Issue 1, 2016

Photocontrol of ion permeation in lipid vesicles with (bola)amphiphilic spirooxazines

Abstract

Three (bola)amphiphilic spirooxazines have been synthesized and their photochromism has been characterized. The large biphotochromic structure of 2 significantly affects its conformational flexibility and the rate constants for thermal ring closure are particularly dependent on the lipid phase state. Two comprehensive ion permeation studies were performed to examine the effect of spirooxazine inclusion and isomerization on membrane permeability. In all cases, the open-ring isomers of these spirooxazines are more disruptive in bilayer membranes than their closed-ring isomers. Further, the rate of ion permeation and net release are highly dependent on the lipid bilayer phase state and the relative position of the photochromic moiety in the bilayer membrane. Moreover, the difference in potassium ion permeability under UV and visible irradiation is more pronounced than previously reported photoresponsive membrane disruptors with reversible photocontrols.

Graphical abstract: Photocontrol of ion permeation in lipid vesicles with (bola)amphiphilic spirooxazines

Supplementary files

Article information

Article type
Paper
Submitted
25 Sep 2015
Accepted
22 Oct 2015
First published
22 Oct 2015

Org. Biomol. Chem., 2016,14, 296-308

Author version available

Photocontrol of ion permeation in lipid vesicles with (bola)amphiphilic spirooxazines

Y. S. Kandasamy, J. Cai, J. G. Ottaviano, K. A. Smith, A. N. Williams, J. Moore, K. M. Louis, L. Selzler, A. Beler, T. Okwuonu and R. S. Murphy, Org. Biomol. Chem., 2016, 14, 296 DOI: 10.1039/C5OB01993A

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