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SML2274

Sigma-Aldrich

DDR1-IN-1

≥98% (HPLC)

Synonym(s):

4-((4-Ethylpiperazin-1-yl)methyl)-N-(4-methyl-3-(2-oxoindolin-5-yloxy)phenyl)-3-(trifluoromethyl)benzamide, N-[3-[(2,3-Dihydro-2-oxo-1H-indol-5-yl)oxy]-4-methylphenyl]-4-[(4-ethyl-1-piperazinyl)methyl]-3-(trifluoromethyl)benzamide

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About This Item

Empirical Formula (Hill Notation):
C30H31F3N4O3
CAS Number:
1449685-96-4
Molecular Weight:
552.59
MDL number:
MFCD28144507
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

CC(C=CC(NC(C1=CC(C(F)(F)F)=C(CN2CCN(CC)CC2)C=C1)=O)=C3)=C3OC4=CC(CC(N5)=O)=C5C=C4

InChI

1S/C30H31F3N4O3/c1-3-36-10-12-37(13-11-36)18-21-6-5-20(15-25(21)30(31,32)33)29(39)34-23-7-4-19(2)27(17-23)40-24-8-9-26-22(14-24)16-28(38)35-26/h4-9,14-15,17H,3,10-13,16,18H2,1-2H3,(H,34,39)(H,35,38)

InChI key

AOZPVMOOEJAZGK-UHFFFAOYSA-N

Biochem/physiol Actions

DDR1-IN-1 is a type II, subtype-selective discoidin domain receptor (DDR) tyrosine kinase inhibitor (DDR1/2 IC50 = 105 nM/413 nM) that effectively blocks collagen-induced DDR1 pY513 autophosphorylation in U2OS cells (EC50 = 86.76 nM) with excellent selectivity over a panel of >380 kinases. DDR1-IN-1 inhibits DDR2-mediated MT1-MMP activation in human rheumatoid synovial fibroblasts (RASF) upon collagen stimulation (IC50 < 2.5 μM) and enhances PI3K/mTOR inhibitor GSK2126458 antiproliferation efficacy in SNU-1040 colorectal cancer culture (123%, 70%, 50% of control, respectively, post 48-hr 250 nM DDR1-IN-1, 82.5 nM GSK2126458, or combined treatment).
DDR1-IN-1 protects cells from apoptosis by inhibiting collagen-mediated Bcl-2-interacting killer (BIK) induction at both mRNA and protein levels.

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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Delphine Assent et al.
PloS one, 10(3), e0116006-e0116006 (2015-03-17)
During tumour dissemination, invading breast carcinoma cells become confronted with a reactive stroma, a type I collagen-rich environment endowed with anti-proliferative and pro-apoptotic properties. To develop metastatic capabilities, tumour cells must acquire the capacity to cope with this novel microenvironment.
A Membrane-Type-1 Matrix Metalloproteinase (MT1-MMP) - Discoidin Domain Receptor 1 Axis Regulates Collagen-Induced Apoptosis in Breast Cancer Cells
Assent D, et al.
PLoS ONE, 10, e0116006-e0116006 (2015)
Yangyang Bian et al.
Nature chemical biology, 12(11), 959-966 (2016-10-19)
We present a new strategy for systematic identification of phosphotyrosine (pTyr) by affinity purification mass spectrometry (AP-MS) using a Src homology 2 (SH2)-domain-derived pTyr superbinder as the affinity reagent. The superbinder allows for markedly deeper coverage of the Tyr phosphoproteome
Iwona Majkowska et al.
The Journal of biological chemistry, 292(16), 6633-6643 (2017-03-09)
Membrane-type 1 matrix metalloproteinase (MT1-MMP) is a membrane-bound MMP that is highly expressed in cells with invading capacity, including fibroblasts and invasive cancer cells. However, pathways of MT1-MMP up-regulation are not clearly understood. A potential physiological stimulus for MT1-MMP expression
Hyung-Gu Kim et al.
ACS chemical biology, 8(10), 2145-2150 (2013-08-01)
The DDR1 receptor tyrosine kinase is activated by matrix collagens and has been implicated in numerous cellular functions such as proliferation, differentiation, adhesion, migration, and invasion. Here we report the discovery of a potent and selective DDR1 inhibitor, DDR1-IN-1, and
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