Computational Studies of the Spin Trapping Behavior of Melatonin and its Derivatives

Authors' Affiliations

Oladun Oladiran, Department of Chemistry, East Tennessee State University. Johnson City, TN. Scott Kirkby, Department of Chemistry, East Tennesee State University.

Location

Ballroom

Start Date

4-12-2019 9:00 AM

End Date

4-12-2019 2:30 PM

Poster Number

43

Faculty Sponsor’s Department

Chemistry

Name of Project's Faculty Sponsor

Dr. Scott Kirkby

Classification of First Author

Graduate Student-Master’s

Type

Poster: Competitive

Project's Category

Quantum Mechanics, Computational Chemistry, Quantum Chemistry

Abstract or Artist's Statement

The presence of excess free radicals in the body can result in severe health consequences because of oxidative damage to cells. Spin traps may be used as a probe to examine radical reactions in cells, but there is a need for less toxic and more lipid soluble examples. Melatonin is one of the numerous antioxidants used to scavenge free radicals in the body and reportedly one of the most efficient radical scavengers known. It is relatively nontoxic and easily crosses the lipid bilayer in cell membranes. Melatonin is thought to undergo a multistep oxidation process and this work investigates the potential for it to be used as a spin trap. The presence of electron withdrawing or donating groups added to melatonin may stabilize an intermediate and allow it to function as a spin trap.

The essence of this study is to conduct a computational inquiry into the relative stability of melatonin, selected derivatives, and the partial oxidation products formed from the scavenging of hydroxyl radical. To determine this, geometries were optimized for each molecule at the DFT/B3LYP/6-31G(d) and HF/6-31G(d) levels of theory.

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Apr 12th, 9:00 AM Apr 12th, 2:30 PM

Computational Studies of the Spin Trapping Behavior of Melatonin and its Derivatives

Ballroom

The presence of excess free radicals in the body can result in severe health consequences because of oxidative damage to cells. Spin traps may be used as a probe to examine radical reactions in cells, but there is a need for less toxic and more lipid soluble examples. Melatonin is one of the numerous antioxidants used to scavenge free radicals in the body and reportedly one of the most efficient radical scavengers known. It is relatively nontoxic and easily crosses the lipid bilayer in cell membranes. Melatonin is thought to undergo a multistep oxidation process and this work investigates the potential for it to be used as a spin trap. The presence of electron withdrawing or donating groups added to melatonin may stabilize an intermediate and allow it to function as a spin trap.

The essence of this study is to conduct a computational inquiry into the relative stability of melatonin, selected derivatives, and the partial oxidation products formed from the scavenging of hydroxyl radical. To determine this, geometries were optimized for each molecule at the DFT/B3LYP/6-31G(d) and HF/6-31G(d) levels of theory.