Diketopyrrolopyrrole-based fluorescent probe for endogenous bisulfite detection and bisulfite triggered phototoxicity specific in liver cancer cells

Jian Wang; Weibo Xu; Yu Wang; Jianli Hua

doi:10.1016/j.saa.2021.120098

Diketopyrrolopyrrole-based fluorescent probe for endogenous bisulfite detection and bisulfite triggered phototoxicity specific in liver cancer cells

Spectrochim Acta A Mol Biomol Spectrosc. 2021 Dec 5:262:120098. doi: 10.1016/j.saa.2021.120098. Epub 2021 Jun 29.

Authors

Jian Wang¹, Weibo Xu², Yu Wang³, Jianli Hua⁴

Affiliations

¹ The Key Laboratory of Resource Chemistry of Ministry of Education, College of Chemistry and Materials Science, Shanghai Normal University, 100 Guilin Rd., Shanghai 200234, PR China; Key Laboratory for Advanced Materials, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 200237 Shanghai, PR China.
² Department of Oncology, Shanghai Medical College, Fudan University, Shanghai 200032, PR China; Department of Head and Neck Surgery, Fudan University Shanghai Cancer Center, Shanghai 200032, PR China.
³ Department of Oncology, Shanghai Medical College, Fudan University, Shanghai 200032, PR China; Department of Head and Neck Surgery, Fudan University Shanghai Cancer Center, Shanghai 200032, PR China. Electronic address: [email protected].
⁴ Key Laboratory for Advanced Materials, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 200237 Shanghai, PR China. Electronic address: [email protected].

PMID: 34252742
DOI: 10.1016/j.saa.2021.120098

Abstract

As the main existing form of SO₂ derivatives, bisulfite showed closely relationship to many diseases. In this work, a new fluorescent probe (SDPP-DM) based on thienyl-substituted diketopyrrolopyrrole (SDPP) was designed and synthesized for the detection of endogenous bisulfite. The probe displayed obvious color changes from green to pink towards bisulfite due to the reduced conjugated length caused by the addition to the α,β-unsaturated double bond of its structure, and the change of the fluorescence intensity of SDPP-DM (I/I₀) was about 16 folds. In addition, SDPP-DM was prepared a test strip for bisulfite identified by naked eye through color and fluorescence changes. Besides, SDPP-DM was successfully applied to imaging and discriminating different endogenous bisulfite levels in normal and cancer cells of liver. More importantly, the ROS generation and cell viability tests showed the phototoxicity of SDPP-DM triggered by bisulfite, indicating the specific phototoxicity of SDPP-DM towards liver cancer cells than normal liver cells.

Keywords: Diketopyrrolopyrrole; Liver cancer cells; Phototoxicity; SO(2) derivatives; Test strip.

MeSH terms

Fluorescent Dyes*
Humans
Ketones
Liver Neoplasms*
Pyrroles
Sulfites / toxicity

Substances

Fluorescent Dyes
Ketones
Pyrroles
Sulfites
diketopyrrolopyrrole dye
hydrogen sulfite