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Article

Solid-Phase Synthesis of Fluorescent Probes for Plasma Membrane Labelling

EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, Edinburgh EH8 9YL, UK
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Author to whom correspondence should be addressed.
Academic Editors: Péter Kele and Takuya Terai
Molecules 2021, 26(2), 354; https://doi.org/10.3390/molecules26020354
Received: 24 November 2020 / Revised: 7 January 2021 / Accepted: 8 January 2021 / Published: 12 January 2021
(This article belongs to the Special Issue Chemical Probe Synthesis and Applications in Chemical Biology)
The cellular plasma membrane plays a fundamental role in biological processes, including cell growth, signaling and transport. The labelling of the plasma membrane with targeted fluorescent probes offers a convenient and non-invasive way to image the morphological changes and dynamics of a membrane in real-time and, despite many examples of fluorescent plasma membrane probes, a “universal targeting/anchoring moiety” is still required. In this study, a small number of stearic acid-based probes labelled with 6-carboxyfluorescein was designed and fabricated via solid-phase synthesis in which variations in both charge and hydrophobicity were explored. To ease the synthesis process, a gram-scale synthesis of the Fmoc-Lys(6-carboxyfluoresein diacetate)-OH building block was developed, allowing the discovery of optimal probes that carried a positively charged amino group and a stearic acid tail that exhibited intense plasma membrane brightness and robust retention. View Full-Text
Keywords: solid-phase synthesis; cell membrane staining; fluorescent probe solid-phase synthesis; cell membrane staining; fluorescent probe
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MDPI and ACS Style

Zhang, S.; Lilienkampf, A.; Bradley, M. Solid-Phase Synthesis of Fluorescent Probes for Plasma Membrane Labelling. Molecules 2021, 26, 354. https://doi.org/10.3390/molecules26020354

AMA Style

Zhang S, Lilienkampf A, Bradley M. Solid-Phase Synthesis of Fluorescent Probes for Plasma Membrane Labelling. Molecules. 2021; 26(2):354. https://doi.org/10.3390/molecules26020354

Chicago/Turabian Style

Zhang, Shuo, Annamaria Lilienkampf, and Mark Bradley. 2021. "Solid-Phase Synthesis of Fluorescent Probes for Plasma Membrane Labelling" Molecules 26, no. 2: 354. https://doi.org/10.3390/molecules26020354

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