| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
|
||
| 250mg |
|
||
| 500mg |
|
||
| 1g |
|
||
| Other Sizes |
| Targets |
The primary targets of α-Cyano-4-hydroxycinnamic acid are monocarboxylate transporters (MCTs), particularly MCT1, for which it acts as a potent, noncompetitive inhibitor. It also targets the mitochondrial pyruvate transporter with a Ki of 6.3 μM. Additional targets include mushroom tyrosinase, where it inhibits both monophenolase and diphenolase activities. The compound also inhibits beta-cell apical anion exchange with an IC50 of 2.4 mM. These diverse targets make it valuable in metabolism, cancer, and analytical research.
|
|---|---|
| ln Vitro |
α-Cyano-4-Hydroxycinnamic Acid (α-Cyano-4-Hydroxycinnamic Acid) prevents monocarboxylates like pyruvate and lactate from being transported [2]. Lung explants' epithelial circumference was lowered and branching morphogenesis was significantly inhibited by α-cyano-4-hydroxycinnamic acid (CHC; 0.5 and 1 mM) at 1 mM in a dose-dependent manner. region[2]. At a dosage of 100 μM, α-Cyano-4-hydroxycinnamic acid inhibits oxidized pyruvate's ability to absorb O2 in rat heart mitochondria quickly and nearly entirely. As low as 1 μM of inhibitor can cause inhibition, however it takes time for inhibition to manifest at this dosage [1].
In vitro, α-Cyano-4-hydroxycinnamic acid inhibits pyruvate transport in rat heart mitochondria with an IC50 value that reflects its potent MCT inhibition. It inhibits the mitochondrial pyruvate transporter with a Ki of 6.3 μM. The compound also inhibits beta-cell apical anion exchange with an IC50 of 2.4 mM. As a MALDI matrix, it facilitates peptide ionization and analysis. These in vitro activities support its use in metabolism research, cancer studies (as MCT inhibitors have antitumoral activity), and analytical chemistry. |
| ln Vivo |
In vivo, α-Cyano-4-hydroxycinnamic acid has demonstrated antitumoral and antiangiogenic activity as an MCT inhibitor. MCT inhibition disrupts lactate transport and metabolism in cancer cells, potentially inhibiting tumor growth. The compound's ability to inhibit pyruvate transport may also affect metabolic pathways in various tissues. However, detailed in vivo efficacy data are limited. Further studies are needed to fully characterize its therapeutic potential in cancer and metabolic disorders.
|
| Enzyme Assay |
In vitro enzyme/receptor binding assays for α-Cyano-4-hydroxycinnamic acid include MCT inhibition assays using cell lines expressing MCT1 or isolated mitochondria. Pyruvate transport is measured using radiolabeled pyruvate or fluorescent probes, with compound concentrations ranging from 0.1-1000 μM. The Ki for mitochondrial pyruvate transporter inhibition is determined to be 6.3 μM. Tyrosinase inhibition is assessed using mushroom tyrosinase and L-DOPA as substrate. Anion exchange inhibition is measured in beta-cell assays with an IC50 of 2.4 mM. All assays include appropriate controls.
|
| Cell Assay |
In vitro cell-based assays for α-Cyano-4-hydroxycinnamic acid are conducted using cancer cell lines to assess MCT inhibition and its effects on cell metabolism and viability. Cells are treated with compound concentrations ranging from 0.1-1000 μM for 24-72 hours. Lactate transport is measured using fluorescent probes or radiolabeled lactate. Cell viability is assessed using MTT assays. Metabolic changes are evaluated by measuring extracellular acidification rate (ECAR) or oxygen consumption rate (OCR) using Seahorse analysis. Experiments include vehicle controls and known MCT inhibitors as positive controls.
|
| Animal Protocol |
In vivo animal studies with α-Cyano-4-hydroxycinnamic acid are conducted in mouse xenograft models to evaluate antitumoral and antiangiogenic activity. The compound is administered via intraperitoneal or intravenous injection at doses ranging from 10-200 mg/kg. Tumor growth is measured by caliper measurements. Angiogenesis is assessed by measuring microvessel density or using angiogenesis assays. Metabolic effects are evaluated by measuring lactate and pyruvate levels in blood and tissues. Each group consists of 6-10 animals with vehicle-treated controls.
|
| ADME/Pharmacokinetics |
Pharmacokinetic properties of α-Cyano-4-hydroxycinnamic acid have not been extensively characterized. As a small, polar molecule (MW 189.17), it is expected to have moderate oral bioavailability with rapid absorption. The compound is soluble in DMSO (10 mg/ml) and methanol (5 mg/ml). It likely undergoes hepatic metabolism, including conjugation, with elimination via renal excretion. The compound's use as a MALDI matrix suggests it is stable under analytical conditions. Detailed PK parameters require further investigation.
|
| Toxicity/Toxicokinetics |
Toxicological data for α-Cyano-4-hydroxycinnamic acid indicate that it is generally well-tolerated at concentrations used for in vitro research. No significant toxicity has been reported in cell-based assays at concentrations up to 100 μM. The compound is used as a MALDI matrix, suggesting it is compatible with biological samples. However, comprehensive toxicological studies have not been conducted. As with all research chemicals, appropriate safety precautions should be taken during handling.
|
| References |
|
| Additional Infomation |
α-Cyano-4-hydroxycinnamic acid is a monohydroxycinnamic acid, a compound in which the α-hydrogen of the carboxyl group in 4-hydroxycinnamic acid is replaced by a cyano group. It can be used as a matrix for matrix-assisted laser desorption/ionization (MALDI) mass spectrometry analysis of peptides and oligonucleotides. It is a nitrile compound, belonging to the phenolic class, and is also a monohydroxycinnamic acid.
See also: α-Cyano-4-hydroxycinnamic acid ester (note moved to). α-Cyano-4-hydroxycinnamic acid is a versatile compound with applications in multiple research areas. It is a potent MCT inhibitor with antitumoral and antiangiogenic activity, making it valuable for cancer metabolism research. It inhibits the mitochondrial pyruvate transporter with a Ki of 6.3 μM. The compound is also the commonly used matrix for MALDI-MS peptide analysis. It has photoprotective properties and is used in sunscreen and skincare product development. Not approved for clinical therapeutic use; intended for research purposes only. |
| Molecular Formula |
C₁₀H₇NO₃
|
|---|---|
| Molecular Weight |
189.17
|
| Exact Mass |
189.042
|
| CAS # |
28166-41-8
|
| PubChem CID |
5328791
|
| Appearance |
Light yellow to yellow solid powder
|
| Density |
1.4±0.1 g/cm3
|
| Boiling Point |
398.1±32.0 °C at 760 mmHg
|
| Melting Point |
245-250 °C(lit.)
|
| Flash Point |
194.5±25.1 °C
|
| Vapour Pressure |
0.0±1.0 mmHg at 25°C
|
| Index of Refraction |
1.674
|
| LogP |
1.53
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
14
|
| Complexity |
292
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C1=CC(=CC=C1/C=C(\C#N)/C(=O)O)O
|
| InChi Key |
AFVLVVWMAFSXCK-VMPITWQZSA-N
|
| InChi Code |
InChI=1S/C10H7NO3/c11-6-8(10(13)14)5-7-1-3-9(12)4-2-7/h1-5,12H,(H,13,14)/b8-5+
|
| Chemical Name |
(E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid
|
| Synonyms |
αCyano4hydroxycinnamic acid α Cyano 4 hydroxycinnamic acid
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
DMSO : ~250 mg/mL (~1321.56 mM)
H2O : < 0.1 mg/mL |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (11.00 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (11.00 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (11.00 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.2863 mL | 26.4313 mL | 52.8625 mL | |
| 5 mM | 1.0573 mL | 5.2863 mL | 10.5725 mL | |
| 10 mM | 0.5286 mL | 2.6431 mL | 5.2863 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
