Date Approved

2010

Degree Type

Open Access Senior Honors Thesis

Department

Chemistry

Abstract

Polyphenolic compounds containing two gallate groups have been shown to be effective inhibitors of Plasminogen Activator Inhibitor-1 (PAI-1). In this work we use Density Functional calculations to examine energetically-accessible configurations of two digallate compounds exhibiting disparate inhibitory activity toward PAI-1. In addition, we examine the partial charges of potentially acidic protons and the relative stability of the respective conjugate bases of a select group of PAI-1 inhibitors. This analysis was carried out to determine whether such characteristics can be used to distinguish between effective and less effective inhibitors. An examination of the stable configurations of CDE-008 and CDE-056 indicates that the range of distances between gallate rings for the poor inhibitor (CDE-008) does not overlap with the range of distances for the better inhibitor (CDE-056). However, no clear differences were observed in the partial charge distribution or relative stability of conjugate bases for the group of inhibitors examined here.

Included in

Chemistry Commons

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