Literature DB >> 27397964

Photo-Triggered Click Chemistry for Biological Applications.

András Herner1, Qing Lin1.   

Abstract

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.

Entities:  

Keywords:  Azirine; Bioorthogonal reaction; Cyclopropenone; Hetero Diels–Alder reaction; Nitrile imine; Photo-triggered reaction; Photoclick; Tetrazole; o-Naphthoquinone methide; o-Quinodimethanes

Mesh:

Substances:

Year:  2015        PMID: 27397964      PMCID: PMC4935935          DOI: 10.1007/s41061-015-0002-2

Source DB:  PubMed          Journal:  Top Curr Chem (Cham)        ISSN: 2364-8961


  68 in total

1.  Bioactive hydrogels: Lighting the way.

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

2.  Selective and Reversible Photochemical Derivatization of Cysteine Residues in Peptides and Proteins.

Authors:  Selvanathan Arumugam; Jun Guo; Ngalle Eric Mbua; Frédéric Friscourt; Nannan Lin; Emmanuel Nekongo; Geert-Jan Boons; Vladimir V Popik
Journal:  Chem Sci       Date:  2014-04-01       Impact factor: 9.825

3.  A bioorthogonal chemistry strategy for probing protein lipidation in live cells.

Authors:  Wenjiao Song; Zhipeng Yu; Michael M Madden; Qing Lin
Journal:  Mol Biosyst       Date:  2010-04-30

4.  Differences in sensitivity between human, mouse and Chinese hamster cells to killing by monochromatic ultraviolet light.

Authors:  R L Wells; A Han
Journal:  Int J Radiat Biol Relat Stud Phys Chem Med       Date:  1985-01

5.  Azirine ligation: fast and selective protein conjugation via photoinduced azirine-alkene cycloaddition.

Authors:  Reyna K V Lim; Qing Lin
Journal:  Chem Commun (Camb)       Date:  2010-09-24       Impact factor: 6.222

6.  Rapid UV light-triggered macromolecular click conjugations via the use of o-quinodimethanes.

Authors:  Till Gruendling; Kim K Oehlenschlaeger; Elena Frick; Mathias Glassner; Christina Schmid; Christopher Barner-Kowollik
Journal:  Macromol Rapid Commun       Date:  2011-04-05       Impact factor: 5.734

7.  A bioorthogonal ligation enabled by click cycloaddition of o-quinolinone quinone methide and vinyl thioether.

Authors:  Qiang Li; Ting Dong; Xiaohui Liu; Xiaoguang Lei
Journal:  J Am Chem Soc       Date:  2013-03-25       Impact factor: 15.419

8.  Apolar peptide models for conformational heterogeneity, hydration, and packing of polypeptide helices: crystal structure of hepta- and octapeptides containing alpha-aminoisobutyric acid.

Authors:  I L Karle; J L Flippen-Anderson; K Uma; P Balaram
Journal:  Proteins       Date:  1990

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.  Sequential "click" - "photo-click" cross-linker for catalyst-free ligation of azide-tagged substrates.

Authors:  Selvanathan Arumugam; Vladimir V Popik
Journal:  J Org Chem       Date:  2014-02-28       Impact factor: 4.354

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  21 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

2.  Selective Modification of Tryptophan Residues in Peptides and Proteins Using a Biomimetic Electron Transfer Process.

Authors:  Samantha J Tower; Wesley J Hetcher; Tyler E Myers; Nicholas J Kuehl; Michael T Taylor
Journal:  J Am Chem Soc       Date:  2020-05-05       Impact factor: 15.419

Review 3.  Photopolymerizable Biomaterials and Light-Based 3D Printing Strategies for Biomedical Applications.

Authors:  Claire Yu; Jacob Schimelman; Pengrui Wang; Kathleen L Miller; Xuanyi Ma; Shangting You; Jiaao Guan; Bingjie Sun; Wei Zhu; Shaochen Chen
Journal:  Chem Rev       Date:  2020-04-23       Impact factor: 60.622

4.  Superfast Tetrazole-BCN Cycloaddition Reaction for Bioorthogonal Protein Labeling on Live Cells.

Authors:  Gangam Srikanth Kumar; Stefano Racioppi; Eva Zurek; Qing Lin
Journal:  J Am Chem Soc       Date:  2021-12-29       Impact factor: 15.419

Review 5.  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

6.  ImmunoPET: Concept, Design, and Applications.

Authors:  Weijun Wei; Zachary T Rosenkrans; Jianjun Liu; Gang Huang; Quan-Yong Luo; Weibo Cai
Journal:  Chem Rev       Date:  2020-03-23       Impact factor: 60.622

Review 7.  Spatiotemporal hydrogel biomaterials for regenerative medicine.

Authors:  Tobin E Brown; Kristi S Anseth
Journal:  Chem Soc Rev       Date:  2017-10-30       Impact factor: 54.564

Review 8.  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 9.  Light-Triggered Click Chemistry.

Authors:  Gangam Srikanth Kumar; Qing Lin
Journal:  Chem Rev       Date:  2020-10-26       Impact factor: 72.087

10.  Enabling In Vivo Photocatalytic Activation of Rapid Bioorthogonal Chemistry by Repurposing Silicon-Rhodamine Fluorophores as Cytocompatible Far-Red Photocatalysts.

Authors:  Chuanqi Wang; He Zhang; Tao Zhang; Xiaoyu Zou; Hui Wang; Julia E Rosenberger; Raghu Vannam; William S Trout; Jonathan B Grimm; Luke D Lavis; Colin Thorpe; Xinqiao Jia; Zibo Li; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2021-07-12       Impact factor: 16.383

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