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cis-Urocanic acid

  Cat. No.:  DC28298   Featured
Chemical Structure
7699-35-6
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More than 5000 active chemicals with high quality for research!
Field of application
cis-Urocanic acid is a 5-HT2A receptor agonist. cis-Urocanic acid binds to 5-HT receptor with relatively high affinity (Kd=4.6 nM). cis-Urocanic acid is an immune modulator that induces immunosuppression by binding to the 5-HT2A receptor.
Chemicals PropertiesBiological activity COA & MSDSRelated productsDatasheet
Cas No.: 7699-35-6
Chemical Name: Urocanic Acid, Cis
Synonyms: Urocanic Acid, Cis;CIS-UROCANIC ACID;(2Z)-3-(1H-Imidazole-4-yl)acrylic acid;(E)-3-(3H-imidazol-4-yl)prop-2-enoic acid;(Z)-2-propenoic acid;(Z)-3-(1H-imidazol-4-yl)-2-propenoic acid;(Z)-3-(1H-imidazol-4-yl)prop-2-enoic acid;(Z)-3-(1H-Imidazol-4-yl)propenoic acid;(Z)-3-(1H-Imidazole-4-yl)acrylic acid;(Z)-Urocanic acid;3-[1H-imidazol-4(5)-yl];Cis-Urocanic Acid-[13C3];Nsc407934;Z-urocanic acid;cis-3-(1H-imidazol-4-yl)-2-propenoic acid;cis-UCA
SMILES: OC(/C=C\C1=CN=CN1)=O
Formula: C6H6N2O2
M.Wt: 138.124041080475
Purity: >98%
Sotrage: 2 years -20°C Powder, 2 weeks 4°C in DMSO, 6 months -80°C in DMSO
Description: cis-Urocanic acid is a 5-HT2A receptor agonist. cis-Urocanic acid binds to 5-HT receptor with relatively high affinity (Kd=4.6 nM). cis-Urocanic acid is an immune modulator that induces immunosuppression by binding to the 5-HT2A receptor[1].
Target: 5-HT2A Receptor
In Vitro: Treatment with 100 μg/mL cis-Urocanic acid (cis-UCA) completely suppresses IL-6 and IL-8 secretion, decreases caspase-3 activity, and improves cell viability against UV-B irradiation. No significant effects on IL-6 or IL-8 secretion, caspase-3 activity, or viability of the non-irradiated cells are observed with 100 μg/mL cis-Urocanic acid in both cell types. The 5000 μg/mL concentration is toxic[1]. Cell Viability Assay[1] Cell Line: Human corneal epithelial cells (HCE-2) and human conjunctival epithelial cells (HCECs) Concentration: 10, 100, 1,000, and 5,000 μg/mL Incubation Time: 24, 48, or 72 hours Result: Treatment with 100 μg/mL completely suppressed IL-6 and IL-8 secretion, decreased caspase-3 activity, and improved cell viability against UV-B irradiation. No significant effects on IL-6 or IL-8 secretion, caspase-3 activity, or viability of the non-irradiated cells were observed with 100 μg/mL in both cell types.
References: [1]. Walterscheid JP, et al. Cis-urocanic acid, a sunlight-induced immunosuppressive factor, activates immune suppression via the 5-HT2A receptor. Proc Natl Acad Sci U S A. 2006 Nov 14;103(46):17420-5. [2]. Viiri J, et al. Cis-urocanic acid suppresses UV-B-induced interleukin-6 and -8 secretion and cytotoxicity in human corneal and conjunctival epithelial cells in vitro. Mol Vis. 2009 Sep 8;15:1799-805.
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MSDS_12351_DC28298_7699-35-6
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