Retrometabolic syntheses of astaxanthin (3,3'-dihydroxy-beta,beta-carotene-4,4'-dione) conjugates: a novel approach to oral and parenteral cardio-protection

Cardiovasc Hematol Agents Med Chem. 2006 Oct;4(4):335-49. doi: 10.2174/187152506784111472.

Abstract

Disodium disuccinate astaxanthin has potent cardioprotective effects in animals, with demonstrated preclinical efficacy in the rat, rabbit, and canine models of experimental infarction. It has been effective in subchronic and acute dosing regimens after parenteral administration, and recently published data in rats demonstrate that oral cardioprotection is also readily achieved. Myocardial salvage in the canine can reach 100% with a 4-day subchronic dosing regimen; single-dose I.V. cardioprotection, when given 2 hours before experimental coronary occlusion, is on average two-thirds of that achieved with the subchronic regimen in dogs. In conscious animals, no effects on hemodynamic parameters have been observed. Recently, the beneficial properties of this prototypical astaxanthin conjugate have been extended to include second- and third-generation compounds with improved pharmacokinetic and/or potency profiles. The primary mechanism of cardioprotection appears to be antioxidant activity: potent direct scavenging of the lynchpin radical in ischemia-reperfusion injury, superoxide anion, has been documented in appropriate model systems. In addition, modulation of serum complement activity, reduction of the levels of deposition of C-reactive protein (CRP) and the membrane attack complex (MAC) in infarcted tissue, and reduction in oxidative stress markers from the arachidonic acid and linoleic acid pathways also suggest a significant anti-inflammatory component to the mechanism of cardioprotection. Favorable plasma protein binding has been demonstrated in vitro for several astaxanthin conjugates; this binding capacity overcomes the supramolecular assembly of the compounds that occurs in aqueous solution, which in itself improves the stability and shelf-life of aqueous formulations. Astaxanthin readily populates cardiac tissue after metabolic hydrolysis of both oral and parenteral administration of the astaxanthin ester derivates, providing a reservoir of cardioprotective agent with a significant half-life due to favorable ADME in mammals. Due to the well-documented safety profile of astaxanthin in humans, disodium disuccinate astaxanthin may well find clinical utility in cardiovascular applications in humans following successful completion of preclinical and clinical pharmacology and toxicology studies in animals and humans, respectively.

Publication types

  • Review

MeSH terms

  • Animals
  • Antioxidants / administration & dosage
  • Antioxidants / chemical synthesis
  • Antioxidants / pharmacokinetics*
  • Antioxidants / pharmacology
  • Drug Design
  • Drug Evaluation, Preclinical
  • Humans
  • Protective Agents / administration & dosage
  • Protective Agents / chemical synthesis
  • Protective Agents / pharmacokinetics*
  • Protective Agents / pharmacology
  • Reactive Oxygen Species / antagonists & inhibitors
  • Reperfusion Injury / drug therapy
  • Reperfusion Injury / prevention & control*
  • Succinates / administration & dosage
  • Succinates / chemical synthesis
  • Succinates / pharmacokinetics*
  • Succinates / pharmacology
  • Xanthophylls / administration & dosage
  • Xanthophylls / biosynthesis
  • Xanthophylls / chemical synthesis
  • Xanthophylls / pharmacokinetics*
  • Xanthophylls / pharmacology

Substances

  • Antioxidants
  • Protective Agents
  • Reactive Oxygen Species
  • Succinates
  • Xanthophylls
  • succinic acid mono-(4-(18-(4-(3-carboxypropionyloxy)-2,6,6-trimethyl-3-oxocyclohex-1-enyl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl)-3,5,5-trimethyl-2-oxocyclohex-3-enyl) ester
  • astaxanthine