Title page for ETD etd-07132005-141738

Type of Document Dissertation
Author Clark, Jeffery Caleb
Author's Email Address jclar21@lsu.edu
URN etd-07132005-141738
Title Synthetic Development and Application of Compounds with Biological Relevance
Degree Doctor of Philosophy (Ph.D.)
Department Chemistry
Advisory Committee
Advisor Name Title
M. Graca H. Vicente Committee Chair
George G. Stanley Committee Member
Julia Y. Chan Committee Member
Kevin M. Smith Committee Member
William E. Crowe Committee Member
Armando B. Corripio Dean's Representative
  • pyrroles
  • carboranylpyrroles
  • peptides
  • linkers
  • porphyrins
  • carboranylporphyrins
Date of Defense 2005-07-06
Availability unrestricted
Nature has provided a vast number of compounds that have medicinal application. The use of these compounds provided by nature however, is limited by the amount of a specific compound that nature provides. The synthesis of these molecules and their derivatives provides an even greater number of compounds for biological screening.

Various pyrroles, the heterocyclic building blocks of porphyrins, can be prepared synthetically over several steps. The implementation of carboranes on pyrrole rings intrinsically provides substrates that can be converted into porphyrins bearing carborane substituents. The condensation of these carboranylpyrroles with carboranylaldehydes provides carboranylporphyrins bearing a higher order of carborane substitution. The conversion of these carboranylporphyrins into their water-soluble nido derivatives provides several compounds whose biological properties are currently being explored.

The use of peptides in the treatment of neurodegenerative diseases such as Alzheimer's provides a need for novel peptides. Peptides typically are synthesized through extensive use of solid-phase chemistry, protecting group chemistry, and linkers. The manipulation of the reactivity of these groups provides more advanced methods for producing novel peptides. The development of novel protecting groups and linkers on solid-phase resins have been attempted and have shown preliminary success.

The preliminary results of the biological studies of two of the molecules from this dissertation have shown positive activity for potential use in cancer therapy. These results as well as future findings will soon be published.

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