Antioxidant multi-walled carbon nanotubes by free radical grafting of gallic acid: new materials for biomedical applications

J Pharm Pharmacol. 2011 Feb;63(2):179-88. doi: 10.1111/j.2042-7158.2010.01211.x. Epub 2010 Nov 16.

Abstract

Objectives: To prove the possibility of covalently functionalizing multi-walled carbon nanotubes (CNTs) by free radical grafting of gallic acid on their surface with the subsequent synthesis of materials with improved biological properties evaluated by specific in-vitro assays.

Methods: Antioxidant CNTs were synthesized by radical grafting of gallic acid onto pristine CNTs. The synthesis of carbon nanotubes was carried out in a fixed-bed reactor and, after the removal of the amorphous carbon, the grafting process was performed. The obtained materials were characterized by fluorescence and Fourier transform infrared spectroscopy (FT-IR) analyses. After assessment of the biocompatibility and determination of the disposable phenolic group content, the antioxidant properties were evaluated in terms of total antioxidant activity and scavenger ability against 2,2'-diphenyl-1-picrylhydrazyl (DPPH), hydroxyl and peroxyl radicals. Finally the inhibition activity on acetylcholinesterase was evaluated.

Key findings: The covalent functionalization of CNTs with gallic acid was confirmed and the amount of gallic acid bound per g of CNTs was found to be 2.1±0.2 mg. Good antioxidant and scavenging properties were recorded in the functionalized CNTs, which were found to be able to inhibit the acetylcholinesterase with potential improved activity for biomedical and pharmaceutical applications.

Conclusions: For the first time, a free radical grafting procedure was proposed as a synthetic approach for the covalent functionalization of CNTs with an antioxidant polyphenol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry*
  • Antioxidants / pharmacology
  • Biphenyl Compounds / chemistry
  • Chick Embryo
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / pharmacology
  • Free Radical Scavengers / chemical synthesis
  • Free Radical Scavengers / chemistry*
  • Free Radical Scavengers / pharmacology
  • Gallic Acid / chemistry*
  • Gallic Acid / pharmacology
  • Hydroxyl Radical / chemistry
  • Lipid Peroxidation / drug effects
  • Materials Testing / methods
  • Nanotubes, Carbon / chemistry*
  • Nanotubes, Carbon / ultrastructure
  • Peroxides / chemistry
  • Picrates / chemistry
  • Spectroscopy, Fourier Transform Infrared / methods

Substances

  • Antioxidants
  • Biphenyl Compounds
  • Cholinesterase Inhibitors
  • Free Radical Scavengers
  • Nanotubes, Carbon
  • Peroxides
  • Picrates
  • perhydroxyl radical
  • Hydroxyl Radical
  • Gallic Acid
  • 1,1-diphenyl-2-picrylhydrazyl