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Merck
CN

PZ0147

PHA-665752 hydrate

≥98% (HPLC)

Synonym(s):

(3Z)-5-[[(2,6-Dichlorophenyl)methyl]sulfonyl]-3-[[3,5-dimethyl-4-[[(2R)-2-(1-pyrrolidinylmethyl)-1-pyrrolidinyl]carbonyl]-1H-pyrrol-2-yl]methylene]-1,3-dihydro-2H-indol-2-one hydrate

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About This Item

Empirical Formula (Hill Notation):
C32H34Cl2N4O4S · xH2O
CAS Number:
477575-56-7
Molecular Weight:
641.61 (anhydrous basis)
NACRES:
NA.77
PubChem Substance ID:
329823732
UNSPSC Code:
12352200
MDL number:
MFCD18632554

Key Documents

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InChI key

MKHQWLQMOSOUEQ-SCLITUASSA-N

SMILES string

O.Cc1[nH]c(\C=C2/C(=O)Nc3ccc(cc23)S(=O)(=O)Cc4c(Cl)cccc4Cl)c(C)c1C(=O)N5CCC[C@@H]5CN6CCCC6

InChI

1S/C32H34Cl2N4O4S.H2O/c1-19-29(35-20(2)30(19)32(40)38-14-6-7-21(38)17-37-12-3-4-13-37)16-24-23-15-22(10-11-28(23)36-31(24)39)43(41,42)18-25-26(33)8-5-9-27(25)34;/h5,8-11,15-16,21,35H,3-4,6-7,12-14,17-18H2,1-2H3,(H,36,39);1H2/b24-16-;/t21-;/m1./s1

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +50 to +70°, c = 0.2 in methanol

color

light yellow to light brown

solubility

DMSO: ≥20 mg/mL

storage temp.

2-8°C

Quality Level

100

Application

PHA-665752 hydrate has been used as a c-Met inhibitor:
  • to study its effects on oxidative stress in human mammary epithelial MCF10A cells with extra centrosomes
  • to study its effects on the clonogenicity of T-cell specific transcription factor/ lymphoid enhancer-binding factor-1 (TCF/LEF-1) responsive promoter to drive expression of green fluorescent protein (TOP-GFP) cancer stem cell (CSC) cultures
  • to study its inhibitory effects on melanoma cell lines

Biochem/physiol Actions

PHA-665752 ia a c-Met kinase inhibitor.
PHA-665752 ia a c-Met kinase inhibitor. PHA-665752 is ATP-competitive, an active-site inhibitor with greater than 50-fold selectivity for c-Met vs a panel of tyrosine and serine-threonine kinases.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Met page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000301928
0000301928
0000185798
0000185798
0000081850

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Registered report: Tumour micro-environment elicits innate resistance to RAF inhibitors through HGF secretion
Blum D, et al.
eLife, 3(4), e04034-e04034 (2014)
Oxidative stress in cells with extra centrosomes drives non-cell-autonomous invasion
Arnandis T, et al.
Developmental Cell, 47(4), 409-424 (2018)
Replication Study: Wnt activity defines colon cancer stem cells and is regulated by the microenvironment
Essex A, et al.
eLife, 8(4), e45426-e45426 (2019)
Anthony Essex et al.
eLife, 8 (2019-06-20)
As part of the Reproducibility Project: Cancer Biology we published a Registered Report (Evans et al., 2015), that described how we intended to replicate selected experiments from the paper 'Wnt activity defines colon cancer stem cells and is regulated by
David Blum et al.
eLife, 3 (2014-12-11)
The Reproducibility Project: Cancer Biology seeks to address growing concerns about reproducibility in scientific research by conducting replications of 50 papers in the field of cancer biology published between 2010 and 2012. This Registered Report describes the proposed replication plan
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