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SML1307

Sigma-Aldrich

K02288

>98% (HPLC)

Sinónimos:

3-[(6-Amino-5-(3,4,5-trimethoxyphenyl)-3-pyridinyl]phenol, 3-[6-Amino-5-(3,4,5-trimethoxyphenyl)-3-pyridinyl]-phenol

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About This Item

Fórmula empírica (notación de Hill):
C20H20N2O4
Número de CAS:
1431985-92-0
Peso molecular:
352.38
Número MDL:
MFCD26936347
Código UNSPSC:
51111800
ID de la sustancia en PubChem:
329825774
NACRES:
NA.77

Nivel de calidad

100

Ensayo

>98% (HPLC)

Formulario

powder

color

white to beige

solubilidad

DMSO: 5 mg/mL, clear (warmed)

temp. de almacenamiento

2-8°C

cadena SMILES

NC1=C(C2=CC(OC)=C(OC)C(OC)=C2)C=C(C3=CC=CC(O)=C3)C=N1

InChI

1S/C20H20N2O4/c1-24-17-9-13(10-18(25-2)19(17)26-3)16-8-14(11-22-20(16)21)12-5-4-6-15(23)7-12/h4-11,23H,1-3H3,(H2,21,22)

Clave InChI

CJLMANFTWLNAKC-UHFFFAOYSA-N

Descripción general

K02288 is a 2-aminopyridine compound.

Acciones bioquímicas o fisiológicas

K02288 is a selective and potent inhibitor of the bone morphogenetic protein (BMP) type I receptor kinases with IC50s in the range 1–2 nM against ALK1 and ALK2. K02288 has IC50 values of 1.1, 1.8, 6.4 nM for ALK2, ALK1 and ALK6 respectively and IC50s of 34.4, 302, 321 and 220 nM for other ALKs (3, 4, 5) and ActRIIA. K02288 specifically inhibited the BMP-induced Smad pathway without affecting TGF-β signaling and induced dorsalization of zebrafish embryos.
K02288 is a selective and potent inhibitor of the bone morphogenetic protein (BMP) type I receptor kinases.
K02288 is functionally similar to dorsomorphin, which is known to be the first small-molecule for BMP signaling inhibition.
BMP signalling is associated with many important physiological processes. It acts a central regulator of developmental processes such as organogenesis, gastrulation, mesoderm induction and endochondral bone formation. BMP signals are also related to diseases including pulmonary hypertension, juvenile polyposis syndrome, fibrodysplasia ossificans progressiva and hereditary hemorrhagic telangiectasia syndrome. BMP signaling inhibition might serve as a tool to study its role in other biological processes.

Pictogramas

Skull and crossbonesCorrosion
GHS06,GHS05

Palabra de señalización

Danger

Frases de peligro

H301,H318

Clasificaciones de peligro

Acute Tox. 3 Oral - Eye Dam. 1

Código de clase de almacenamiento

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000011810
0000011810
0000122498
0000110742
0000035605

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Stem Cell Aging: Mechanisms, Consequences, Rejuvenation (2015)
Dorsomorphin inhibits BMP signals required for embryogenesis and iron metabolism.
Paul B Y, et al.
Nature Chemical Biology, 4(1), 33-33 (2008)
Charlene Watterston et al.
PLoS genetics, 15(5), e1008163-e1008163 (2019-05-16)
As small regulatory transcripts, microRNAs (miRs) act as genetic 'fine tuners' of posttranscriptional events, and as genetic switches to promote phenotypic switching. The miR miR26a targets the BMP signalling effector, smad1. We show that loss of miR26a leads to hemorrhage
Matteo Malinverno et al.
Nature communications, 10(1), 2761-2761 (2019-06-27)
Cerebral cavernous malformation (CCM) is a neurovascular familial or sporadic disease that is characterised by capillary-venous cavernomas, and is due to loss-of-function mutations to any one of three CCM genes. Familial CCM follows a two-hit mechanism similar to that of tumour suppressor
Georgina Kerr et al.
Angiogenesis, 18(2), 209-217 (2015-01-06)
Activin receptor-like kinase 1 (ALK1, encoded by the gene ACVRL1) is a type I BMP/TGF-β receptor that mediates signalling in endothelial cells via phosphorylation of SMAD1/5/8. During angiogenesis, sprouting endothelial cells specialise into tip cells and stalk cells. ALK1 synergises

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