Recent Advances in Chemiluminescent Enzyme Substrates

Akhavan-Tafti, Hashem; Silva, R. De; Thakur, Kshema; Eickholt, Robert A.; Chrovian, Christa C.; Lauwers, K.; Handley, R.; Siripurapu, Sarada; Endreszl, C.; Schaap, A. Paul

doi:10.1142/9789812811158_0053

Cited by 5 publications

(5 citation statements)

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“…Since the first reports on the development of boronate-based redox probes (Lo and Chu, 2003 ; Chang et al, 2004 ; Akhavan-Tafti et al, 2005 ), numerous authors have claimed the selectivity of this class of probes toward H 2 O 2 . However, analysis of the scientific literature on the chemical reactivity of arylboronates clearly points to the ability of other nucleophilic oxidants to convert them to corresponding phenols.…”

Section: Chemical Reactivity Of Boronates Toward Biological Oxidantsmentioning

confidence: 99%

Boronate-Based Probes for Biological Oxidants: A Novel Class of Molecular Tools for Redox Biology

et al. 2020

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Boronate-based molecular probes are emerging as one of the most effective tools for detection and quantitation of peroxynitrite and hydroperoxides. This review discusses the chemical reactivity of boronate compounds in the context of their use for detection of biological oxidants, and presents examples of the practical use of those probes in selected chemical, enzymatic, and biological systems. The particular reactivity of boronates toward nucleophilic oxidants makes them a distinct class of probes for redox biology studies. We focus on the recent progress in the design and application of boronate-based probes in redox studies and perspectives for further developments.

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Section: Chemical Reactivity Of Boronates Toward Biological Oxidantsmentioning

confidence: 99%

Boronate-Based Probes for Biological Oxidants: A Novel Class of Molecular Tools for Redox Biology

et al. 2020

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“…The amination of heteroaromatic halides containing two oxygen, nitrogen, or sulfur atoms, such as halo-thiazoles or -imidazoles, has been equally limited, − despite the importance of 2-amino-thiazoles and -imidazoles in pharmaceutical applications. , Most reported aminations of these heterocyclic halides have been conducted with BINAP as ligand; only one published 33 and one patented example conducted with palladium catalysts bearing sterically hindered monodentate ligands have been reported, and no studies that evaluate the scope of these aminations with these recently developed catalysts have been conducted. It is unclear if catalysts containing these ligands would show high activity for reactions of heteroaryl halides.…”

Section: Introductionmentioning

confidence: 99%

Scope and Mechanism of Palladium-Catalyzed Amination of Five-Membered Heterocyclic Halides

2003

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Detailed studies have been conducted to determine the activity of palladium catalysts for the amination of five-membered heterocyclic halides and to determine the factors that control the scope of this reaction. Palladium-catalyzed aminations of the electron-rich furanyl, thiophenyl, and indolyl halides and of the related 2-halogenated thiazoles, benzimidazole, and benzoxazole have been shown to occur with a subset of amines. Various combinations of palladium precursors and P(t)Bu(3) were tested as catalysts for reaction of 3-bromothiophene with N-methylaniline, and the fastest reactions occurred with the Pd(I) dimer, [PdBr(P(t)Bu(3))](2). The fastest aminations of thiazoles, benzimidazoles, and benzoxazoles occurred with the combination of palladium trifluoroacetate and P(t)Bu(3) as catalyst.

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“…This reagent, also known as Appel’s salt, has been previously used to synthesize both benzothiazole and benzimidazole scaffolds from anilines. 21 Appel’s salt condenses readily with arylamines, and the resulting iminodithiazoles can be easily opened with a variety of nucleophiles. 22 If the nucleophile is present on the aniline itself (as in the case of ortho -amino anilines), cyanobenzimidazole structures can be isolated directly.…”

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confidence: 99%

Expedient Synthesis of Electronically Modified Luciferins for Bioluminescence Imaging

et al. 2012

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Bioluminescence imaging with luciferase enzymes requires access to light-emitting, small molecule luciferins. Here, we describe a rapid method to synthesize d-luciferin, the substrate for firefly luciferase (Fluc), along with a novel set of electronically modified analogs. Our procedure utilizes a relatively rare, but synthetically useful dithiazolium reagent to generate heteroaromatic scaffolds in a divergent fashion. Two of the luciferin analogs produced with this approach emit light with Fluc in vitro and in live cells. Collectively, our work increases the number of substrates that can be used for bioluminescence imaging and provides a general strategy for synthesizing new collections of luciferins.

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Recent Advances in Chemiluminescent Enzyme Substrates

Cited by 5 publications

References 0 publications

Boronate-Based Probes for Biological Oxidants: A Novel Class of Molecular Tools for Redox Biology

Boronate-Based Probes for Biological Oxidants: A Novel Class of Molecular Tools for Redox Biology

Scope and Mechanism of Palladium-Catalyzed Amination of Five-Membered Heterocyclic Halides

Expedient Synthesis of Electronically Modified Luciferins for Bioluminescence Imaging

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