7-Diethylaminocoumarin-3-carboxylic acid

Names

[ Name ]:
7-Diethylaminocoumarin-3-carboxylic acid

[Synonym ]:
7-diethylaminocoumarin-3-carboxylic acid
7-(Diethylamino)coumarin-3-carboxylic Acid
2H-1-Benzopyran-3-carboxylic acid, 7-(diethylamino)-2-oxo-
7-(Diethylamino)-2-oxo-2H-chromene-3-carboxylic acid
7-(diethylamino)-2-oxochromene-3-carboxylic acid
7ACC1

Biological Activity

[Description]:

7ACC1(DEAC; Coumarin D 1421; D 1421) selectively interfere with lactate fluxes in the lactate-rich tumor microenvironment; inhibits lactate influx but not efflux in tumor cells expressing MCT1 and MCT4 transporters.IC50 value: 0.86 uM(Lactate uptake inhibition) [1]Target: MCT inhibitor; lactate transport inhibitorContrary to the reference MCT1 inhibitor AR-C155858, 7ACC unexpectedly inhibited lactate influx but not efflux in tumor cells expressing MCT1 and MCT4 transporters. 7ACC delayed the growth of cervix SiHa tumors, colorectal HCT116 tumors, and orthoptopic MCF-7 breast tumors. MCT target engagement was confirmed by the lack of activity of 7ACC on bladder UM-UC-3 carcinoma that does not express functional MCT. 7ACC also inhibited SiHa tumor relapse after treatment with cisplatin. Finally, we found that contrary to AR-C155858, 7ACC did not prevent the cell entry of the substrate-mimetic drug 3-bromopyruvate (3BP) through MCT1, and contributed to the inhibition of tumor relapse after 3BP treatment.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Monocarboxylate Transporter

Research Areas >> Cancer

[References]

[1]. Draoui N, et al. Antitumor activity of 7-aminocarboxycoumarin derivatives, a new class of potent inhibitors of lactate influx but not efflux. Mol Cancer Ther. 2014 Jun;13(6):1410-8.

[Related Small Molecules]

AZD3965 | UK-5099 | AR-C155858 | 7ACC2

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
464.7±45.0 °C at 760 mmHg

[ Melting Point ]:
222-224ºC (dec.)(lit.)

[ Molecular Formula ]:
C₁₄H₁₅NO₄

[ Molecular Weight ]:
261.273

[ Flash Point ]:
234.9±28.7 °C

[ Exact Mass ]:
261.100098

[ PSA ]:
70.75000

[ LogP ]:
3.34

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.618

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2932209090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932209090

[ Summary ]:
2932209090. other lactones. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Photophysical properties of 7-(diethylamino)coumarin-3-carboxylic acid in the nanocage of cyclodextrins and in different solvents and solvent mixtures.

Photochem. Photobiol. , (2012)

The photophysical properties of 7-(diethylamino) coumarin-3-carboxylic acid (7-DCCA) were studied in cyclodextrins (α, β, γ,-CDs), different neat solvents and solvent mixtures by using steady state ab...

Cholesterol-dependent formation of GM1 ganglioside-bound amyloid beta-protein, an endogenous seed for Alzheimer amyloid.

J. Biol. Chem. 276(27) , 24985-90, (2001)

GM1 ganglioside-bound amyloid beta-protein (GM1/Abeta), found in brains exhibiting early pathological changes of Alzheimer's disease (AD) including diffuse plaques, has been suggested to be involved i...

Interactions of amyloid beta-protein with various gangliosides in raft-like membranes: importance of GM1 ganglioside-bound form as an endogenous seed for Alzheimer amyloid.

Biochemistry 41(23) , 7385-90, (2002)

GM1 ganglioside-bound amyloid beta-protein (GM1-Abeta), found in brains exhibiting early pathological changes of Alzheimer's disease (AD) plaques, has been suggested to accelerate amyloid fibril forma...