1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide Chemical Properties

Boiling point:

627.0±65.0 °C(Predicted)

Density 

1.53±0.1 g/cm3(Predicted)

storage temp. 

room temp

solubility 

DMSO: ≥5mg/mL

form 

Tan solid

pka

0.85±0.30(Predicted)

color 

white to beige

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.

InChI

InChI=1S/C18H12N6OS/c1-2-6-12(7-3-1)10-24-16-15(22-23-24)17(20-11-19-16)26-18-21-13-8-4-5-9-14(13)25-18/h1-9,11H,10H2

InChIKey

HZSOKHVVANONPV-UHFFFAOYSA-N

SMILES

C1=NC(SC2=NC3=CC=CC=C3O2)=C2N=NN(CC3=CC=CC=C3)C2=N1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide Usage And Synthesis

Description

VAS-2870 (722456-31-7) is a NAD(P)H oxidase (Nox) inhibitor. Abolishes PDGF-mediated Nox activation and ROS production (100% at 10 μM). Inhibits PMA-induced oxidative burst in HL-60 cells (IC50=2 μM). VAS-2870 enhances TGF-β-induced apoptosis in liver tumor cells.

Uses

VAS 2870, is a NADPH oxidase (NOX) inhibitor.

Uses

VAS2870 has been used as a nicotinamide adenine dinucleotide phosphate (NADPH) oxidase (NOX) inhibitor:

• to study the importance of NOX-derived reactive oxygen species in cytoskeletal organization, proper localization of E-cadherin and cell motility during zebrafish epiboly
• to study the function of Nox2 and Nox4 in lipopolysaccharide (LPS)-induced intestinal injury in high-fat diet (HFD) fed mice
• to reduce the reactive oxygen species level and study its influence on inhibiting the induction of trained innate immunity in monocytes

General Description

A cell-permeable thiotriazolopyrimidine compound that acts as an effective NADPH oxidase (NOX) inhibitor (IC₅₀ = 10.6 μM against NOX activity in human neutrophil lysates) and is widely used for studying NOX-dependent cellular ROS formations in various cultures, including oxLDL-treated HUVEC (complete inhibition at 5 μM), PDGF-induced primary rat VSMC (vascular smooth muscle cells; complete inhibition at 10 μM), as well as aortic sections from spontaneously hypertensive rats (SHRs) (72% inhibition at 10 μM). Also shown to inhibit PDGF-BB-induced murine EB (embryonid body) vacularization (74% inhibition at 50 μM) and improve ACh-induced vasorelaxation of isolated rat aortic rings from both SHRs and non-hypertensive rats ex vivo (by 41.7 and 34.5%, respectively, at 10 μM).

Biochem/physiol Actions

VAS2870 is a cell-permeable and specific NADPH oxidase (NOX) inhibitor that effectively suppresses growth factor-mediated ROS liberation in VSMC.

storage

Store at +4°C

References

[1] HENRIK TEN FREYHAUS. Novel Nox inhibitor VAS2870 attenuates PDGF-dependent smooth muscle cell chemotaxis, but not proliferation.[J]. Cardiovascular Research, 2006, 71 2: 331-341. DOI:10.1016/j.cardiores.2006.01.022
[2] CLAUDIA STIELOW . Novel Nox inhibitor of oxLDL-induced reactive oxygen species formation in human endothelial cells[J]. Biochemical and biophysical research communications, 2006, 344 1: Pages 200-205. DOI:10.1016/j.bbrc.2006.03.114
[3] PATRICIA SANCHO  Isabel F. The NADPH oxidase inhibitor VAS2870 impairs cell growth and enhances TGF-β-induced apoptosis of liver tumor cells[J]. Biochemical pharmacology, 2011, 81 7: Pages 917-924. DOI:10.1016/j.bcp.2011.01.007

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