Nitrosyl-cobinamide, a new and direct nitric oxide releasing drug effective in vivo

Exp Biol Med (Maywood). 2007 Dec;232(11):1432-40. doi: 10.3181/0703-RM-70.

Abstract

A limited number of nitric oxide (NO)-generating drugs are available for clinical use for acute and chronic conditions. Most of these agents are organic nitrates, which do not directly release NO; tolerance to the drugs develops, in part, as a consequence of their conversion to NO. We synthesized nitrosyl-cobinamide (NO-Cbi) from cobinamide, a structural analog of cobalamin (vitamin B12). NO-Cbi is a direct NO-releasing agent that we found was stable in water, but under physiologic conditions, it released NO with a half-life of 30 mins to 1 h. We show in five different biological systems that NO-Cbi is an effective NO-releasing drug. First, in cultured rat vascular smooth muscle cells, NO-Cbi induced phosphorylation of vasodilator-stimulated phosphoprotein, a downstream target of cGMP and cGMP-dependent protein kinase. Second, in isolated Drosophila melanogaster Malpighian tubules, NO-Cbi-stimulated fluid secretion was similar to that stimulated by Deta-NONOate and a cGMP analog. Third, in isolated mouse hearts, NO-Cbi increased coronary flow much more potently than nitroglycerin. Fourth, in contracted mouse aortic rings, NO-Cbi induced relaxation, albeit to a lesser extent than sodium nitroprusside. Fifth, in intact mice, a single NO-Cbi injection rapidly reduced blood pressure, and blood pressure returned to normal after 45 mins; repeated NO-Cbi injections induced the expected fall in blood pressure. These studies indicate that NO-Cbi is a useful NO donor that can be used experimentally in the laboratory; moreover, it could be developed into a vasodilating drug for treating hypertension and potentially other diseases such as angina and congestive heart failure.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Angina Pectoris / drug therapy
  • Angina Pectoris / metabolism
  • Animals
  • Aorta / metabolism
  • Blood Pressure / drug effects
  • Cobamides / chemical synthesis
  • Cobamides / chemistry
  • Cobamides / pharmacology*
  • Coronary Circulation / drug effects
  • Drosophila melanogaster
  • Drug Evaluation, Preclinical
  • Heart Failure / drug therapy
  • Heart Failure / metabolism
  • Hypertension / drug therapy
  • Hypertension / metabolism
  • Malpighian Tubules / metabolism
  • Mice
  • Muscle Relaxation / drug effects
  • Muscle, Smooth, Vascular / metabolism
  • Myocardium / metabolism
  • Nitric Oxide / metabolism*
  • Nitric Oxide Donors / chemical synthesis
  • Nitric Oxide Donors / chemistry
  • Nitric Oxide Donors / pharmacology*
  • Nitroso Compounds / chemical synthesis
  • Nitroso Compounds / chemistry
  • Nitroso Compounds / pharmacology*
  • Organ Culture Techniques
  • Rats
  • Vasodilator Agents / chemical synthesis
  • Vasodilator Agents / chemistry
  • Vasodilator Agents / pharmacology*

Substances

  • Cobamides
  • Nitric Oxide Donors
  • Nitroso Compounds
  • Vasodilator Agents
  • cobinamide
  • Nitric Oxide