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SML1907

Sigma-Aldrich

ESI-05

≥98% (HPLC)

Synonym(s):

1,3,5-Trimethyl-2-[(4-methylphenyl)sulfonyl]-benzene, Mesityl (4-methylphenyl) sulfone

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About This Item

Empirical Formula (Hill Notation):
C16H18O2S
CAS Number:
5184-64-5
Molecular Weight:
274.38
MDL number:
MFCD00091573
UNSPSC Code:
12352200
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

room temp

SMILES string

CC1=CC=C(S(C2=C(C)C=C(C)C=C2C)(=O)=O)C=C1

InChI

1S/C16H18O2S/c1-11-5-7-15(8-6-11)19(17,18)16-13(3)9-12(2)10-14(16)4/h5-10H,1-4H3

InChI key

CGPHOZWFSFNOEQ-UHFFFAOYSA-N

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Show Differences

1 of 4

This Item
SML1726SML1920SML2657
ESI-05 ≥98% (HPLC)

SML1907

ESI-05

MSAB ≥95% (HPLC)

SML1726

MSAB

ML364 ≥98% (HPLC)

SML1920

ML364

MP-A08 ≥98% (HPLC)

SML2657

MP-A08

assay

≥98% (HPLC)

assay

≥95% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

form

powder

form

powder

form

powder

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

room temp

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMSO: 20 mg/mL, clear

solubility

DMSO: 25 mg/mL, clear

solubility

DMSO: 20 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

color

white to beige

color

off-white to purple

color

white to beige

color

white to beige

Application

ESI-05 has been used to study the effect of protein exchange directly activated by cAMP 2 on traumatic brain injury.[1]

Biochem/physiol Actions

ESI-05 is a selective inhibitor against cAMP-regulated guanine nucleotide exhange factor (GEF) EPAC2 (Exchange factor directly activated by cAMP 2) activation by targeting an EPAC2-specific allosteric site at the interface of the two cAMP-binding domains.
ESI-05 is a selective inhibitor against cAMP-regulated guanine nucleotide exhange factor (GEF) EPAC2 (Exchange factor directly activated by cAMP 2) activation by targeting an EPAC2-specific allosteric site at the interface of the two cAMP-binding domains. ESI-05 inhibits EAPC2, but not EPAC1 or PKA, activation by cAMP in a highly potent (IC50 = 430 nM; 25 μM cAMP) and cAMP-competitive manner in cell-free assays, and suppresses cAMP analog 007-AM-induced cellular Rap1 activation in EPAC2-, but not EPAC1-, expressing HEK293 transfectants.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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    Lot/Batch Number
    027M4612V

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    Tamara Tsalkova et al.
    Proceedings of the National Academy of Sciences of the United States of America, 109(45), 18613-18618 (2012-10-24)
    The major physiological effects of cAMP in mammalian cells are transduced by two ubiquitously expressed intracellular cAMP receptors, protein kinase A (PKA) and exchange protein directly activated by cAMP (EPAC), as well as cyclic nucleotide-gated ion channels in certain tissues.
    Haijun Chen et al.
    Journal of medicinal chemistry, 56(3), 952-962 (2013-01-05)
    EPAC1 and EPAC2, two isoforms of exchange proteins directly activated by cAMP (EPAC), respond to the second messenger cAMP and regulate a wide variety of intracellular processes under physiological and pathophysiological circumstances. Herein, we report the chemical design, synthesis, and
    Eva Calderón-Sánchez et al.
    PloS one, 11(2), e0147375-e0147375 (2016-02-04)
    Urocortin-1 (Ucn-1) is an endogenous peptide that protects heart from ischemia and reperfusion (I/R) injuries. Ucn-1 is known to prevent cardiac cell death, but its role in the transcription of specific genes related to survival signaling pathway has not been
    Ling Zhang et al.
    Frontiers in neuroscience, 12, 263-263 (2018-05-10)
    Traumatic brain injury (TBI) is a major cause of mortality and disability worldwide. TBI-induced neuronal apoptosis is one of the main contributors to the secondary injury process. The aim of this study is to investigate the involvement of Exchange protein

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