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

Catalog No.S8612 Batch:S861202

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.

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.

References

[4] Sonveaux P, et al. J Clin Invest. 2008, 118(12):3930-42.

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Selleck's α-cyano-4-hydroxycinnamic acid(α-CHCA) has been cited by 5 publications

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
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