Intramolekulare 1,3‐dipolare Cycloadditionen von Diarylnitriliminen aus 2,5‐Diaryltetrazolen

Meier, H.; Heimgartner, Heinz

doi:10.1002/hlca.19850680524

Cited by 47 publications

(23 citation statements)

References 78 publications

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“…This mechanism is consistent with a literature report in which quenching of the in situ generated diaryl nitrile imine by an excess carboxylic acid produced the N ′-acyl- N ′-aryl-benzohydrazide product in good yield. 24 It is conceivable that other nucleophiles such as Cys (Figure S9), 12 if they are in close proximity, may also participate in the cross-linking reactions with ACT for other targets. Since a recent report 25 suggested that the photoreactivity of diaryltetrazole can be harnessed for photo-cross-linking with target proteins through their acidic side chains, we compared the intrinsic reactivity of the carboxy-nitrile imine to that of the diaryl-nitrile imine toward glutamic acid (10 mM) in mixed PBS/acetonitrile (1:1) solution.…”

Section: Resultsmentioning

confidence: 99%

2-Aryl-5-carboxytetrazole as a New Photoaffinity Label for Drug Target Identification

et al. 2016

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Photoaffinity labels are powerful tools for dissecting ligand–protein interactions, and they have a broad utility in medicinal chemistry and drug discovery. Traditional photoaffinity labels work through nonspecific C–H/X–H bond insertion reactions with the protein of interest by the highly reactive photogenerated intermediate. Herein, we report a new photoaffinity label, 2-aryl-5-carboxytetrazole (ACT), that interacts with the target protein via a unique mechanism in which the photogenerated carboxynitrile imine reacts with a proximal nucleophile near the target active site. In two distinct case studies, we demonstrate that the attachment of ACT to a ligand does not significantly alter the binding affinity and specificity of the parent drug. Compared with diazirine and benzophenone, two commonly used photoaffinity labels, in two case studies ACT showed higher photo-cross-linking yields toward their protein targets in vitro based on mass spectrometry analysis. In the in situ target identification studies, ACT successfully captured the desired targets with an efficiency comparable to the diazirine. We expect that further development of this class of photoaffinity labels will lead to a broad range of applications across target identification, and validation and elucidation of the binding site in drug discovery.

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Section: Resultsmentioning

confidence: 99%

2-Aryl-5-carboxytetrazole as a New Photoaffinity Label for Drug Target Identification

et al. 2016

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“…Recently, Lin and co‐workers15 re‐discovered a light‐induced ligation methodology based on the nitrile imine‐mediated 1,3‐dipolar cycloaddition of a tetrazole and an ene (NITEC) which was first reported by Huisgen and Sustmann16 in 1967 and has been very rarely employed since 17. Starting with a tetrazole‐containing compound, the reaction is initiated by UV irradiation.…”

Section: Introductionmentioning

confidence: 99%

Photoclickable Surfaces for Profluorescent Covalent Polymer Coatings

Dietrich

Delaittre

Blinco

et al. 2011

Adv Funct Materials

144

114

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The nitrile imine‐mediated tetrazole‐ene cycloaddition reaction (NITEC) is introduced as a powerful and versatile conjugation tool to covalently ligate macromolecules onto variable (bio)surfaces. The NITEC approach is initiated by UV irradiation and proceeds rapidly at ambient temperature yielding a highly fluorescent linkage. Initially, the formation of block copolymers by the NITEC methodology is studied to evidence its efficacy as a macromolecular conjugation tool. The grafting of polymers onto inorganic (silicon) and bioorganic (cellulose) surfaces is subsequently carried out employing the optimized reaction conditions obtained from the macromolecular ligation experiments and evidenced by surface characterization techniques, including X‐ray photoelectron spectroscopy and FT‐IR microscopy. In addition, the patterned immobilization of variable polymer chains onto profluorescent cellulose is achieved through a simple masking process during the irradiation.

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“…The cycloaddition is faster in water thanks to the hydrophobic effect [19]. Despite these favorable features, tetrazoles were used mostly in the synthesis of heterocyclic compounds [20, 21] and in polymer and material sciences [22] for a long time.…”

Section: Photoinduced 13-dipolar Cycloaddition Reaction Between Tementioning

confidence: 99%

Photo-Triggered Click Chemistry for Biological Applications

2015

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In the last decade and a half, numerous bioorthogonal reactions have been developed with a goal to study biological processes in their native environment, i.e., in living cells and animals. Among them, the photo-triggered reactions offer several unique advantages including operational simplicity with the use of light rather than toxic metal catalysts and ligands, and exceptional spatiotemporal control through the application of an appropriate light source with pre-selected wavelength, light intensity and exposure time. While the photoinduced reactions have been studied extensively in materials research, e.g., on macromolecular surface, the adaptation of these reactions for chemical biology applications is still in its infancy. In this chapter, we review the recent efforts in the discovery and optimization the photo-triggered bioorthogonal reactions, with a focus on those that have shown broad utility in biological systems. We discuss in each cases the chemical and mechanistic background, the kinetics of the reactions and the biological applicability together with the limiting factors.

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Intramolekulare 1,3‐dipolare Cycloadditionen von Diarylnitriliminen aus 2,5‐Diaryltetrazolen

Cited by 47 publications

References 78 publications

2-Aryl-5-carboxytetrazole as a New Photoaffinity Label for Drug Target Identification

2-Aryl-5-carboxytetrazole as a New Photoaffinity Label for Drug Target Identification

Photoclickable Surfaces for Profluorescent Covalent Polymer Coatings

Photo-Triggered Click Chemistry for Biological Applications

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