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R0158

Sigma-Aldrich

RepSox

≥98% (HPLC), solid, TGF-β RI kinase inhibitor

Synonym(s):

E-616452; 2-[3-(6-Methyl-2-pyridinyl)-1H-pyrazol-4-yl]-1,5-naphthyridine

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About This Item

Empirical Formula (Hill Notation):
C17H13N5
CAS Number:
446859-33-2
Molecular Weight:
287.32
MDL number:
MFCD09037561
UNSPSC Code:
51111800
PubChem Substance ID:
329823975
NACRES:
NA.77

product name

RepSox, ≥98% (HPLC)

Quality Level

100

Assay

≥98% (HPLC)

form

solid

solubility

DMSO: >20 mg/mL

storage temp.

2-8°C

SMILES string

Cc1cccc(n1)-c2n[nH]cc2-c3ccc4ncccc4n3

InChI

1S/C17H13N5/c1-11-4-2-5-16(20-11)17-12(10-19-22-17)13-7-8-14-15(21-13)6-3-9-18-14/h2-10H,1H3,(H,19,22)

InChI key

LBPKYPYHDKKRFS-UHFFFAOYSA-N

Application

RepSox has been used as an inhibitor of autophosphorylation of the transforming growth factor β type I receptor kinase (ALK5). It has also been used as a basal media component for culturing human Pluripotent stem cells.

Biochem/physiol Actions

RepSox Inhibits TGF-beta receptor signaling. Retroviral transduction of Sox2, Oct4, and Klf4 genes results in direct reprogramming of somatic cells into induced pluripotent stem cells (iPSCs).
RepSox inhibits osteoclast differentiation, resorption in bone tissues and ovariectomy (OVX)‐induced osteoporosis (OP) through repression of the SMAD family member 3 (Smad3) and c-Jun N-terminal kinase (JNK) pathway/ activator protein 1 (AP-1) pathways.

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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Establishment of a normal-derived estrogen receptor-positive cell line comparable to the prevailing human breast cancer subtype
Hopkinson B, et al.
Testing, 8(6), 10580-10580 (2017)
Phosphorylation of NEUROG3 links endocrine differentiation to the cell cycle in pancreatic progenitors
Krentz N, et al.
Developmental Cell, 41(2), 129-142 (2017)
Yumiko Mihara et al.
The Journal of clinical endocrinology and metabolism, 105(12) (2020-09-03)
To identify the upstream regulators (URs) involved in the onset and pathogenesis of ovarian endometrioma. Recently, a method called Significance-based Modules Integrating the Transcriptome and Epigenome (SMITE) that uses transcriptome data in combination with publicly available data for identifying URs
Small molecule inhibitor RepSox prevented ovariectomy-induced osteoporosis by suppressing osteoclast differentiation and bone resorption
Mei L, et al.
Journal of Cellular Physiology, 233(12) (2018)
Alice C Newman et al.
Nature communications, 8(1), 1537-1537 (2017-11-18)
Macroautophagy can regulate cell signalling and tumorigenesis via elusive molecular mechanisms. We establish a RAS mutant cancer cell model where the autophagy gene ATG5 is dispensable in A549 cells in vitro, yet promotes tumorigenesis in mice. ATG5 represses transcriptional activation
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