α-cyano-4-hydroxycinnamic acid(α-CHCA)

For research use only.

Catalog No.S8612

α-cyano-4-hydroxycinnamic acid(α-CHCA) Chemical Structure

CAS No. 28166-41-8

4-Chloro-α-cyanocinnamic acid (α-CHCA) is a classic monocarboxylate transporters (MCT) inhibitor. α-cyano-4-hydroxycinnamate (CHC) has a 10-fold selectivity for MCT1 compared to other MCTs.

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Description 4-Chloro-α-cyanocinnamic acid (α-CHCA) is a classic monocarboxylate transporters (MCT) inhibitor. α-cyano-4-hydroxycinnamate (CHC) has a 10-fold selectivity for MCT1 compared to other MCTs.
Targets
MCT [1]
()
In vitro

Most glioma cell lines are sensitive to CHC, with the exception of SW1088 and SW1783 cells, which show lower sensitivity. The effect of CHC on U251 and SW1088 total cell biomass appears to be related to lactate transport activity. Accordingly, U251 cells presents higher levels of MCT1 and CD147 at the plasma membrane than did SW1088, and consequently, CHC decreases glucose consumption and lactate production in U251, but not in SW1088 cells. In the sensitive U251 cells, CHC is able to inhibit cell proliferation and induce cell death, having a cytotoxic effect; however, in the less sensitive SW1088 cells, CHC only inhibits cell proliferation but did not induce cell death, having only a cytostatic effect. CHC does not enter the cell because its inhibitory effect is dependent on interactions with membrane proteins accessible from the outside of the cell[1]. CHC can inhibit different MCT isoforms. However, they have different sensitivities. In this context, in addition to MCT1, CHC could also inhibit MCT4 activity; however, the latter should happen at much higher concentrations, because MCT4 has much lower affinity for CHC (Ki values are 5-10 times higher than for MCT1; 50-100 mM). Transport by MCT1, 2, and 4 is competitively inhibited by CHC whereas transport by MCT3 is insensitive to this inhibitor[1][2]. CHC is also a small-molecule inhibitor of lactate transport[3].

In vivo CHC effects in the normal brain tissue are minimal and do not have a significant impact in the neuron-astrocyte lactate shuttle[1].

Protocol

Cell Research:

[1]

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  • Cell lines: Glioma cells
  • Concentrations: 0.6-12 mM
  • Incubation Time: 24, 48, and 72 h
  • Method:

    Cells are plated into 96-well plates, at a density of 3 × 103 cells per well. The effect of treatment with CHC (0.6-12 mM) on cell number (total biomass) is determined at 24, 48, and 72 h by the sulforhodamine B assay. IC50 values (i.e., CHC concentration that corresponds to 50% of cell growth inhibition) are estimated from 3 independent experiments, each one in triplicate, using GraphPad Software. Cell proliferation assay is performed and assessed under the treatment conditions previously described, for 5 mM and 10 mM of CHC. After CHC treatment, cells are incubated with BrdU and its incorporation is assessed at 450 nm (λref = 655 nm).


    (Only for Reference)
Animal Research:

[4]

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  • Animal Models: RJ:NMRI mice
  • Dosages: 1 mmol/Kg
  • Administration: i.p.
    (Only for Reference)

Solubility (25°C)

In vitro DMSO 37 mg/mL (195.59 mM)
Ethanol 8 mg/mL (42.29 mM)
Water Insoluble

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 189.17
Formula

C10H7NO3

CAS No. 28166-41-8
Storage powder
in solvent
Synonyms N/A
Smiles C1=CC(=CC=C1C=C(C#N)C(=O)O)O

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Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID