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Chemical Compound Review

SureCN15418     3-(3H-imidazol-4-yl)prop-2- enoic acid

Synonyms: AG-A-49511, AG-H-07542, SureCN1136889, ACMC-20h5tq, ANW-55452, ...
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Disease relevance of urocanic acid

  • Based on (a) the close fit of its absorption spectrum to the action spectrum, (b) its superficial location in the stratum corneum, and (c) its photochemical properties, the hypothesis is advanced that the photoreceptor for systemic UV-induced immunosuppression of contact hypersensitivity may be urocanic acid [1].
  • The photochemistry of Urocanic acid, a chromophore present in human skin and linked to photoimmunosuppression and skin cancer, is investigated theoretically by means of time-dependent density functional theory [2].
  • In this study, the efferent suppression of delayed-type hypersensitivity by UV-irradiated urocanic acid is demonstrated to be due to 2 phenotypically distinct T cells, (Thy1+, L3T4-, Ly2+) and (Thy1+, L3T4+, Ly2-) [3].
  • Two phenotypically distinct T cells are involved in ultraviolet-irradiated urocanic acid-induced suppression of the efferent delayed-type hypersensitivity response to herpes simplex virus, type 1 in vivo [3].
  • This situation parallels the generation of 2 distinct T-suppressor cells for HSV-1 by UV irradiation of mice and provides further evidence for the involvement of urocanic acid in the generation of UVB suppression [3].

High impact information on urocanic acid


Chemical compound and disease context of urocanic acid


Biological context of urocanic acid


Anatomical context of urocanic acid


Associations of urocanic acid with other chemical compounds


Gene context of urocanic acid

  • Enhancement of riboflavin-mediated photo-oxidation of glucose 6-phosphate dehydrogenase by urocanic acid [26].
  • Based on the excretion of urocanic acid it is estimated that NEUT2 mice catabolize approximately 40 micromol/day via the deamination pathway [27].
  • Incubation of urocanase from Pseudomonas putida with either its substrate, urocanic acid, or product, 4'(5')-imidazolone-5'(4')-propionic acid, resulted in an oxygen-dependent inhibition of enzyme activity [28].
  • While distinct molecular requirements exist for biphenylimidazole and imidazoleacrylic acid binding, these results suggest that Val108 is a common structural determinant of nonpeptide recognition on the AT1 receptor [29].
  • The presence of urocanic acid in the skin suggests that significant degradation of ADR could occur in the presence of biologically relevant concentrations of riboflavin if patients treated with ADR are exposed to sunlight [30].

Analytical, diagnostic and therapeutic context of urocanic acid


  1. 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. De Fabo, E.C., Noonan, F.P. J. Exp. Med. (1983) [Pubmed]
  2. A TD-DFT study of the photochemistry of urocanic acid in biologically relevant ionic, rotameric, and protomeric forms. Danielsson, J., Ulicný, J., Laaksonen, A. J. Am. Chem. Soc. (2001) [Pubmed]
  3. Two phenotypically distinct T cells are involved in ultraviolet-irradiated urocanic acid-induced suppression of the efferent delayed-type hypersensitivity response to herpes simplex virus, type 1 in vivo. Ross, J.A., Howie, S.E., Norval, M., Maingay, J. J. Invest. Dermatol. (1987) [Pubmed]
  4. Urocanic acid enhances IL-10 production in activated CD4+ T cells. Holán, V., Kuffová, L., Zajícová, A., Krulová, M., Filipec, M., Holler, P., Jancárek, A. J. Immunol. (1998) [Pubmed]
  5. Regulation of tumor antigen presentation by urocanic acid. Beissert, S., Mohammad, T., Torri, H., Lonati, A., Yan, Z., Morrison, H., Granstein, R.D. J. Immunol. (1997) [Pubmed]
  6. Cloning and expression of rat histidase. Homology to two bacterial histidases and four phenylalanine ammonia-lyases. Taylor, R.G., Lambert, M.A., Sexsmith, E., Sadler, S.J., Ray, P.N., Mahuran, D.J., McInnes, R.R. J. Biol. Chem. (1990) [Pubmed]
  7. Interaction between the nonpeptide angiotensin antagonist SKF-108,566 and histidine 256 (HisVI:16) of the angiotensin type 1 receptor. Schambye, H.T., Hjorth, S.A., Weinstock, J., Schwartz, T.W. Mol. Pharmacol. (1995) [Pubmed]
  8. Singlet oxygen generation by UVA light exposure of endogenous photosensitizers. Baier, J., Maisch, T., Maier, M., Engel, E., Landthaler, M., Bäumler, W. Biophys. J. (2006) [Pubmed]
  9. Effect of excess dietary L-histidine on plasma cholesterol levels in weanling rats. Solomon, J.K., Geison, R.L. J. Nutr. (1978) [Pubmed]
  10. Urocanic acid analogues and the suppression of the delayed type hypersensitivity response to Herpes simplex virus. Norval, M., Simpson, T.J., Bardshiri, E., Howie, S.E. Photochem. Photobiol. (1989) [Pubmed]
  11. High transfection efficiency of poly(4-vinylimidazole) as a new gene carrier. Ihm, J.E., Han, K.O., Han, I.K., Ahn, K.D., Han, D.K., Cho, C.S. Bioconjug. Chem. (2003) [Pubmed]
  12. Construction of a urocanic acid-producing strain of Serratia marcescens by transduction. Kisumi, M., Nakanishi, N., Takagi, T., Chibata, I. Appl. Environ. Microbiol. (1978) [Pubmed]
  13. Urocanic acid photobiology. Photooxidation and superoxide formation. Morrison, H., Deibel, R.M. Photochem. Photobiol. (1988) [Pubmed]
  14. Direct comparison of DNA damage, isomerization of urocanic acid and edema in the mouse produced by three commonly used artificial UV light sources. Yarosh, D.B., Kibitel, J., Ullrich, S.E., Kim, T.H., Ananthaswamy, H.N., Krien, P., Fourtanier, A., Kripke, M.L. Photochem. Photobiol. (1999) [Pubmed]
  15. Seasonal variation in urocanic acid isomers in human skin. de Fine Olivarius, F., Wulf, H.C., Crosby, J., Norval, M. Photochem. Photobiol. (1997) [Pubmed]
  16. Effect of phototherapy and urocanic acid isomers on natural killer cell function. Gilmour, J.W., Vestey, J.P., George, S., Norval, M. J. Invest. Dermatol. (1993) [Pubmed]
  17. Ultraviolet-irradiated urocanic acid suppresses delayed-type hypersensitivity to herpes simplex virus in mice. Ross, J.A., Howie, S.E., Norval, M., Maingay, J., Simpson, T.J. J. Invest. Dermatol. (1986) [Pubmed]
  18. Histamine and cis-urocanic acid augment tumor necrosis factor-alpha mediated induction of keratinocyte intercellular adhesion molecule-1 expression. Mitra, R.S., Shimizu, Y., Nickoloff, B.J. J. Cell. Physiol. (1993) [Pubmed]
  19. Molecular characterization of histidinemia: identification of four missense mutations in the histidase gene. Kawai, Y., Moriyama, A., Asai, K., Coleman-Campbell, C.M., Sumi, S., Morishita, H., Suchi, M. Hum. Genet. (2005) [Pubmed]
  20. Comparative potency of different UV sources in reducing the density and antigen-presenting capacity of Langerhans cells in C3H mice. El-Ghorr, A.A., Pierik, F., Norval, M. Photochem. Photobiol. (1994) [Pubmed]
  21. Stereospecific modulation of GABA(A) receptor function by urocanic acid isomers. Uusi-Oukari, M., Soini, S.L., Heikkilä, J., Koivisto, A., Neuvonen, K., Pasanen, P., Sinkkonen, S.T., Laihia, J.K., Jansén, C.T., Korpi, E.R. Eur. J. Pharmacol. (2000) [Pubmed]
  22. Photosensitized reactions of nucleic acids. Cadet, J., Berger, M., Decarroz, C., Wagner, J.R., van Lier, J.E., Ginot, Y.M., Vigny, P. Biochimie (1986) [Pubmed]
  23. Urocanic acid photobiology. Photocycloaddition of N,N-dimethylthymine to urocanic acid. Morrison, H., Bernasconi, C., Pandey, G. Photochem. Photobiol. (1983) [Pubmed]
  24. Biochemical study of malnutrition. Part VI: Histidine and its metabolites. Antener, I., Verwilghen, A.M., Van Geert, C., Mauron, J. International journal for vitamin and nutrition research. Internationale Zeitschrift für Vitamin- und Ernährungsforschung. Journal international de vitaminologie et de nutrition. (1983) [Pubmed]
  25. Effects of low concentrations of cis- and trans-urocanic acid on cytokine elaboration by keratinocytes. Redondo, P., García-Foncillas, J., Cuevillas, F., España, A., Quintanilla, E. Photodermatology, photoimmunology & photomedicine. (1996) [Pubmed]
  26. Enhancement of riboflavin-mediated photo-oxidation of glucose 6-phosphate dehydrogenase by urocanic acid. Silva, E., Herrera, L., Edwards, A.M., de la Fuente, J., Lissi, E. Photochem. Photobiol. (2005) [Pubmed]
  27. Disruption of histidine catabolism in NEUT2 mice. Cook, R.J. Arch. Biochem. Biophys. (2001) [Pubmed]
  28. Substrate-mediated inactivation of urocanase from Pseudomonas putida. Evidence for an essential sulfhydryl group. Matherly, L.H., Phillips, A.T. Biochemistry (1980) [Pubmed]
  29. Interaction of biphenylimidazole and imidazoleacrylic acid nonpeptide antagonists with valine 108 in TM III of the AT1 angiotensin receptor. Nirula, V., Zheng, W., Sothinathan, R., Sandberg, K. Br. J. Pharmacol. (1996) [Pubmed]
  30. The enhancement of riboflavin-mediated photo-oxidation of doxorubicin by histidine and urocanic acid. Ramu, A., Mehta, M.M., Leaseburg, T., Aleksic, A. Cancer Chemother. Pharmacol. (2001) [Pubmed]
  31. Interference-based electrochemical biosensor for the measurement of the concentration and isomer ratio of urocanic acid. Tatsuma, T., Okamura, K., Komori, K., Fujishima, A. Anal. Chem. (2002) [Pubmed]
  32. Analysis of Z and E isomers of urocanic acid by high-performance liquid chromatography. Morrison, H., Avnir, D., Zarrella, T. J. Chromatogr. (1980) [Pubmed]
  33. A non-invasive chamber sampling technique for HPLC analysis of human epidermal urocanic acid isomers. Jansén, C.T., Lammintausta, K., Pasanen, P., Neuvonen, K., Varjonen, E., Kalimo, K., Ayräs, P. Acta Derm. Venereol. (1991) [Pubmed]
  34. Effect of psoriasis heliotherapy on epidermal urocanic acid isomer concentrations. Snellman, E., Koulu, L., Pasanen, P., Lammintausta, K., Neuvonen, K., Ayräs, P., Jansén, C.T. Acta Derm. Venereol. (1992) [Pubmed]
  35. Measurement of the skin urocanic acid content in normal and histidinemic infants. Yokoya, S., Tokuhiro, E., Suwa, S., Maesaka, H. Eur. J. Pediatr. (1983) [Pubmed]
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