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SML1307

Sigma-Aldrich

K02288

>98% (HPLC)

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Synonym(s):
3-[(6-Amino-5-(3,4,5-trimethoxyphenyl)-3-pyridinyl]phenol, 3-[6-Amino-5-(3,4,5-trimethoxyphenyl)-3-pyridinyl]-phenol
Empirical Formula (Hill Notation):
C20H20N2O4
CAS Number:
1431985-92-0
Molecular Weight:
352.38
MDL number:
MFCD26936347
UNSPSC Code:
51111800
PubChem Substance ID:
329825774
NACRES:
NA.77

Quality Level

100

Assay

>98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

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)

InChI key

CJLMANFTWLNAKC-UHFFFAOYSA-N

General description

K02288 is a 2-aminopyridine compound.

Biochem/physiol Actions

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 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.

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301,H318

Hazard Classifications

Acute Tox. 3 Oral - Eye Dam. 1

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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Dorsomorphin inhibits BMP signals required for embryogenesis and iron metabolism.
Paul B Y, et al.
Nature Chemical Biology, 4(1), 33-33 (2008)
Stem Cell Aging: Mechanisms, Consequences, Rejuvenation (2015)
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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