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Anastasiia Tikhomirova final.pdf (12.08 MB)

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Studies of Photoinduced DNA Damage by Phenanthrene Dihydrodioxin and Light-driven Electron Delocalization in Pyridinium Molecules

Tikhomirova, Anastasiia
http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1561918589357022

Abstract Details

2019, Doctor of Philosophy (Ph.D.), Bowling Green State University, Photochemical Sciences.
Ever since the discovery of the DNA molecular structure, this molecule became a desirable target for the researchers aiming to develop anticancer drugs and therapies. The main emphasis of this dissertation was placed on the design, development and studies of photochemical properties of a novel photo activated DNA damaging agent. Upon light irradiation of compound the release of highly reactive 9,10-phenanthrenequinone was observed. Studies of phenanthrene dihydrodioxin interaction with DNA demonstrated the intercalative mode of binding and slightly preferential binding affinity to the AT-rich DNA sequences. The synthesized agent induced a partial transition from B to Z form of DNA. The phenanthrene dihydrodioxin compound proved to be an efficient single-strand DNA photocleaver upon visible light irradiation. This further demonstrates the potential of photomasked ortho-quinones as efficient DNA damaging agents. This work also describes an unusual transformation from pyridinium substituted methane to the corresponding gem-diol in the mild conditions in the presence of air. Proposed mechanism of the reaction involves the formation of reactive oxygen species (ROS). ROS are known to be highly toxic to biomolecules, including DNA. It is demonstrated in this work that the production of ROS intermediates in the reaction of the gem-diol formation can lead to DNA damage in the dark. In the continuous interest of our research group, a series of bis(pyridinium) and bis(3-carboxamidepyridinium) alkane salts were synthesized in order to study through-space electron delocalization and formation of dimer radical cation species upon electrochemical and photoreduction. Investigation of photoinduced charge separation is important for the development of artificial photosynthetic systems and molecular electronics. Studies of unsubstituted and meta-substituted pyridines connected by the alkyl linker of different length provided additional information on the efficiency of the pyridinium dimers in delocalizing the electron density. The systems were studied by means of cyclic voltammetry and transient absorption spectroscopy.
R. Marshall Wilson, Prof. (Advisor)
Farida Selim, Prof. (Other)
Pavel Anzenbacher, Prof. (Committee Member)
Alexander Tarnovsky, Prof. (Committee Member)
264 p.
Biochemistry; Chemistry; Organic Chemistry; Physical Chemistry
DNA damage; DNA binding; DNA intercalation; Reactive Oxygen Species; ROS; Photolysis; geminal diol; cyanine dye; pyridinium salts; pimerization; aerobic oxidation; photochemistry; organic chemistry; spectroscopy

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Citations

  • Tikhomirova, A. (2019). Studies of Photoinduced DNA Damage by Phenanthrene Dihydrodioxin and Light-driven Electron Delocalization in Pyridinium Molecules [Doctoral dissertation, Bowling Green State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1561918589357022

    APA Style (7th edition)

  • Tikhomirova, Anastasiia. Studies of Photoinduced DNA Damage by Phenanthrene Dihydrodioxin and Light-driven Electron Delocalization in Pyridinium Molecules. 2019. Bowling Green State University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1561918589357022.

    MLA Style (8th edition)

  • Tikhomirova, Anastasiia. "Studies of Photoinduced DNA Damage by Phenanthrene Dihydrodioxin and Light-driven Electron Delocalization in Pyridinium Molecules." Doctoral dissertation, Bowling Green State University, 2019. http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1561918589357022

    Chicago Manual of Style (17th edition)

bgsu1561918589357022
310
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This open access ETD is published by Bowling Green State University and OhioLINK.