Conjugation of Bioactive Molecules to a Fluorescent Dithiomaleimide by Photoin­duced and BEt<sub>3</sub>‐Initiated Thio‐Click Reactions

Lázár, László; Nagy, Miklós; Borbás, Anikó; Herczegh, Pál; Zsuga, Miklós; Kéki, Sándor

doi:10.1002/ejoc.201501116

Cited by 6 publications

(2 citation statements)

References 32 publications

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“…[23] This method, which proceeds withouth eatingo rU Vactivation, was successfully used to link thiols on allyl glycosides as well as thiosugarst om aleimide. [24] Thus, thiol-ene reactions of diallylglycoluril were carried out with av ariety of thiols by using Et 3 B/ TBC (Table1,e ntries 1-7, method B). As indicated, all symmetric dithioether glycolurils 7a-g were isolated in moderate to good yields (entries1-7, 30-82 %, method B).…”

Section: Resultsmentioning

confidence: 99%

“…Then, we tested the hydrothiolation method, reported by the group of Renaud, using triethylborane (Et 3 B) as a radical initiator and 4‐ tert ‐butylcatechol (TBC) as a co‐reagent . This method, which proceeds without heating or UV activation, was successfully used to link thiols on allyl glycosides as well as thiosugars to maleimide . Thus, thiol–ene reactions of diallylglycoluril were carried out with a variety of thiols by using Et 3 B/TBC (Table , entries 1–7, method B).…”

Section: Resultsmentioning

confidence: 99%

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Functionalization of Bambusurils by a Thiol–Ene Click Reaction and a Facile Method for the Preparation of Anion‐Free Bambus[6]urils

Azazna

Lafosse

Rivollier

et al. 2018

Chemistry A European J

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Sulfide-functionalized bambus[4]urils ((RS) BU[4]) and bambus[6]urils ((RS) BU[6]) were synthesized through thiol-ene click coupling reactions (TEC) of allylbambus[n]urils. Thiosugars were grafted to BU[4] and BU[6]. Synthesis of BU[6] derivatives always requires the use of a template anion (iodide, chloride, or bromide), which is enclosed in the cavity of BU[6]. We show that this anion influences the reactivity of bambus[6]urils. An encapsulated iodide makes allyl functions of allyl BU[6] less reactive towards TEC and hydrogenation reactions in comparison to the corresponding chloride or bromide inclusion complexes. This is critical for the chemical reactivity of BU[6] and even more to determine their anion-binding properties. We report a new, facile and fast method using AgSbF to prepare anion-free BU[6]. NMR spectroscopic methods were used to estimate association constants of these new empty BU[6] with different anions. Quantum chemical calculations were employed to rationalize the observed results. These new functionalized bambusuril scaffolds in alternate conformations could find applications as multivalent binders.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Functionalization of Bambusurils by a Thiol–Ene Click Reaction and a Facile Method for the Preparation of Anion‐Free Bambus[6]urils

Azazna

Lafosse

Rivollier

et al. 2018

Chemistry A European J

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Thiomaleimide Functionalization for Selective Biological Fluorescence Detection of Peroxynitrite as Tested in HeLa and RAW 264.7 Cells

Yudhistira

Mulay

Lee

et al. 2017

Chemistry An Asian Journal

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The role of fluorescent molecules in diagnosis, treatment as well as in biomedical research has great current medicinal significance and is the focus of concentrated effort across the scientific research spectrum. Related research continues to reveal new practical sensing systems that bear enhanced features for interfacing of substituted molecules with biological systems. As part of an effort to better understand chalcogenide systems, a new dithiomaleimide BODIPY (BDP-NGM) probe has been designed, synthesized and characterized. The fluorescence of BDP-NGM was quenched by the incorporation of [3,4-bis(phenylthio)] on the maleimide-4-phenyl moiety which is, in turn, placed at the meso-position of the BODIPY system. The probe shows a turn-on fluorescence response upon reaction with ONOO ; mass spectral evidence reveals peaks in agreement with products involving oxidation of the sulfur groups to sulfone groups. An about 18.0-fold emission intensity enhancement was found. By comparison, the emission signal from another ROS/RNS, superoxide, gave a modest turn on signal (≈5.0-fold). The reaction is complete within 10 min, judging from the monitoring of the turn-on fluorescence process; the detection limit was found to be 0.4 μm. BDP-NGM can be used for the detection of ONOO under both acidic and basic conditions. Live cell imaging showed that the current probe can be used for the selective detection of ONOO in living systems.

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Promotion of a Reaction by Cooling: Stereoselective 1,2‐cis‐α‐Thioglycoconjugation by Thiol‐Ene Coupling at −80 °C

Eszenyi

Kelemen

Balogh

et al. 2018

Chemistry A European J

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The photoinitiated thiol-ene coupling reactions of 2-substituted glycals were studied as a generally applicable strategy for stereoselective 1,2-cis-α-thioconjugation. Although all glycals reacted with full α-selectivity, the efficacy of the reactions varied in a broad range depending on their configuration and glycals bearing axial acetoxy substituents reacted with very low efficacy at room temperature. The study revealed that the reaction progress could be promoted by cooling and inhibited by heating. At -80 °C, the equilibrium of the rapidly reversible addition of the thiyl radical to alkenes is shifted almost completely toward products, leading to efficient addition reactions. By exploiting this unique temperature effect a series of α-thio-l-fucosides, -d-galactosides, and d-GlcNAc derivatives were prepared with high efficacy and complete stereoselectivity.

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Conjugation of Bioactive Molecules to a Fluorescent Dithiomaleimide by Photoinduced and BEt₃‐Initiated Thio‐Click Reactions

Cited by 6 publications

References 32 publications

Functionalization of Bambusurils by a Thiol–Ene Click Reaction and a Facile Method for the Preparation of Anion‐Free Bambus[6]urils

Functionalization of Bambusurils by a Thiol–Ene Click Reaction and a Facile Method for the Preparation of Anion‐Free Bambus[6]urils

Thiomaleimide Functionalization for Selective Biological Fluorescence Detection of Peroxynitrite as Tested in HeLa and RAW 264.7 Cells

Promotion of a Reaction by Cooling: Stereoselective 1,2‐cis‐α‐Thioglycoconjugation by Thiol‐Ene Coupling at −80 °C

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Conjugation of Bioactive Molecules to a Fluorescent Dithiomaleimide by Photoin­duced and BEt3‐Initiated Thio‐Click Reactions

Cited by 6 publications

References 32 publications

Functionalization of Bambusurils by a Thiol–Ene Click Reaction and a Facile Method for the Preparation of Anion‐Free Bambus[6]urils

Functionalization of Bambusurils by a Thiol–Ene Click Reaction and a Facile Method for the Preparation of Anion‐Free Bambus[6]urils

Thiomaleimide Functionalization for Selective Biological Fluorescence Detection of Peroxynitrite as Tested in HeLa and RAW 264.7 Cells

Promotion of a Reaction by Cooling: Stereoselective 1,2‐cis‐α‐Thioglycoconjugation by Thiol‐Ene Coupling at −80 °C

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Conjugation of Bioactive Molecules to a Fluorescent Dithiomaleimide by Photoinduced and BEt₃‐Initiated Thio‐Click Reactions