Skip NavigationSkip to Content
Our Science Seminars Synthesis Core Resources Women In Chemistry Fellows

Compound Information

Compound Name: Disodium 1-[(2-Carboxylato)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate

Compound

Figure: PROLI/NO Structure

  1. Category Information
  2. Nickname: PROLI/NO
  3. CAS Registry Number: 178948-42-0
  4. Molecular Formula: C5H7N3O4Na2
  5. Molecular Weight: 251 (as methanol solvate, C5H7N3O4Na2.MeOH)
  6. Half-life at pH 7.4 and 37oC: 2 sec
  7. Moles of NO/Mole of Compound: 2
  8. Solubility: Aqueous media at high pH
  9. UV Spectrum

          λmax(nm):

          ε(mM-1cm-1):      

    252 in 0.1 M NaOH

    8.4
  10. X-Ray Crystallographic Data:
  11. Special Comments: An ultrafast NO generator. Wth its 2-second half-life at physiological temperature and pH, PROLI/NO reversed cerebral vasospasm without inducing systemic hypertension or other toxic effects in a primate model. Also used to induce penile erection in male cats. In contrast to many other diazeniumdiolates, the corresponding N-nitroso derivative is considered non-carcinogenic, a major advantage for potential clinical applications. This compound is known to be commercially available.

Reference and Patent Information

Reference TypeKeywordsReferenceText
Biological  Saavedra, J. E.; Southan, G. J.; Davies, K. M.; Lundell, A.; Markou, C.; Hanson, S. R.; Adrie, C.; Hurford, W. E.; Zapol, W. M.; Keefer, L. K. Localizing antithrombotic and vasodilatory activity with a novel, ultrafast nitric oxide donor. J. Med. Chem. 1996, 39, 4361-4365. Pubmed Abstract
Biological  Adrie, C.; Hirani, W. M.; Holzmann, A.; Keefer, L.; Zapol, W. M.; Hurford, W. E. Selective pulmonary vasodilation by intravenous infusion of an ultrashort half-life nucleophile/nitric oxide adduct. Anesthesiology 1998, 88, 190-195. Pubmed Abstract
BiologicalCytostasis Chen, C.; Hanson, S. R.; Keefer, L. K.; Saavedra J. E.; Davies, K. M.; Hutsell, T. C.; Hughes, J. D.; Ku, D. N; Lumsden, A. B. Boundary layer infusion of nitric oxide reduces early smooth muscle cell proliferation in the endarterectomized canine artery. J. Surg. Res. 1997, 67, 26-32. Pubmed Abstract
BiologicalErectile Function Champion, H. C.; Bivalacqua, T. J.; Wang, R.; Kadowitz, P. J.; Keefer, L. K.; Saavedra, J. E.; Hrabie, J. A.; Doherty, P. C.; Hellstrom, W. J. G. Induction of penile erection by intracavernosal and transurethral administration of novel nitric oxide donors in the cat. J. Urol. 1999, 161, 2013-2019. Pubmed Abstract
BiologicalMechanism of Action Vavra, A. K.; Havelka, G. E.; Martinez, J.; Lee, V. R.; Fu, B.; Jiang, Q.; Keefer, L. K.; Kibbe, M. R. Insights into the effect of nitric oxide and its metabolites nitrite and nitrate at inhibiting neointimal hyperplasia. Nitric Oxide 2011 25 (1), 22-30. Pubmed Abstract
BiologicalMechanism of Action Weyerbrock, A.; Walbridge, S.; Saavedra, J. E.; Keefer, L. K.; Oldfield, E. H. Differential effects of nitric oxide on blood–brain barrier integrity and cerebral blood flow in intracerebral C6 gliomas.Neuro-Oncology 2011 13 (2), 203–211. Pubmed Abstract
BiologicalNeointimal Hyperplasia Varu, V. N.; Ahanchi, S. S.; Hogg, M. E.; Bhikhapurwala, H. A.; Chen, A.; Popowich, D. A.; Vavra, A. K.; Martinez, J.; Jiang, Q.; Saavedra, J. E.; Hrabie, J. A.; Keefer L. K.; Kibbe, M. R. Insulinenhances the effect of nitric oxide at inhibiting neointimal hyperplasia in a ratmodel of type 1 diabetes. Am. J. Physiol.: Heart Circ. Physiol. 2010, 299 (3), H772-H779. Pubmed Abstract
BiologicalNeointimal Hyperplasia Pearce C. G.; Najjar S. F.; Kapadia M. R.; Murar J.; Eng J.; Lyle B.; Aalami O. O.; Jiang Q.; Hrabie J. A.; Saavedra J. E.; Keefer L. K.; Kibbe M. R. Beneficial effect of a short-acting NO donor for the prevention of neointimal hyperplasia. Free Rad. Bio. Med. 2008, 44 (1), 73-81. Pubmed Abstract
BiologicalNeointimal Hyperplasia Ahanchi S. S.; Varu V. N.; Tsihlis N. D.; Martinez J.; Pearce C. G.; Kapadia M. R.; Jiang Q.; Saavedra J. E.; Keefer L. K.; Hrabie J. A.; Kibbe M. R. Heightened efficacy of nitric oxide-based therapies in type II diabetes mellitus and metabolic syndrome. Am. J. Physiol. 2008, 295 (6, Pt. 2), H2388-H2398. Pubmed Abstract
BiologicalNeointimal Hyperplasia Hogg, M. E.; Varu, V. N.; Vavra, A. K.; Popowich, D. A.; Banerjee, M. N.; Martinez, J.;Jiang, Q.; Saavedra, J. E.; Keefer, L. K.; Kibbe, M. R. Effect of nitric oxide on neointimal hyperplasia based on sex and hormone status. Free Rad. Bio. Med 2011, 50 (9), 1065-1074. Pubmed Abstract
1 - 10 of 15 results

NIH...Turning Discovery Into Health®

U.S. Department of Health and Human Services | National Institutes of Health | National Cancer Institute | USA.gov |

Home | Contact | Policies | Accessibility | Viewing Files | FOIA |