Identifier

etd-01092009-122836

Degree

Doctor of Philosophy (PhD)

Department

Chemistry

Document Type

Dissertation

Abstract

Phthalocyanines (Pcs) are excellent candidates for use as fluorophores for near-infrared (near-IR) fluorescent tagging of biomolecules and as photodynamic therapy (PDT) agents. Synthesis of Pcs with asymmetrical substitution on the periphery is often difficult due to the problems during the purification of the Pc mixtures obtained. The objective of this project is to design and synthesize chemically robust near-IR fluorophores for bioanalytical applications and to develop new synthetic methods for rapid synthesis of the target compounds. A novel synthetic route was developed utilizing a hydrophilic, polyethylene glycol-based (PEG) support with different types of linkers. The Pcs were functionalized with either hydroxyl or amine groups for covalent conjugation purposes and were decorated with solubilizing groups such as carboxylic acids and short PEG chains. Monohydroxyl and mono-amine functionalized oligoethylene glycol substituted Pcs were synthesized via a solid-phase phthalonitrile tetramerization reaction. In order to alter the photophysical properties of the desired compounds different metals were inserted in the cavity of the macrocycle. The potential of several of the compounds for PDT has been evaluated in vitro. Generally, these compounds are readily taken up in cells, have very low dark toxicity, exhibit rapid toxicity in near-infrared light, and are broadly dispersed in the cell including in lysosomes and in the endoplasmic reticulum.

Date

2008

Document Availability at the Time of Submission

Secure the entire work for patent and/or proprietary purposes for a period of one year. Student has submitted appropriate documentation which states: During this period the copyright owner also agrees not to exercise her/his ownership rights, including public use in works, without prior authorization from LSU. At the end of the one year period, either we or LSU may request an automatic extension for one additional year. At the end of the one year secure period (or its extension, if such is requested), the work will be released for access worldwide.

Committee Chair

Robert P. Hammer

Included in

Chemistry Commons

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