An Octupolar Donor-Acceptor Dye Exploiting Aggregation-Induced Intersystem Crossing for Efficient ROS Generation

Abstract

Photodynamic therapy (PDT) requires photosensitizers (PSs) that efficiently generate reactive oxygen species (ROS) or otherwise induce cell damage, even under the hypoxic conditions typical of solid tumor environments. Here, we report a heavy-atom-free octupolar donor-acceptor dye, 3CN, designed with a triphenylamine core and three cyanovinylbenzothiazole acceptors. This dye harnesses aggregation-induced intersystem crossing (AI-ISC) to promote efficient triplet state population. In aqueous solutions, 3CN spontaneously self-assembles into stable nanoaggregates (3CNAgg ) that exhibit excellent colloidal stability and prolonged triplet-state lifetimes. These aggregates demonstrate superior Type I photosensitization capabilities, generating the superoxide anion radical (O2•-) with significantly greater efficiency under white light irradiation than the reference PS, rose bengal. In encapsulated formulation, 3CNEn , exhibits remarkable therapeutic efficacy with IC50 values of 8.6 μM against triple-negative human breast cancer cells (MDA-MB-231), while maintaining potent photocytotoxicity even under severely hypoxic conditions (1% O2). In vivo studies using mouse models bearing MDA-MB-231 tumors demonstrate 100% inhibition of tumor growth with minimal dark cytotoxicity and inherent tumor-targeting properties.

Supplementary files

Article information

Article type
Paper
Submitted
25 Aug 2025
Accepted
26 Sep 2025
First published
29 Sep 2025

J. Mater. Chem. B, 2025, Accepted Manuscript

An Octupolar Donor-Acceptor Dye Exploiting Aggregation-Induced Intersystem Crossing for Efficient ROS Generation

D. Kang, Y. Luo, T. Kim, J. Oh, J. Bae and Y. Kim, J. Mater. Chem. B, 2025, Accepted Manuscript , DOI: 10.1039/D5TB01914A

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