Design of Environmentally Sensitive Fluorescent Nucleosides and their Applications

Bag, Subhendu Sekhar; Saito, Isao

doi:10.1002/9781119179320.ch7

Cited by 5 publications

(3 citation statements)

References 130 publications

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“…The fluorophore sensitivity to the environmental polarity in biological membranes can be related to the dipole moment of the molecule in their excited state when compared to the ground state. The phenomenon of solvatochromism is the ability for a solvent to lower the fluorophore excited state that can shift its emission maximum . Hence, solvatochromic fluorescent lipid probes have been used to explore the polarity of membranes .…”

Section: Strategies For Building Fluorescent Glycerophospholipidsmentioning

confidence: 99%

Emergent Glycerophospholipid Fluorescent Probes: Synthesis and Applications

et al. 2019

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Fluorescent labeling through bioconjugation is the preferred tool for the investigation of biological functions involving lipids, namely for clarifying metabolic pathways and molecular mechanisms of diseases. The lack of functionalized lipid probes with biological and physicochemical properties suitable for these studies is still a major limitation. Moreover, the synthesis of these probes is challenging and strongly dependent on the application envisioned. The objective of this Review is to highlight advances in the application of fluorescent glycerophospholipid probes through innovative approaches in the synthesis reported in the past decade. The reaction pathways, choice of fluorophore, and location of fluorophore in the glycerophospholipid structure are critically addressed. The relevance of these bioconjugates is exemplified with applications using advanced analysis by fluorescence enhancement or quenching to unravel biomembrane structure features and phospholipase activity. Finally, this Review reinforces the need for innovative and more efficient routes for the synthesis of tailored glycerophospholipids fluorescent conjugates.

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Section: Strategies For Building Fluorescent Glycerophospholipidsmentioning

confidence: 99%

Emergent Glycerophospholipid Fluorescent Probes: Synthesis and Applications

et al. 2019

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“…7,8 The synthetic design is even more challenging when optimal photophysical properties and/ or intramolecular charge transfer characteristics towards microenvironment sensitivity are needed for live-cell imaging. [9][10][11] Chemical modifications to generate FNAs normally involve decorating commercial pyrimidines and purines with bulky and highly conjugated groups at C-2 or C-8, respectively, through cross-coupling condensation reactions. 12 The main constraints of FNAs for efficient and environmentally safe syntheses include the use of costly precursors and hazardous metal catalysts.…”

Section: Introductionmentioning

confidence: 99%

2,4,5-Triaminopyrimidines as blue fluorescent probes for cell viability monitoring: synthesis, photophysical properties, and microscopy applications

Gonçalves,

Sousa

et al. 2024

Org. Biomol. Chem.

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“…As a part of our continuous research efforts in the design of solvofluorochromic molecules/biomolecular building blocks, , we thought that it would be worthwhile to design dual-emissive modified nucleosides. Based on our experience, literature reports, and wider applicability, we considered design of C-5-labeled uridines as model nucleoside probes useable for DNA analysis in the future. ,, However, there is no report wherein C5-position of 2′-deoxyuridine is linked by an electron-donor unit as a postsynthetically modifiable functional group which effectively can generate a modulated fluorescence property of a fluorophore if attached at the terminus or the terminal alkyne can be reacted with a fluorophoric azide functionality. Previously, we have shown the “installation/modulation of fluorescence response” of various small fluorescent molecules and an interesting dual-emission behavior from pyrene when attached to the N,N -dimethylanilino triazole donor unit .…”

Section: Introductionmentioning

confidence: 99%

Design of “Click” Fluorescent Labeled 2′-deoxyuridines via C5-[4-(2-Propynyl(methyl)amino)]phenyl Acetylene as a Universal Linker: Synthesis, Photophysical Properties, and Interaction with BSA

Bag

Gogoi

2018

J. Org. Chem.

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Microenvironment-sensitive fluorescent nucleosides present attractive advantages over single-emitting dyes for sensing inter-biomolecular interactions involving DNA. Herein, we report the rational design and synthesis of triazolyl push-pull fluorophore-labeled uridines via the intermediacy of C5-[4-(2-propynyl(methyl)amino)]phenyl acetylene as a universal linker. The synthesized nucleosides showed interesting solvatochromic characteristic and/or intramolecular charge transfer (ICT) features. A few of them also exhibited dual-emitting characteristics evidencing our designing concept. The HOMO-LUMO distribution showed that the emissive states of these nucleosides were characterized with more significant electron redistribution between the C5-[4-(2-propynyl(methyl)amino)]phenyl triazolyl donor moiety and the aromatic chromophores linked to it, leading to modulated emission property. The solvent polarity sensitivity of these nucleosides was also tested. The synthesized triazolyl benzonitrile (10C), naphthyl (10E), and pyrenyl (10G) nucleosides were found to exhibit interesting ICT and dual (LE/ICT) emission properties. The dual-emitting pyrenyl nucleoside maintained a good ratiometric response in the BSA protein microenvironment, enabling the switch-on ratiometric sensing of BSA as the only protein biomolecule. Thus, it is expected that the new fluorescent nucleoside analogues would be useful in designing DNA probes for nucleic acid analysis or studying DNA-protein interactions via a drastic change in fluorescence response due to a change in micropolarity.

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Design of Environmentally Sensitive Fluorescent Nucleosides and their Applications

Cited by 5 publications

References 130 publications

Emergent Glycerophospholipid Fluorescent Probes: Synthesis and Applications

Emergent Glycerophospholipid Fluorescent Probes: Synthesis and Applications

2,4,5-Triaminopyrimidines as blue fluorescent probes for cell viability monitoring: synthesis, photophysical properties, and microscopy applications

Design of “Click” Fluorescent Labeled 2′-deoxyuridines via C5-[4-(2-Propynyl(methyl)amino)]phenyl Acetylene as a Universal Linker: Synthesis, Photophysical Properties, and Interaction with BSA

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