Prodrug activation by 4,4'-bipyridine-mediated aromatic nitro reduction.
Journal
Nature communications
ISSN: 2041-1723
Titre abrégé: Nat Commun
Pays: England
ID NLM: 101528555
Informations de publication
Date de publication:
05 Oct 2024
05 Oct 2024
Historique:
received:
17
10
2023
accepted:
16
09
2024
medline:
6
10
2024
pubmed:
6
10
2024
entrez:
5
10
2024
Statut:
epublish
Résumé
Unleashing prodrugs through nitro-reduction is a promising strategy in cancer treatment. In this study, we present a unique bioorthogonal reaction for aromatic nitro reduction, mediated by 4,4'-bipyridine. The reaction is a rare example of organocatalyst-mediated bioorthogonal reaction. This bioorthogonal reaction demonstrates broad substrate scope and proceeds at low micromolar concentrations under biocompatible conditions. Our mechanistic study reveals that water is essential for the reaction to proceed at biorelevant substrate concentrations. We illustrate the utility of our reaction for controlled prodrug activation in mammalian cells, bacteria, and mouse models. Furthermore, a nitro-reduction-annulation cascade is developed for the synthesis of indole derivatives in living cells.
Identifiants
pubmed: 39368987
doi: 10.1038/s41467-024-52604-y
pii: 10.1038/s41467-024-52604-y
doi:
Substances chimiques
Prodrugs
0
4,4'-bipyridyl
X4O2OD61CB
Indoles
0
Pyridines
0
Nitro Compounds
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
8643Subventions
Organisme : Tsinghua University (THU)
ID : Dushi plan
Informations de copyright
© 2024. The Author(s).
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