(6R)-5,6,7,8-tetrahydro-L-biopterin and its stereoisomer prevent ischemia reperfusion injury in human forearm

Arterioscler Thromb Vasc Biol. 2007 Jun;27(6):1334-9. doi: 10.1161/ATVBAHA.107.142257. Epub 2007 Apr 5.

Abstract

Objective: 6R-5,6,7,8-tetrahydro-L-biopterin (6R-BH4) is a cofactor for endothelial nitric oxide synthase but also has antioxidant properties. Its stereo-isomer 6S-5,6,7,8-tetrahydro-L-biopterin (6S-BH4) and structurally similar pterin 6R,S-5,6,7,8-tetrahydro-D-neopterin (NH4) are also antioxidants but have no cofactor function. When endothelial nitric oxide synthase is 6R-BH4-deplete, it synthesizes superoxide rather than nitric oxide. Reduced nitric oxide bioavailability by interaction with reactive oxygen species is implicated in endothelial dysfunction (ED). 6R-BH4 corrects ED in animal models of ischemia reperfusion injury (IRI) and in patients with cardiovascular risks. It is uncertain whether the effect of exogenous 6R-BH4 on ED is through its cofactor or antioxidant action.

Methods and results: In healthy volunteers, forearm blood flow was measured by venous occlusion plethysmography during intra-arterial infusion of the endothelium-dependent vasodilator acetylcholine, or the endothelium-independent vasodilator glyceryl trinitrate, before and after IRI. IRI reduced plasma total antioxidant status (P=0.03) and impaired vasodilatation to acetylcholine (P=0.01), but not to glyceryl trinitrate (P=0.3). Intra-arterial infusion of 6R-BH4, 6S-BH4 and NH4 at approximately equimolar concentrations prevented IRI.

Conclusion: IRI causes ED associated with increased oxidative stress that is prevented by 6R-BH4, 6S-BH4, and NH4, an effect mediated perhaps by an antioxidant rather than cofactor function. Regardless of mechanism, 6R-BH4, 6S-BH4, or NH4 may reduce tissue injury during clinical IRI syndromes.

Publication types

  • Controlled Clinical Trial
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholine / pharmacology
  • Adult
  • Antioxidants / chemistry
  • Antioxidants / pharmacology
  • Antioxidants / therapeutic use*
  • Biopterins / analogs & derivatives*
  • Biopterins / blood
  • Biopterins / chemistry
  • Biopterins / pharmacology
  • Biopterins / therapeutic use
  • Coenzymes / blood
  • Coenzymes / chemistry
  • Coenzymes / pharmacology
  • Coenzymes / therapeutic use*
  • Dose-Response Relationship, Drug
  • Endothelium, Vascular / drug effects*
  • Endothelium, Vascular / metabolism
  • Endothelium, Vascular / physiopathology
  • Female
  • Forearm / blood supply*
  • Humans
  • Male
  • Nitric Oxide / blood
  • Nitric Oxide Synthase / metabolism
  • Oxidative Stress / drug effects
  • Regional Blood Flow / drug effects
  • Reperfusion Injury / metabolism
  • Reperfusion Injury / physiopathology
  • Reperfusion Injury / prevention & control*
  • Stereoisomerism
  • Time Factors
  • Vasodilation / drug effects*
  • Vasodilator Agents / pharmacology

Substances

  • Antioxidants
  • Coenzymes
  • Vasodilator Agents
  • Biopterins
  • tetrahydroneopterin
  • Nitric Oxide
  • Nitric Oxide Synthase
  • sapropterin
  • Acetylcholine