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SYNTHESIS OF NEW PHOTOACTIVATABLE NITROXYL (HNO) DONORS BASED ON THE 6,2-HNM PHOTOTRIGGER

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2018, BS, Kent State University, College of Arts and Sciences / Department of Chemistry and Biochemistry.
Nitroxyl (HNO) is a simple molecule that has been found to have high physiological relevance. HNO is a vasodilator, a positive lusitrope (increases myocardial relaxation), and a positive inotrope (increases the strength of a myocardial muscle contraction) that works independently of cAMP. It has been shown in recent studies to be useful for the treatment of patients with acute heart failure. A complication with HNO is that it rapidly dimerizes and, in order to study the chemistry and mechanisms of the reactions of HNO with biomolecules, there is a need for a rapidly releasing HNO donor. Our group is developing photoactivatable HNO donors that have promise for the rapid release of HNO “on demand”. One system under investigation incorporates a hydroxy-2-naphthalenyl (HNM) phototrigger. Our first generation of HNO donors showed a competing photoredox side reaction pathway that did not lead to HNO generation. However, the use the 6,2-HNM phototrigger in compound 1 showed a better selectivity for HNO release. The impact of adding additional substituents at the C* position in 1 is being studied in order to increase HNO generation relative to the unwanted photoredox side reaction. Adding a methyl group to the C* in the first generation of HNO donors showed an increase in the selectivity for HNO generation. In the present work, the effect of the addition of a phenyl group at this position is under study.
Paul Sampson (Advisor)
Alexander Seed (Advisor)
Ruth Leslie (Committee Member)
Douglas Kline (Committee Member)
101 p.

Recommended Citations

Citations

  • Brandle, G. C. (2018). SYNTHESIS OF NEW PHOTOACTIVATABLE NITROXYL (HNO) DONORS BASED ON THE 6,2-HNM PHOTOTRIGGER [Undergraduate thesis, Kent State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors152571105724107

    APA Style (7th edition)

  • Brandle, Greggory. SYNTHESIS OF NEW PHOTOACTIVATABLE NITROXYL (HNO) DONORS BASED ON THE 6,2-HNM PHOTOTRIGGER. 2018. Kent State University, Undergraduate thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors152571105724107.

    MLA Style (8th edition)

  • Brandle, Greggory. "SYNTHESIS OF NEW PHOTOACTIVATABLE NITROXYL (HNO) DONORS BASED ON THE 6,2-HNM PHOTOTRIGGER." Undergraduate thesis, Kent State University, 2018. http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors152571105724107

    Chicago Manual of Style (17th edition)