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Synthesis and Fate of Oligonucleotides Containing the Oxidative Damage Product 3'-Oxothymidine

Bedi, Fernand Mel
http://rave.ohiolink.edu/etdc/view?acc_num=toledo1429183009

Abstract Details

2015, Doctor of Philosophy, University of Toledo, Medicinal Chemistry.
Oxidative events that take place during normal oxygen metabolism can lead to the formation of organic or inorganic radicals. Unchecked, the interaction of these radicals with macromolecules in the organism and with DNA in particular can to lead to DNA lesions, cell damage and apoptosis. Independent generation of DNA lesions resulting from oxidative damage can be used to promote the study of their effects on biological systems. Here we report the synthesis and characterization of a DNA damage product emanating from hydrogen abstraction at the 3'-carbon of thymidine. A phosphoramidite building block was chemically synthesized and incorporated into a DNA single strand using “reverse” oligonucleotide synthesis. The DNA lesion was then successfully generated by oxidative cleavage using sodium periodate. Our studies indicate that although the lesion is observed, it quickly degrades. Alternative conditions for oligomer isolation are warranted for full characterization of the lesion. Such studies will allow us to determine the effect that this damage product has on biological systems.
Amanda Bryant-Friedrich, PhD. (Committee Chair)
Viranga Tillekeratne , PhD. (Committee Member)
Paul Erhardt, PhD. (Committee Member)
Ming-Cheh Liu, PhD. (Committee Member)
135 p.
Biochemistry; Biomedical Research; Chemistry
oligonucleotides; oxothymidine; oxidative damage; DNA lesions; phosphoramidite; reverse oligonucleotide synthesis; radicals; hydrogen abstraction

Recommended Citations

Citations

  • Bedi, F. M. (2015). Synthesis and Fate of Oligonucleotides Containing the Oxidative Damage Product 3'-Oxothymidine [Doctoral dissertation, University of Toledo]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=toledo1429183009

    APA Style (7th edition)

  • Bedi, Fernand. Synthesis and Fate of Oligonucleotides Containing the Oxidative Damage Product 3'-Oxothymidine. 2015. University of Toledo, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=toledo1429183009.

    MLA Style (8th edition)

  • Bedi, Fernand. "Synthesis and Fate of Oligonucleotides Containing the Oxidative Damage Product 3'-Oxothymidine." Doctoral dissertation, University of Toledo, 2015. http://rave.ohiolink.edu/etdc/view?acc_num=toledo1429183009

    Chicago Manual of Style (17th edition)

toledo1429183009
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© 2015, all rights reserved.
This open access ETD is published by University of Toledo and OhioLINK.