Photochemistry of Masked Pyrene-4,5-Dione
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Bowling Green State University / OhioLINK
2013
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| Online Access: | http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1371083757 |
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ndltd-OhioLink-oai-etd.ohiolink.edu-bgsu13710837572021-08-03T05:24:02Z Photochemistry of Masked Pyrene-4,5-Dione Karabaeva, Kanykey E. Chemistry photochemistry dihydrodioxin ortho-quinone caged molecule DNA cutting agent ultrafast The photochemistry of 1,2-dipyridinium dihydrodioxin, 1,1-di(2-pyridyl) dihydrodioxin, 1,1-di(2-pyridyl) dihydrodioxin-Cu<sup>2+</sup>, pyrene-4,5-dione, and their complexes with DNA were studied. Also, quantum yields of pyrene-4,5-dione release from 1,2-dipyridinium dihydrodioxin, 1,1-di(2-pyridyl) dihydrodioxin, and 1,1-di(2-pyridyl) dihydrodioxin-Cu<sup>2+</sup> were calculated to be 10<sup>-4</sup>, 0.1, and 0.3 respectively. In case of 1,2-dipyridinium dihydrodioxin, it was found that DNA damage happens due to electron transfer from pyrene ring of 1,2-dipyridinium dihydrodioxin to DNA stack under excitation by UV-light. Evidence is given that release of pyrene-4,5-dione is not responsible for DNA cleavage, as it was believed before. After treatment of DNA with pyrene-4,5-dione under UV-light no decomposition of DNA was noticed. Pyrene-4,5-dione forms solvent separated radical-ion pair with Guanine of DNA after which both molecules go back to ground state. Unfortunately, 1,1-di(2-pyridyl) dihydrodioxin and 1,1-di(2-pyridyl) dihydrodioxin-Cu<sup>2+</sup> do not dissolve in water and cannot be used as DNA-cutting agents. Although, photoexcitation of 1,1-di(2-pyridyl) dihydrodioxin-Cu<sup>2+</sup> gives better understanding of the mechanism of electron transfer from the pyrene-ring to an acceptor. 1,1-di(2-pyridyl) dihydrodioxin does not have a good electron acceptor in its structure therefore electron transfer does not occur. Electron transfer from pyrene-ring of dihydrodioxin to electron acceptor, such as DNA molecule, water or Cu<sup>2+</sup>, forms stable radical-cation species which has an absorption band at 450 nm and can be recognized. 1,2-dipyridinium dihydrodioxin in water, 1,2-dipyridinium dihydrodioxin with DNA, and 1,1-di(2-pyridyl) dihydrodioxin-Cu<sup>2+</sup> showed in transient absorption spectra the presence of stable 450 nm band with a lifetime of more than 1 ns. 2013-07-23 English text Bowling Green State University / OhioLINK http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1371083757 http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1371083757 unrestricted This thesis or dissertation is protected by copyright: some rights reserved. It is licensed for use under a Creative Commons license. Specific terms and permissions are available from this document's record in the OhioLINK ETD Center. |
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NDLTD |
| language |
English |
| sources |
NDLTD |
| topic |
Chemistry photochemistry dihydrodioxin ortho-quinone caged molecule DNA cutting agent ultrafast |
| spellingShingle |
Chemistry photochemistry dihydrodioxin ortho-quinone caged molecule DNA cutting agent ultrafast Karabaeva, Kanykey E. Photochemistry of Masked Pyrene-4,5-Dione |
| author |
Karabaeva, Kanykey E. |
| author_facet |
Karabaeva, Kanykey E. |
| author_sort |
Karabaeva, Kanykey E. |
| title |
Photochemistry of Masked Pyrene-4,5-Dione |
| title_short |
Photochemistry of Masked Pyrene-4,5-Dione |
| title_full |
Photochemistry of Masked Pyrene-4,5-Dione |
| title_fullStr |
Photochemistry of Masked Pyrene-4,5-Dione |
| title_full_unstemmed |
Photochemistry of Masked Pyrene-4,5-Dione |
| title_sort |
photochemistry of masked pyrene-4,5-dione |
| publisher |
Bowling Green State University / OhioLINK |
| publishDate |
2013 |
| url |
http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1371083757 |
| work_keys_str_mv |
AT karabaevakanykeye photochemistryofmaskedpyrene45dione |
| _version_ |
1719419678699290624 |