Title page for ETD etd-10312012-113031


Type of Document Dissertation
Author Ongarora, Benson Getenga
URN etd-10312012-113031
Title Syntheses and Characterization of Water-Soluble Phthalocyanines for Diagnosis and Treatment of Cancer
Degree Doctor of Philosophy (Ph.D.)
Department Chemistry
Advisory Committee
Advisor Name Title
Vicente, M. Graҫa H. Committee Chair
Choi, Jin-Woo Committee Member
Stanley, George G. Committee Member
Taylor, Carol M. Committee Member
Keywords
  • synthesis
  • cationic
  • phthalocyanines
  • cellular studies
  • photophysical studies
  • carcinoembryonic antigen
  • cytotoxicity
Date of Defense 2012-10-15
Availability unrestricted
Abstract
Ongarora, Benson Getenga, B.S., Moi University, 2005

Doctor of Philosophy, Fall Commencement, 2012

Major: Chemistry

Syntheses and Characterization of Water-Soluble Phthalocyanines for Diagnosis and Treatment of Cancer

Dissertation directed by Professor M.Graҫa H. Vicente

Pages in dissertation, xi. Words in abstract, 251.

ABSTRACT

Chapter 1 describes the general properties of phthalocyanines, synthesis of metallo-phthalocyanines, their photophysical features and their uses. The concepts of PDT and targeted therapeutics are also introduced.

Chapter 2 describes the syntheses, characterization, photophysical studies and biological evaluation of cationic phthalocyanines. The trimethylaminophenoxy substituted phthalocyanines were synthesized through statistical condensation method, which gave a statistical mixture of isomers. Di-cationic phthalocyanines were found to be more cytotoxic. The amphiphilicity of the phthalocyanines played an important role.

Chapter 3 covers the conjugation of phthalocyanines to peptides and is in pursuit of targeted therapeutics. The conjugation of two peptides, EGFR L1 (six amino acid residues) and EGFR L2 (twelve amino acid residues), gave conjugates with different charge, length, and hydrophobicity. The bioconjugates were synthesized via SPS method using typical peptide coupling agents. Cellular and animal studies are described for the conjugates.

Chapter 4 is a description of the syntheses and characterization of pure regiomeric phthalocyanines. Previous chapters described, mostly, statistical mixture of Pcs. In this chapter, strategy to the synthesis of monomeric isomers and their characterization is presented.

Chapter 5 describes the syntheses, characterization and cellular studies of a series of di-cationic and pegylated phthalocyanines. Statistical condensation was used in the synthesis of macrocycles. Phthalocyanines with cationic charge at close proximity and on α-substitution position of the macrocycle were found to be more cytotoxic. In addition, Pc-antibody bioconjugates are discussed. The biological studies are described for both cationic Pcs and Pc-conjugates. Just like Chapter 3, this chapter is also in pursuit of targeted therapeutics.

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