Olefin Metathesis-Based Fluorescent Probes for the Selective Detection of Ethylene in Live Cells

Ethylene is an important plant hormone that is involved in a variety of developmental processes including agriculturally important ripening of certain fruits. Owing to its significant roles, a number of approaches have previously been developed to detect ethylene via molecular interactions. However,...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2018-10, Vol.140 (41), p.13151-13155
Main Authors: Toussaint, Sacha N. W, Calkins, Ryan T, Lee, Sumin, Michel, Brian W
Format: Article
Language:English
Subjects:
Boron Compounds - chemical synthesis
Boron Compounds - chemistry
Chlamydomonas reinhardtii
Ethylenes - analysis
Ethylenes - chemistry
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
HEK293 Cells
Humans
Hydrolysis
Limit of Detection
Mangifera - chemistry
Microscopy, Confocal - methods
Microscopy, Fluorescence - methods
Musa - chemistry
Organometallic Compounds - chemical synthesis
Organometallic Compounds - chemistry
Organophosphorus Compounds - chemistry
Plant Growth Regulators - analysis
Plant Growth Regulators - chemistry
Ruthenium - chemistry
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Summary:Ethylene is an important plant hormone that is involved in a variety of developmental processes including agriculturally important ripening of certain fruits. Owing to its significant roles, a number of approaches have previously been developed to detect ethylene via molecular interactions. However, there are no current approaches for detection that are selective via a discrete homogeneous molecular interaction. Here we report two profluorescent chemodosimeters for the selective detection of the plant hormone ethylene. The approach consists of a BODIPY fluorophore with a pendant ruthenium recognition element based on a Hoveyda–Grubbs second generation catalysts. A marked increase in fluorescence is observed upon exposure to ethylene and selectivity is observed for ethylene over other alkenes, providing a unique approach toward ethylene detection. Imaging in live cells demonstrated that ethylene could be detected from multiple relevant sources.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.8b05191