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

Catalog No.S8612 Batch:S861203

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Technical Data

Formula

C10H7NO3
Molecular Weight 189.17 CAS No. 28166-41-8
Solubility (25°C)* In vitro DMSO 38 mg/mL (200.87 mM)
Ethanol 38 mg/mL (200.87 mM)
Water Insoluble
* <1 mg/ml means slightly soluble or 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.
* Room temperature shipping (Stability testing shows this product can be shipped without any cooling measures.)

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Biological Activity

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 (from reference)

Cell Assay:

[1]
  • 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).
Animal Study:

[4]
  • Animal Models

    RJ:NMRI mice

  • Dosages

    1 mmol/Kg

  • Administration

    i.p.

Selleck's α-cyano-4-hydroxycinnamic acid(α-CHCA) has been cited by 6 publications

GPR65 sensing tumor-derived lactate induces HMGB1 release from TAM via the cAMP/PKA/CREB pathway to promote glioma progression [ J Exp Clin Cancer Res, 2024, 43(1):105] PubMed: 38576043
PDGF-BB accelerates TSCC via fibroblast lactates limiting miR-26a-5p and boosting mitophagy [ Cancer Cell Int, 2024, 24(1):5] PubMed: 38169376
ENO1 Promotes OSCC Migration and Invasion by Orchestrating IL-6 Secretion from Macrophages via a Positive Feedback Loop [ Int J Mol Sci, 2023, 24(1)737] PubMed: 36614179
Aerobic glycolysis enhances HBx-initiated hepatocellular carcinogenesis via NF-κBp65/HK2 signalling [ J Exp Clin Cancer Res, 2022, 41(1):329] PubMed: 36411480
Autoregulation of H+/lactate efflux prevents monocarboxylate transport (MCT) inhibitors from reducing glycolytic lactic acid production [ Br J Cancer, 2022, 10.1038/s41416-022-01910-7] PubMed: 35840734
Proteogenomic characterization identifies clinically relevant subgroups of intrahepatic cholangiocarcinoma [ Cancer Cell, 2021, S1535-6108(21)00659-0] PubMed: 34971568

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SHIPPING AND STORAGE
Selleck products are transported at room temperature. If you receive the product at room temperature, please rest assured, the Selleck Quality Inspection Department has conducted experiments to verify that the normal temperature placement of one month will not affect the biological activity of powder products. After collecting, please store the product according to the requirements described in the datasheet. Most Selleck products are stable under the recommended conditions.

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