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Key Documents

SML0814

Sigma-Aldrich

ESI-09

≥98% (HPLC)

Synonym(s):

α-[2-(3-Chlorophenyl)hydrazinylidene]-5-(1,1-dimethylethyl)-b-oxo-3-isoxazolepropanenitrile

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About This Item

Empirical Formula (Hill Notation):
C16H15ClN4O2
CAS Number:
263707-16-0
Molecular Weight:
330.77
UNSPSC Code:
41106305
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

, faint yellow to dark orange

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

InChI

1S/C16H15ClN4O2/c1-16(2,3)14-8-12(21-23-14)15(22)13(9-18)20-19-11-6-4-5-10(17)7-11/h4-8,19H,1-3H3/b20-13+

InChI key

DXEATJQGQHDURZ-DEDYPNTBSA-N

Application

ESI-09 has been used as an antagonist for exchange factor directly activated by cAMP (EPAC).

Biochem/physiol Actions

ESI-09 is a potent, specific inhibitor of EPAC (exchange protein directly activated by cAMP). ESI-09 inhibits EPAC1 and EPAC2 with IC50 values of 3.2 and 1.4 μM, respectively, with no activity against PKA at 25 μM. In pancreatic cell lines, the compound blocks phosphorylation of Akt and insulin secretion. ESI-09 inhibits migration of pancreatic cancer cell lines.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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AKAP-mediated feedback control of cAMP gradients in developing hippocampal neurons.
Gorshkov K, et al.
Nature Chemical Biology, 13(4), 425-425 (2017)
Transforming growth factor β2 promotes transcription of COX2 and EP4, leading to a prostaglandin E2-driven autostimulatory loop that enhances virulence of Theileria annulata transformed macrophages.
Haidar M, et al.
Infection and Immunity, 83(5), 1869-1880 (2015)
Different cAMP sources are critically involved in G protein?coupled receptor CRHR1 signaling.
Inda C, et al.
The Journal of Cell Biology, 214(2), 181-195 (2016)
α-Viniferin Improves Facial Hyperpigmentation via Accelerating Feedback Termination of cAMP/PKA-Signaled Phosphorylation Circuit in Facultative Melanogenesis.
Yun C Y, et al.
Theranostics, 8(7), 2031-2031 (2018)
Wei Liu et al.
The Journal of experimental medicine, 217(4) (2020-01-10)
Progressive loss of retinal ganglion cells (RGCs) leads to irreversible visual deficits in glaucoma. Here, we found that the level of cyclic AMP and the activity and expression of its mediator Epac1 were increased in retinas of two mouse models
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