Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

SML0333

Sigma-Aldrich

NVP-BHG712

≥98% (HPLC)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C26H20F3N7O
CAS Number:
940310-85-0
Molecular Weight:
503.48
MDL number:
MFCD20272929
UNSPSC Code:
12352200
PubChem Substance ID:
329825338
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

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)

InChI key

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.

Biochem/physiol Actions

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.

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

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
126M4752V
124M4703V
042M4735V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Identification of Eph receptor signaling as a regulator of autophagy and a therapeutic target in colorectal carcinoma
DiPrima M, et al.
Molecular Oncology, 13(11), 2441-2459 (2019)
Clinton D Protack et al.
Scientific reports, 7(1), 15386-15386 (2017-11-15)
Low rates of arteriovenous fistula (AVF) maturation prevent optimal fistula use for hemodialysis; however, the mechanism of venous remodeling in the fistula environment is not well understood. We hypothesized that the embryonic venous determinant Eph-B4 mediates AVF maturation. In human
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
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
Jeannette Rudzitis-Auth et al.
British journal of pharmacology, 177(14), 3225-3239 (2020-03-08)
The development of endometriotic lesions is crucially dependent on the formation of new blood vessels. In the present study, we analysed whether this process is regulated by erythropoietin-producing hepatoma receptor B4 (EphB4) signalling. We first assessed the anti-angiogenic action of
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service