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SML0501

Sigma-Aldrich

SB-590885

≥98% (HPLC)

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Synonym(s):
5-(2-(4-(2-Dimethylaminoethoxy)phenyl)-5-(4-pyridinyl)-1H-imidazol-4-yl)-2,3-dihydro-1H-inden-1-one oxime
Empirical Formula (Hill Notation):
C27H27N5O2
CAS Number:
405554-55-4
Molecular Weight:
453.54
MDL number:
MFCD16038645
UNSPSC Code:
12352200
PubChem Substance ID:
329825450
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL (clear solution, warmed)

storage temp.

2-8°C

SMILES string

CN(C)CCOc1ccc(cc1)-c2nc(-c3ccc4c(CC\C4=N\O)c3)c([nH]2)-c5ccncc5

InChI

1S/C27H27N5O2/c1-32(2)15-16-34-22-7-3-19(4-8-22)27-29-25(18-11-13-28-14-12-18)26(30-27)21-5-9-23-20(17-21)6-10-24(23)31-33/h3-5,7-9,11-14,17,33H,6,10,15-16H2,1-2H3,(H,29,30)/b31-24-

InChI key

MLSAQOINCGAULQ-QLTSDVKISA-N

Application

SB-590885 has been used as a component of a mixture to maintain naive human pluripotent stem cells (PSCs).It has also been used as B-Raf (BRAF) inhibitor to study its effects on lung adenocarcinoma cell lines.

Biochem/physiol Actions

SB-590885 is a potent and selective ATP competitive inhibitor of B-Raf kinase with Kd = 300 pM for B-Raf, and >1000-fold selectivity over a panel of 22 commonly studied cellular kinases

Features and Benefits

This compound is featured on the MAPKKKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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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Comprehensive cell surface protein profiling identifies specific markers of human naive and primed pluripotent states
Collier A J, et al.
Cell Stem Cell, 20(6), 874-890 (2017)
An integrative pharmacogenomic approach identifies two-drug combination therapies for personalized cancer medicine
Liu Y, et al.
Scientific Reports, 6(6), 22120-22120 (2016)
S Tiwary et al.
Oncogenesis, 3, e110-e110 (2014-07-08)
Melanoma is curable when it is at an early phase but is lethal once it becomes metastatic. The recent development of BRAF(V600E) inhibitors (BIs) showed great promise in treating metastatic melanoma, but resistance developed quickly in the treated patients, and

Articles

MAPKKKs

The extracellular signal regulated kinase (ERK1 and ERK2) pathways are activated by mitogens and play an important role in controlling cell growth and differentiation.

Naive Pluripotent Stem Cell Culture in Serum-Free Media

Naive pluripotent stem cells cultured in vitro using specialized media and inhibitors mimic "ground-state" cells from blastocysts.

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