Structure of SNAP
CAS No.: 67776-06-1
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
SNAP is a nitric oxide donor used as a stable platelet aggregation inhibitor.
Synonyms: S-Nitroso-N-acetyl-DL-penicillamine
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CAS No. : | 67776-06-1 |
Formula : | C7H12N2O4S |
M.W : | 220.25 |
SMILES Code : | CC(C)(SN=O)C(C(O)=O)NC(C)=O |
Synonyms : |
S-Nitroso-N-acetyl-DL-penicillamine
|
MDL No. : | MFCD00272624 |
InChI Key : | ZIIQCSMRQKCOCT-UHFFFAOYSA-N |
Pubchem ID : | 5231 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
In Vitro:
Cell Line
|
Concentration | Treated Time | Description | References |
Human platelets | 0.01-10 µM | 10 min | Increase in intraplatelet cGMP concentrations | Br J Pharmacol. 1994 Aug;112(4):1071-6 |
Human platelets | 3-10 µM | 5 min | Inhibition of P-selectin release | Br J Pharmacol. 1994 Aug;112(4):1071-6 |
Human platelets | 0.01-10 µM | 1 min | Inhibition of collagen-induced platelet aggregation and ATP release | Br J Pharmacol. 1994 Aug;112(4):1071-6 |
Human platelets | 3 or 10 µM | 1-2 min | To study the inhibitory effect of SNAP on collagen-induced platelet aggregation, and found that ONOO- reversed the inhibitory effect of SNAP | Proc Natl Acad Sci U S A. 1994 Jul 5;91(14):6702-6 |
Dorsal root ganglia neurons | 0.1-1 mM | 1200 seconds | SNAP induced concentration-dependent increase in fluorescence intensity of DAF-treated neurons, and L-cysteine did not affect SNAP-induced fluorescence increase. | Neuropharmacology. 2013 Aug;71:1-9 |
Guinea-pig trachea strips with NK2 receptor antagonist SR 48968 | 100 µM | 20 minutes | Examined SNAP's effect on acetylcholine release after NK2 receptor blockade. SNAP significantly inhibited release (78±3% of control). | Br J Pharmacol. 2000 Sep;131(1):94-8 |
Capsaicin-pretreated guinea-pig trachea strips | 100 and 300 µM | 20 minutes | Studied SNAP's effect on acetylcholine release after capsaicin pretreatment. SNAP's facilitatory effect was reversed to inhibition (74±4% and 78±2% of control), which was prevented by ODQ. | Br J Pharmacol. 2000 Sep;131(1):94-8 |
Epithelium-free preparation of guinea-pig trachea | 100 and 300 µM | 20 minutes | Investigated the effect of SNAP on electrically evoked [3H]-acetylcholine release. SNAP significantly increased release (121±4% and 124±10% of control), an effect abolished by the soluble guanylyl cyclase inhibitor ODQ (1 μM). | Br J Pharmacol. 2000 Sep;131(1):94-8 |
Rat colonic mucosal cells | 0.1 – 1000 µM | 20 minutes | To assess the extent of damage to colonic mucosal cells by SNAP, results showed increased cell damage as evaluated by Trypan blue dye uptake and lysosomal enzyme release. | Br J Pharmacol. 1999 Nov;128(6):1268-74 |
Arabidopsis nuclear extracts | 10-1000 µM | 20 minutes | To evaluate the effect of SNAP on HDAC activity; SNAP significantly inhibited nuclear HDAC activity (60% inhibition at 500 μM), reversible by DTT | Plant Physiol. 2017 Feb;173(2):1434-1452 |
BALB/cJ mouse peritoneal macrophages | 500 µM | 24 hours | SNAP inhibited the growth of MHV-3 in peritoneal macrophages from BALB/cJ mice. | J Virol. 1998 Sep;72(9):7084-90 |
A/J mouse peritoneal macrophages | 500 µM | 24 hours | SNAP inhibited the growth of MHV-3 in peritoneal macrophages from A/J mice. | J Virol. 1998 Sep;72(9):7084-90 |
RAW 264.7 cells | 500 µM | 24 hours | SNAP inhibited the growth of MHV-3 in RAW 264.7 cells, while NAP (an inactive analog of SNAP) had no effect. | J Virol. 1998 Sep;72(9):7084-90 |
NAc neurons | 100 µM | 30 minutes | Increased surface GluR2 expression by enhancing NSF S-nitrosylation and GluR2-NSF interactions | J Neurosci. 2014 Mar 5;34(10):3493-508 |
Human platelets | 0.01-10 µM | 5 min | Induction of disaggregation of ADP-aggregated platelets | Br J Pharmacol. 1994 Aug;112(4):1071-6 |
HEK293 cells | 100 µM | 5 minutes | To investigate the inhibitory effect of SNAP on N-type Ca2+ channel currents. Results showed that SNAP significantly inhibited N-type Ca2+ channel currents, and this effect was reversed by DTT. | J Biol Chem. 2015 Dec 18;290(51):30616-23 |
SHR rat coronary endothelial cells | 100 µM | 5 minutes | SNAP failed to modulate the α-thrombin-induced calcium transient. | Br J Pharmacol. 2000 Aug;130(7):1468-76 |
WKY rat coronary endothelial cells | 10–100 µM | 5 minutes | SNAP dose-dependently reduced the peak and decay time of α-thrombin-induced calcium transient. In one-third of the cells analyzed, 100 μM SNAP completely abolished the α-thrombin-induced calcium transient. | Br J Pharmacol. 2000 Aug;130(7):1468-76 |
SHR rat cardiomyocytes | 1-200 µM | 5 minutes | SNAP failed to further increase cGMP content | Br J Pharmacol. 2001 Oct;134(3):596-602 |
WKY rat cardiomyocytes | 1-200 µM | 5 minutes | SNAP dose-dependently increased cGMP content | Br J Pharmacol. 2001 Oct;134(3):596-602 |
Rat liver sinusoidal endothelial cells | 2 mM | 6 hours | To evaluate the cytotoxicity of low-concentration SNAP, results showed 15% cell death under hypoxic conditions. | Biochem J. 1996 Sep 15;318 ( Pt 3)(Pt 3):789-95 |
Rat liver sinusoidal endothelial cells | 10 mM | 6 hours | To assess the cytotoxicity of high-concentration SNAP, results showed 80% cell death under normoxic conditions. | Biochem J. 1996 Sep 15;318 ( Pt 3)(Pt 3):789-95 |
Human platelets | 1 µM | 60 min | Evaluation of stability of SNAP and SNFP, SNPL inhibitory activity decayed over time | Br J Pharmacol. 1994 Aug;112(4):1071-6 |
Arabidopsis protoplasts | 500 µM | 60 minutes | To assess SNAP's effect on HDAC activity in protoplasts; concentration-dependent inhibition (20% at 500 μM), blocked by cPTIO | Plant Physiol. 2017 Feb;173(2):1434-1452 |
Leishmania donovani amastigotes | 10 to 160 μg/ml | 72 hours | To assess the resistance of PMM-resistant strains to NO, showing enhanced resistance to NO at the intracellular amastigote stage. | Antimicrob Agents Chemother. 2019 Dec 20;64(1):e00904-19 |
Rat liver sinusoidal endothelial cells | 5 mM | 8 hours | To evaluate the cytotoxicity of SNAP under hypoxic conditions, results showed a significant increase in cell death to 90% under hypoxia compared to 45% under normoxia. | Biochem J. 1996 Sep 15;318 ( Pt 3)(Pt 3):789-95 |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
Zucker rats | Obese Zucker rats (OZR) and lean Zucker rats (LZR) | In vitro (microvascular myographs) | 0.3 nM | 30 minutes | To assess the effect of ET-1 on endothelium-dependent and -independent relaxant responses in penile arteries, it was found that ET-1 inhibits NO-mediated endothelial relaxations via NADPH oxidase-dependent ROS generation and enhances vasoconstriction in obese animals. | Br J Pharmacol. 2014 Dec;171(24):5682-95 |
Sprague-Dawley rats | Cocaine behavioral sensitization model | Bilateral NAc injection | 0.5 or 1 μg/side | Single injection, tested after 30 min | Dose-dependently attenuated the expression of cocaine-induced behavioral sensitization | J Neurosci. 2014 Mar 5;34(10):3493-508 |
BALB/c mice | CT26 colorectal cancer and 4T1 triple-negative breast cancer models | Intratumoral injection | 1 μmol Hf (0.24 μmol SNAP) | 4T1 model: 4 fractions of 2 Gy; CT26 model: 3 fractions of 3 Gy | SNAP/MOL(+) plus low-dose X-ray significantly inhibited tumor growth (TGI 81.2% in 4T1 model, 95.4% in CT26 model) and reduced lung metastasis | Adv Sci (Weinh). 2025 Feb;12(8):e2413518 |
Rats | Migraine model | Topical application | 10 μM | 30 minutes | To study the effect of SNAP on the mechanical sensitivity of meningeal nociceptors, results showed that SNAP promoted a delayed increase in mechanical sensitivity of nociceptors | Ann Neurol. 2013 Jun;73(6):741-50 |
Rats | Carrageenin-induced mechanical hyperalgesia | Local administration | 200 µg/paw | Single dose, 30 minutes | SNAP inhibited carrageenin-induced mechanical hyperalgesia, and L-cysteine did not affect SNAP-induced anti-hyperalgesia. | Neuropharmacology. 2013 Aug;71:1-9 |
Rat | Isolated perfused heart model | Aortic cannula perfusion | 5-10 nM | Single administration, lasting 30 sec | To investigate the protective effect of S-nitroso-N-acetyl-DL-penicillamine against peroxynitrite-induced vascular dysfunction. Results showed that SNAP at low concentrations did not induce vasodilatation but prevented the inhibition of vasodilator responses by peroxynitrite. | Proc Natl Acad Sci U S A. 1994 Dec 20;91(26):12383-7 |
Tags: S-Nitroso-N-acetyl-DL-penicillamine | SNAP | NO Synthase | Nitric oxide synthases | NOS | inhibitor | 67776-06-1 |
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