Urocanic Acid Photochemistry and Photobiology

Photochemistry and Photobiology

Volumn 69, Issue 2, 1999, Pages 115-135

  Mohammad, Taj ^a,c   Morrison, Harry ^a,c   HogenEsch, Harm ^b  

^a Department of Chemistry ^*  (United States)

^b PURDUE UNIVERSITY   (United States)

^c PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; SUPEROXIDE; UROCANIC ACID; VIRUS DNA;

BIOLOGY; CHEMICAL MODEL; DIMERIZATION; IMMUNE SYSTEM; ISOMERISM; METABOLISM; PHOTOCHEMISTRY; REVIEW;

DIMERIZATION; DNA; DNA, VIRAL; IMMUNE SYSTEM; ISOMERISM; MODELS, CHEMICAL; PHOTOBIOLOGY; PHOTOCHEMISTRY; SUPEROXIDES; UROCANIC ACID;

EID: 0033071696     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1999.tb03264.x     Document Type: Review

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126. Kanne, D., K. Straub, J. E. Hearst and H. Rapoport (1982) Isolation and characteriztion of pyrimidine-psoralen-pyrimidine photoadducts from DNA. J. Am. Chem. Soc. 104, 6754-6764.
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129. 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.
130. Maleski, R. and H. Morrison (1972) Organic photochemistry. XXI. Photocycloaddition of 1,3-dimethylthymine to in situ generated ethylene. Mol. Photochem. 4, 55-59.
131. Wexler, A. J., J. A. Hyatt, P. W. Raynolds, C. Cottrell and J. S. Swenton (1978) A comparison of lhe 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.
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136. Wood, P. D. and L. J. Johnston (1997) Generation and characterization of psoralen radical cations. Photochem. Photobiol. 66, 642-648.
137. Deibel, R. M., H. Morrison and W. M. Baird (1987) Urocanic acid photobiology. Photochemical binding of urocanic acid to bovine serum albumin. Photochem. Photobiol. 45, 421-123.
138. Yoshikawa, K., N. Mori, S. Sakakihara, N. Mizuno and P.-S. Song (1979) Photoconjugation of 8-methoxypsoralen with proteins. Photochem. Photobiol. 29, 1127-1133.
139. Sinha, B. K. and C. F. Chignell (1983) Binding of anthracene to cellular macromolecules in the presence of light. Photochem. Photobiol. 37, 33-37.
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141. Kochevar, I. E. and L. C. Harber (1977) Photoreactions of 3,3′,4′,5-tetrachlorosalicylanilide with proteins. J. Invest. Dermaiol. 68, 151-156.
142. Clive, D., R. McCuen, J. F. S. Spector, C. Piper and K. H. Mavournin (1983) Specific gene mutations in L5178Y cells in culture. Mutat. Res. 115, 225-251.
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145. Reeve, V. E., M. Bosnic, W. G. Reilly and R. D. Ley (1991) Urocanic acid photobiology in the hairless mouse. Photochem. Photobiol. 53, 88S. [Abstract]
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147. Muhammad, T. and H. Morrison (1996) Evidence for the photosensitized formation of singlet oxygen by UVB irradiation of 2′-deoxyguanosine 5′-monophosphate. J. Am. Chem. Soc. 118, 1221-1222.
148. Hanson, K. M. and J. D. Simon (1998) The origin of the wavelength-dependent photoreactivity of trans-urocanic acid. Photochem. Photobiol. 67, 538-540.
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151. Norval, M., T. J. Simpson, E. Bardshiri and S. E. M. Howie (1989) Urocanic acid analogues and the suppression of the delayed type hypersensitivity response to Herpes simplex virus. Photochem. Photobiol. 49, 633-639.
152. Houghtaling, M. A., M. A. Kennedy, T. Mohammad, I. Tessman and H. Morrison (1996) Photochemistry and photobiology of imidazole-4(5)-methylidene malonic acid: an analog of both E- and Z-urocanic acid. Photochem. Photobiol. 64, 216-219.
153. Lewis, F. D. and A. B. Yoon (1995) The influence of intramolecular hydrogen bonding on the structure and E ↔ Z photoisomerization of urocanic acid derivatives. Res. Chem. Intermed. 21, 749-763.
154. Franceschi, S., V. Andreu, N. de Viguerie, M. Riviere, A. Lattes and A. Moisand (1998) Synthesis and aggregation behaviour of two-headed surfactants containing the urocanic acid moiety. New J. Chem., 225-231.
155. Kripke, M. L. (1998) President's lecture: photoimmunology - a personal odyssey. Photochem. Photobiol. 67, 83S. [Abstract]
156. Ross, J. A., S. E. Howie, M. Norval, J. Maingay and T. J. Simpson (1986) Ultraviolet-irradiated urocanic acid suppresses delayed-type hypersensitivity to herpes simplex virus in mice. J. Invest. Dermatol. 87, 630-633.
157. Guymer, R. H. and T. E. Mandel (1993) Urocanic acid as an immunosuppressant in allotransplantation in mice. Transplantation 55, 36-43.
158. Gieseler, R. K., F. Klemp, M. Bredt, R. Mentlein, R. Kuhn, B. von Gaudecker, J. H. Peters and R. Schlemminger (1994) Prolongation of survival of small bowel transplant recipients after treatment with cis-urocanic acid. Transplant. Proc. 26, 1601-1603.
159. Filipec, M., E. Letko, Z. Haskova, D. Jenickova, P. Holler, A. Jancarek and V. Holan (1998) The effect of urocanic acid on graft rejection in an experimental model of orthotopic corneal transplantation in rabbits. Graefes Arch. Clin. Exp. Ophthalmol. 236, 65-68.
160. Noonan, F. P., E. C. De Fabo and H. Morrison (1988) Cis- urocanic acid, a product formed by ultraviolet B irradiation of the skin, initiates an antigen presentation defect in splenic dendritic cells in vivo. J Invest. Dermatol. 90, 92-99.
161. Lappin, M. B., J. M. Weiss, E. Scopf, M. Norval and J. C. Simon (1997) Physiologic doses of urocanic acid do not alter the allostimulatory function or the development of murine dendritic cells in vitro. Photodermatol. Photoimmunol. Photomed. 13, 163-168.
162. Hurks, H. M., C. Out-Luiting, R. G. Van den Molen, B. J. Vermeer. F. H. Claas and A. M. Mommaas (1997) Differential suppression of the human mixed epidermal cell lymphocyte reaction (MECLR) and mixed lymphocyte reaction (MLR) by cis-urocanic acid. Photochem. Photobiol. 65, 616-621.
163. Rattis, F.-M., J. Peguet-Navarro, P. Courtellemont, G. Redziniak and D. Schmitt (1995) cis-Urocanic acid failed to affect in vitro human Langerhans cell allostimulatory function. Photochem. Photobiol. 62, 914-916.
164. Dai, R. and J. W. Streilein (1997) Ultraviolet B-exposed and soluble factor - pre-incubated epidermal Langerhans cells fail to induce contact hypersensitivity and promote DNP-specific tolerance. J. Invest. Dermatol. 108, 721-726.
165. Beissert, S., T. Mohammad, H. Torri, A. Lonati, Z. Yan, H. Morrison and R. D. Granstein (1997) Regulation of tumor antigen presentation by urocanic acid. J. Immunol. 159, 92-96.
166. Redondo, P., J. Garcia-Foncillas, F. Cuevillas, A. Espana and E. Quintanilla (1996) Effects of low concentrations of cis- and trans-urocanic acid on cytokine elaboration by keratinocytes. Photodermatol. Photoimmunol. Photomed. 12, 237-243.
167. Bacci, S., T. Nakamura and J. W. Streilein (1996) Failed antigen presentation after UVB radiation correlates with modifications of Langerhans cell cytoskeleton. J. Invest. Dermatol. 107, 838-843.
168. Norval, M., J. W. Gilmour and T. J. Simpson (1990) The effect of histamine receptor antagonists on immunosuppression induced by the cis-isomer of urocanic acid. Photodermatol. Photoimmunol. Photomed. 7, 243-248.
169. 2 production and suppresses indirectly tumor necrosis factor-alpha levels. J. Immunol. 150, 4514-4523.
170. 2 production by human keratinocytes: link to indomethacin-inhibitable UVB-induced immunosuppression. Photochem. Photobiol. 61, 303-309.
171. 1 3 receptors. J. Invest. Dermatol. 107, 664. [Abstract]
172. Hart, P. H., A. Jaksic, G. Swift, M. Norval, A. A. El-Ghorr and J. J. Finlay Jones (1997) Histamine involvement in UVB- and cis-urocanic acid-induced systemic suppression of contact hypersensitivity responses. Immunology 91, 601-608.
173. Wille, J. J. and A. Kydonieus (1995) Abrogation of contact hypersensitivity in mice by topically-applied mast cell degranulating agents. J. Invest. Dermatol. 104, 679. [Abstract]
174. Malaviya, R., A. R. Morrison and A. P. Pentland (1996) Histamine in human epidermal cells is induced by ultraviolet light injury. J. Invest. Dermatol. 106, 785-789.
175. Jun, B. D., L. K. Roberts, B. H. Cho. B. Robertson and R. A. Daynes (1988) Parallel recovery of epidermal antigen-presenting cell activity and contact hypersensitivity responses in mice exposed to ultraviolet irradiation: the role of a prostaglandin- dependent mechanism. J. Invest. Dermatol. 90, 311-316.
176. 2, IL-4, and IL-10 is responsible for UV-induced systemic immune suppression. J. Immunol. 160, 3783-3789.
177. Enk, A. H., V. L. Angeloni, M. C. Udey and S. I. Katz (1993) Inhibition of Langerhans cell antigen-presenting function by IL-10. J. Immunol. 151, 2390-2398.
178. Beissert, S., J. Hosoi, S. Grabbe, A. Asahina and R. D. Granstein (1995) IL-10 inhibits tumor antigen presentation by epidermal antigen-presenting cells. J. Immunol. 54, 1280-1286.
179. Van der Pouw Kraan, T. C. T. M., L. C. M. Boeije, R. J. T. Smeenk. J. Wijdenes and L. A. Aarden (1995) Prostaglandin- E2 is a potent inhibitor of human interleukin 12 production. J. Exp. Med. 181, 775-779.
180. Muller, G., J. Saloga, T. Germann, G. Schuler, J. Knop and A. H. Enk (1995) IL-12 as mediator and adjuvant for the induction of contact sensitivity in vivo. J. Immunol. 155, 4661-4668.
181. Reeve, V. E., M. Bosnic and N. Nishimura (1998) Role of interferon-γ in protection by UVA (320-400 nm) radiation against UVB (280-320 nm)-induced immunosuppression. Photochem. Photobiol. 67, 46S. [Abstract]
182. Rivas, J. M. and S. E. Ullrich (1994) The role of IL-4, IL-10, and TNF-α in the immune suppression induced by ultraviolet radiation. J. Leukocyte Biol. 56, 769-775.
183. Kurimoto, I. and J. W. Streilein (1992) Cis-urocanic acid suppression of contact hypersensitivity induction is mediated via tumor necrosis factor-alpha. J. Immunol. 148, 3072-3078.
184. El-Ghorr, A. A. and M. Norval (1997) The effect of chronic treatment of mice with urocanic acid isomers. Photochem. Photobiol. 65, 866-872.
185. Olivarius, F. D. F., J. Lock-Andersen, F. G. Larsen, H. C. Wulf, J. Crosby and M. Norval (1998) Urocanic acid isomers in patients with basal cell carcinoma and cutaneous malignant melanoma. Br. J. Dermatol. 138, 986-992.
186. Donawho, C. K., M. Norval and D. B. Yarosh (1998) Molecular target of UV-B radiation in the melanoma enhancing effect of UV irradiation in a murinc model. Photochem. Photobiol. 67, 64S. [Abstract]