Literature DB >> 27218228

New Red-Emitting Tetrazine-Phenoxazine Fluorogenic Labels for Live-Cell Intracellular Bioorthogonal Labeling Schemes.

Gergely Knorr1, Eszter Kozma1, András Herner1, Edward A Lemke2, Péter Kele3.   

Abstract

The synthesis of a set of tetrazine-bearing fluorogenic dyes suitable for intracellular labeling of proteins in live cells is presented. The red excitability and emission properties ensure minimal autofluorescence, while through-bond energy-transfer-based fluorogenicity reduces nonspecific background fluorescence of unreacted dyes. The tetrazine motif efficiently quenches fluorescence of the phenoxazine core, which can be selectively turned on chemically upon bioorthogonal inverse-electron-demand Diels-Alder reaction with proteins modified genetically with strained trans-cyclooctenes.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  dyes/pigments; energy transfer; fluorescent probes; imaging agents; proteins

Mesh：

Substances：

Year:  2016        PMID： 27218228     DOI： 10.1002/chem.201600590

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  17 in total

1.  Tetrazine Carbon Nanotubes for Pretargeted In Vivo "Click-to-Release" Bioorthogonal Tumour Imaging.

Authors:  He Li; João Conde; Ana Guerreiro; Gonçalo J L Bernardes
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-07       Impact factor: 15.336

2.  Developing bioorthogonal probes to span a spectrum of reactivities.

Authors:  Sean S Nguyen; Jennifer A Prescher
Journal:  Nat Rev Chem       Date:  2020-07-21       Impact factor: 34.035

3.  Optimizing the Genetic Incorporation of Chemical Probes into GPCRs for Photo-crosslinking Mapping and Bioorthogonal Chemistry in Live Mammalian Cells.

Authors:  Robert Serfling; Lisa Seidel; Thore Böttke; Irene Coin
Journal:  J Vis Exp       Date:  2018-04-09       Impact factor: 1.355

4.  Two-Tier Screening Platform for Directed Evolution of Aminoacyl-tRNA Synthetases with Enhanced Stop Codon Suppression Efficiency.

Authors:  Andrew E Owens; Katherine T Grasso; Christine A Ziegler; Rudi Fasan
Journal:  Chembiochem       Date:  2017-05-16       Impact factor: 3.164

5.  Advances in Tetrazine Bioorthogonal Chemistry Driven by the Synthesis of Novel Tetrazines and Dienophiles.

Authors:  Haoxing Wu; Neal K Devaraj
Journal:  Acc Chem Res       Date:  2018-04-11       Impact factor: 22.384

6.  Computationally guided discovery of a reactive, hydrophilic trans-5-oxocene dienophile for bioorthogonal labeling.

Authors:  William D Lambert; Samuel L Scinto; Olga Dmitrenko; Samantha J Boyd; Ronald Magboo; Ryan A Mehl; Jason W Chin; Joseph M Fox; Stephen Wallace
Journal:  Org Biomol Chem       Date:  2017-08-09       Impact factor: 3.876

7.  Green- to far-red-emitting fluorogenic tetrazine probes - synthetic access and no-wash protein imaging inside living cells.

Authors:  Achim Wieczorek; Philipp Werther; Jonas Euchner; Richard Wombacher
Journal:  Chem Sci       Date:  2016-10-21       Impact factor: 9.825

Review 8.  Bio-orthogonal Fluorescent Labelling of Biopolymers through Inverse-Electron-Demand Diels-Alder Reactions.

Authors:  Eszter Kozma; Orsolya Demeter; Péter Kele
Journal:  Chembiochem       Date:  2017-02-01       Impact factor: 3.164

9.  Bioorthogonal Fluorescence Turn-On Labeling Based on Bicyclononyne-Tetrazine Cycloaddition Reactions that Form Pyridazine Products.

Authors:  Sebastian J Siegl; Juraj Galeta; Rastislav Dzijak; Martin Dračínský; Milan Vrabel
Journal:  Chempluschem       Date:  2019-05-14       Impact factor: 2.863

10.  Dermacozine N, the First Natural Linear Pentacyclic Oxazinophenazine with UV-Vis Absorption Maxima in the Near Infrared Region, along with Dermacozines O and P Isolated from the Mariana Trench Sediment Strain Dermacoccus abyssi MT 1.1T.

Authors:  Bertalan Juhasz; Dawrin Pech-Puch; Jioji N Tabudravu; Bastien Cautain; Fernando Reyes; Carlos Jiménez; Kwaku Kyeremeh; Marcel Jaspars
Journal:  Mar Drugs       Date:  2021-06-03       Impact factor: 5.118
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