Dendritic receptors designed to bind polyanions in both organic and aqueous media

John G. Hardy, Ian Ashworth, Colin Brennan, David K. Smith*

*Corresponding author for this work

Research output: Contribution to journalArticle

3 Citations (Scopus)
194 Downloads (Pure)

Abstract

This paper reports the synthesis of dendrons containing a spermine unit at their focal point. The dendritic branching is based on L-lysine building blocks, and has terminal oligo(ethyleneglycol) units on the surface. As a consequence of the solubilising surface groups, these dendrons have high solubility in solvents with widely different polarities (e.g., dichloromethane and water). The protonated spermine unit at the focal point is an effective anion binding fragment and, as such, these dendrons are able to bind to polyanions. This paper demonstrates that polyanions can be bound in both dichloromethane (using a dye solubilisation assay) and in water (competitive ATP binding assay). In organic media the dendritic branching appears to have a pro-active effect on the solubilisation of the dye, with more dye being solubilised by higher generations of dendron. On the other hand, in water the degree of branching has no impact on the anion binding process. We propose that in this case, the spermine unit is effectively solvated by the bulk solvent and the dendritic branching does not need to play an active role in assisting solubility. Dendritic effects on anion binding have therefore been elucidated in different solvents. The dendritic branching plays a pro-active role in providing the anion binding unit with good solubility in apolar solvent media.

Original languageEnglish
Pages (from-to)900-906
Number of pages7
JournalOrganic & biomolecular chemistry
Volume5
Issue number6
DOIs
Publication statusPublished - 2007

Keywords

  • SUPRAMOLECULAR CHEMISTRY
  • BUILDING-BLOCKS
  • CONTROLLABLE NANOMATERIALS
  • SELECTIVE RECOGNITION
  • ANION RECEPTORS
  • DENDRIMERS
  • CORE
  • DENDRONS
  • DNA
  • SOLUBILIZATION

ASJC Scopus subject areas

  • Chemistry(all)
  • Biomaterials

Cite this