Student Scholar Symposium Abstracts and Posters

Document Type


Publication Date

Spring 5-2021

Faculty Advisor(s)

Dr. Matthew Gartner


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.


Presented at the virtual Spring 2021 Student Scholar Symposium at Chapman University.


-Opioids are important pain-relieving drugs but also carry a risk of harmful side effects.

-Decreasing the pKa of the opioid amine group promotes selective binding in inflamed tissue.
-Fluorinated morphine derivatives are calculated to have lower pKa’s for pH -specific binding.