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Solid-Phase Synthesis of Fluorescent Probes for Plasma Membrane Labelling.

ABSTRACT: 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.

SUBMITTER: Zhang S

PROVIDER: S-EPMC7827822 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

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Solid-Phase Synthesis of Fluorescent Probes for Plasma Membrane Labelling.

Zhang Shuo S Lilienkampf Annamaria A Bradley Mark M

Molecules (Basel, Switzerland) 20210112 2

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 la ...[more]

PMID: 33445514

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