Live‐Cell Imaging of Sterculic Acid—a Naturally Occurring 1,2‐Cyclopropene Fatty Acid—by Bioorthogonal Reaction with Turn‐On Tetrazine‐Fluorophore Conjugates **

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Abstract: In the field of lipid research, bioorthogonal chemistry has made the study of lipid uptake and processing in living systems possible, whilst minimising biological properties arising from detectable pendant groups. To allow the study of unsaturated free fatty acids in live cells, we here report the use of sterculic acid, a 1,2‐cyclopropene‐containing oleic acid analogue, as a bioorthogonal probe. We show that this lipid can be readily taken up by dendritic cells without toxic side effects, and that it can subsequently be visualised using an inverse electron‐demand Diels–Alder reaction with quenched tetrazine‐fluorophore conjugates. In addition, the lipid can be used to identify changes in protein oleoylation after immune cell activation. Finally, this reaction can be integrated into a multiplexed bioorthogonal reaction workflow by combining it with two sequential copper‐catalysed Huisgen ligation reactions. This allows for the study of multiple biomolecules in the cell simultaneously by multimodal confocal imaging.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Live‐Cell Imaging of Sterculic Acid—a Naturally Occurring 1,2‐Cyclopropene Fatty Acid—by Bioorthogonal Reaction with Turn‐On Tetrazine‐Fluorophore Conjugates ** ; day:08 ; month:08 ; year:2022 ; extent:1
Angewandte Chemie / International edition. International edition ; (08.08.2022) (gesamt 1)

Creator: Bertheussen, Kristine
van de Plassche, Merel
Bakkum, Thomas
Gagestein, Berend
Ttofi, Iakovia
Sarris, Alexi J. C.
Overkleeft, Herman S.
van der Stelt, Mario
van Kasteren, Sander I.

DOI: 10.1002/anie.202207640

URN: urn:nbn:de:101:1-2022080915044943528704

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:38 AM CEST

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Associated

Bertheussen, Kristine
van de Plassche, Merel
Bakkum, Thomas
Gagestein, Berend
Ttofi, Iakovia
Sarris, Alexi J. C.
Overkleeft, Herman S.
van der Stelt, Mario
van Kasteren, Sander I.

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