Synthetic and structural studies of Calix[4]pyrogallolarenes: towards biological applications

This work presented in this thesis details efforts towards understanding what factors control the formation of the myriad of architectures in calix[4]pyrogallolarenes, leading towards biological application. A variety of C-alkyl-calix[4]pyrogallolarenes have been synthesised and their solidstate and in-solution behaviour has been studied by diffusion NMR spectroscopy and single crystal X-ray diffraction. It has been found that calix nano-capsules can be formed by calix[4]pyrogallolarenes in polar protic solvents when the alkyl chain is substituted with bromine at its terminus. This is speculated to be due to formation of a dipolar interaction between the bromine atoms of adjacent calix[4]pyrogallolarene molecules. Calix[4]pyrogallolarenes with pendant chains bearing hydroxyl and cyano groups have been synthesised, and their behaviour in the solid state have been investigated by single crystal X-ray diffraction. They have been shown to form head-to-tail packing interactions in the solid state. As the hydroxyl functional group offers opportunity for further synthetic manipulations, in future investigations these molecules will provide a key intermediate in the synthesis of therapeutic delivery vectors. Preliminary investigation of cellular toxicity of the calixarenes has also been performed and indicates that this class of molecules does not appear to possess a high degree of toxicity towards dendritic cells and peripheral blood mononuclear cells which are the envisioned target of this delivery vector.

Name dc:type.qualificationname

phd

Level dc:type.qualificationlevel

doctoral

Grantor dc:publisher.institution

Nottingham Trent University

Year dc:date.issued

2008

Author dc:creator

• Bowley, N

Language dc:language

en