Modular Design and Scaffold-Synthesis of Multi-Functional Fluorophores for Targeted Cellular Imaging and Pyroptosis.

Autor: Zhang L; School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, 211816, Nanjing, China.; Physical and Synthetic Biology, Faculty of Biology, Ludwig-Maximilians-Universität München, Großhadernerstr. 2-4, 82152, Planegg-Martinsried, Germany.; Biophysical Chemistry, Faculty of Chemistry and Chemical Biology, Technische Universität Dortmund, Otto-Hahn-Str. 4a, 44227, Dortmund, Germany., Wang C; School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, 211816, Nanjing, China., Li Y; School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, 211816, Nanjing, China., Wang H; Digestive Endoscopy Department, The First Affiliated Hospital with Nanjing Medical University, 300 Guangzhou Road, 210029, Nanjing, China., Sun K; School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, 211816, Nanjing, China., Lu S; Physical and Synthetic Biology, Faculty of Biology, Ludwig-Maximilians-Universität München, Großhadernerstr. 2-4, 82152, Planegg-Martinsried, Germany.; Biophysical Chemistry, Faculty of Chemistry and Chemical Biology, Technische Universität Dortmund, Otto-Hahn-Str. 4a, 44227, Dortmund, Germany., Wang Y; School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, 211816, Nanjing, China., Jing S; School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, 211816, Nanjing, China., Cordes T; Physical and Synthetic Biology, Faculty of Biology, Ludwig-Maximilians-Universität München, Großhadernerstr. 2-4, 82152, Planegg-Martinsried, Germany.; Biophysical Chemistry, Faculty of Chemistry and Chemical Biology, Technische Universität Dortmund, Otto-Hahn-Str. 4a, 44227, Dortmund, Germany.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Nov 18, pp. e202415627. Date of Electronic Publication: 2024 Nov 18.
DOI: 10.1002/anie.202415627
Abstrakt: Fluorophores are essential tools for optical imaging and biomedical research. Their synthetic modification to incorporate new functions, however, remains a challenging task. Conventional strategies rely on linear synthesis in which a parent framework is gradually extended. We here designed and synthesized a versatile library of multi-functional fluorophores via a scaffold-based Ugi four-component reaction (U-4CR). The adaptability of the scaffold is achieved through modification of starting materials. This allows to use a small range of starting materials for the creation of fluorogenic probes that can detect reactive-oxygen species and where the localization into subcellular organelles or membranes can be controlled. We present reaction yields ranging from 60 % to 90 % and discovered that some compounds can even function as imaging and therapeutic agents via Fenton chemistry inducing pyroptosis in living cancer cells. Our study underlines the potential of scaffold-based synthesis for versatile creation of functional fluorophores and their applications.
(© 2024 The Author(s). Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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