Identifier

etd-07102017-141916

Degree

Doctor of Philosophy (PhD)

Department

Chemistry

Document Type

Dissertation

Abstract

Abstract Chapter 1 provides a brief introduction to colorectal cancer (CRC), methods of detection, photodynamic therapy (PDT), and EGFR as an attractive targeting strategy for imaging CRC. Chapter 2 details the synthesis of ten peptide sequences for targeting EGFR receptors at the site of CRC, as a collaborative work with Dr. Seetharama Jois. This chapter also investigates the efficacy of these peptides for EGFR. Chapter 3 offers the first synthetic strategy for developing BODIPY-peptide conjugates via amide linkages. All conjugates were optimized for the best reaction conditions and good yields were observed. Each conjugate was subjected to photophysical, SPR, and characterization studies. Cell studies obtained by Mrs. Zehua Zhou suggesting the conjugate bearing the hydrophobic peptide sequence had a greater cellular uptake then compared to conjugates containing a charged peptide sequence. Chapter 4 details the conjugation strategy via NCS- chemistry. NCS-BODIPY dyes were conjugated to two pegylated peptides. These conjugates were synthesized in 30 minutes with excellent yields. Tests administered by Mrs. Zehua Zhou determined the conjugates to have low dark and phototoxicity to human carcinoma HEp2 cells over-expressing EGFR, and to be taken up in to cells efficiently. Chapter 5 discusses the conjugation of BODIPY dyes and peptides via click chemistry to build peptide-BODIPY conjugates with cyclic or linear peptide sequences. The conjugates were synthesized efficiently in 24 hours with great yields and minimal side products were observed. Preliminary cell studies suggest conjugates bearing mono-styryl group were

Date

2017

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

Vicente, Graca

Available for download on Saturday, February 23, 2019

Included in

Chemistry Commons

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