Selective Mercuration of 2-Hydroxy Nile Red and Its Application towards Chemodosimetric Hg<sup>2+</sup>-selective Signaling

Lee, Haekyung; Choi, Myung Gil; Yu, Hyo-Yeon; Ahn, Sangdoo; Chang, Suk‐Kyu

doi:10.5012/bkcs.2010.31.12.3539

Cited by 8 publications

(4 citation statements)

References 37 publications

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“…Mercuration of a fluorescence dye can be used for designing a Hg 2+ -selective chemodosimeter (Scheme ). The 2-hydroxy derivative of Nile Red 75 exhibits a significant fluorescent change with Hg 2+ ions in aqueous environments by selective dimercuration at the 1,6-positions. This has been confirmed by 1 H NMR measurements.…”

Section: Luminescent Chemodosimeters For Metal Cationsmentioning

confidence: 99%

Luminescent Chemodosimeters for Bioimaging

et al. 2012

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Section: Luminescent Chemodosimeters For Metal Cationsmentioning

confidence: 99%

Luminescent Chemodosimeters for Bioimaging

et al. 2012

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“…Direct metalation of dyes is much rarer. The only examples of this in the literature were benzo[ a ]phenoxazines metalated directly with mercury ( 58 ) …”

Section: Synthesis Of Nile Blue and Nile Red Analoguesmentioning

confidence: 99%

Nile Red and Nile Blue: Applications and Syntheses of Structural Analogues

Martinez

Henary

2016

Chemistry A European J

182

157

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Nile red and Nile blue are highly fluorescent and photostable organic dyes from the benzo[a]phenoxazine family. They have been used as histological stains for imaging lysosomes and lipids in vitro. The dyes' high quantum yields and solvent-dependent optical properties make them ideal scaffolds for the development of pH probes and local polarity indicators. Reviews of the literature in this area are scarce with only one review ever published in 2006. It has been 10 years since and the field has evolved. This review aims to expand upon topics covered by the previous reviewers and to report on recent advances in the literature. As authors, we hope to convey a sense of scope and to spark renewed interest in this useful niche of dye chemistry.

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“…Other solvents were purchased from Biosolve except the deuterated solvents, which were purchased from Cambridge Isotopes Laboratories. 2-Hydroxy Nile red, 55 Nile redalkyne, 56 BTA-NH 2 , and BTA-N 3 were prepared following literature procedures. 27 Synthesis of Nile Red-NH 2 .…”

Section: ■ Introductionmentioning

confidence: 99%

Elucidating the Stability of Single-Chain Polymeric Nanoparticles in Biological Media and Living Cells

2021

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The controlled folding of synthetic polymer chains into single-chain polymeric nanoparticles (SCPNs) of defined size and shape in water is a viable way to create compartmentalized, nanometer-sized structures for a range of biological applications. Understanding the relationship between the polymer’s microstructure and the stability of folded structures is crucial to achieving desired applications. Here, we introduce the solvatochromic dye Nile red into SCPNs and apply a combination of spectroscopic and microscopic techniques to relate polymer microstructure to nanoparticle stability in complex biological media and cellular environments. Our experimental data show that the polymer’s microstructure has little effect on the stability of SCPNs in biological media and cytoplasm of living cells, but only SCPNs comprising supramolecular benzene-1,3,5-tricarboxamide (BTA) motifs showed good stability in lysosomes. The results indicate that the polymer’s microstructure is vital to ensure nanoparticle stability in highly competitive environments: both hydrophobic collapse and a structured interior are required. Our study provides an accessible way of probing the stability of SCPNs in cellular environments and paves the way for designing highly stable SCPNs for efficient bio-orthogonal catalysis and sensing applications.

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Selective Mercuration of 2-Hydroxy Nile Red and Its Application towards Chemodosimetric Hg²⁺-selective Signaling

Cited by 8 publications

References 37 publications

Luminescent Chemodosimeters for Bioimaging

Luminescent Chemodosimeters for Bioimaging

Nile Red and Nile Blue: Applications and Syntheses of Structural Analogues

Elucidating the Stability of Single-Chain Polymeric Nanoparticles in Biological Media and Living Cells

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Selective Mercuration of 2-Hydroxy Nile Red and Its Application towards Chemodosimetric Hg2+-selective Signaling

Cited by 8 publications

References 37 publications

Luminescent Chemodosimeters for Bioimaging

Luminescent Chemodosimeters for Bioimaging

Nile Red and Nile Blue: Applications and Syntheses of Structural Analogues

Elucidating the Stability of Single-Chain Polymeric Nanoparticles in Biological Media and Living Cells

Contact Info

Product

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Selective Mercuration of 2-Hydroxy Nile Red and Its Application towards Chemodosimetric Hg²⁺-selective Signaling