Student Scholar Symposium Abstracts and Posters
Document Type
Poster
Publication Date
Spring 5-2021
Faculty Advisor(s)
Dr. Matthew Gartner
Abstract
Opioids such as morphine are important pain-relieving drugs but also carry a risk of harmful side effects including addiction. Morphine is active in both healthy and inflamed tissue, however, decreasing the pKa of the biochemically-active amine group can promote selective binding in the more acidic conditions of inflamed tissue and reduce harmful side effects associated with opioids. Herein, we explore the impact of fluorination on the pKa of fluoromorphine derivatives to identify which will bind selectively in inflamed tissue. Theoretical pKa values are determined at the M06-2X(SMD)/aug-cc-pVDZ level of theory to calculate the ΔGaq" role="presentation" style="box-sizing: border-box; margin: 0px; padding: 0px; display: inline-block; line-height: normal; font-size: 16.2px; word-spacing: normal; overflow-wrap: normal; white-space: nowrap; float: none; direction: ltr; max-width: none; max-height: none; min-width: 0px; min-height: 0px; border: 0px; position: relative;">ΔGaq values for the amine deprotonation reactions.
Recommended Citation
Alexander, Nayiri; Augenstein, Makena; Sorensen, Angelina; and Gartner, Matthew, "Computational Design of β-Fluorinated Morphine Derivatives for pH-specific Binding" (2021). Student Scholar Symposium Abstracts and Posters. 460.
https://digitalcommons.chapman.edu/cusrd_abstracts/460
Included in
Chemicals and Drugs Commons, Medicinal and Pharmaceutical Chemistry Commons, Pharmaceutics and Drug Design Commons
Comments
Presented at the virtual Spring 2021 Student Scholar Symposium at Chapman University.
Highlights:
-Opioids are important pain-relieving drugs but also carry a risk of harmful side effects.