cis-Urocanic acid

Cis-Urocanic acid
Identifiers
	IUPAC name (Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid;
CAS Number	7699-35-6;
PubChem CID	1549103;
ChemSpider	1266070;
UNII	5LM7WD7VIC;
ChEBI	CHEBI:30818;
ChEMBL	ChEMBL1316726;
Chemical and physical data
Formula	C6H6N2O2
Molar mass	138.126 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=C(NC=N1)/C=C\C(=O)O;
	InChI InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1-; Key:LOIYMIARKYCTBW-UPHRSURJSA-N;

cis-Urocanic acid (cis-UCA) is a chemical compound produced by ultraviolet irradiation of trans-urocanic acid, a metabolite naturally formed in the body from histidine. cis-Urocanic acid is suspected of involvement in the development of skin cancer. It acts as an immunosuppressant through action as an agonist of the 5-HT_2A receptor, and blocking this receptor has been shown to reduce cis-UCA mediated photocarcinogenesis.^[1]^[2]^[3] However the immunomodulatory effects of cis-UCA are complex and also involve other pathways, and at low levels it shows antiinflammatory actions and may be protective against UV damage in the cornea and retina.^[4]^[5]^[6]^[7]^[8]^[9]

References[edit]

^ Walterscheid JP, Nghiem DX, Kazimi N, Nutt LK, McConkey DJ, Norval M, Ullrich SE (November 2006). "Cis-urocanic acid, a sunlight-induced immunosuppressive factor, activates immune suppression via the 5-HT2A receptor". Proceedings of the National Academy of Sciences of the United States of America. 103 (46): 17420–17425. doi:10.1073/pnas.0603119103. PMC 1859944. PMID 17085585.
^ Shen L, Ji HF (September 2009). "Molecular basis for cis-urocanic acid as a 5-HT(2A) receptor agonist". Bioorganic & Medicinal Chemistry Letters. 19 (18): 5307–5309. doi:10.1016/j.bmcl.2009.07.143. PMID 19683920.
^ Menezes AC, Raposo S, Simões S, Ribeiro H, Oliveira H, Ascenso A (March 2016). "Prevention of Photocarcinogenesis by Agonists of 5-HT1A and Antagonists of 5-HT2A Receptors". Molecular Neurobiology. 53 (2): 1145–1164. doi:10.1007/s12035-014-9068-z. PMID 25589005. S2CID 14282500.
^ Norval M, El-Ghorr AA (September 2002). "Studies to determine the immunomodulating effects of cis-urocanic acid". Methods. 28 (1): 63–70. doi:10.1016/s1046-2023(02)00210-4. PMID 12231189.
^ Schwarz T (December 2005). "Mechanisms of UV-induced immunosuppression" (PDF). The Keio Journal of Medicine. 54 (4): 165–71. doi:10.2302/kjm.54.165. PMID 16452825.
^ Ullrich SE (August 2007). "Sunlight and skin cancer: lessons from the immune system". Molecular Carcinogenesis. 46 (8): 629–633. doi:10.1002/mc.20328. PMC 2661262. PMID 17443748.
^ Lucas RM, Byrne SN, Correale J, Ilschner S, Hart PH (October 2015). "Ultraviolet radiation, vitamin D and multiple sclerosis". Neurodegenerative Disease Management. 5 (5): 413–424. doi:10.2217/nmt.15.33. PMID 26477548.
^ Korhonen E, Bisevac J, Hyttinen JM, Piippo N, Hytti M, Kaarniranta K, et al. (April 2020). "UV-B-Induced Inflammasome Activation Can Be Prevented by Cis-Urocanic Acid in Human Corneal Epithelial Cells". Investigative Ophthalmology & Visual Science. 61 (4): 7. doi:10.1167/iovs.61.4.7. PMC 7401861. PMID 32271889.
^ Korhonen E, Piippo N, Hytti M, Kaarniranta K, Kauppinen A (October 2023). "Cis-urocanic acid improves cell viability and suppresses inflammasome activation in human retinal pigment epithelial cells". Biochemical Pharmacology. 216: 115790. doi:10.1016/j.bcp.2023.115790. PMID 37683842.

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[1] Walterscheid JP, Nghiem DX, Kazimi N, Nutt LK, McConkey DJ, Norval M, Ullrich SE (November 2006). "Cis-urocanic acid, a sunlight-induced immunosuppressive factor, activates immune suppression via the 5-HT2A receptor". Proceedings of the National Academy of Sciences of the United States of America. 103 (46): 17420–17425. doi:10.1073/pnas.0603119103. PMC 1859944. PMID 17085585.

[2] Shen L, Ji HF (September 2009). "Molecular basis for cis-urocanic acid as a 5-HT(2A) receptor agonist". Bioorganic & Medicinal Chemistry Letters. 19 (18): 5307–5309. doi:10.1016/j.bmcl.2009.07.143. PMID 19683920.

[3] Menezes AC, Raposo S, Simões S, Ribeiro H, Oliveira H, Ascenso A (March 2016). "Prevention of Photocarcinogenesis by Agonists of 5-HT1A and Antagonists of 5-HT2A Receptors". Molecular Neurobiology. 53 (2): 1145–1164. doi:10.1007/s12035-014-9068-z. PMID 25589005. S2CID 14282500.

[4] Norval M, El-Ghorr AA (September 2002). "Studies to determine the immunomodulating effects of cis-urocanic acid". Methods. 28 (1): 63–70. doi:10.1016/s1046-2023(02)00210-4. PMID 12231189.

[5] Schwarz T (December 2005). "Mechanisms of UV-induced immunosuppression" (PDF). The Keio Journal of Medicine. 54 (4): 165–71. doi:10.2302/kjm.54.165. PMID 16452825.

[pmid16452825-6] Ullrich SE (August 2007). "Sunlight and skin cancer: lessons from the immune system". Molecular Carcinogenesis. 46 (8): 629–633. doi:10.1002/mc.20328. PMC 2661262. PMID 17443748.

[7] Lucas RM, Byrne SN, Correale J, Ilschner S, Hart PH (October 2015). "Ultraviolet radiation, vitamin D and multiple sclerosis". Neurodegenerative Disease Management. 5 (5): 413–424. doi:10.2217/nmt.15.33. PMID 26477548.

[8] Korhonen E, Bisevac J, Hyttinen JM, Piippo N, Hytti M, Kaarniranta K, et al. (April 2020). "UV-B-Induced Inflammasome Activation Can Be Prevented by Cis-Urocanic Acid in Human Corneal Epithelial Cells". Investigative Ophthalmology & Visual Science. 61 (4): 7. doi:10.1167/iovs.61.4.7. PMC 7401861. PMID 32271889.

[9] Korhonen E, Piippo N, Hytti M, Kaarniranta K, Kauppinen A (October 2023). "Cis-urocanic acid improves cell viability and suppresses inflammasome activation in human retinal pigment epithelial cells". Biochemical Pharmacology. 216: 115790. doi:10.1016/j.bcp.2023.115790. PMID 37683842.

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