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SML0333

Sigma-Aldrich

NVP-BHG712

≥98% (HPLC)

Synonyme(s) :

4-Methyl-3-[[1-methyl-6-(3-pyridinyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]amino]-N-[3-(trifluoromethyl)phenyl]-benzamide

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About This Item

Formule empirique (notation de Hill):
C26H20F3N7O
Numéro CAS:
940310-85-0
Poids moléculaire :
503.48
Numéro MDL:
MFCD20272929
Code UNSPSC :
12352200
ID de substance PubChem :
329825338
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Essai

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

−20°C

Chaîne SMILES 

Cc1ccc(cc1Nc2nc(nc3n(C)ncc23)-c4cccnc4)C(=O)Nc5cccc(c5)C(F)(F)F

InChI

1S/C26H20F3N7O/c1-15-8-9-16(25(37)32-19-7-3-6-18(12-19)26(27,28)29)11-21(15)33-23-20-14-31-36(2)24(20)35-22(34-23)17-5-4-10-30-13-17/h3-14H,1-2H3,(H,32,37)(H,33,34,35)

Clé InChI

ZCCPLJOKGAACRT-UHFFFAOYSA-N

Application

NVP-BHG712 has been used as an ephrin type-B receptor 4 (Eph-B4) inhibitor to study its effect on Eph-B4 phosphorylation in ephrin-B2/Fc stimulated mouse lung endothelial cells.
NVP-BHG712 has been used as an epinephrine type-B receptor 4 (Eph-B4) inhibitor:
  • to study its effects on human colorectal cancer cell growth in vitro and the growth of tumor cells in mice.
  • to study the regulation of endothelial nitric oxide synthase.
  • to study its effects on vascularization and growth of endometriotic lesions.

Actions biochimiques/physiologiques

NVP-BHG712 (4-methyl-3-(1-methyl-6-(pyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)-N-(3-(trifluoromethyl)phenyl)benzamide) inhibits the activity of ABC transporter subfamily C member 10 (ABCC10), which is responsible for mediating paclitaxel resistance. Therefore, NVP-BHG712 in combination with paclitaxel is effective against cancers that are resistant to paclitaxel due to the expression of the ABCC10.
NVP-BHG712 is a very potent, selective inhbitor of the receptor tyrosine kinase EphB4 (ED50 = 25 nM). NVP-BHG712 blocks Ephrin receptor autophosphorylation and VEGF-induced angiogenesis.
NVP-BHG712 obstructs angiogenesis mediated by vascular endothelial growth factor in vivo. It also blocks the efflux of ATP-binding cassette (ABC) transporter subfamily C member 10 (ABCC10) into the HEK293 cells by overexpressing the ABCC10 transporter.

Caractéristiques et avantages

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

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000183336
0000183336
0000138398
0000086887
0000086886

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Consulter la Bibliothèque de documents

Yujia Wang et al.
The Journal of biological chemistry, 290(22), 14235-14244 (2015-04-24)
EPH kinases are the largest family of receptor tyrosine kinases, and their ligands, ephrins (EFNs), are also cell surface molecules. This work presents evidence that EPHB4 on vascular smooth muscle cells (VSMCs) is involved in blood pressure regulation. We generated
Eph-B4 mediates vein graft adaptation by regulation of endothelial nitric oxide synthase
Wang M, et al.
Journal of Vascular Surgery, 65(1), 179-189 (2017)
Christin Neuber et al.
Molecules (Basel, Switzerland), 25(21) (2020-11-07)
In a previous study, EphB4 was demonstrated to be a positive regulator of A375-melanoma growth but a negative regulator of tumor vascularization and perfusion. To distinguish between EphB4 forward and ephrinB2 reverse signaling, we used the commercially available EphB4 kinase
Mo Wang et al.
Journal of vascular surgery, 65(1), 179-189 (2016-01-29)
Vein graft adaptation is characterized by loss of expression of the tyrosine kinase receptor Eph-B4, the embryonic determinant of venous identity, without increased expression of its ligand ephrin-B2, the embryonic determinant of arterial identity. Endothelial nitric oxide synthase (eNOS) is
Inhibition of erythropoietin-producing hepatoma receptor B4 (EphB4) signalling suppresses the vascularisation and growth of endometriotic lesions
Rudzitis-Auth J, et al.
British Journal of Pharmacology, 65(1), 179-189 (2020)
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