(+/-)-S-Nitroso-N-acetylpenicillamineA cysteine protease inhibitor and spontaneous NO donor in physiological conditions

(±)-S-Nitroso-N-acetylpenicillamine (CAS 79032-48-7)

(±)-S-Nitroso-N-acetylpenicillamine | CAS 79032-48-7 is rated 5.0 out of 5 by 2.
  • y_2019, m_10, d_20, h_9
  • bvseo_bulk, prod_bvrr, vn_bulk_2.0.13
  • cp_1, bvpage1
  • co_hasreviews, tv_0, tr_2
  • loc_en_US, sid_200319, prod, sort_[SortEntry(order=SUBMISSION_TIME, direction=DESCENDING)]
  • clientName_scbt
  • bvseo_sdk, java_sdk, bvseo-3.2.0
  • CLOUD, getAggregateRating, 76ms
  • REVIEWS, PRODUCT
5
2
4
0
3
0
2
0
1
0
Synonym: S-Nitroso-N-acetyl-DL-penicillamine; SNAP;N-Acetyl-3-(nitrosothio)-DL-valine
Application: A cysteine protease inhibitor and spontaneous NO donor in physiological conditions
CAS Number: 79032-48-7
Purity: ≥98%
Molecular Weight: 220.25
Molecular Formula: C7H12N2O4S
* Refer to Certificate of Analysis for lot specific data (including water content).
Submit a review for this product and receive 15 CruzCredits

(±)-S-Nitroso-N-acetylpenicillamine (SNAP) is a NO donor and cysteine protease inhibitor. The unique NO releasing properties of SNAP make it an ideal agent for studying the pharmacological and physiological actions of NO since it is a potent vasodilator in vitro that does not induce pharmacological tolerance. Research shows that SNAP dose-dependently inhibits serum-induced thymidine incorporation in rat aortic smooth muscle cells, activates GCS (soluble guanylyl cyclase) and relaxes isolated bovine coronary artery rings (EC50=0.13 μM). SNAP has also been shown to inhibit vascular smooth muscle cell mitogenesis and proliferation, as well as leukocyte adherence to the endothelium.


References

1. Hogg, N., et al., 1992. Production of hydroxyl radicals from the simultaneous generation of superoxide and nitric oxide. The Biochemical journal. 281 ( Pt 2)(): 419-24. PMID: 1310595

2. Shaffer, J E., et al., 1992. Lack of tolerance to a 24-hour infusion of S-nitroso N-acetylpenicillamine (SNAP) in conscious rabbits. The Journal of pharmacology and experimental therapeutics. 260(1): 286-93. PMID: 1731043

3. Garg, U C., et al., 1989. Nitric oxide-generating vasodilators and 8-bromo-cyclic guanosine monophosphate inhibit mitogenesis and proliferation of cultured rat vascular smooth muscle cells. The Journal of clinical investigation. 83(5): 1774-7. PMID: 2540223

4. Henry, P J., et al., 1989. Nitroglycerin-induced tolerance affects multiple sites in the organic nitrate bioconversion cascade. The Journal of pharmacology and experimental therapeutics. 248(2): 762-8. PMID: 2563771

5. Kowaluk, E A., et al., 1987. Tolerance to relaxation in rat aorta: comparison of an S-nitrosothiol with nitroglycerin. European journal of pharmacology. 144(3): 379-83. PMID: 3126076

6. Ascenzi, P., et al., 2001. Inhibition of cysteine protease activity by NO-donors. Current protein & peptide science. 2(2): 137-53. PMID: 12370021

Usage :
SNAP spontaneously releases NO under physiological conditions. Prepare solutions fresh daily. Half-life in aqueous medium exposed to air is 4.6 hours.
Appearance :
Powder
Physical State :
Solid
Solubility :
Soluble in water (2 mg/ml), DMSO (25 mg/ml), ethanol (25 mg/ml), methanol, PBS (pH 7.2) (~11 mg/ml), and DMF (~25 mg/ml).
Storage :
Store at -20° C
Melting Point :
>140° C (dec.)
Density :
~1.4 g/cm3 (Predicted)
Refractive Index :
n20D 1.56
IC50 :
relaxation of isolated bovine coronary artery rings: EC5050 = 130 nM
pK Values :
pKa: 3.06
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
5231
MDL Number :
MFCD00272624
SMILES :
CC(=O)NC(C(=O)O)C(C)(C)SN=O

Download SDS (MSDS)

Certificate of Analysis

Adobe Acrobat Reader is required to reliably view,
print and comment on PDF documents

(+/-)-S-Nitroso-N-acetylpenicillamine  Product Citations

See how others have used (+/-)-S-Nitroso-N-acetylpenicillamine. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 13 total

PMID: # 31067462  Coulombe, P. et al. 2019. Cell Rep. 27: 1769-1780.e4.

PMID: # 31229545  Zahid, AA. et al. 2019. Int. J. Biol. Macromol. 136: 901-910.

PMID: # 30918325  Lee, KC.|Hsieh, YC.|Chan, CC.|Sun, HJ.|Huang, YH.|Hou, MC.|Lin, HC.| et al. 2019. Lab. Invest. 99: 1203-1216.

PMID: # 29560858  Ricca, BL. et al. 2018. Elife. 7:

PMID: # 29673242  Lee, IH. et al. 2018. J Exerc Nutrition Biochem. 22: 22-28.

PMID: # 30425239  Aulas, A. et al. 2018. Cell Death Dis. 9: 1129.

PMID: # 26980442  Ding, Y. et al. 2016. Science signaling. 9: ra29.

PMID: # 27064847  Guerra, D. et al. 2016. Biochemistry. 55: 2452-64.

PMID: # 25326127  2015. Circ. Res. 116: 46-55.

PMID: # 24626957  Swain, L. et al. 2014. Journal of leukocyte biology. 96: 365-75.

Citations 1 to 10 of 13 total

Hello, is this product sterile or do I need to sterilize it myself prior to use? I cannot seem to find this information in the data sheet. Thank you, Anne

Asked by: AnneDK
Thank you for your question. This product is not sterile.
Answered by: Technical Support
Date published: 2017-11-09

Hello, How long would SNAP dissolved in 100% DMSO last in -20C? By "prepare solutions daily", does this mean that I have to measure out the tiny amount of the powder every time, as opposed to storing it dissolved in DMSO? Thanks, Peter

Asked by: Pmin91
Thank you for your question. You correct, due to the products instability in solution, we recommend reconstituting just prior to use.
Answered by: Technical Support
Date published: 2017-01-16
  • y_2019, m_10, d_20, h_9CST
  • bvseo_bulk, prod_bvqa, vn_bulk_2.0.13
  • cp_1, bvpage1
  • co_hasquestionsanswers, tq_2
  • loc_en_US, sid_200319, prod, sort_[SortEntry(order=LAST_APPROVED_ANSWER_SUBMISSION_TIME, direction=DESCENDING)]
  • clientName_scbt
  • bvseo_sdk, java_sdk, bvseo-3.2.0
  • CLOUD, getContent, 81ms
  • QUESTIONS, PRODUCT
Rated 5 out of 5 by from Worked well! We used this reagent to treat cell at 100 uM, which wrok well.
Date published: 2018-02-05
Rated 5 out of 5 by from Megson et al Megson et al. (PubMed ID 10188974) found that the slow decomposition of ( )-S-Nitroso-N-acetylpenicillamine (SNAP) within arterial endothelium generated enough nitric oxide to prolong vasodilation. -SCBT Publication Review
Date published: 2015-05-19
  • y_2019, m_10, d_20, h_9
  • bvseo_bulk, prod_bvrr, vn_bulk_2.0.13
  • cp_1, bvpage1
  • co_hasreviews, tv_0, tr_2
  • loc_en_US, sid_200319, prod, sort_[SortEntry(order=SUBMISSION_TIME, direction=DESCENDING)]
  • clientName_scbt
  • bvseo_sdk, java_sdk, bvseo-3.2.0
  • CLOUD, getReviews, 32ms
  • REVIEWS, PRODUCT

Santa Cruz Biotechnology, Inc. is a world leader in the development of products for the biomedical research market. Call us Toll Free at 1-800-457-3801.
Copyright © 2007-2019 Santa Cruz Biotechnology, Inc. All Rights Reserved. "Santa Cruz Biotechnology", and the Santa Cruz Biotechnology, Inc. logo, "Santa Cruz Animal Health", "San Juan Ranch", "Supplement of Champions", the San Juan Ranch logo, "Ultracruz", "Chemcruz", "Immunocruz", "Exactacruz", and "EZ Touch" are registered trademarks of Santa Cruz Biotechnology, Inc.
All trademarks are the property of their respective owners.