SML1047
GW2580
≥98% (HPLC)
Synonym(s):
5-[[3-Methoxy-4-[(4-methoxyphenyl)methoxy]phenyl]methyl]-2,4-Pyrimidinediamine, 5-[[3-Methoxy-4-[(4-methoxyphenyl)methoxy]phenyl]methyl]pyrimidine-2,4-diamine, GW 2580, GW-2580
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About This Item
Empirical Formula (Hill Notation):
C20H22N4O3
CAS Number:
Molecular Weight:
366.41
UNSPSC Code:
12352200
NACRES:
NA.77
Quality Level
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 10 mg/mL, clear (warmed)
storage temp.
−20°C
SMILES string
Nc1nc(c(cn1)Cc2cc(c(cc2)OCc3ccc(cc3)OC)OC)N
InChI
1S/C20H22N4O3/c1-25-16-6-3-13(4-7-16)12-27-17-8-5-14(10-18(17)26-2)9-15-11-23-20(22)24-19(15)21/h3-8,10-11H,9,12H2,1-2H3,(H4,21,22,23,24)
InChI key
MYQAUKPBNJWPIE-UHFFFAOYSA-N
Application
GW2580 has been used to study its effect on paracrine signaling from stretched cardiomyocyte on cardiac fibroblast phenotype.
Biochem/physiol Actions
GW2580 is a cell-permeable, potent and selective ATP-competitive inhibitor of cFMS kinase, receptor for macrophage-colony stimulating factor, M-CSF or CSF-1, and a key regulator of macrophage and osteoclast activation and differentiation.
GW2580 is a cell-permeable, potent and selective ATP-competitive inhibitor of cFMS kinase, receptor for macrophage-colony stimulating factor, M-CSF or CSF-1, and a key regulator of macrophage and osteoclast activation and differentiation. FMS is a type III receptor tyrosine kinase that binds to the macrophage or monocyte colony-stimulating factor (M-CSF or CSF-1). Overexpression of CSF-1 and/or FMS has been implicated in a number of disease states including the growth of metastasis of some types of cancer, in promoting osteoclast proliferation in bone osteolysis, and in several inflammatory disorders. GW2580 selectively inhibits cFMS-mediated cellular functions in vitro at 0.06 μM as well as CSF-1-dependent tumor growth in vivo. GW2580 was inactive against 26 other 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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Yi Rang Na et al.
Cell reports, 31(6), 107643-107643 (2020-05-14)
As current therapies benefit only a minority of cancer patients, additional therapeutic targets are needed. Tumor-associated macrophages (TAMs) have attracted attention for improving therapeutic responses, yet regulatory strategies remain elusive. Here, we show that the protein kinase A catalytic subunit
Silvia Lonardi et al.
Cancer immunology research, 8(6), 829-841 (2020-04-03)
Langerhans cell histiocytosis (LCH) is a rare disorder characterized by tissue accumulation of CD1a+CD207+ LCH cells. In LCH, somatic mutations of the BRAF V600E gene have been detected in tissue LCH cells, bone marrow CD34+ hematopoietic stem cells, circulating CD14+
Kate M Herum et al.
Molecular biology of the cell, 28(14), 1871-1882 (2017-05-05)
Cardiac fibrosis is a serious condition currently lacking effective treatments. It occurs as a result of cardiac fibroblast (CFB) activation and differentiation into myofibroblasts, characterized by proliferation, extracellular matrix (ECM) production and stiffening, and contraction due to the expression of