Analysis of pH-Induced Conformational Switching in Novel Amide-Based Amphiphiles Using Various 1H-NMR Spectroscopy Techniques

Authors

Carim van Beek, University of the PacificFollow
Marcos Beltran-Sanchez, University of the PacificFollow
Nataliya Samoshina, University of the PacificFollow
Vyacheslav V. Samoshin, vsamoshin@pacific.eduFollow

Poster Number

1a

Lead Author Affiliation

Organic Chemistry

Lead Author Status

Doctoral Student

Second Author Affiliation

Organic Chemistry

Second Author Status

Masters Student

Fourth Author Affiliation

Chemistry Department

Fourth Author Status

Faculty

Introduction/Abstract

A series of amide-based amphiphiles able to perform a conformational switch upon protonation (flipid) has been synthesized and studied using NMR spectroscopy

Purpose

These amphiphiles are to be incorporated as acid-sensitive components into a lipid bilayer, forming pH-responsive liposomes for targeted drug delivery. The acid-induced conformational flips disrupt the liposomal membrane and trigger a cargo release in the acidic environment.

Method

To determine the conformation and potential shift in conformation of the amide-based model, ¹H-NMR titration and ¹H-NMR Nuclear Overhauser Effect (NOE) techniques were employed

Results

Using one specific model, the shift between conformations was observed using ¹H-NMR titration techniques, yielding a successful proof-of-concept.

Significance

After establishing the proper composition of the flipids for efficient conformational switching, their potential to disrupt the the lipid bilayer in liposomal formulations will be evaluated. When successful, this can yield an efficient system for targeted drug delivery in response to a local lowered pH (e.g. inflammation or tumor site)

Location

DeRosa University Center

Format

Poster Presentation

Poster Session

Afternoon 1pm-3pm