1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide
Synonym(s):1,3-Benzoxazol-2-yl-3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide;7-(1,3-Benzoxazol-2-ylsulfanyl)-3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine;7-(2-Benzoxazolylthio)-3-(phenylmethyl)-3H-1,2,3-triazolo[4,5-d]pyrimidine;
- CAS NO.:722456-31-7
- Empirical Formula: C18H12N6OS
- Molecular Weight: 360.39
- MDL number: MFCD03407188
- Update Date: 2024-11-08 20:21:46
What is 1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide?
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.
The Uses of 1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide
VAS 2870, is a NADPH oxidase (NOX) inhibitor.
The Uses of 1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide
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
What are the applications of Application
VAS-2870 is a cell permeable specific NADPH oxidase inhibitor
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) Freyhaus et al. (2006), Novel Nox inhibitor VAS2870 attenuates PDGF-dependent smooth muscle cell chemotaxis, but not proliferation; Cardiovasc. Res. 71 331 2) Stielow et al. (2006), Novel Nox inhibitor of oxLDL-induced reactive oxygen species formation in human endothelial cells; Biochem. Biophys. Res. Commun. 344 200 3) Sancho et al. (2011), The NADPH oxidase inhibitor VAS2870 impairs cell growth and enhances TGF-β-induced apoptosis of liver tumor cells; Biochem. Pharmacol. 81 917
Properties of 1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide
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. |
Safety information for 1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral |
Precautionary Statement Codes |
P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide
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