Substituent effects on the apparent pK of the reversible open-to-closed transition of sultams derived from sulforhodamine dyes

Corrie, John E. T.; Munasinghe, V. Ranjit N.

doi:10.1016/j.dyepig.2008.01.008

Cited by 3 publications

(1 citation statement)

References 14 publications

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“…The morpholino derivatives 18 and 18 D showed a substantial shift to lower values ( K L–Z < 0.2), due in part to the inductive electron-withdrawing properties of the oxygen atom. 29 Like the TMR scaffold, where the deuterated 1 D showed a higher Φ f value compared to the parent dye 1 (Φ f,D /Φ f,H = 1.22), other deuterated rhodamines showed an increase in Φ f , including dyes containing pyrrolidine ( 5 / 5 D ; Φ f,D /Φ f,H = 1.14), piperidine ( 17 / 17 D ; Φ f,D /Φ f,H = 1.50), and morpholine ( 18 / 18 D ; Φ f,D /Φ f,H = 1.18; Table 1 ). Notably, the azetidine- d 6 compound ( 6 D ) showed no improvement in Φ f over 6 ( Table 1 ).…”

Section: Resultsmentioning

confidence: 99%

A General Method to Improve Fluorophores Using Deuterated Auxochromes

Grimm

Xie

Casler

et al. 2021

JACS Au

167

121

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Fluorescence microscopy relies on dyes that absorb and then emit photons. In addition to fluorescence, fluorophores can undergo photochemical processes that decrease quantum yield or result in spectral shifts and irreversible photobleaching. Chemical strategies that suppress these undesirable pathways—thereby increasing the brightness and photostability of fluorophores—are crucial for advancing the frontier of bioimaging. Here, we describe a general method to improve small-molecule fluorophores by incorporating deuterium into the alkylamino auxochromes of rhodamines and other dyes. This strategy increases fluorescence quantum yield, inhibits photochemically induced spectral shifts, and slows irreparable photobleaching, yielding next-generation labels with improved performance in cellular imaging experiments.

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Section: Resultsmentioning

confidence: 99%

A General Method to Improve Fluorophores Using Deuterated Auxochromes

Grimm

Xie

Casler

et al. 2021

JACS Au

167

121

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Rapid Synthesis of Unsymmetrical Sulforhodamines Through Nucleophilic Amination of a Monobrominated Sulfoxanthene Dye

Chevalier

Renault

Boschetti³

et al. 2014

Eur J Org Chem

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A transition‐metal‐free method for the synthesis of N‐substituted unsymmetrical sulforhodamine fluorophores from an unusual monobrominated sulfoxanthene dye and primary or secondary amines by direct SNAr‐type reactions is presented. The simplicity and effectiveness of this “postamination” procedure were demonstrated through the rapid preparation of a library of multifunctional red‐emitting rhodamine analogues. Some of these analogues are equipped with a reactive handle and retain the two water‐solubilizing sulfonic acid moieties of the starting halogenated derivative; this makes them ideal candidates for biolabeling applications. The potential utility of this expeditious strategy to finely tune the photophysical (Stokes shift) and physicochemical properties (amphiphilic character and water solubility) of the sulforhodamine scaffold was also demonstrated through the appendage of a fluorescent amine to create a fluorescence resonance energy transfer (FRET) pair, a long‐chain amine, and tetraazamacrocycles derived from cyclen.

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A Palette of Bridged Bicycle-Strengthened Fluorophores

Zhang,

Wang

et al. 2024

Preprint

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Organic fluorophores are the keystone of advanced biological imaging. The vast chemical space of fluorophores has been extensively explored in seek of molecules with ideal properties. However, within the current molecular constraints, there appears to be a trade-off between high brightness, robust photostability, and tunable biochemical properties. Herein we report a general strategy to systematically boost the performance of donor-acceptor-type fluorophores by leveraging SO2 and O-substituted azabicyclo[3.2.1] octane auxochromes. These bicyclic heterocycles give rise to a collection of 'Bridged' dyes (BD) spanning the UV and visible range with top-notch quantum efficiencies, enhanced water solubility, and tunable cell-permeability. Notably, these azabicyclic fluorophores showed remarkable photostability than its tetramethyl or azatidine analogue, at the same time completely resistant to oxidative photobluing rendered by the Bredt's rule. Functionalized BD dyes are tailored for applications in single-molecule imaging, super-resolution imaging (STED and SIM) in fixed or live mammalian cells and plant cells, and live zebrafish imaging or chemigenetic voltage imaging. Synergizing with advanced imaging methods, the bridge bicycle dyes represent a versatile palette for biological researches.

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Substituent effects on the apparent pK of the reversible open-to-closed transition of sultams derived from sulforhodamine dyes

Cited by 3 publications

References 14 publications

A General Method to Improve Fluorophores Using Deuterated Auxochromes

A General Method to Improve Fluorophores Using Deuterated Auxochromes

Rapid Synthesis of Unsymmetrical Sulforhodamines Through Nucleophilic Amination of a Monobrominated Sulfoxanthene Dye

A Palette of Bridged Bicycle-Strengthened Fluorophores

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