Synthetic Host-Guest Assembly in Cells and Tissues: Fast, Stable, and Selective Bioorthogonal Imaging via Molecular Recognition.

Analytical Chemistry
Ranjan SasmalSarit S Agasti

Abstract

Bioorthogonal strategies are continuing to pave the way for new analytical tools in biology. Although a significant amount of progress has been made in developing covalent reaction based bioorthogonal strategies, balanced reactivity, and stability are often difficult to achieve from these systems. Alternatively, despite being kinetically beneficial, the development of noncovalent approaches that utilize fully synthetic and stable components remains challenging due to the lack of selectivity in conventional noncovalent interactions in the living cellular environment. Herein, we introduce a bioorthogonal assembly strategy based on a synthetic host-guest system featuring Cucurbit[7]uril (CB[7]) and adamantylamine (ADA). We demonstrate that highly selective and ultrastable host-guest interaction between CB[7] and ADA provides a noncovalent mechanism for assembling labeling agents, such as fluorophores and DNA, in cells and tissues for bioorthogonal imaging of molecular targets. Additionally, by combining with covalent reaction, we show that this CB[7]-ADA based noncovalent interaction enables simultaneous bioorthogonal labeling and multiplexed imaging in cells as well as tissue sections. Finally, we show that interaction between CB...Continue Reading

References

Jul 3, 2007·Nature Methods·Andreas HennigWerner M Nau
Aug 29, 2009·Angewandte Chemie·Ellen M Sletten, Carolyn R Bertozzi
Dec 22, 2009·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Pedro Montes-NavajasHermenegildo García
Dec 30, 2009·Angewandte Chemie·Hoang D NguyenLuc Brunsveld
May 14, 2010·PloS One·Gaya HettiarachchiVolker Briken
May 28, 2011·Journal of the American Chemical Society·Alberto Gomez-CasadoJurriaan Huskens
Sep 3, 2011·Angewandte Chemie·Sander S van BerkelJan C M van Hest
Oct 5, 2011·Journal of the American Chemical Society·Leigh A LogsdonAdam R Urbach
Nov 25, 2011·Angewandte Chemie·Sarit S AgastiRalph Weissleder
Jan 31, 2012·Journal of the American Chemical Society·Jason L SeitchikRyan A Mehl
Jun 30, 2012·Angewandte Chemie·Ghyslain BudinRalph Weissleder
Oct 18, 2012·Journal of the American Chemical Society·David M PattersonJennifer A Prescher
Nov 6, 2012·Angewandte Chemie·Qi AnPascal Jonkheijm
Mar 29, 2013·Chemical Communications : Chem Comm·Pauline NeirynckLuc Brunsveld
Jul 26, 2013·Journal of the American Chemical Society·Leigh A Logsdon, Adam R Urbach
Sep 17, 2013·Angewandte Chemie·Liping CaoLyle Isaacs
Jan 21, 2014·ACS Chemical Biology·David M PattersonJennifer A Prescher
Mar 13, 2014·Angewandte Chemie·Carmen StoffelenJurriaan Huskens
May 31, 2014·Analytical Chemistry·Bo YanVincent M Rotello
Sep 23, 2014·Chemistry & Biology·Craig S McKay, M G Finn
Oct 16, 2014·Chemical Society Reviews·Khaleel I Assaf, Werner M Nau
Aug 14, 2015·Journal of the American Chemical Society·Heather E MurreyDouglas S Johnson
Aug 14, 2015·Bioconjugate Chemistry·Shrikrishnan SankaranPascal Jonkheijm
Nov 14, 2015·Journal of the American Chemical Society·Jong Wha LeeHugh I Kim
Nov 14, 2015·Chemical Reviews·Steven J BarrowOren A Scherman
Jun 18, 2016·Chemical Communications : Chem Comm·Wei LiAdam R Urbach
Sep 28, 2016·Journal of the American Chemical Society·Alexandra I LazarWerner M Nau
Nov 3, 2016·Journal of the American Chemical Society·Soumen K SamantaLyle Isaacs
Dec 22, 2016·Journal of the American Chemical Society·Andrew T BockusAdam R Urbach
Dec 28, 2016·Angewandte Chemie·Arcadio VázquezMilan Vrabel
Feb 2, 2017·Angewandte Chemie·James MurrayKimoon Kim
Feb 14, 2017·Chemical Society Reviews·Wenqi LiuLyle Isaacs
Apr 20, 2017·Journal of the American Chemical Society·Yulin TianQing Lin
May 19, 2017·Langmuir : the ACS Journal of Surfaces and Colloids·Shrikrishnan SankaranPascal Jonkheijm

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Citations

May 22, 2019·Organic & Biomolecular Chemistry·Weijian XueLyle Isaacs
Nov 19, 2019·Chemical Communications : Chem Comm·Ranjan SasmalSarit S Agasti
Oct 2, 2019·Frontiers in Chemistry·Debapratim DasWerner M Nau
Nov 19, 2020·Chemical Communications : Chem Comm·Ekaterina Y Chernikova, Daria V Berdnikova
Jun 1, 2019·Nature Reviews. Chemistry·Cynthia L Schreiber, Bradley D Smith
Oct 22, 2019·Journal of the American Chemical Society·Suman Kr GhoshKimoon Kim
Oct 21, 2021·ACS Chemical Biology·Anna Kataki-AnastasakouEllen M Sletten
Dec 1, 2021·Chemical Communications : Chem Comm·Madushani DharmarwardanaBradley D Smith

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Methods Mentioned

BETA
Structured Illumination Microscopy
fluorescence imaging
fluorescence microscopy
Fluorescence Activated Cell Shorting

Software Mentioned

Zen
Origin
ImageJ

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