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primary topic: Systematic Tuning of Rhodamine Spirocyclization

Systematic Tuning of Rhodamine Spirocyclization
type: Article
abstract: Fluorescence microscopy is a powerful method to examine cellular structures and biological processes with high spatial and temporal resolution. The development of novel microscopy techniques and labeling systems has expanded the limits of cellular imaging. However, this progress also relies on the availability of suitable fluorescent probes, thereby creating a need for new synthetic strategies that enable systematic modification of fluorophores. Rhodamine derivatives are widely used fluorophores, which exist in an equilibrium between a non-fluorescent, cell-permeable spirocyclic form and a fluorescent zwitterion. This spirocyclization equilibrium affects crucial properties of rhodamines regarding their applicability in cellular imaging, including fluorogenicity, cell-permeability and blinking behavior. Strategies that provide control over this equilibrium therefore hold the potential to generate suitable fluorescent probes for different microscopy techniques and labeling systems. This thesis describes the development and application of a synthetic strategy, which allows systematic tuning of the spirocyclization equilibrium of rhodamines. To this end, the ortho-carboxy group of various rhodamine derivatives was transformed into amides with different substituents. Introduction of substituted acyl benzenesulfonamides enables to control the spirocyclization equilibrium with unprecedented precision and to specifically optimize the fluorogenicity for HaloTag and SNAP-tag labeling. The resulting probes show suitable properties for live-cell, no-wash confocal and stimulated emission depletion (STED) microscopy. Replacing the ortho-carboxy group with more electron-rich amides strongly shifts the position of the equilibrium toward the spirocyclic state and results in spontaneous blinking. This led to the development of fluorophores for single molecule localization microscopy (SMLM). The generality of this synthetic strategy allowed conversion of various rhodamine-based scaffo…
date: 2022
author list: authors
type: EPrint
type: DoctoralThesisEPrint
is part of: repository
has document: Systematic Tuning of Rhodamine Spirocyclization (PDF)
has document: Systematic Tuning of Rhodamine Spirocyclization (Other)
subject: 540 Chemie

Systematic Tuning of Rhodamine Spirocyclization (PDF)
type: Document
has file: Thesis_Lardon_220227.pdf
has part: Thesis_Lardon_220227.pdf

Nicolas Marcel Lardon
type: Person
given name: Nicolas Marcel
family name: Lardon

Systematic Tuning of Rhodamine Spirocyclization (Other)
type: Document
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Systematic Tuning of Rhodamine Spirocyclization (Other)
type: Document
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Systematic Tuning of Rhodamine Spirocyclization (Other)
type: Document
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Systematic Tuning of Rhodamine Spirocyclization (Other)
type: Document
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Systematic Tuning of Rhodamine Spirocyclization (Other)
type: Document
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HTML Summary of #31526 Systematic Tuning of Rhodamine Spirocyclization
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primary topic: Systematic Tuning of Rhodamine Spirocyclization

540 Chemie
type: Concept
preferred label: 540 Chemistry and allied sciences @en