A novel SWCNT platform bearing DOTA and β-cyclodextrin units. "One shot" multidecoration under microwave irradiation

Org Biomol Chem. 2014 Jul 14;12(26):4708-15. doi: 10.1039/c4ob00611a.

Abstract

The functionalization of single-walled carbon nanotubes (SWCNTs) via microwave-assisted grafting reactions enables efficient multidecoration in a single step. A novel water-soluble SWCNT platform was prepared via the simple 1,3-dipolar cycloaddition of azomethine ylides under dielectric heating. Thanks to a single grafting reaction the CNT surface binds in a 1 : 1 ratio an amino acidic β-cyclodextrin (β-CD) derivative and the DOTAMA moiety (1,4,7,10-tetraazacyclododecane-N,N',N'',N'''-tetraacetic acid monoamide). This novel "one shot" synthesis, compared with multistep functionalizations, preserves the SWCNT's structural integrity (TEM images). Besides thermogravimetric analyses, the determination of the amount of β-CD and DOTA moieties grafting onto the SWCNT's surface was performed on the basis of phenolphthalein and gadolinium complexation, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Cell Survival
  • Chemistry, Organic / methods*
  • Cycloaddition Reaction
  • Decarboxylation
  • Heterocyclic Compounds, 1-Ring / chemistry*
  • Humans
  • Microwaves*
  • Nanotubes, Carbon / chemistry*
  • Nanotubes, Carbon / ultrastructure
  • Spectrophotometry, Ultraviolet
  • Temperature
  • beta-Cyclodextrins / chemical synthesis
  • beta-Cyclodextrins / chemistry*

Substances

  • Heterocyclic Compounds, 1-Ring
  • Nanotubes, Carbon
  • beta-Cyclodextrins
  • 1,4,7,10-tetraazacyclododecane- 1,4,7,10-tetraacetic acid
  • betadex