Carbon nanotubes functionalized with folic acid attached via biomimetic peptide linker

Nanomedicine (Lond). 2017 Sep;12(18):2161-2182. doi: 10.2217/nnm-2017-0120. Epub 2017 Aug 17.

Abstract

Aim: Anchoring folic acid (FA) with a biomimetic peptidic linker resistant to proteolytic degradation to act as a homing device on functionalized carbon nanotubes.

Materials & methods: Ethylenediamine was attached to oxidized multiwalled carbon nanotubes (MWNTs) using 4-(4,6-dimethoxy-[1,3,5]triazin-2-yl)-4-methylmorpholinium tetrafluoroborate. FA was coupled with 6-aminohexanoic acid and derivatives of β-alanine, affording four intermediates, which connected to the MWNTs via peptidic linkers of various lengths.

Results: Biomimetic nanomaterials were produced with FA as a homing molecule. The structure and properties of the nanomaterials were analyzed, confirming the versatility of the peptides used as linkers.

Conclusion: Conjugates of FA attached to MWNTs via peptide linkers prepared from β-alanine residues are resistant to proteolytic degradation. Viability in colon cancer cells and normal colonocytes confirmed their lack of cytotoxicity.

Keywords: biomimetics; carbon nanotubes; folate derivative; peptide linker; triazine-based coupling reagent.

MeSH terms

  • Aminocaproic Acid / chemistry
  • Biomimetic Materials / chemistry*
  • Borates / chemistry
  • Cell Line
  • Cell Survival
  • Drug Delivery Systems
  • Ethylenediamines / chemistry
  • Folic Acid / chemistry*
  • HT29 Cells
  • Humans
  • Hydrolysis
  • Nanotubes, Carbon / chemistry*
  • Nanotubes, Carbon / toxicity
  • Oligopeptides / chemistry*
  • Particle Size
  • Surface Properties
  • beta-Alanine / analogs & derivatives*
  • beta-Alanine / chemistry*

Substances

  • Borates
  • Ethylenediamines
  • Nanotubes, Carbon
  • Oligopeptides
  • beta-Alanine
  • ethylenediamine
  • Folic Acid
  • fluoroboric acid
  • Aminocaproic Acid