Literature DB >> 33429851

Concise Synthesis of Functionalized Cyclobutene Analogues for Bioorthogonal Tetrazine Ligation.

Jiayu Sun1, Jie Li1, Hongbao Sun1, Chunling Li2,3, Haoxing Wu1.   

Abstract

Novel bioorthogonal tools enable the development of new biomedical applications. Here we report the concise synthesis of a series of aryl-functionalized cyclobutene analogues using commercially available starting materials. Our study demonstrates that cyclobutene acts as a small, strained dienophile to generate stable substrates suitable for bioorthogonal tetrazine ligation.

Entities:  

Keywords:  bioorthogonal chemistry; concise synthesis; functionalized cyclobutene analogues; tetrazine ligation

Mesh：

Substances：

Year:  2021        PMID： 33429851      PMCID： PMC7827859          DOI： 10.3390/molecules26020276

Source DB:  PubMed          Journal:  Molecules        ISSN： 1420-3049            Impact factor:   4.411


  32 in total

1.  Alkene-tetrazine ligation for imaging cellular DNA.

Authors:  Ulrike Rieder; Nathan W Luedtke
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-30       Impact factor: 15.336

2.  A General Strategy to Design Highly Fluorogenic Far-Red and Near-Infrared Tetrazine Bioorthogonal Probes.

Authors:  Wuyu Mao; Jie Tang; Liqun Dai; Xinyu He; Jie Li; Larry Cai; Ping Liao; Ruotian Jiang; Jingwei Zhou; Haoxing Wu
Journal:  Angew Chem Int Ed Engl       Date:  2020-12-01       Impact factor: 15.336

3.  Synthesis and reactivity comparisons of 1-methyl-3-substituted cyclopropene mini-tags for tetrazine bioorthogonal reactions.

Authors:  Jun Yang; Yong Liang; Jolita Šečkutė; K N Houk; Neal K Devaraj
Journal:  Chemistry       Date:  2014-02-24       Impact factor: 5.236

4.  Tetrazine-Mediated Bioorthogonal System for Prodrug Activation, Photothermal Therapy, and Optoacoustic Imaging.

Authors:  Xin Xie; Bowen Li; Jie Wang; Chenyue Zhan; Yong Huang; Fang Zeng; Shuizhu Wu
Journal:  ACS Appl Mater Interfaces       Date:  2019-10-31       Impact factor: 9.229

5.  Isomeric cyclopropenes exhibit unique bioorthogonal reactivities.

Authors:  David N Kamber; Lidia A Nazarova; Yong Liang; Steven A Lopez; David M Patterson; Hui-Wen Shih; K N Houk; Jennifer A Prescher
Journal:  J Am Chem Soc       Date:  2013-09-06       Impact factor: 15.419

6.  Acylazetine as a dienophile in bioorthogonal inverse electron-demand Diels-Alder ligation.

Authors:  Sander B Engelsma; Lianne I Willems; Claudia E van Paaschen; Sander I van Kasteren; Gijsbert A van der Marel; Herman S Overkleeft; Dmitri V Filippov
Journal:  Org Lett       Date:  2014-05-05       Impact factor: 6.005

7.  Triggered Drug Release from an Antibody-Drug Conjugate Using Fast "Click-to-Release" Chemistry in Mice.

Authors:  Raffaella Rossin; Sander M J van Duijnhoven; Wolter Ten Hoeve; Henk M Janssen; Laurens H J Kleijn; Freek J M Hoeben; Ron M Versteegen; Marc S Robillard
Journal:  Bioconjug Chem       Date:  2016-06-29       Impact factor: 4.774

8.  Rapid and efficient tetrazine-induced drug release from highly stable benzonorbornadiene derivatives.

Authors:  Minghao Xu; Julian Tu; Raphael M Franzini
Journal:  Chem Commun (Camb)       Date:  2017-06-06       Impact factor: 6.222

9.  Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity.

Authors:  Melissa L Blackman; Maksim Royzen; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2008-09-18       Impact factor: 15.419

Review 10.  The Future of Bioorthogonal Chemistry.

Authors:  Neal K Devaraj
Journal:  ACS Cent Sci       Date:  2018-07-23       Impact factor: 14.553
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