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Metabolic labelling of DNA in cells by means of the “photoclick” reaction triggered by visible light

Rieger, Lisa 1; Pfeuffer, Bastian 1; Wagenknecht, Hans-Achim 1
1 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)

Abstract:

Two pyrene-tetrazole conjugates were synthesized as photoreactive chromophores that allow for the first time the combination of metabolic labelling of DNA in cells and subsequent bioorthogonal “photoclick” modification triggered by visible light. Two strained alkenes and three alkene-modified nucleosides were used as reactive counterparts and revealed no major differences in their “photoclick” reactivity. This is a significant advantage because it allows 5-vinyl-2′-deoxyuridine to be applied as the smallest possible alkene-modified nucleoside for metabolic labelling of DNA in cells. Both pyrene-tetrazole conjugates show fluorogenicity during the “photoclick” reactions, which is a second advantage for cellular imaging. Living HeLa cells were incubated with 5-vinyl-2′-deoxyuridine for 48 h to ensure one cell division. After fixation, the newly synthesized genomic DNA was successfully labelled by irradiation with visible light at 405 nm and 450 nm. This method is an attractive tool for the visualization of genomic DNA in cells with full spatiotemporal control by the use of visible light as a reaction trigger.


Verlagsausgabe §
DOI: 10.5445/IR/1000162654
Veröffentlicht am 29.09.2023
Originalveröffentlichung
DOI: 10.1039/D3CB00150D
Scopus
Zitationen: 3
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Zitationen: 4
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2023
Sprache Englisch
Identifikator ISSN: 2633-0679
KITopen-ID: 1000162654
Erschienen in RSC Chemical Biology
Verlag Royal Society of Chemistry (RSC)
Bemerkung zur Veröffentlichung Gefördert durch den KIT-Publikationsfonds
Vorab online veröffentlicht am 30.08.2023
Nachgewiesen in Scopus
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