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An Emerging Molecular Design Approach to Heavy-Atom-Free Photosensitizers for Enhanced Photodynamic Therapy under Hypoxia

Authors
Van-Nghia NguyenQi, SujieKim, SanginKwon, NahyunKim, GyoungmiYim, YubinPark, SungnamYoon, Juyoung
Issue Date
16-10월-2019
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.141, no.41, pp.16243 - 16248
Indexed
SCIE
SCOPUS
Journal Title
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume
141
Number
41
Start Page
16243
End Page
16248
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/62500
DOI
10.1021/jacs.9b09220
ISSN
0002-7863
Abstract
A novel strategy for designing highly efficient and activatable photosensitizers that can effectively generate reactive oxygen species (ROS) under both normoxia and hypoxia is proposed. Replacing both oxygen atoms in conventional naphthalimides (RNI-O) with sulfur atoms led to dramatic changes in the photophysical properties. The remarkable fluorescence quenching (Phi(PL) approximate to 0) of the resulting thionaphthalimides (RNI-S) suggested that the intersystem crossing from the singlet excited state to the reactive triplet state was enhanced by the sulfur substitution. Surprisingly, the singlet oxygen quantum yield of RNI-S gradually increased with increasing electron-donating ability of the 4-R substituents (MANI-S, Phi(Delta) approximate to 1.00, in air-saturated acetonitrile). Theoretical studies revealed that small singlet-triplet energy gaps and large spin-orbit coupling could be responsible for the efficient population of the triplet state of RNI-S. In particular, the ROS generation ability of MANI-S was suppressed under physiological conditions due to their self-assembly and was significantly recovered in cancer cells. More importantly, cellular experiments showed that MANI-S still produced a considerable amount of ROS even under severely hypoxic conditions (1% O-2) through a type-I mechanism.
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