Issue 1, 2023

Solid-state emitting twisted π-conjugate as AIE-active DSE-gen: in vitro anticancer properties against FaDu and 4T1 with biocompatibility and bioimaging

Abstract

Dual-state emissive fluorogens (DSE-gens) are currently defining their importance as a transpiring tool in biological and biomedical applications. This work focuses on designing and synthesizing indole-anthracene-based solid-state emitting twisted π-conjugates using a metal-free protocol to achieve AIE-active DSE-gens, expanding their scope in biological applications. Special effort has been made to introduce proficient and photo/thermostable DSE-gens that inhibit cancer but not normal cells. Here, the lead DSE-gen initially detects cancer and normal cells by bioimaging; however, it could also confirm and distinguish cancer cells from normal cells by its abated fluorescence signal after killing cancer cells. In contrast, the fluorescence signals for a normal cell remain unscathed. Surprisingly, these molecules displayed decent anticancer properties against FaDu and 4T1 but not MCF-7 cell lines. From a series of newly designed indole-based molecules, we report one single 2,3,4-trimethoxybenzene-linked DSE-gen (the lead), exhibiting high ROS generation, less haemolysis, and less cytotoxicity than doxorubicin (DOX) for normal cells, crucial parameters for a biocompatible in vitro anticancer probe. Thus, we present a potentially applicable anticancer drug, offering a bioactive material with bioimaging efficacy and a way to detect dead cancer cells selectively. The primary mechanism behind the identified outcomes is deciphered with the support of experimental (steady-state and time-resolved fluorescence, biological assays, cellular uptake) and molecular docking studies.

Graphical abstract: Solid-state emitting twisted π-conjugate as AIE-active DSE-gen: in vitro anticancer properties against FaDu and 4T1 with biocompatibility and bioimaging

Supplementary files

Article information

Article type
Paper
Submitted
29 Sept. 2022
Accepted
25 Nov. 2022
First published
25 Nov. 2022

J. Mater. Chem. B, 2023,11, 188-203

Solid-state emitting twisted π-conjugate as AIE-active DSE-gen: in vitro anticancer properties against FaDu and 4T1 with biocompatibility and bioimaging

S. Bhuin, P. Sharma, P. Chakraborty, O. P. Kulkarni and M. Chakravarty, J. Mater. Chem. B, 2023, 11, 188 DOI: 10.1039/D2TB02078E

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