Intramolecular Electrostatic Interactions Regulate Reactivity of Zwitterionic Functionalities in Amphiphilic Assemblies

Author:

Das Ritam1,Dutta Ranit1,Yi Jun1,Qiu Jingyi2,Krishna Jithu1,Tzafriri Gideon1,Lin Zhou1,Thayumanavan S.12ORCID

Affiliation:

1. Department of Chemistry University of Massachusetts Amherst Amherst MA 01003 United States

2. Department of Biomedical Engineering and Centre for Bioactive Delivery-Institute for Applied Life Sciences University of Massachusetts Amherst Amherst MA 01003 United States

Abstract

AbstractThe consequences of intramolecular ionic interactions in determining the reactivity of functional groups are of interest because they provide insights into how nature deploys seemingly reactive functionalities to be rather ubiquitous. Of specific interest are the quaternary ammonium ions in lipids. In this work, we investigate the effect of intramolecular electrostatic interactions in zwitterionic functionalities by judiciously incorporating them as leaving groups at the α‐position of α,β‐unsaturated ester‐based lipid head groups. We find that electrostatic stabilization indeed plays a critical role in both the reaction kinetics with nucleophiles and the thermodynamics of lipid formation. We further leverage these findings to fabricate both triggerable assembly and disassembly of liposomal supramolecular assemblies in the presence of nucleophiles.

Funder

Army Research Office

Publisher

Wiley

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