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SML0273

Sigma-Aldrich

VAS2870

≥97% (HPLC)

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, VAS 2870, VAS-2870

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About This Item

Empirical Formula (Hill Notation):
C18H12N6OS
CAS Number:
722456-31-7
Molecular Weight:
360.39
MDL number:
MFCD03407188
UNSPSC Code:
12352200
PubChem Substance ID:
329825281
NACRES:
NA.77

Quality Level

100

Assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: ≥5 mg/mL

storage temp.

room temp

SMILES string

C(c1ccccc1)n2nnc3c(Sc4nc5ccccc5o4)ncnc23

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

InChI key

HZSOKHVVANONPV-UHFFFAOYSA-N

Application

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

Biochem/physiol Actions

In addition to NOX4 inhibition, VAS2870 is also known to supress the reactive oxygen species (ROS) production in several cell types. It effectively impairs cell growth and increases apoptosis induced by transforming growth factor β (TGF-β) in liver cancer cells. Thus, inhibition of NOX enzymes by VAS2870 may be considered as a potential therapeutic strategy for liver cancer.
VAS2870 is a cell-permeable and specific NADPH oxidase (NOX) inhibitor that effectively suppresses growth factor-mediated ROS liberation in VSMC.

Storage Class Code

11 - Combustible Solids

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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Sigma-Aldrich

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Sigma-Aldrich

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Austin T Robinson et al.
American journal of physiology. Heart and circulatory physiology, 312(5), H896-H906 (2017-02-27)
High blood pressure has been shown to elicit impaired dilation in the vasculature. The purpose of this investigation was to elucidate the mechanisms through which high pressure may elicit vascular dysfunction and determine the mechanisms through which regular aerobic exercise
Patricia Sancho et al.
Biochemical pharmacology, 81(7), 917-924 (2011-02-01)
Liver tumor cells show several molecular alterations which favor pro-survival signaling. Among those, we have proposed the NADPH oxidase NOX1 as a prosurvival signal for liver tumor cells. On the one side, we have described that FaO rat hepatoma cells
Qi-An Sun et al.
Free radical biology & medicine, 52(9), 1897-1902 (2012-03-13)
Specific inhibitors of the production of reactive oxygen species (ROS) by the NADPH oxidases (Nox's) are potentially important therapeutic agents in the wide range of human diseases that are characterized by excessive ROS production. It has been proposed that VAS2870
Jing Yang et al.
International journal of molecular medicine, 42(1), 123-130 (2018-04-06)
NADPH oxidases (NOXs) are important in the pathophysiology of fibrotic diseases. The expression and activity of NOXs are regulated by growth factors, including transforming growth factor (TGF‑β). The proliferation of retinal pigment epithelial (RPE) cells following epithelial‑ to‑mesenchymal transition (EMT) is
I-Jung Tsai et al.
International journal of molecular sciences, 20(18) (2019-09-13)
Patients with a relapse of idiopathic nephrotic syndrome have significantly increased levels of serum complement component 5a (C5a), and proteinuria has been noted in mice treated with C5a via changes in permeability of kidney endothelial cells (KECs) in established animal
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