Recyclable Cu(i)/melanin dots for cycloaddition, bioconjugation and cell labelling

Sun, Yao; Hong, Suhyun; Ma, Xiaowei; Cheng, Kai; Wang, Jing; Zhang, Zhe; Yang, Meng; Jiang, Yuxin; Hong, Xuechuan; Cheng, Zhen

doi:10.1039/c6sc01536k

Title: Recyclable Cu(i)/melanin dots for cycloaddition, bioconjugation and cell labelling

Abstract

We successfully transferred melanin into a novel catalytic platform. Ligand-free, water-soluble, recyclable and biocompatible Cu(i)-loaded melanin dots [Cu(i)/M-dots] was easily prepared and demonstrate excellent properties for classic CuAAC, bioconjugation and cell labelling.

Authors:

Sun, Yao ^[1]; Hong, Suhyun ^[2]; Ma, Xiaowei ^[2]; Cheng, Kai ^[2]; Wang, Jing ^[2]; Zhang, Zhe ^[2]; Yang, Meng ^[3]; Jiang, Yuxin ^[3]; Hong, Xuechuan ^[4]; Cheng, Zhen ^[2]

Stanford University, Stanford, CA (United States); Wuhan Univ. School of Pharmaceutical Sciences, Wuhan (China)
Stanford University, Stanford, CA (United States)
Chinese Academy of Medical Science, Beijing (China)
Wuhan Univ. School of Pharmaceutical Sciences, Wuhan (China)

Publication Date:: Fri May 20 00:00:00 EDT 2016

Research Org.:: Stanford University, Stanford, CA (United States). Molecular Imaging Program at Stanford (MIPS), Bio-X Program, Department of Radiology, Canary Center at Stanford for Cancer Early Detection

Sponsoring Org.:: USDOE Office of Science (SC), Biological and Environmental Research (BER)

OSTI Identifier:: 1437938

Grant/Contract Number:: SC0008397

Resource Type:: Accepted Manuscript

Journal Name:: Chemical Science

Additional Journal Information:: Journal Volume: 7; Journal Issue: 9; Journal ID: ISSN 2041-6520

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

Subject:: 59 BASIC BIOLOGICAL SCIENCES

Citation Formats


                    Sun, Yao, Hong, Suhyun, Ma, Xiaowei, Cheng, Kai, Wang, Jing, Zhang, Zhe, Yang, Meng, Jiang, Yuxin, Hong, Xuechuan, and Cheng, Zhen. Recyclable Cu(i)/melanin dots for cycloaddition, bioconjugation and cell labelling.  United States: N. p., 2016. 
Web.  doi:10.1039/c6sc01536k.

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                    Sun, Yao, Hong, Suhyun, Ma, Xiaowei, Cheng, Kai, Wang, Jing, Zhang, Zhe, Yang, Meng, Jiang, Yuxin, Hong, Xuechuan, & Cheng, Zhen. Recyclable Cu(i)/melanin dots for cycloaddition, bioconjugation and cell labelling.  United States.  https://doi.org/10.1039/c6sc01536k

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                    Sun, Yao, Hong, Suhyun, Ma, Xiaowei, Cheng, Kai, Wang, Jing, Zhang, Zhe, Yang, Meng, Jiang, Yuxin, Hong, Xuechuan, and Cheng, Zhen. Fri .  
"Recyclable Cu(i)/melanin dots for cycloaddition, bioconjugation and cell labelling".  United States.  https://doi.org/10.1039/c6sc01536k.  https://www.osti.gov/servlets/purl/1437938.

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@article{osti_1437938,

  title        = {Recyclable Cu(i)/melanin dots for cycloaddition, bioconjugation and cell labelling},

  author       = {Sun, Yao and Hong, Suhyun and Ma, Xiaowei and Cheng, Kai and Wang, Jing and Zhang, Zhe and Yang, Meng and Jiang, Yuxin and Hong, Xuechuan and Cheng, Zhen},

  abstractNote = {We successfully transferred melanin into a novel catalytic platform. Ligand-free, water-soluble, recyclable and biocompatible Cu(i)-loaded melanin dots [Cu(i)/M-dots] was easily prepared and demonstrate excellent properties for classic CuAAC, bioconjugation and cell labelling.},

  doi          = {10.1039/c6sc01536k},

  journal      = {Chemical Science},

  number       = 9,

  volume       = 7,

  place        = {United States},

  year         = {Fri May 20 00:00:00 EDT 2016},

  month        = {Fri May 20 00:00:00 EDT 2016}

}

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Title: Recyclable Cu(i)/melanin dots for cycloaddition, bioconjugation and cell labelling

Abstract

Citation Formats

Analysis and Optimization of Copper-Catalyzed Azideâ€“Alkyne Cycloaddition for Bioconjugation journal, December 2009

A Fluorogenic Probe for the Copper(I)-Catalyzed Azide−Alkyne Ligation Reaction: Modulation of the Fluorescence Emission via 3 (n,π*) − 1 (π,π*) Inversion journal, July 2004

Conformational Modulation of in Vitro Activity of Cyclic RGD Peptides via Aziridine Aldehyde-Driven Macrocyclization Chemistry journal, June 2012

In Vitro and In Vivo Near-Infrared Photothermal Therapy of Cancer Using Polypyrrole Organic Nanoparticles journal, August 2012

Discovery and Characterization of Catalysts for Azide−Alkyne Cycloaddition by Fluorescence Quenching journal, August 2004

Development and Bioorthogonal Activation of Palladium-Labile Prodrugs of Gemcitabine journal, June 2014

Tyrosinase as a multifunctional reporter gene for Photoacoustic/MRI/PET triple modality molecular imaging journal, March 2013

Engineering Melanin Nanoparticles as an Efficient Drug-Delivery System for Imaging-Guided Chemotherapy journal, July 2015

The physical and chemical properties of eumelanin journal, December 2006

Copper toxicity, oxidative stress, and antioxidant nutrients journal, July 2003

Self-assembly and characterization of small and monodisperse dye nanospheres in a protein cage journal, January 2014

Copper-Chelating Azides for Efficient Click Conjugation Reactions in Complex Media journal, April 2014

Fast, Cell-Compatible Click Chemistry with Copper-Chelating Azides for Biomolecular Labeling journal, May 2012

Strained Cyclooctyne as a Molecular Platform for Construction of Multimodal Imaging Probes journal, March 2015

Surpassing the Use of Copper in the Click Functionalization of Polymeric Nanostructures: A Strain-Promoted Approach journal, April 2009

Research Highlights journal, September 2011

High correlation between pentosidine protein crosslinks and pigmentation implicates ascorbate oxidation in human lens senescence and cataractogenesis. journal, November 1991

Transferring Biomarker into Molecular Probe: Melanin Nanoparticle as a Naturally Active Platform for Multimodality Imaging journal, October 2014

The Oxidative Damage of Plasmid DNA by Ascorbic Acid Derivativesin vitro: The First Research on the Relationship between the Structure of Ascorbic Acid and the Oxidative Damage of Plasmid DNA journal, September 2006

Engineering DNA aptamers for novel analytical and biomedical applications journal, January 2011

Labeling Live Cells by Copper-Catalyzed Alkyne−Azide Click Chemistry journal, October 2010

Melanin acts as a potent UVB photosensitizer to cause an atypical mode of cell death in murine skin journal, October 2004

Transition metal-mediated bioorthogonal protein chemistry in living cells journal, January 2014

Hybrid Cu x O/TiO 2 Nanocomposites As Risk-Reduction Materials in Indoor Environments journal, January 2012

Metal swap between Zn7-metallothionein-3 and amyloid-β–Cu protects against amyloid-β toxicity journal, May 2008

Hybrid Nanotrimers for Dual T 1 and T 2 -Weighted Magnetic Resonance Imaging journal, October 2014

In situ conversion of porphyrin microbubbles to nanoparticles for multimodality imaging journal, March 2015

Recent Advances on the Development of Pharmacotherapeutic Agents on the Basis of Human Serum Albumin journal, March 2015

Chemistry in living systems journal, June 2005

Peptidotriazoles on Solid Phase [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides journal, May 2002

Fast, Cell-Compatible Click Chemistry with Copper-Chelating Azides for Biomolecular Labeling journal, May 2012

Strained Cyclooctyne as a Molecular Platform for Construction of Multimodal Imaging Probes journal, March 2015

Research Highlights journal, February 2011

Metal swap between Zn7metallothionein–3 and amyloid–β–Cu protects against amyloid–β toxicity text, January 2008

A photo-responsive macroscopic switch constructed using a chiral azo-calix[4]arene functionalized silicon surface journal, January 2018

Facile Cu( ii )-mediated conjugation of thioesters and thioacids to peptides and proteins under mild conditions journal, January 2018

Multimodality imaging of naturally active melanin nanoparticles targeting somatostatin receptor subtype 2 in human small-cell lung cancer journal, January 2019

Mn-Loaded apolactoferrin dots for in vivo MRI and NIR-II cancer imaging journal, January 2019

Analysis and Optimization of Copper-Catalyzed Azideâ€“Alkyne Cycloaddition for Bioconjugation
journal, December 2009

A Fluorogenic Probe for the Copper(I)-Catalyzed Azide−Alkyne Ligation Reaction: Modulation of the Fluorescence Emission via ³ (n,π) − ¹ (π,π) Inversion
journal, July 2004

Conformational Modulation of in Vitro Activity of Cyclic RGD Peptides via Aziridine Aldehyde-Driven Macrocyclization Chemistry
journal, June 2012

In Vitro and In Vivo Near-Infrared Photothermal Therapy of Cancer Using Polypyrrole Organic Nanoparticles
journal, August 2012

Discovery and Characterization of Catalysts for Azide−Alkyne Cycloaddition by Fluorescence Quenching
journal, August 2004

Development and Bioorthogonal Activation of Palladium-Labile Prodrugs of Gemcitabine
journal, June 2014

Tyrosinase as a multifunctional reporter gene for Photoacoustic/MRI/PET triple modality molecular imaging
journal, March 2013

Engineering Melanin Nanoparticles as an Efficient Drug-Delivery System for Imaging-Guided Chemotherapy
journal, July 2015

The physical and chemical properties of eumelanin
journal, December 2006

Copper toxicity, oxidative stress, and antioxidant nutrients
journal, July 2003

Self-assembly and characterization of small and monodisperse dye nanospheres in a protein cage
journal, January 2014

Copper-Chelating Azides for Efficient Click Conjugation Reactions in Complex Media
journal, April 2014

Fast, Cell-Compatible Click Chemistry with Copper-Chelating Azides for Biomolecular Labeling
journal, May 2012

Strained Cyclooctyne as a Molecular Platform for Construction of Multimodal Imaging Probes
journal, March 2015

Surpassing the Use of Copper in the Click Functionalization of Polymeric Nanostructures: A Strain-Promoted Approach
journal, April 2009

Research Highlights
journal, September 2011

High correlation between pentosidine protein crosslinks and pigmentation implicates ascorbate oxidation in human lens senescence and cataractogenesis.
journal, November 1991

Transferring Biomarker into Molecular Probe: Melanin Nanoparticle as a Naturally Active Platform for Multimodality Imaging
journal, October 2014

The Oxidative Damage of Plasmid DNA by Ascorbic Acid Derivativesin vitro: The First Research on the Relationship between the Structure of Ascorbic Acid and the Oxidative Damage of Plasmid DNA
journal, September 2006

Engineering DNA aptamers for novel analytical and biomedical applications
journal, January 2011

Labeling Live Cells by Copper-Catalyzed Alkyne−Azide Click Chemistry
journal, October 2010

Melanin acts as a potent UVB photosensitizer to cause an atypical mode of cell death in murine skin
journal, October 2004

Transition metal-mediated bioorthogonal protein chemistry in living cells
journal, January 2014

Hybrid Cu _x O/TiO ₂ Nanocomposites As Risk-Reduction Materials in Indoor Environments
journal, January 2012

Metal swap between Zn7-metallothionein-3 and amyloid-β–Cu protects against amyloid-β toxicity
journal, May 2008

Hybrid Nanotrimers for Dual T ₁ and T ₂ -Weighted Magnetic Resonance Imaging
journal, October 2014

In situ conversion of porphyrin microbubbles to nanoparticles for multimodality imaging
journal, March 2015

Recent Advances on the Development of Pharmacotherapeutic Agents on the Basis of Human Serum Albumin
journal, March 2015

Chemistry in living systems
journal, June 2005

Peptidotriazoles on Solid Phase [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides
journal, May 2002

Fast, Cell-Compatible Click Chemistry with Copper-Chelating Azides for Biomolecular Labeling
journal, May 2012

Strained Cyclooctyne as a Molecular Platform for Construction of Multimodal Imaging Probes
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Research Highlights
journal, February 2011

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text, January 2008

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journal, January 2019

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journal, January 2019