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SML1976

Sigma-Aldrich

DIM-C-pPhCO2Me

≥98% (HPLC)

Sinônimo(s):

4-(di-1H-Indol-3-ylmethyl)-benzoic acid methyl ester, Benzoic acid, 4-(di-1H-indol-3-ylmethyl)-, methyl ester

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About This Item

Fórmula empírica (Notação de Hill):
C25H20N2O2
Número CAS:
151358-48-4
Peso molecular:
380.44
Código UNSPSC:
12352200
NACRES:
NA.77

Ensaio

≥98% (HPLC)

Formulário

powder

cor

pink to light red

solubilidade

DMSO: 2 mg/mL, clear

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

O=C(OC)C1=CC=C(C(C2=CNC3=C2C=CC=C3)C4=CNC5=CC=CC=C54)C=C1

InChI

1S/C25H20N2O2/c1-29-25(28)17-12-10-16(11-13-17)24(20-14-26-22-8-4-2-6-18(20)22)21-15-27-23-9-5-3-7-19(21)23/h2-15,24,26-27H,1H3

Ações bioquímicas/fisiológicas

DIM-C-pPhCO2Me is a NR4A1 (Nur77) antagonist that exhibit potent anticancer activity in pancreatic, colon, breast, kidney, and rhabdomyosarcoma cells. DIM-C-pPhCO2Me decreases expression of PAX3-FOXO1A and β1-integrin proteins in Rh30 rhabdomyosarcoma and MDA-MB-231 breast cancer cells. DIM-C-pPhCO2Me inhibits migration of Rh30 and MDA-MB-231 cancer cells.
DIM-C-pPhCO2Me is also known as 1,1-bis(3′-indolyl)-1-(p-carboxymethylphenyl)methane. In pancreatic and colon cancer cells, DIM-C-pPhCO2Me plays an inhibitory role on cell migration. DIM-C-pPhCO2Me prevents the action of mechanistic target of rapamycin (mTOR) and reduces the multiplication and survival of cancer cells. It stimulates reactive oxygen species (ROS) in various cancer cell lines.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

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Erik Hedrick et al.
Molecular and cellular biology, 36(9), 1383-1394 (2016-03-02)
Overexpression of the nuclear receptor 4A1 (NR4A1) in breast cancer patients is a prognostic factor for decreased survival and increased metastasis, and this has been linked to NR4A1-dependent regulation of transforming growth factor β (TGF-β) signaling. Results of RNA interference
The nuclear orphan receptor Nr4a1 regulates beta1-integrin expression in pancreatic and colon cancer cells and can be targeted by Nr4a1 antagonists
Hedrick E, et al.
Molecular Carcinogenesis, 56(9), 2066-2075 (2017)
Syng-Ook Lee et al.
Molecular endocrinology (Baltimore, Md.), 28(10), 1729-1739 (2014-08-08)
1,1-Bis(3'-indolyl)-1-(p-substituted phenyl)methane (C-DIM) compounds exhibit antineoplastic activity in multiple cancer cell lines and the p-hydroxyphenyl analog (DIM-C-pPhOH) inactivates nuclear receptor 4A1 (NR4A1) in lung and pancreatic cancer cell lines. Using a series of 14 different p-substituted phenyl C-DIMs, we show
Alexandra Lacey et al.
Cancer research, 77(3), 732-741 (2016-11-20)
Alveolar rhabdomyosarcoma (ARMS) is a devastating pediatric disease driven by expression of the oncogenic fusion gene PAX3-FOXO1A. In this study, we report overexpression of the nuclear receptor NR4A1 in rhabdomyosarcomas that is sufficient to drive high expression of PAX3-FOXO1A there.

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