Journal Article

PUBDB-2024-00333

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png A Tri PPP ro‐Nucleotide Reporter with Optimized Cell‐Permeable Dyes for Metabolic Labeling of Cellular and Viral DNA in Living Cells

Sterrenberg, V. T. ; Stalling, D.Extern* ; Knaack, J. I. H. ; Soh, T.Extern*CSSB* ; Bosse, J. B. (Corresponding author)Extern*CSSB* ; Meier, C. (Corresponding author)CSSB*

2023
Wiley-VCH Weinheim

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Please use a persistent id in citations: doi:10.1002/anie.202308271  doi:10.3204/PUBDB-2024-00333

Abstract: The metabolic labeling of nucleic acids in living cells is highly desirable to track the dynamics of nucleic acid metabolism in real-time and has the potential to provide novel insights into cellular biology as well as pathogen-host interactions. Catalyst-free inverse electron demand Diels–Alder reactions (iEDDA) with nucleosides carrying highly reactive moieties such as axial 2-trans-cyclooctene (2TCOa) would be an ideal tool to allow intracellular labeling of DNA. However, cellular kinase phosphorylation of the modified nucleosides is needed after cellular uptake as triphosphates are not membrane permeable. Unfortunately, the narrow substrate window of most endogenous kinases limits the use of highly reactive moieties. Here, we apply our TriPPPro (triphosphate pronucleotide) approach to directly deliver a highly reactive 2TCOa-modified 2′-deoxycytidine triphosphate reporter into living cells. We show that this nucleoside triphosphate is metabolically incorporated into de novo synthesized cellular and viral DNA and can be labeled with highly reactive and cell-permeable fluorescent dye-tetrazine conjugates via iEDDA to visualize DNA in living cells directly. Thus, we present the first comprehensive method for live-cell imaging of cellular and viral nucleic acids using a two-step labeling approach.

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Contributing Institute(s):

1. CSSB-MHH-JB (CSSB-MHH-JB)

Research Program(s):

1. 899 - ohne Topic (POF4-899) (POF4-899)
2. DFG project 390874280 - EXC 2155: RESIST - Resolving Infection Susceptibility (390874280) (390874280)

Experiment(s):

1. No specific instrument

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Database coverage:
; ; ; Chemical Reactions ; Clarivate Analytics Master Journal List ; Current Contents - Life Sciences ; Current Contents - Physical, Chemical and Earth Sciences ; DEAL Wiley ; Ebsco Academic Search ; Essential Science Indicators ; IF >= 15 ; Index Chemicus ; JCR ; Nationallizenz ; SCOPUS ; Science Citation Index Expanded ; Web of Science Core Collection

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