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Issue 7, 2020
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Fine-tuning thio-pyridazinediones as SMDC scaffolds (with intracellular thiol release via a novel self-immolative linker)

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Abstract

Herein we report the synthesis of a library of thioalkyl- and thioaryl-pyridazinediones for thiol-based self-immolative release of cargo. A bisthioaryl-pyridazinedione is shown to be stable to serum protein albumin but unstable in intracellular conditions. A derivatised analogue underwent self-immolative degradation in cellular thiol conditions as evidenced by LC-MS/release of a turn-on fluorescence fluorophore; versatility of the thiol-pyridazinedione is demonstrated through synthesis of SMDC precursors that contain three different functional groups on the same central molecule.

Graphical abstract: Fine-tuning thio-pyridazinediones as SMDC scaffolds (with intracellular thiol release via a novel self-immolative linker)

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Supplementary files

Article information


Submitted
08 Nov 2019
Accepted
17 Dec 2019
First published
18 Dec 2019

This article is Open Access

Chem. Commun., 2020,56, 1125-1128
Article type
Communication

Fine-tuning thio-pyridazinediones as SMDC scaffolds (with intracellular thiol release via a novel self-immolative linker)

M. Fernández, A. Shamsabadi and V. Chudasama, Chem. Commun., 2020, 56, 1125
DOI: 10.1039/C9CC08744C

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