Intracellular modulation of excited-state dynamics in a chromophore dyad: differential enhancement of photocytotoxicity targeting cancer cells
Author
Kolemen, S.
Işık, M.
Kim, G. M.
Kim D.
Geng, H.
Buyuktemiz, M.
Karatas, T.
Zhang, X. F.
Dede, Y.
Yoon, J.
Akkaya, E. U.
Date
2015Source Title
Angewandte Chemie (International Edition)
Print ISSN
1433-7851
Electronic ISSN
1521-3773
Publisher
Wiley-VCH Verlag
Volume
54
Issue
18
Pages
5340 - 5344
Language
English
Type
ArticleItem Usage Stats
111
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175
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Abstract
The photosensitized generation of reactive oxygen
species, and particularly of singlet oxygen [O2(a1Dg)], is the
essence of photodynamic action exploited in photodynamic
therapy. The ability to switch singlet oxygen generation on/off
would be highly valuable, especially when it is linked to
a cancer-related cellular parameter. Building on recent findings
related to intersystem crossing efficiency, we designed a dimeric
BODIPY dye with reduced symmetry, which is ineffective as
a photosensitizer unless it is activated by a reaction with
intracellular glutathione (GSH). The reaction alters the
properties of both the ground and excited states, consequently
enabling the efficient generation of singlet oxygen. Remarkably, the designed photosensitizer can discriminate between
different concentrations of GSH in normal and cancer cells
and thus remains inefficient as a photosensitizer inside
a normal cell while being transformed into a lethal singlet
oxygen source in cancer cells. This is the first demonstration of
such a difference in the intracellular activity of a photosensitizer.