Selective photosensitization through an AND logic response: optimization of the pH and glutathione response of activatable photosensitizers

Sundus Erbas-Cakmak; Fatma Pir Cakmak; Seda Demirel Topel; Taha Bilal Uyar; Engin U. Akkaya

doi:10.1039/C5CC01261A

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Selective photosensitization through an AND logic response: optimization of the pH and glutathione response of activatable photosensitizers†

Sundus Erbas-Cakmak,^a Fatma Pir Cakmak,^b Seda Demirel Topel,^c Taha Bilal Uyar^a and Engin U. Akkaya*^ab

Author affiliations

* Corresponding authors

^a UNAM-National Nanotechnology Research Center, Bilkent University, Ankara, Turkey
E-mail: eua@fen.bilkent.edu.tr

^b Department of Chemistry, Bilkent University, Ankara, Turkey

^c Akdeniz University, Department of Chemistry, Antalya, Turkey

Abstract

A series of pH and GSH responsive photosensitizers were designed and synthesized. pK_a values were optimized by adjusting the inductive contribution of substituents to reach a pH range (6.0–7.4) relevant to the tumour microenvironment. pH-Activatable behaviour and redox mediated release of the quencher from the PS by GSH allow the construction of an AND logic operator for selective photodynamic action in aqueous solutions.

This article is part of the themed collection: Molecular Logic Gates and Information Processing

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Article information

DOI: https://doi.org/10.1039/C5CC01261A
Article type: Communication
Submitted: 10 Feb 2015
Accepted: 22 Jun 2015
First published: 22 Jun 2015

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Chem. Commun., 2015,51, 12258-12261

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Selective photosensitization through an AND logic response: optimization of the pH and glutathione response of activatable photosensitizers

S. Erbas-Cakmak, F. P. Cakmak, S. D. Topel, T. B. Uyar and E. U. Akkaya, Chem. Commun., 2015, 51, 12258 DOI: 10.1039/C5CC01261A

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Chemical Communications

Selective photosensitization through an AND logic response: optimization of the pH and glutathione response of activatable photosensitizers†

Abstract

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Selective photosensitization through an AND logic response: optimization of the pH and glutathione response of activatable photosensitizers

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