2-(ACETYLOXY)-4-[(NITROOXY)METHYL]PHENYL ESTER, BENZOIC ACID

Names

[ Name ]:
2-(ACETYLOXY)-4-[(NITROOXY)METHYL]PHENYL ESTER, BENZOIC ACID

[Synonym ]:
[4-(nitrooxymethyl)phenyl] 2-acetyloxybenzoate

Biological Activity

[Description]:

NCX4040 (NO-Aspirin), a non-steroidal anti-inflammatory drug (NSAID), is a nitric oxide (NO) releasing form of Aspirin. NCX4040 induces apoptosis in PC3 metastatic prostate cancer cells. NCX4040 has anti-inflammatory and anti-cancer effects[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

[In Vitro]

NCX4040 significantly induces hydrogen peroxide formation with ensuing oxidative stress and mitochondrial depolarization resulting in lipid peroxidation, cell cycle arrest, inhibition of colony growth and induction of apoptosis in PC3 cells[1]. NCX4040 (10-50 μM) inhibits migration potential of PC3 cells by depolymerizing F-actin and promoting anoikis[1]. NCX4040 down regulates cyclin D1 expression in PC3 cells. Western blot analysis revealed that significant down regulation of key anti-apoptotic markers such as cellular inhibitor of apoptosis protein-1 (cIAP1), X-linked inhibitor of apoptosis (XIAP), survivin, and Cellular-Myc (c-Myc)[1]. NCX4040-treated cells showes upregulation of phosho histone H2AX (pH2AX), cleaved caspase3 and cleaved Poly [ADP-ribose] polymerase 1 (PARP1)[1].

[References]

[1]. Somaiah Chinnapaka, et al. Nitro aspirin (NCX4040) induces apoptosis in PC3 metastatic prostate cancer cells via hydrogen peroxide (H 2 O 2)-mediated oxidative stress. Free Radic Biol Med. 2019 Nov 1;143:494-509.

Chemical & Physical Properties

[ Molecular Formula ]:
C₁₆H₁₃NO₇

[ Molecular Weight ]:
331.27700

[ Exact Mass ]:
331.06900

[ PSA ]:
107.65000

[ LogP ]:
3.06260

[ Storage condition ]:
20°C

Safety Information

[ Symbol ]:

GHS05, GHS07, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H317-H318-H400

[ Precautionary Statements ]:
P273-P280-P305 + P351 + P338

[ Hazard Codes ]:
C

[ Risk Phrases ]:
41-43

[ Safety Phrases ]:
26-36/37-39

[ RIDADR ]:
UN 3077 9 / PGIII

Articles

Dispersal of human and plant pathogens biofilms via nitric oxide donors at 4 °C.

AMB Express 6 , 49, (2016)

Recent studies suggest that nitric oxide donors capable of manipulating nitric oxide-mediated signaling in bacteria could induce dispersal of biofilms. Encased in extracellular polymeric substances, h...

Study of molecular mechanisms of pro-apoptotic activity of NCX 4040, a novel nitric oxide-releasing aspirin, in colon cancer cell lines.

J. Transl. Med. 5 , 52, (2008)

Despite numerous studies aimed at verifying the antitumor activity of nitric oxide-releasing nonsteroidal antiflammatory drugs (NO-NSAIDs), little is known about the molecular targets responsible for ...

In vitro and in vivo evaluation of NCX 4040 cytotoxic activity in human colon cancer cell lines.

J. Transl. Med. 3 , 7, (2005)

BACKGROUND: Nitric oxide-releasing nonsteroidal antiinflammatory drugs (NO-NSAIDs) are reported to be safer than NSAIDs because of their lower gastric toxicity. We compared the effect of a novel NO-re...