Exploring the Condensation Reaction between Aromatic Nitriles and Amino Thiols To Optimize In Situ Nanoparticle Formation for the Imaging of Proteases and Glycosidases in Cells

被引：52

作者：

Chen, Zixin ^{[1
,2
]}

Chen, Min ^{[1
,2
]}

Cheng, Yunfeng ^{[1
,2
]}

Kowada, Toshiyuki ^{[3
]}

Xie, Jinghang ^{[1
,2
]}

Zheng, Xianchuang ^{[1
,2
]}

Rao, Jianghong ^{[1
,2
]}

机构：

[1] Stanford Univ, Sch Med, Mol Imaging Program Stanford, Dept Radiol, Stanford, CA 94305 USA

[2] Stanford Univ, Sch Med, Mol Imaging Program Stanford, Dept Chem, Stanford, CA 94305 USA

[3] Tohoku Univ, Inst Multidisciplinary Res Adv Mat, Aoba Ku, 2-1-1 Katahira, Sendai, Miyagi 9808577, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 08期

关键词：

bioorthogonal reactions; enzyme activity imaging; fluorescent probes; nanoparticles; self-assembly; AZIDE-ALKYNE CYCLOADDITION; PHOTOCLICK-CHEMISTRY; CLICK CHEMISTRY; COPPER-FREE; PROTEIN; LIGATION; HYDROGELS; F-18-C-SNAT; ACTIVATION; SURFACES;

D O I：

10.1002/anie.201913314

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The condensation reaction between 6-hydroxy-2-cyanobenzothiazole (CBT) and cysteine has been shown for various applications such as site-specific protein labelling and in vivo cancer imaging. This report further expands the substrate scope of this reaction by varying the substituents on aromatic nitriles and amino thiols and testing their reactivity and ability to form nanoparticles for cell imaging. The structure-activity relationship study leads to the identification of the minimum structural requirement for the macrocyclization and assembly process in forming nanoparticles. One of the scaffolds made of 2-pyrimidinecarbonitrile and cysteine joined by a benzyl linker was applied to design fluorescent probes for imaging caspase-3/7 and beta-galactosidase activity in live cells. These results demonstrate the generality of this system for imaging hydrolytic enzymes.

引用

页码：3272 / 3279

页数：8

共 70 条

[21] Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation [J].

Kiick, KL ;

Saxon, E ;

Tirrell, DA ;

Bertozzi, CR .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (01) :19-24

[22] Genetic Encoding of Bicyclononynes and trans-Cyclooctenes for Site-Specific Protein Labeling in Vitro and in Live Mammalian Cells via Rapid Fluorogenic Diels-Alder Reactions [J].

Lang, Kathrin ;

Davis, Lloyd ;

Wallace, Stephen ;

Mahesh, Mohan ;

Cox, Daniel J. ;

Blackman, Melissa L. ;

Fox, Joseph M. ;

Chin, Jason W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) :10317-10320

[23] Genetically encoded norbornene directs site-specific cellular protein labelling via a rapid bioorthogonal reaction [J].

Lang, Kathrin ;

Davis, Lloyd ;

Torres-Kolbus, Jessica ;

Chou, Chungjung ;

Deiters, Alexander ;

Chin, Jason W. .

NATURE CHEMISTRY, 2012, 4 (04) :298-304

[24] Visible Light-Initiated Bioorthogonal Photoclick Cycloaddition [J].

Li, Jinbo ;

Kong, Hao ;

Huang, Lei ;

Cheng, Bo ;

Qin, Ke ;

Zheng, Mengmeng ;

Yan, Zheng ;

Zhang, Yan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (44) :14542-14546

[25]

Liang G., 2011, ANGEW CHEM, V123, P6407

[26]

Liang G. L., 2011, ANGEW CHEM, V123, P2323

[27] Controlled Self-Assembling of Gadolinium Nanoparticles as Smart Molecular Magnetic Resonance Imaging Contrast Agents [J].

Liang, Gaolin ;

Ronald, John ;

Chen, Yuanxin ;

Ye, Deju ;

Pandit, Prachi ;

Ma, Man Lung ;

Rutt, Brian ;

Rao, Jianghong .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) :6283-6286

[28]

Liang GL, 2010, NAT CHEM, V2, P54, DOI [10.1038/nchem.480, 10.1038/NCHEM.480]

[29]

Liu S., 2015, ANGEW CHEM, V127, P3710

[30] Oligomeric Hydrogels Self-Assembled from Reduction-Controlled Condensation [J].

Liu, Shuang ;

Tang, Anming ;

Xie, Maolin ;

Zhao, Yundan ;

Jiang, Jun ;

Liang, Gaolin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (12) :3639-3642

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