» Articles » PMID: 33445514

Solid-Phase Synthesis of Fluorescent Probes for Plasma Membrane Labelling

Overview
Journal Molecules
Publisher MDPI
Specialty Biology
Date 2021 Jan 15
PMID 33445514
Citations 1
Authors
Affiliations
Soon will be listed here.
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.

Citing Articles

Design, Synthesis, Application and Research Progress of Fluorescent Probes.

Jiang X, Yang R, Lei X, Xue S, Wang Z, Zhang J J Fluoresc. 2023; 34(3):965-975.

PMID: 37498366 DOI: 10.1007/s10895-023-03344-7.

References
1.
de Fatima Martins M, Honorio-Ferreira A, Martins P, Goncalves C . Presence of sialic acids in bronchioloalveolar cells and identification and quantification of N-acetylneuraminic and N-glycolylneuraminic acids in the lung. Acta Histochem. 2019; 121(6):712-717. DOI: 10.1016/j.acthis.2019.06.004. View

2.
Upadhyay A, Kandi R, Pulla Rao C . Wheat germ agglutinin modified magnetic iron oxide nanocomplex as a cell membrane specific receptor target material for killing breast cancer cells. J Mater Chem B. 2020; 6(36):5729-5737. DOI: 10.1039/c8tb01170b. View

3.
Sarin V, Kent S, Tam J, MERRIFIELD R . Quantitative monitoring of solid-phase peptide synthesis by the ninhydrin reaction. Anal Biochem. 1981; 117(1):147-57. DOI: 10.1016/0003-2697(81)90704-1. View

4.
Zhang X, Zhang J, Liu L . Fluorescence properties of twenty fluorescein derivatives: lifetime, quantum yield, absorption and emission spectra. J Fluoresc. 2014; 24(3):819-26. DOI: 10.1007/s10895-014-1356-5. View

5.
Xu S, Liu H, Yin X, Yuan L, Huan S, Zhang X . A cell membrane-anchored fluorescent probe for monitoring carbon monoxide release from living cells. Chem Sci. 2019; 10(1):320-325. PMC: 6333233. DOI: 10.1039/c8sc03584a. View