Interactions of a paracyclophane-based conjugated oligoelectrolyte with biological membranes

Jakkarin Limwongyut; Yang Liu; Gayatri Shankar Chilambi; Thomas Seviour; Jamie Hinks; Yuguang Mu; Guillermo C Bazan

doi:10.1039/c8ra08069k

Interactions of a paracyclophane-based conjugated oligoelectrolyte with biological membranes

RSC Adv. 2018 Nov 29;8(70):39849-39853. doi: 10.1039/c8ra08069k. eCollection 2018 Nov 28.

Authors

Jakkarin Limwongyut¹, Yang Liu², Gayatri Shankar Chilambi³, Thomas Seviour³, Jamie Hinks³, Yuguang Mu², Guillermo C Bazan^{1

4

5}

Affiliations

¹ Center for Polymers and Organic Solids, Department of Chemistry and Biochemistry, University of California Santa Barbara CA 93106 USA bazan@chem.ucsb.edu.
² School of Biological Sciences, Nanyang Technological University 637551 Singapore.
³ Singapore Centre on Environmental Life Sciences Engineering (SCELSE), Nanyang Technological University 637551 Singapore.
⁴ Materials Department, University of California Santa Barbara CA 93106 USA.
⁵ School of Chemical and Biomedical Engineering, Nanyang Technological University 637551 Singapore.

Abstract

A three-dimensional conjugated oligoelectrolyte (COE) bearing a [2.2]paracyclophane unit (COE2-3-pCp) was synthesized. Its biological activity was determined both in vivo and in silico within the context of membrane perturbation and biocompatibility. Molecular dynamics simulations indicate that, compared to its linear analog (COE2-3C), COE2-3-pCp introduces more lipid disorder with higher extent of membrane thinning. COE2-3-pCp also exhibits a higher MIC towards E. coli K12 and yeast, while maintaining similar levels of membrane permeabilization. These findings suggest a new design of COEs as biocompatible cell permeabilizers.