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PTIO (CAS 18390-00-6)

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Alternate Names:
2-Phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide
Application:
PTIO is a nitric oxide (NO) radical scavenger used to inhibit physiological effects of NO
CAS Number:
18390-00-6
Purity:
≥98%
Molecular Weight:
233.29
Molecular Formula:
C13H17N2O2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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PTIO, 2-phenyl-4,4,5,5-tetramethylimidazolineoxyl-1-oxyl-3-oxide, is a stable radical compound used to scavenge and trap NO radicals. The reaction between PTIO and NO produces NO2 and derivatives of 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl. This reaction can be monitored with ESR spectroscopy. PTIO and its water soluble derivative Carboxy-PTIO (sc-200352) are demonstrated to block many biological actions mediated by NO. PTIO reaction with NO is described to suppress the pathogenicity of excessively produced NO in endotoxin shock and to inhibit endothelium-dependent vascular relaxation mediated by NO in an ex vivo system. The vasorelaxant effects of NO on rabbit aorta smooth muscle was inhibited by both PTIO compounds and Carboxy-PTIO was shown to inhibit vasorelaxation almost two-fold more strongly than by inhibitors of NO synthesis N-omega-nitro-L-arginine and N-omega-monomethyl-L-arginine. NO-induced enhancement of tumor vascular permeability was also blocked by the PTIO compounds. The PTIO radical compounds directly extinguish cellular NO without affecting the activity of NOS (nitric acid synthase), distinguishing this mechanism of action from other methods of NO perturbation.


PTIO (CAS 18390-00-6) References

  1. Reactions of PTIO and carboxy-PTIO with *NO, *NO2, and O2-*.  |  Goldstein, S., et al. 2003. J Biol Chem. 278: 50949-55. PMID: 12954619
  2. Diaphorase can metabolize some vasorelaxants to NO and eliminate NO scavenging effect of 2-phenyl-4,4,5,5,-tetramethylimidazoline-1-oxyl-3-oxide (PTIO).  |  Bartík, P., et al. 2004. Physiol Res. 53: 615-20. PMID: 15588129
  3. Netrin-1 induces angiogenesis via a DCC-dependent ERK1/2-eNOS feed-forward mechanism.  |  Nguyen, A. and Cai, H. 2006. Proc Natl Acad Sci U S A. 103: 6530-5. PMID: 16611730
  4. Lipoamide dehydrogenase and diaphorase catalyzed conversion of some NO donors to NO and reduction of NO scavenger 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide (PTIO).  |  Stibingerová, A., et al. 2009. Gen Physiol Biophys. 28: 384-90. PMID: 20097961
  5. 2-Phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-Oxide (PTIO•) Radical Scavenging: A New and Simple Antioxidant Assay In Vitro.  |  Li, X. 2017. J Agric Food Chem. 65: 6288-6297. PMID: 28689421
  6. 2-Phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide Radical (PTIO•) Trapping Activity and Mechanisms of 16 Phenolic Xanthones.  |  Li, X., et al. 2018. Molecules. 23: PMID: 29997352
  7. pH Effect and Chemical Mechanisms of Antioxidant Higenamine.  |  Xie, Y., et al. 2018. Molecules. 23: PMID: 30158440
  8. A large kinetic isotope effect in the reaction of ascorbic acid with 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide (PTIO˙) in aqueous buffer solutions.  |  Nakanishi, I., et al. 2020. Chem Commun (Camb). 56: 11505-11507. PMID: 32945829
  9. Vasodilator effect of carboxy-2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl in the coronary circulation: in vivo and in vitro studies.  |  Tsunoda, R., et al. 1994. Eur J Pharmacol. 262: 55-63. PMID: 7813579
  10. Multiple functions of nitric oxide in pathophysiology and microbiology: analysis by a new nitric oxide scavenger.  |  Maeda, H., et al. 1994. J Leukoc Biol. 56: 588-92. PMID: 7964166
  11. Therapeutic effects of imidazolineoxyl N-oxide against endotoxin shock through its direct nitric oxide-scavenging activity.  |  Yoshida, M., et al. 1994. Biochem Biophys Res Commun. 202: 923-30. PMID: 8048966
  12. Antagonistic action of imidazolineoxyl N-oxides against endothelium-derived relaxing factor/.NO through a radical reaction.  |  Akaike, T., et al. 1993. Biochemistry. 32: 827-32. PMID: 8422387
  13. Depletion of nitric oxide causes cell cycle alterations, apoptosis, and oxidative stress in pulmonary cells.  |  Janssen, YM., et al. 1998. Am J Physiol. 275: L1100-9. PMID: 9843847

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

PTIO, 25 mg

sc-202782
25 mg
$56.00

PTIO, 100 mg

sc-202782A
100 mg
$158.00