Research output: Contribution to Journal/Magazine › Journal article › peer-review
Research output: Contribution to Journal/Magazine › Journal article › peer-review
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TY - JOUR
T1 - Dendritic receptors designed to bind polyanions in both organic and aqueous media
AU - Hardy, John G.
AU - Ashworth, Ian
AU - Brennan, Colin
AU - Smith, David K.
PY - 2007
Y1 - 2007
N2 - 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.
AB - 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.
KW - SUPRAMOLECULAR CHEMISTRY
KW - BUILDING-BLOCKS
KW - CONTROLLABLE NANOMATERIALS
KW - SELECTIVE RECOGNITION
KW - ANION RECEPTORS
KW - DENDRIMERS
KW - CORE
KW - DENDRONS
KW - DNA
KW - SOLUBILIZATION
KW - Chemistry(all)
KW - Biomaterials
U2 - 10.1039/b618063a
DO - 10.1039/b618063a
M3 - Journal article
VL - 5
SP - 900
EP - 906
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 6
ER -