Photocontrol of ion permeation in lipid vesicles with (bola)amphiphilic spirooxazines.
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.
Department of Chemistry and Biochemistry, Research and Innovation Centre, University of Regina, 3737 Wascana Parkway, Regina, SK S4S 0A2, Canada. scott.murphy.uregina@gmail.com.
Yamuna S
YS
Kandasamy
Department of Chemistry and Biochemistry, Research and Innovation Centre, University of Regina, 3737 Wascana Parkway, Regina, SK S4S 0A2, Canada. scott.murphy.uregina@gmail.com.
Jianxin
J
Cai
Department of Chemistry and Biochemistry, Research and Innovation Centre, University of Regina, 3737 Wascana Parkway, Regina, SK S4S 0A2, Canada. scott.murphy.uregina@gmail.com.
John G
JG
Ottaviano
Department of Chemistry and Biochemistry, Research and Innovation Centre, University of Regina, 3737 Wascana Parkway, Regina, SK S4S 0A2, Canada. scott.murphy.uregina@gmail.com.
Kelti A
KA
Smith
Department of Chemistry and Biochemistry, Research and Innovation Centre, University of Regina, 3737 Wascana Parkway, Regina, SK S4S 0A2, Canada. scott.murphy.uregina@gmail.com.
Ashley N
AN
Williams
Department of Chemistry and Biochemistry, Research and Innovation Centre, University of Regina, 3737 Wascana Parkway, Regina, SK S4S 0A2, Canada. scott.murphy.uregina@gmail.com.
Jarod
J
Moore
Department of Chemistry and Biochemistry, Research and Innovation Centre, University of Regina, 3737 Wascana Parkway, Regina, SK S4S 0A2, Canada. scott.murphy.uregina@gmail.com.
Kristen M
KM
Louis
Department of Chemistry and Biochemistry, Research and Innovation Centre, University of Regina, 3737 Wascana Parkway, Regina, SK S4S 0A2, Canada. scott.murphy.uregina@gmail.com.
Lindsay
L
Selzler
Department of Chemistry and Biochemistry, Research and Innovation Centre, University of Regina, 3737 Wascana Parkway, Regina, SK S4S 0A2, Canada. scott.murphy.uregina@gmail.com.
Alisha
A
Beler
Department of Chemistry and Biochemistry, Research and Innovation Centre, University of Regina, 3737 Wascana Parkway, Regina, SK S4S 0A2, Canada. scott.murphy.uregina@gmail.com.
Tobechi
T
Okwuonu
Department of Chemistry and Biochemistry, Research and Innovation Centre, University of Regina, 3737 Wascana Parkway, Regina, SK S4S 0A2, Canada. scott.murphy.uregina@gmail.com.
R Scott
RS
Murphy
D007477:Ions / Q000737:chemistry; D008051:Lipid Bilayers / Q000737:chemistry*; D008055:Lipids / Q000737:chemistry*; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis / Q000737:chemistry*; D055668:Photochemical Processes; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000737:chemistry*
D007477:Ions; D008051:Lipid Bilayers; D008055:Lipids; D010078:Oxazines; D013141:Spiro Compounds; D013501:Surface-Active Agents