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Synthesis, Characterization, DNA Binding and Photocleavage Studies of a Di-Ruthenated Porphyrin

Wilson, Dale F.
http://rave.ohiolink.edu/etdc/view?acc_num=dayton1398882510

Abstract Details

2014, Master of Science (M.S.), University of Dayton, Bioengineering.
A novel di-runthenated porphyrin has been synthesized that is capable of photocleaving plasmid DNA within the photodynamic therapy window of 600-800nm. The desired porphyrin was synthesized through reaction of 4-pyridine carboxaldehyde, 4-trifuorlomethyl benzaldehyde and pyrrole under reflux in propionic acid and isolated through column chromatography using methylene chloride/methanol as the eluent. Coordination of cis-Ru(bipy)2Cl2 moieties was achieved through reflux under nitrogen in glacial acetic acid to give the bis-Ru(bipy)2Cl]2[5,15-(4-pyridyl)-10,20-(p-trifluoromethylphenyl)-porphyrin. UV-Vis spectra of the porphyrin and its ruthenated analog revealed an intense Soret band at 410 nm and Q-bands at 500 and 650nm. Cyclic voltammetry was used to determine the oxidative and reductive characteristics of the porphyrin and its ruthenated analog. DNA titrations using buffered solutions of the ruthenated porphyrin and calf thymus DNA were performed spectrophotometrically. The binding constant of the ruthenated porphyrin was determined to be 1.30 x 106 M-1. The ability of the ruthenated porphyrin to photocleave DNA was evaluated by irradiating aqueous samples of plasmid DNA and the complex at a ratio of 5 base pairs to 1 complex using a mercury arc lamp with a 500nm filter. Use of the 500nm filter allowed for observation of the photodynamic therapy window of 600-800nm. Samples were taken at 5 minute intervals and compared using gel electrophoresis to confirm the formation of the photocleaved nicked form of the plasmid DNA.
Shawn Swavey (Advisor)
Doug Dudis (Committee Member)
Robert Wilkens (Committee Member)
Donald Comfort (Committee Member)
Chemistry; Inorganic Chemistry
porphyrin; ruthenium; DNA photocleavage; coordination chemistry; DNA binding; bioinorganic chemistry

Recommended Citations

Citations

  • Wilson, D. F. (2014). Synthesis, Characterization, DNA Binding and Photocleavage Studies of a Di-Ruthenated Porphyrin [Master's thesis, University of Dayton]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=dayton1398882510

    APA Style (7th edition)

  • Wilson, Dale. Synthesis, Characterization, DNA Binding and Photocleavage Studies of a Di-Ruthenated Porphyrin. 2014. University of Dayton, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=dayton1398882510.

    MLA Style (8th edition)

  • Wilson, Dale. "Synthesis, Characterization, DNA Binding and Photocleavage Studies of a Di-Ruthenated Porphyrin." Master's thesis, University of Dayton, 2014. http://rave.ohiolink.edu/etdc/view?acc_num=dayton1398882510

    Chicago Manual of Style (17th edition)

dayton1398882510
971
© , some rights reserved.Creative Commons License Synthesis, Characterization, DNA Binding and Photocleavage Studies of a Di-Ruthenated Porphyrin by Dale F. Wilson is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. Based on a work at etd.ohiolink.edu.
This open access ETD is published by University of Dayton and OhioLINK.