Literature DB >> 20481508

Development of a bioorthogonal and highly efficient conjugation method for quantum dots using tetrazine-norbornene cycloaddition.

Hee-Sun Han1, Neal K Devaraj, Jungmin Lee, Scott A Hilderbrand, Ralph Weissleder, Moungi G Bawendi.   

Abstract

We present a bioorthogonal and modular conjugation method for efficient coupling of organic dyes and biomolecules to quantum dots (QDs) using a norbornene-tetrazine cycloaddition. The use of noncoordinating functional groups combined with the rapid rate of the cycloaddition leads to highly efficient conjugation. We have applied this method to the in situ targeting of norbornene-coated QDs to live cancer cells labeled with tetrazine-modified proteins.

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Year:  2010        PMID： 20481508      PMCID： PMC2892974          DOI： 10.1021/ja101677r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  11 in total

1.  Click Chemistry: Diverse Chemical Function from a Few Good Reactions.

Authors:  Hartmuth C. Kolb; M. G. Finn; K. Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2001-06-01       Impact factor: 15.336

Review 2.  Quantum dot bioconjugates for imaging, labelling and sensing.

Authors:  Igor L Medintz; H Tetsuo Uyeda; Ellen R Goldman; Hedi Mattoussi
Journal:  Nat Mater       Date:  2005-06       Impact factor: 43.841

3.  Compact biocompatible quantum dots via RAFT-mediated synthesis of imidazole-based random copolymer ligand.

Authors:  Wenhao Liu; Andrew B Greytak; Jungmin Lee; Cliff R Wong; Jongnam Park; Lisa F Marshall; Wen Jiang; Peter N Curtin; Alice Y Ting; Daniel G Nocera; Dai Fukumura; Rakesh K Jain; Moungi G Bawendi
Journal:  J Am Chem Soc       Date:  2010-01-20       Impact factor: 15.419

4.  InAs(ZnCdS) quantum dots optimized for biological imaging in the near-infrared.

Authors:  Peter M Allen; Wenhao Liu; Vikash P Chauhan; Jungmin Lee; Alice Y Ting; Dai Fukumura; Rakesh K Jain; Moungi G Bawendi
Journal:  J Am Chem Soc       Date:  2010-01-20       Impact factor: 15.419

5.  Tetrazine-based cycloadditions: application to pretargeted live cell imaging.

Authors:  Neal K Devaraj; Ralph Weissleder; Scott A Hilderbrand
Journal:  Bioconjug Chem       Date:  2008-12       Impact factor: 4.774

6.  Fast and sensitive pretargeted labeling of cancer cells through a tetrazine/trans-cyclooctene cycloaddition.

Authors:  Neal K Devaraj; Rabi Upadhyay; Jered B Haun; Scott A Hilderbrand; Ralph Weissleder
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

7.  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

8.  Copper-free click chemistry for dynamic in vivo imaging.

Authors:  Jeremy M Baskin; Jennifer A Prescher; Scott T Laughlin; Nicholas J Agard; Pamela V Chang; Isaac A Miller; Anderson Lo; Julian A Codelli; Carolyn R Bertozzi
Journal:  Proc Natl Acad Sci U S A       Date:  2007-10-17       Impact factor: 11.205

9.  How to very efficiently functionalize gold nanoparticles by "click" chemistry.

Authors:  Elodie Boisselier; Lionel Salmon; Jaime Ruiz; Didier Astruc
Journal:  Chem Commun (Camb)       Date:  2008-10-01       Impact factor: 6.222

10.  Second-generation difluorinated cyclooctynes for copper-free click chemistry.

Authors:  Julian A Codelli; Jeremy M Baskin; Nicholas J Agard; Carolyn R Bertozzi
Journal:  J Am Chem Soc       Date:  2008-08-05       Impact factor: 15.419
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  48 in total

1.  Synthesis and evaluation of a series of 1,2,4,5-tetrazines for bioorthogonal conjugation.

Authors:  Mark R Karver; Ralph Weissleder; Scott A Hilderbrand
Journal:  Bioconjug Chem       Date:  2011-10-24       Impact factor: 4.774

Review 2.  The surface science of nanocrystals.

Authors:  Michael A Boles; Daishun Ling; Taeghwan Hyeon; Dmitri V Talapin
Journal:  Nat Mater       Date:  2016-02       Impact factor: 43.841

3.  Synthesis of macrocyclic tetrazoles for rapid photoinduced bioorthogonal 1,3-dipolar cycloaddition reactions.

Authors:  Zhipeng Yu; Reyna K V Lim; Qing Lin
Journal:  Chemistry       Date:  2010-12-03       Impact factor: 5.236

4.  Ultrabright and bioorthogonal labeling of cellular targets using semiconducting polymer dots and click chemistry.

Authors:  Changfeng Wu; Yuhui Jin; Thomas Schneider; Daniel R Burnham; Polina B Smith; Daniel T Chiu
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-03       Impact factor: 15.336

5.  Covalent Protein Labeling and Improved Single-Molecule Optical Properties of Aqueous CdSe/CdS Quantum Dots.

Authors:  Sara M Wichner; Victor R Mann; Alexander S Powers; Maya A Segal; Mustafa Mir; Jigar N Bandaria; Mark A DeWitt; Xavier Darzacq; Ahmet Yildiz; Bruce E Cohen
Journal:  ACS Nano       Date:  2017-06-21       Impact factor: 15.881

6.  Orthogonal amplification of nanoparticles for improved diagnostic sensing.

Authors:  Vanessa M Peterson; Cesar M Castro; Hakho Lee; Ralph Weissleder
Journal:  ACS Nano       Date:  2012-03-23       Impact factor: 15.881

7.  3,6-Substituted-1,2,4,5-tetrazines: tuning reaction rates for staged labeling applications.

Authors:  Danzhu Wang; Weixuan Chen; Yueqin Zheng; Chaofeng Dai; Ke Wang; Bowen Ke; Binghe Wang
Journal:  Org Biomol Chem       Date:  2014-06-21       Impact factor: 3.876

8.  Spatial charge configuration regulates nanoparticle transport and binding behavior in vivo.

Authors:  Hee-Sun Han; John D Martin; Jungmin Lee; Daniel K Harris; Dai Fukumura; Rakesh K Jain; Moungi Bawendi
Journal:  Angew Chem Int Ed Engl       Date:  2012-12-17       Impact factor: 15.336

9.  Optimization of a Pretargeted Strategy for the PET Imaging of Colorectal Carcinoma via the Modulation of Radioligand Pharmacokinetics.

Authors:  Brian M Zeglis; Christian Brand; Dalya Abdel-Atti; Kathryn E Carnazza; Brendon E Cook; Sean Carlin; Thomas Reiner; Jason S Lewis
Journal:  Mol Pharm       Date:  2015-08-31       Impact factor: 4.939

10.  Monocyte-directed RNAi targeting CCR2 improves infarct healing in atherosclerosis-prone mice.

Authors:  Maulik D Majmudar; Edmund J Keliher; Timo Heidt; Florian Leuschner; Jessica Truelove; Brena F Sena; Rostic Gorbatov; Yoshiko Iwamoto; Partha Dutta; Gregory Wojtkiewicz; Gabriel Courties; Matt Sebas; Anna Borodovsky; Kevin Fitzgerald; Marc W Nolte; Gerhard Dickneite; John W Chen; Daniel G Anderson; Filip K Swirski; Ralph Weissleder; Matthias Nahrendorf
Journal:  Circulation       Date:  2013-04-24       Impact factor: 29.690
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