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SML3156

Sigma-Aldrich

ALW-II-41-27

≥98% (HPLC)

Synonym(s):

ALW-II-247, N-(5-(4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenylcarbamoyl)-2-methylphenyl)-5-(thiophen-2-yl)nicotinamide, N-[4-[(4-Ethyl-1-piperazinyl)methyl]-3-(trifluoromethyl)phenyl]-4-methyl-3-[[[5-(2-thienyl)-3-pyridinyl]carbonyl]amino]benzamide

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About This Item

Empirical Formula (Hill Notation):
C32H32F3N5O2S
CAS Number:
1186206-79-0
Molecular Weight:
607.69
MDL number:
MFCD25372028
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(NC1=CC=C(CN2CCN(CC)CC2)C(C(F)(F)F)=C1)C3=CC=C(C)C(NC(C4=CC(C5=CC=CS5)=CN=C4)=O)=C3

InChI

1S/C32H32F3N5O2S/c1-3-39-10-12-40(13-11-39)20-23-8-9-26(17-27(23)32(33,34)35)37-30(41)22-7-6-21(2)28(16-22)38-31(42)25-15-24(18-36-19-25)29-5-4-14-43-29/h4-9,14-19H,3,10-13,20H2,1-2H3,(H,37,41)(H,38,42)

InChI key

HYWXBDQAYLPMIX-UHFFFAOYSA-N

Biochem/physiol Actions

ALW-II-41-27 is an RG-25 (RG25) structural analog that exhibits enhanced type II kinase inhibitor activity against ephrin type-A receptor 2/EphA2/ECK (IC50 = 11 nM vs 770 nM with NG25) by targeting the ATP-binding pocket and an allosteric site next to the “DFG” motif. ALW-II-41-27 inhibits constitutive and ephrin A1-induced EphA2 tyrosine phosphorylation (0.1-1 μM; H358), effectively suppressing EphA2-dependent cancer survival in vitro (0.1-1 μM for 72 hrs; NSCLC) and xenograft tumor growth in mice in vivo (15-30 mg/kg b.i.d. i.p.; H358 NSCLC & A375 melanoma). Note: ALW-II-41-27 and RG-25 (RG25) display very similar kinase-targeting profiles with EphA2 being a notable exception, RG25 can therefore serve as a control for ALW-II-41-27 when probing EphA2-mediated cellular functions.

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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Katherine R Amato et al.
The Journal of clinical investigation, 124(5), 2037-2049 (2014-04-10)
Genome-wide analyses determined previously that the receptor tyrosine kinase (RTK) EPHA2 is commonly overexpressed in non-small cell lung cancers (NSCLCs). EPHA2 overexpression is associated with poor clinical outcomes; therefore, EPHA2 may represent a promising therapeutic target for patients with NSCLC.
Katherine R Amato et al.
Cancer research, 76(2), 305-318 (2016-01-09)
Despite the success of treating EGFR-mutant lung cancer patients with EGFR tyrosine kinase inhibitors (TKI), all patients eventually acquire resistance to these therapies. Although various resistance mechanisms have been described, there are currently no FDA-approved therapies that target alternative mechanisms
Characterization of DDR2 Inhibitors for the Treatment of DDR2 Mutated Nonsmall Cell Lung Cancer.
Terai, et al.
ACS chemical biology, 10, 2687-2696 (2018)
Yongmun Choi et al.
Bioorganic & medicinal chemistry letters, 19(15), 4467-4470 (2009-06-26)
The Eph family of receptor tyrosine kinases has drawn growing attention due to their role in regulating diverse biological phenomena. However, pharmacological interrogation of Eph kinase function has been hampered by a lack of potent and selective Eph kinase inhibitors.
Azadeh Arabzadeh et al.
Oncotarget, 8(61), 104330-104346 (2017-12-22)
We have shown that carcinoembryonic antigen cell adhesion molecule 1 long isoform (CEACAM1-L) expression in MC38 metastatic colorectal cancer (CRC) cells results in liver metastasis inhibition via CCL2 and STAT3 signaling. But other molecular mechanisms orchestrating CEACAM1-L-mediated metastasis inhibition remain
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