochem. Photobiol. 48, 153– 156. 50 Anglin, J. H., Jr. and W. H. Batten (1970) Structure of urocanic acid photodimers. Photochem. Photobiol. 11, 271– 277. 51 D'Auria, M. and R. Racioppi (1998) Photochemical dimerization of esters of urocanic acid. J. Photochem. Photobiol. A Chem. 112, 145– 148. 52 Baden, H. P. and M. A. Pathak (1967) The metabolism and function of urocanic acid in skin. J. Invest. Dermatol. 48, 11– 17. 53 Morrison, H., D. Avnir, C. Bernasconi and G. Fagan (1980) Z/E photoisomerization of urocanic acid. Photochem. Photobiol. 32, 711– 714. 54 McGrath, H., Jr., J. M. Bell and J. W. Haycock (1994) Fluorescent light activates the immunomodulator cis-urocanic acid in vitro: implications for patients with systemic lupus erythe-matosus. Ann. Rheum. Dis. 53, 396– 399. 55 Rihner, M. and H. McGrath (1992) Fluorescent light photosensitivity in patients with systemic lupus erythe-matosus. Arthritis Rheum. 35, 949– 952. 56 El-Ghorr, A. A. and M. Norval (1997) Biological effects of narrow-band (311 nm TLOl) UVB irradiation: a review. J. Photochem. Photobiol. B Biol. 38, 99– 106. 57 Gibbs, N. K., M. Norval, N. J. Traynor, J. C. Crosby, G. Lowe and B. E. Johnson (1993) Comparative potency of broad-band and narrow-band phototherapy to induce edema, sunburn cells and urocanic acid photoisomerization in hairless mouse skin. Photochem. Photobiol. 58, 643– 647. 58 Mohammad, T., I. Tessman, H. Morrison, M. A. Kennedy and S. W. Simmonds (1994) Photosensitized inactivation of infectrous DNA by urocanic acid, indoleacrylic acid and rhodium complexes. Photochem. Photobiol. 59, 189– 196. 59 Morrison, H., C. Bernasconi and G. Pandey (1984) A wavelength effect on urocanic acid photoisomerization. Photochem. Photobiol. 40, 549– 550. 60 Ullman, E. F., E. Babad and M. Sung (1969) Wavelength-dependent photochemistry of α, β-unsaturated carboxylate anions. J. Am. Chem. Soc. 91, 5792– 5797. 61 Saltiel, J., D. F. Sears, Jr., Y.-P. Sun and J.-O. Choi (1991) Evidence for ground-state s-cis conformers in the fluorescence spectra of all-trans-1, 6-diphcnyl-1,3,5-hexatriene, J. Am. Chem. Soc. 114, 3607– 3612. 62 Wallace-Williams, S. E., S. Møller, R. A. Goldbeck, K. M. Hanson, I. W. Lewis, W. A. Yee and D. S. Kliger (1993) Excited-state s-cis rotamers produced by extreme edge excitation of all-trans-1.4-diphcnyl-1.3-butadiene. J. Phys. Chem. 97, 9587– 9592. 63 Shuhla, M. K. and P. C. Misra (1995) Electronic spectra, structure and photoisomerization of urocanic acid. Spectrochim. Acta 51A, 831– 838. 64 Lahti, A., M. Hotokka, K. Ncuvonen and P. Äyräs (1995) A theoretical study of the conformers of trans-and cis-urocanic acid. J. Mol. Struct. (Theochem.) 331, 169– 179. 65 Li, B., K. M. Hanson and J. D. Simon (1997) Primary processes of the electronic excited states of trans-urocanic acid. J. Phys. Chem. A 101, 969– 972. 66 Lamola, A. A. (1968) Applications of electronic energy transfer in solution. Photochem. Photobiol. 8, 601– 616. 67 Lamola, A. A. (1966) Molecular mechanisms in nucleic acid photochemistry. I. Sensitized photochemical splitting of thymine dimer. J. Am. Chem. Soc. 88, 813– 819. 68 Murov, S. L., I. Carmichael and G. L. Hug (1993) Handbook of Photochemistry. Marcel Dekker, New York . 69 Morrison, H., C. Bernasconi and G. Pandey (1983) Urocanic acid photobiology. Photocycloaddition of N, N-dimethylthymine to urocanic acid. Photochem. Photobiol. 38, 23– 27. 70 Vigny, P. and M. Duquesne (1976) On the fluorescence properties of nucleotides and polynucleotides at room temperature. In Excited States of Biological Molecules. Proceedings of an International Conference (Edited by J. S. Birks). pp. 167– 177. John Wiley & Sons. New York . 71 Oraevshy, A. A., A. V. Sharkob and D. N. Nikogosyan (1981) Picosecond study of electronically excited singlet states of nucleic acid components. Chem. Phys. Lett. 83, 276– 280. 72 Nikogosyan, D. N., D. A. Angelov and A. A. Oraevsky (1982) Determination of parameters of excited states of DNA and RNA bases hy laser UV photolysis. Photochem. Photobiol. 35, 627– 635. 73 Kleopfer, R. and H. Morrison (1972) Organic photochemistry. XVII. The solution-phase photodimerization of dimethylthymine. J. Am Chem. Soc., 94, 255– 264. 74 Otten, J. G., C. S. Yeh, S. Byrn and H. Morrison (1977) Solution phase photodimerization of tetramethyluracil. Further studies on the photochemistry of ground-state aggregates. J. Am. Chem. Soc. 99, 6353– 6359. 75 Rodighiero, G., F. Dall'Acqua and D. Averbeck (1988) New psoralen and angelicin derivatives. In Psoralen DNA Photobiology, Vol. 1 (Edited by F. P. Gasparro). pp. 37– 114. CRC Press. Boca Raton . FL . 76 Gibbs, N. K., G. Torr and B. E. Johnson (1996) Evidence that certain phototoxic drugs photosensitize urocanic acid isomerization. J. Photochem. Photobiol. B Biol. 34, 63– 66. 77 Craw, M., R. V. Bensasson, J. C. Ronfard-Haret, M. T. SaeMelo and T. G. Truscott (1983) Some photophysical properties of 3-carbethosypsoralen. 8-methoxypsoralen and 5-methoxypsoralen triplet states. Photochem., Photobiol. 37, 611– 615. 78 Poppe, W. and L. L. Grosaweiner (1975) Photodynamic sensitization by, 8-methoxypsoralen via singlet oxygen mechanism. Photochem. Photobiol. 22, 217– 219. 79 Kpissay, A., C. N. Kuhl, T. Mohammad, K. Haber and H. Morrison (1997) Evidence for azidyl radical initiated olefin isomerization. One-way isonierization of (Z)-urocanic acid. Tetrahedron Lett. 38, 8435– 8438. 80 Hug, D. H. and J. K. Hunter (1995) Microorganisms from skin metabolize cis-urocanic acid. Photochem. Photobiol. 61, 21S. [Abstract]. 81 Schwarz, W., H. Schell, G. Huettinger, H. Wasmeier and T. Diepgen (1987) Effects of UVA on human stratum corneum histidine and urocanic acid isomers. Photodermatology 4, 269– 271. 82 Olivarius, F. de Fine, H. C. Wulf, J. Crosby and M. Norval (1997) Seasonal variation in urocanic acid isomers in human shin. Photochem. Photobiol. 66, 119– 123. 83 van der Molen, R. G., C. Out-Luiting, A. M. Weerheim, H. K. Koerten and A. M. Mommaas (1998) Efficacy of sunscreem in protection against UV-induced isomerization of urocanic acid in human skin. Photochem. Photobiol. 67, 71S. [Abstract]. 84 Gibbs, N. K., M. Norval, N. J. Traynor, M. Wolf, B. E. Johnson and J. Crosby (1993) Action spectra for the trans to cis photoisomerization of urocanic acid in vitro and in mouse skin. Photochem. Photobiol. 57, 584– 590. correction. Photochem. Photobiol. (1993) 58, 769. 85 Laihia, J. K. and C. T. Jansén (1994) Urocanic acid photoconversion in relation to erythematogenicity of radiation from different types of phototherapy equipment. Photodermatol. Photoimmunol. Photomed. 10, 13– 16. 86 Kammeyer, A., M. B. M. Teunissen, S. Pawl, M. A. De Rie and J. D. Bos (1995) Photoisomerization spectrum of urocanic acid in human skin and in vitro: effects of simulated solar and artificial ultraviolet radiation. Br. J. Dermatol. 132, 884– 891. 87 Hanson, K. M. and J. D. Simon (1997) The photochemical isomerization kinetics of urocanic acid and their effects upon the in vitro and in vivo photoisomerization action spectra. Photochem. Photobiol. 66, 817– 820. correction. Photochem. Photobiol. (1998) 67, 473. 88 Morrison, H., B. Mauclair, R. M. Deibel, G. Pandey and W. M. Baird (1985) Urocanic acid photobiology. Photochemical binding to calf-thymus DNA. Photochem. Photobiol. 41, 251– 257. 89 De Fabo, E. C. and F. P. Noonan (1992) Urocanic acid, photoimmunology and ozone depletion: human health implications. In Biological Effects of Light. Proceedings of a Symposium (Edited by M. F. Holick and A. M. Kligman). pp. 387– 396. de Gruyter. Berlin , Germany . 90 Young, A. R. (1997) Chromophores in human skin. Phys. Med. Biol. 42, 789– 802. 91 Garssen, J., M. Norval, A. El-Ghorr, N. K. Gibbs, C. D. Jones, D. Cerimele C. De Simone, S. Caffieri, F. Dall'Acqua, F. R. De Gruijl, Y. Sontag and H. Van Loveren (1998) Estimation of the effect of increasing UVB exposure on the human immune system and related resistance to infectious diseases and tumours. J. Photochem. Photobiol. B Biol. 42, 167– 179. 92 Tessman, I., H. Morrison, C. Bernasconi, G. Pandey and L. Ekanayake (1983) Photochemical inactivation of single-stranded viral DNA in the presence of urocanic acid. Photochem. Photobiol. 38, 29– 35. 93 Patrick, M. H. and R. O. Rahn (1976) Photochemistry of DNA and polynucleotides: photoproducts. In Photochemistry and Photobiology qf Nucleic Acids, Vol. II (Edited by S. Y. Wang). pp. 35– 95. Academic Press, New York . 94 Sancar, A. (1994) Structure and function of DNA photolyase. Biochemistry 33, 2– 9. 95 Terrian, D. L., C. N. Kuhl, I. Tessman and H. Morrison (1996) On the role of urocanic acid in photoimmunosuppression: attempted photorepair of urocanic acid—DNA cyclobutane adducts with DNA photolyase. Photochem. Photobiol. 63, 898– 900. 96 Tessman, I. (1990) SOS repair can be about as effective for single-stranded DNA as for double-stranded DNA and even more so. J. Bacteriol. 172, 5503– 5505. 97 Lias, S. G., J. E. Bartrness, J. F. Liebman, J. L. Holmes, R. D. Levin and W. G. Mallard (1988) Gas-phase ion and neutral thermochemistry. J. Phys. Chem. Ref. Data 17, (Suppl. 1). 388. 98 Sinsheimer, R. L., B. Starman, C. Nagler and G. Guthrie (1962) The process of infection with bacteriophage φX174. I. Evidence for a "replicative form." J. Mol. Biol. 4, 142– 160. 99 Tessman, I., S.-K. Liu and M. A. Kennedy (1992) Mechanism of SOS mutagenesis of UV-irradiated DNA: mostly error-free processing of deaminated cytosine. Proc. Natl. Acad. Sci. USA 89, 1159– 1163. 100 Tessman, I. (1992) Bypass of UV lesions by E. coli DNA polymerase in vivo. Photochem. Photobiol. 55, 80s. [Abstract]. 101 Sancar, G. B., F. W. Smith, R. Reid, G. Payne, M. Levy and A. Sancar (1987) Action mechanism of Escherichia coli DNA photolyase. I. Formation of the enzyme—substrate complex. J. Biol. Chem. 262, 478– 485. 102 Tessman, I. and M. A. Kennedy (1991) The two-step model of UV mutagenesis reassessed: deamination of cytosine in cyclobutane diners as the likely source of the mutations associated with photoreactivation. Mol. Gen. Genet. 227, 144– 148. 103 Armitage, B. (1998) Photocleavage of nucleic acids. Chem. Rev. 98, 1171– 1200. 104 Paillous, N. and P. Vicendo (1993) Mechanisms of photosensitized DNA cleavage. J. Photochem. Photobiol. B Biol. 20, 203– 209. 105 Kochevar, I. E. and D. A. Dunn (1990) Photosensitized reactions of DNA: cleavage and addition. In Bioorganic Photochemistry, Vol. I (Edited by H. Morrison), pp. 273– 315. John Wiley & Sons. New York . 106 Stubbe, J., J. W. Kozarich, W. Wu and D. E. Vanderwall (1996) Bleomycins: a structural model for specificity, binding, and double strand cleavage. Ace. Chem. Res. 29, 322– 330. 107 Begley, T. (1994) Photoenzymes: a novel class of biological catalysts. Acc. Chem. Res. 27, 394– 401. 108 Dandliker, P. J., M. E. Núñez and J. K. Barton (1998) Oxidative charge transfer to repair thymine dimers and damage guanine bases in DNA assemblies containing tethered metallointercalators. Biochemistry 37, 6491– 6502. 109 Hartzfeld, D. G. and S. D. Rose (1993) Efficient pyrimidine dimer radical anion splitting in low polarity solvents. J. Am. Chem. Soc. 115, 850– 854. 110 Heelis, P. F., R. F. Hartman and S. D. Rose (1993) Detection of radical ion intermediates in flavin-photosensitized pyrimidine dimer splitting. Photochem. Photobiol. 57, 442– 446. 111 Yang, D.-Y. and T. P. Begley (1993) Mechanistic studies on DNA photolyase VIII: studies on the fragmentation of the radical anion and cation of a uracil—alkene photoadduct. Tetrahedron Lett. 34, 1709– 1712. 112 Pouwels, P. J. W., R. F. Hartman, S. D. Rose and R. Kaptein (1994) CIDNP evidence for reversibility of the photosensitized splitting of pyrimidine dimers. J. Am. Chem. Soc. 116, 6967– 6968. 113 Pouwels, P. J. W., R. F. Hartman, S. D. Rose and R. Kaptein (1995) Photo-CIDNP study of pyrimidine dimer splitting I: reactions involving pyrimidine radical cation intermediates. Photochem. Photobiol. 61, 563– 574. 114 Pouwels, P. J. W., R. F. Hartman, S. D. Rose and R. Kaptein (1995) Photo-CIDNP study of pyrimidine dimer splitting 11: reactions involving pyrimidine radical anion intermediates. Photochem. Photobiol. 61, 575– 583. 115 Brancaleon, L., D. Brousmiche, V. Jayathirtha Rao, L. J. Johnston and V. Ramamurthy (1998) Photoinduced electron transfer reactions within zeolites: detection of radical cations and dimerization of arylalkenes. J. Am. Chem. Soc. 120, 4926– 4933. 116 Reeve, V. E., G. E. Greenoak, P. J. Canfield, C. Boehm-Wilcox and C. H. Gallagher (1989) Topical urocanic acid enhances UV-induced tumor yield and malignancy in the hairless mouse. Photochem. Photobiol. 49, 459– 464. 117 Cleaver, J. and G. Thomas (1981) Measurement of unscheduled synthesis by autoradiography. In DNA Repair: A Laboratory, Manual of Research Procedures, Vol. 1B (Edited by E. C. Friedberg and P. Hanawalt). pp. 277– 287. Marcel Dekker, New York . 118 Uland, S. A. J., F. P. Noonan, S. Ceryak, D. P. T. Steenvoorden, B. Bouscarel, D. Hug, G. M. J. Beijersbergen van Henegouwen and E. C. De Fabo (1998) Urocanic acid does not photobind to DNA in mice irradiated with immunosuppressive doses of UVB. Photochem. Photobiol. 67, 222– 226. 119 Farrow, S. J., T. Mohammad, W. Baird and H. Morrison (1990) Photolytic covalent binding of indoleacrylic acid to DNA. Photochem. Photobiol. 51, 263– 271. 120 Mohammad, T., W. M. Baird and H. Morrison (1991) Photochemical covalent binding of p-methoxycinnamic acid to calf thymus DNA. Bioorg. Chem. 19, 88– 100. 121 Reddy, M. V. and K. Randerath (1986) Nuclease P1-mediated enhancement of sensitivity of 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis 7, 1543– 1548. 122 Herbert, M. A., J. C. LeBlanc, D. Weinblum and H. E. Johns (1969) Properties of thymine dimers. Photochem. Photobiol. 9, 33– 43. 123 Kanne, D., K. Straub, J. E. Hearst and H. Rapoport (1981) Isolation and characterization of pyrimidine-psoralen-pyrimdine photoadducts from DNA. J. Am. Chem. Soc. 104, 6754– 6764. 124 Kripke, M. L., P. A. Cox, L. G. Alas and D. B. Yarosh (1992) Pyrimidine dimers in DNA initiate systemic immunosuppression in UV-irradiated mice. Proc. Natl. Acad. Sci. USA 89, 7516– 7520. 125 Kim, S.-T. and A. Sancar (1991) Effect of base, pentose, and phosphodiester backbone structures on binding and repair of pyrimidine dimers by Escherichia coli DNA photolyase. Biochemistry 30, 8623– 8630. 126 Ou, C. N., C. W. Tsai, K. J. Tapley, Jr. and P.-S. Song (1978) Photobinding of 8-methoxypsoralen and 5, 6-dimethoxycoumarin to DNA and its effect on template activity. Biochemistry 17, 1047– 1053. 127 Maleski, R. and H. Morrison (1972) Organic photochemistry. XXI. Photocycloaddition of 1, 3-dimethylthymine to in situ generated ethylene. Mol. Photochem. 4, 55– 59. 128 Wexler, A. J., J. A. Hyatt, P. W. Raynolds, C. Cottrell and J. S. Swenton (1978) A comparison of the photoaddition reactions of nucleic acid nitrogen bases and cyclohexenones with isobutylene. The role of rigidity in product formation. J. Am. Chem. Soc. 100, 512– 520. 129 Kellogg, R. E. and W. T. Simpson (1965) Perturbation of singlet—singlet transition energies. J. Am. Chem. Soc. 87, 4230– 4234. 130 Kasper, A. M. (1991) The photochemistry of urocanic acid with 2′-deoxyadenosine and a study of aryl/ester orbital interactions in the excited state. Ph.D. Dissertation, Purdue University, West Lafayette , IN . 131 Peterkofsky, A. (1962) The mechanism of action of histidase: aminoenzyme formation and partial reac

Referência(s)