Literature DB >> 20597509

Rapid covalent ligation of fluorescent peptides to water solubilized quantum dots.

Juan B Blanco-Canosa1, Igor L Medintz, Dorothy Farrell, Hedi Mattoussi, Philip E Dawson.   

Abstract

Water solubilized nanoparticles such as CdSe-ZnS core-shell nanocrystals (quantum dots, QDs) have great potential in bioimaging and sensing applications due to their excellent photophysical properties. However, the efficient modification of QDs with complex biomolecules represents a significant challenge. Here, we describe a straightforward arylhydrazone approach for the chemoselective covalent modification of QDs that is compatible with neutral pH and micromolar concentrations of the peptide target. The kinetics of covalent modification can be monitored spectroscopically at 354 nm in the presence of the QD and average peptide/QD ratios from 2:1 to 11:1 were achieved with excellent control over the desired valency. These results suggest that aniline catalyzed hydrazone ligation has the potential to provide a general method for the controlled assembly of a variety of nanoparticle-biomolecule hybrids.

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Year:  2010        PMID: 20597509      PMCID: PMC3182822          DOI: 10.1021/ja910988d

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


  39 in total

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Authors:  H Tetsuo Uyeda; Igor L Medintz; Jyoti K Jaiswal; Sanford M Simon; Hedi Mattoussi
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Review 2.  Quantum dots for live cells, in vivo imaging, and diagnostics.

Authors:  X Michalet; F F Pinaud; L A Bentolila; J M Tsay; S Doose; J J Li; G Sundaresan; A M Wu; S S Gambhir; S Weiss
Journal:  Science       Date:  2005-01-28       Impact factor: 47.728

3.  Proteolytic activity monitored by fluorescence resonance energy transfer through quantum-dot-peptide conjugates.

Authors:  Igor L Medintz; Aaron R Clapp; Florence M Brunel; Theresa Tiefenbrunn; H Tetsuo Uyeda; Eddie L Chang; Jeffrey R Deschamps; Philip E Dawson; Hedi Mattoussi
Journal:  Nat Mater       Date:  2006-06-25       Impact factor: 43.841

4.  Synthesis and application of quantum dots FRET-based protease sensors.

Authors:  Lifang Shi; Vania De Paoli; Nitsa Rosenzweig; Zeev Rosenzweig
Journal:  J Am Chem Soc       Date:  2006-08-16       Impact factor: 15.419

5.  Nucleophilic catalysis of oxime ligation.

Authors:  Anouk Dirksen; Tilman M Hackeng; Philip E Dawson
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-20       Impact factor: 15.336

6.  Kinetic parameters for small-molecule drug delivery by covalent cell surface targeting.

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7.  Quantum dot-fluorescent protein pairs as novel fluorescence resonance energy transfer probes.

Authors:  Allison M Dennis; Gang Bao
Journal:  Nano Lett       Date:  2008-04-16       Impact factor: 11.189

8.  Quantum dot bioconjugates for ultrasensitive nonisotopic detection.

Authors:  W C Chan; S Nie
Journal:  Science       Date:  1998-09-25       Impact factor: 47.728

9.  Poly(ethylene glycol) carbodiimide coupling reagents for the biological and chemical functionalization of water-soluble nanoparticles.

Authors:  Hongyan Shen; Ali M Jawaid; Preston T Snee
Journal:  ACS Nano       Date:  2009-04-28       Impact factor: 15.881

10.  Site-specific (18)F-labeling of the protein hormone leptin using a general two-step ligation procedure.

Authors:  Robert R Flavell; Paresh Kothari; Maya Bar-Dagan; Michael Synan; Shankar Vallabhajosula; Jeffrey M Friedman; Tom W Muir; Giovanni Ceccarini
Journal:  J Am Chem Soc       Date:  2008-06-21       Impact factor: 15.419

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  11 in total

Review 1.  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

2.  Thiol antioxidant-functionalized CdSe/ZnS quantum dots: synthesis, characterization, cytotoxicity.

Authors:  Hong Zheng; Luke J Mortensen; Lisa A DeLouise
Journal:  J Biomed Nanotechnol       Date:  2013-03       Impact factor: 4.099

3.  Aromatic aldehyde and hydrazine activated peptide coated quantum dots for easy bioconjugation and live cell imaging.

Authors:  Gopal Iyer; Fabien Pinaud; Jianmin Xu; Yuval Ebenstein; Jack Li; Jessica Chang; Maxime Dahan; Shimon Weiss
Journal:  Bioconjug Chem       Date:  2011-05-16       Impact factor: 4.774

4.  Selecting improved peptidyl motifs for cytosolic delivery of disparate protein and nanoparticle materials.

Authors:  Kelly Boeneman; James B Delehanty; Juan B Blanco-Canosa; Kimihiro Susumu; Michael H Stewart; Eunkeu Oh; Alan L Huston; Glyn Dawson; Sampat Ingale; Ryan Walters; Miriam Domowicz; Jeffrey R Deschamps; W Russ Algar; Stassi Dimaggio; Janet Manono; Christopher M Spillmann; Darren Thompson; Travis L Jennings; Philip E Dawson; Igor L Medintz
Journal:  ACS Nano       Date:  2013-05-28       Impact factor: 15.881

5.  3,4-Dihydroxyphenylalanine Peptides as Nonperturbative Quantum Dot Sensors of Aminopeptidase.

Authors:  Valle Palomo; Sebastián A Díaz; Michael H Stewart; Kimihiro Susumu; Igor L Medintz; Philip E Dawson
Journal:  ACS Nano       Date:  2016-05-27       Impact factor: 15.881

6.  Reversible control of nanoparticle functionalization and physicochemical properties by dynamic covalent exchange.

Authors:  Flavio della Sala; Euan R Kay
Journal:  Angew Chem Int Ed Engl       Date:  2015-03-27       Impact factor: 15.336

Review 7.  Protein-Templated Fragment Ligations-From Molecular Recognition to Drug Discovery.

Authors:  Mike Jaegle; Ee Lin Wong; Carolin Tauber; Eric Nawrotzky; Christoph Arkona; Jörg Rademann
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-31       Impact factor: 15.336

8.  Proteintemplat-gesteuerte Fragmentligationen - von der molekularen Erkennung zur Wirkstofffindung.

Authors:  Mike Jaegle; Ee Lin Wong; Carolin Tauber; Eric Nawrotzky; Christoph Arkona; Jörg Rademann
Journal:  Angew Chem Weinheim Bergstr Ger       Date:  2017-05-31

9.  Fine tuning of spatial arrangement of enzymes in a PCNA-mediated multienzyme complex using a rigid poly-L-proline linker.

Authors:  Tomoaki Haga; Hidehiko Hirakawa; Teruyuki Nagamune
Journal:  PLoS One       Date:  2013-09-05       Impact factor: 3.240

10.  Reversible Control of Nanoparticle Functionalization and Physicochemical Properties by Dynamic Covalent Exchange.

Authors:  Flavio Della Sala; Euan R Kay
Journal:  Angew Chem Weinheim Bergstr Ger       Date:  2015-01-14
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