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Medicinal Chemistry is a course offered by Winona State University that focuses on the chemical structure - biological activity relationship (SAR). The course is offered to chemistry and biology students who have previously taken organic chemistry and intend to further their knowledge of pharmacokinetics and pharmacodynamics. Project-based learning utilizing in silico molecular docking simulations is a primary method to help students actively learn the concept and the application of the SAR in medicinal chemistry. A drug target with a known three-dimensional structure is chosen and the amino acid residues at the binding site of the protein structure were analyzed. A lead compound was chosen and common modeling programs and lead modification strategies were employed to change the structure of the lead compound. In this presentation, rotigotine analogs and the structure-activity relationship of analog binding to the human dopamine D3 receptor was analyzed. A single substituent was modified several times resulting in a definitive relationship of functional groups and their corresponding binding affinity. It was found that hydrophobic substituents at C1 of rotigotine increased the binding affinity while electron donating and withdrawing substituents had little effect.1 This was due to the presence of hydrophobic amino acid residues at the binding pocket for the C1 substituent. When compared to the original rotigotine compound, it was found that replacing the original alcohol group on C1 to a hydrogen increased the binding affinity by ~300%, and by replacing the alcohol with a t-Bu an increase of ~1,800%; indicating a definitive relationship between the hydrophobicity of the functional group and the inhibition constant.3

Content Notes

Poster, Final Report Form

First Advisor

Myoung Lee



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