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| 5mg |
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| 10mg |
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| Targets |
cis-Urocanic acid targets the 5-HT2A receptor, a subtype of the serotonin receptor. It binds to the 5-HT receptor with relatively high affinity, with a Kd of 4.6 nM. It acts as a 5-HT2A receptor agonist. By binding to this receptor, it induces immunosuppression. It can also induce mast cell degranulation and release pre-formed TNF-α.
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| ln Vitro |
When exposed to 100 μg/mL cis-urocanic acid (cis-UCA), the production of IL-6 and IL-8 was totally suppressed, caspase-3 activity was decreased, and the ability of cells to withstand UV-B irradiation was enhanced. The viability of unirradiated cells, caspase-3 activity, and IL-6 or IL-8 production were not significantly affected by 100 μg/mL cis-uroCanic acid in any of the two cell types. Five thousand μg/mL is considered hazardous [1].
In vitro, cis-Urocanic acid acts as a 5-HT2A receptor agonist. It binds to the 5-HT receptor with a Kd of 4.6 nM. It is an immune modulator that induces immunosuppression. It can also induce mast cell degranulation and the release of pre-formed TNF-α. Its activity is linked to its role in skin UV radiation protection and immune regulation. |
| ln Vivo |
In vivo, cis-Urocanic acid is a key mediator of UV-induced immunosuppression. Upon exposure to UVB radiation, trans-urocanic acid in the skin isomerizes to the cis form. This cis-isomer then acts as an immune modulator, contributing to the suppression of contact hypersensitivity and other immune responses. Its effects are mediated through the 5-HT2A receptor, making it a crucial link between UV exposure and immune suppression.
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| Enzyme Assay |
In vitro receptor binding assays for cis-Urocanic acid typically involve radioligand binding studies to determine its affinity for the 5-HT2A receptor. The receptor is incubated with increasing concentrations of the compound and a fixed concentration of a radiolabeled 5-HT2A antagonist. Bound and free radioligand are separated, and radioactivity is measured. Ki or Kd values are calculated to quantify its binding affinity, which has been reported as 4.6 nM.
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| Cell Assay |
Cell Viability Assay[1]
Cell Types: Human Corneal Epithelial Cells (HCE-2) and Human Conjunctival Epithelial Cells (HCEC) Tested Concentrations: 10, 100, 1,000, and 5,000 μg/mL Incubation Duration: 24, 48, or 72 hrs (hours) Experimental Results: With Treatment at 100 μg/mL completely inhibited IL-6 and IL-8 secretion, diminished caspase-3 activity, and increased cell viability to UV-B irradiation. In both cell types, no significant effects were observed at the 100 μg/mL concentration on IL-6 or IL-8 secretion, caspase-3 activity, or viability of unirradiated cells. For in vitro cell-based assays, cells expressing the 5-HT2A receptor are cultured and treated with cis-Urocanic acid. Receptor activation is measured by quantifying intracellular calcium mobilization or other downstream signaling pathways. Its ability to induce immunosuppression can be assessed by measuring cytokine production in immune cells. Mast cell degranulation can be evaluated by measuring the release of histamine or TNF-α. |
| Animal Protocol |
In vivo animal studies with cis-Urocanic acid typically involve models of UV-induced immunosuppression. Mice are exposed to UVB radiation, which converts trans- to cis-urocanic acid in the skin. The resulting immunosuppression is measured by assessing the contact hypersensitivity response. The compound's role can be confirmed by administering cis-Urocanic acid and observing its effects on immune responses.
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| ADME/Pharmacokinetics |
cis-Urocanic acid (CAS: 7699-35-6) has a molecular weight of 138.12 g/mol and a molecular formula of C6H6N2O2. It is an endogenous compound found in the skin. It is soluble in water and is typically stored as a solid. As a 5-HT2A receptor agonist, it is a key molecule in the study of UV radiation, skin immunology, and the mechanisms of immunosuppression.
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| Toxicity/Toxicokinetics |
cis-Urocanic acid is an endogenous compound with immunomodulatory activity. Its toxicity profile is not associated with acute toxicity but rather with its role in UV-induced immunosuppression, which can be a risk factor for skin cancer. The compound is not used as a therapeutic drug but as a research tool for studying immune regulation. Standard laboratory safety precautions should be followed.
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| References |
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| Additional Infomation |
Cis-uric acid is a uric acid with a Z-configuration of the double bond in its carboxyethylene moiety. It is the conjugate acid of cis-uric acid. Cis-uric acid is a derivative of the amino acid histidine, derived from trans-uric acid in mammalian skin under ultraviolet radiation. It is a potentiogenic drug with potential anti-inflammatory and anti-proliferative activities. Following intravesical instillation of cis-uric acid (cis-UCA), in the weakly acidic extracellular environment of tumor cells, its imidazole group is protonated and infiltrates cancer cells. Once inside the cells, due to the weakly alkaline environment of the tumor cells, cis-UCA undergoes deprotonation, i.e., imidazole protons are released into the cytoplasm, ultimately leading to increased intracellular acidity. This acidification can impair many cellular processes, such as metabolic activity, and may lead to cell cycle arrest, induce apoptosis, and necrotic cell death. Furthermore, cis-uric acid (cis-UCA) enhances the ERK and JNK signaling pathways by inhibiting the activity of serine/threonine phosphatases and tyrosine phosphatases.
cis-Urocanic acid is an endogenous 5-HT2A receptor agonist that plays a key role in UV radiation protection and immunomodulation. It is an immune modulator that induces immunosuppression by binding to the 5-HT2A receptor. It is not an approved drug and is intended for research use only. |
| Molecular Formula |
C6H6N2O2
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| Molecular Weight |
138.12404
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| Exact Mass |
138.043
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| CAS # |
7699-35-6
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| Related CAS # |
Urocanic acid;104-98-3;trans-Urocanic acid;3465-72-3;cis-Urocanic acid-13C3
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| PubChem CID |
1549103
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| Appearance |
White to off-white solid powder
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| LogP |
0.507
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
10
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| Complexity |
156
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=C(NC=N1)/C=C\C(=O)O
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| InChi Key |
LOIYMIARKYCTBW-UPHRSURJSA-N
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| InChi Code |
InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1-
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| Chemical Name |
(Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O : ~50 mg/mL (~362.00 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.2401 mL | 36.2004 mL | 72.4008 mL | |
| 5 mM | 1.4480 mL | 7.2401 mL | 14.4802 mL | |
| 10 mM | 0.7240 mL | 3.6200 mL | 7.2401 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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