Literature DB >> 25022432

Photoclick chemistry: a fluorogenic light-triggered in vivo ligation reaction.

Carlo P Ramil1, Qing Lin2.   

Abstract

The ability to use chemical reactivity to monitor and control biomolecular processes with a spatial and temporal precision motivated the development of light-triggered in vivo chemistries. To this end, the photoinduced tetrazole-alkene cycloaddition, also termed 'photoclick chemistry' offers a very rapid chemical ligation platform for the manipulation of biomolecules and matrices in vivo. Here we outline the recent developments in the optimization of this chemistry, ranging from the search for substrates that offer two-photon photoactivatability, superior reaction kinetics, and/or genetic encodability, to the study of the reaction mechanism. The applications of the photoclick chemistry in protein labeling in vitro and in vivo as well as in preparing 'smart' hydrogels for 3D cell culture are highlighted.
Copyright © 2014 Elsevier Ltd. All rights reserved.

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Year:  2014        PMID: 25022432      PMCID: PMC4149939          DOI: 10.1016/j.cbpa.2014.05.024

Source DB:  PubMed          Journal:  Curr Opin Chem Biol        ISSN: 1367-5931            Impact factor:   8.822


  41 in total

1.  Analysis of the ultraviolet B response in primary human keratinocytes using oligonucleotide microarrays.

Authors:  Angela Sesto; Manuel Navarro; Frank Burslem; José L Jorcano
Journal:  Proc Natl Acad Sci U S A       Date:  2002-02-26       Impact factor: 11.205

2.  Design and synthesis of minimalist terminal alkyne-containing diazirine photo-crosslinkers and their incorporation into kinase inhibitors for cell- and tissue-based proteome profiling.

Authors:  Zhengqiu Li; Piliang Hao; Lin Li; Chelsea Y J Tan; Xiamin Cheng; Grace Y J Chen; Siu Kwan Sze; Han-Ming Shen; Shao Q Yao
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-10       Impact factor: 15.336

3.  Bioactive hydrogels: Lighting the way.

Authors:  Daniel L Alge; Kristi S Anseth
Journal:  Nat Mater       Date:  2013-11       Impact factor: 43.841

Review 4.  Photoinducible bioorthogonal chemistry: a spatiotemporally controllable tool to visualize and perturb proteins in live cells.

Authors:  Reyna K V Lim; Qing Lin
Journal:  Acc Chem Res       Date:  2011-05-20       Impact factor: 22.384

5.  No-wash protein labeling with designed fluorogenic probes and application to real-time pulse-chase analysis.

Authors:  Shin Mizukami; Shuji Watanabe; Yuri Akimoto; Kazuya Kikuchi
Journal:  J Am Chem Soc       Date:  2012-01-06       Impact factor: 15.419

6.  Live-cell imaging of cyclopropene tags with fluorogenic tetrazine cycloadditions.

Authors:  Jun Yang; Jolita Šečkutė; Christian M Cole; Neal K Devaraj
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-13       Impact factor: 15.336

7.  Functionalized cyclopropenes as bioorthogonal chemical reporters.

Authors:  David M Patterson; Lidia A Nazarova; Bryan Xie; David N Kamber; Jennifer A Prescher
Journal:  J Am Chem Soc       Date:  2012-11-01       Impact factor: 15.419

8.  Synthesis and evaluation of photoreactive tetrazole amino acids.

Authors:  Yizhong Wang; Qing Lin
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

9.  Fluorogenic, two-photon-triggered photoclick chemistry in live mammalian cells.

Authors:  Zhipeng Yu; Tymish Y Ohulchanskyy; Peng An; Paras N Prasad; Qing Lin
Journal:  J Am Chem Soc       Date:  2013-10-31       Impact factor: 15.419

10.  Expanding the genetic code of an animal.

Authors:  Sebastian Greiss; Jason W Chin
Journal:  J Am Chem Soc       Date:  2011-08-22       Impact factor: 15.419

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  20 in total

1.  Fluorescent bioorthogonal labeling of class B GPCRs in live cells.

Authors:  Srikanth Kumar Gangam; Qing Lin
Journal:  Methods Enzymol       Date:  2020-06-15       Impact factor: 1.600

Review 2.  Covalent modification of biological targets with natural products through Paal-Knorr pyrrole formation.

Authors:  Alexander Kornienko; James J La Clair
Journal:  Nat Prod Rep       Date:  2017-08-30       Impact factor: 13.423

Review 3.  Photocrosslinking probes for capture of carbohydrate interactions.

Authors:  Han Wu; Jennifer Kohler
Journal:  Curr Opin Chem Biol       Date:  2019-11-06       Impact factor: 8.822

4.  A Method to Generate and Analyze Modified Myristoylated Proteins.

Authors:  Huanyao Gao; Wei Sun; Zhiquan Song; Yanbao Yu; Li Wang; Xian Chen; Qisheng Zhang
Journal:  Chembiochem       Date:  2017-01-03       Impact factor: 3.164

5.  Sterically Shielded, Stabilized Nitrile Imine for Rapid Bioorthogonal Protein Labeling in Live Cells.

Authors:  Peng An; Tracey M Lewandowski; Tuğçe G Erbay; Peng Liu; Qing Lin
Journal:  J Am Chem Soc       Date:  2018-04-02       Impact factor: 15.419

Review 6.  Lights on 2,5-diaryl tetrazoles: applications and limits of a versatile photoclick reaction.

Authors:  Valentina Pirota; Alessandra Benassi; Filippo Doria
Journal:  Photochem Photobiol Sci       Date:  2022-02-21       Impact factor: 4.328

7.  A photocaged, cyclopropene-containing analog of the amino acid neurotransmitter glutamate.

Authors:  Pratik Kumar; David Shukhman; Scott T Laughlin
Journal:  Tetrahedron Lett       Date:  2016-11-11       Impact factor: 2.415

8.  Rapid Bioorthogonal Chemistry Turn-on through Enzymatic or Long Wavelength Photocatalytic Activation of Tetrazine Ligation.

Authors:  Han Zhang; William S Trout; Shuang Liu; Gabriel A Andrade; Devin A Hudson; Samuel L Scinto; Kevin T Dicker; Yi Li; Nikifar Lazouski; Joel Rosenthal; Colin Thorpe; Xinqiao Jia; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2016-04-27       Impact factor: 15.419

Review 9.  Photo-controllable bioorthogonal chemistry for spatiotemporal control of bio-targets in living systems.

Authors:  Jinbo Li; Hao Kong; Chenghong Zhu; Yan Zhang
Journal:  Chem Sci       Date:  2020-03-10       Impact factor: 9.825

Review 10.  Photo-affinity labeling (PAL) in chemical proteomics: a handy tool to investigate protein-protein interactions (PPIs).

Authors:  Dhiraj P Murale; Seong Cheol Hong; Md Mamunul Haque; Jun-Seok Lee
Journal:  Proteome Sci       Date:  2017-06-24       Impact factor: 2.480

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