Issue 70, 2018, Issue in Progress
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RSC Advances

Interactions of a paracyclophane-based conjugated oligoelectrolyte with biological membranes†

Jakkarin Limwongyut, ORCID logo a   Yang Liu,c   Gayatri Shankar Chilambi,d   Thomas Seviour,d   Jamie Hinks,d   Yuguang Muc  and  Guillermo C. Bazan ORCID logo *abe  

* Corresponding authors

a Center for Polymers and Organic Solids, Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA, USA
E-mail: bazan@chem.ucsb.edu

b Materials Department, University of California, Santa Barbara, CA, USA

c School of Biological Sciences, Nanyang Technological University, Singapore

d Singapore Centre on Environmental Life Sciences Engineering (SCELSE), Nanyang Technological University, Singapore

e School of Chemical and Biomedical Engineering, Nanyang Technological University, 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.

Graphical abstract: Interactions of a paracyclophane-based conjugated oligoelectrolyte with biological membranes

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Article information

DOI
https://doi.org/10.1039/C8RA08069K
Article type
Paper
Submitted
28 Sep 2018
Accepted
14 Nov 2018
First published
29 Nov 2018
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2018,8, 39849-39853

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Interactions of a paracyclophane-based conjugated oligoelectrolyte with biological membranes

J. Limwongyut, Y. Liu, G. S. Chilambi, T. Seviour, J. Hinks, Y. Mu and G. C. Bazan, RSC Adv., 2018, 8, 39849 DOI: 10.1039/C8RA08069K

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