Design of Turn-On Near-Infrared Fluorescent Probes for Highly Sensitive and Selective Monitoring of Biopolymers

被引:11
作者
Ducharme, Gerard T. [1 ]
LaCasse, Zane [2 ]
Sheth, Tanya [2 ]
Nesterova, Irina V. [2 ]
Nesterov, Evgueni E. [1 ,2 ]
机构
[1] Louisiana State Univ, Dept Chem, Baton Rouge, LA 70803 USA
[2] Northern Illinois Univ, Dept Chem & Biochem, De Kalb, IL 60115 USA
基金
美国国家科学基金会;
关键词
aggregation; biosensors; EGFR tyrosine kinase; fluorescent probes; phthalocyanines; GROWTH-FACTOR RECEPTOR; IRREVERSIBLE INHIBITOR; TETRAZINE PROBES; BINDING MODE; KINASE; CANCER; IR; PHTHALOCYANINES; PET; NANOPARTICLES;
D O I
10.1002/anie.202000108
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Simple, sensitive, and selective detection of specific biopolymers is critical in a broad range of biomedical and technological areas. We present a design of turn-on near-infrared (NIR) fluorescent probes with intrinsically high signal-to-background ratio. The fluorescent signal generation mechanism is based on the aggregation/de-aggregation of phthalocyanine chromophores controlled by selective binding of small-molecule "anchor" groups to a specific binding site of a target biopolymer. As a proof-of-concept, we demonstrate a design of a sensor for EGFR tyrosine kinase-an important target in cancer research. The universality of the fluorescent signal generation mechanism, as well as the dependence of the response selectivity on the choice of the small-molecule "anchor" group, make it possible to use this approach to design reliable turn-on NIR fluorescent sensors for detecting specific protein targets present in the low-nanomolar concentration range.
引用
收藏
页码:8440 / 8444
页数:5
相关论文
共 70 条
[1]   Evaluation of radiolabeled ML04, a putative irreversible inhibitor of epidermal growth factor receptor, as a bioprobe for PET imaging of EGFR-overexpressing tumors [J].
Abourbeh, Galith ;
Dissoki, Samar ;
Jacobson, Orit ;
Litchi, Amir ;
Ben Daniel, Revital ;
Laki, Desirediu ;
Levitzki, Alexander ;
Mishani, Eyal .
NUCLEAR MEDICINE AND BIOLOGY, 2007, 34 (01) :55-70
[2]   Comparison of visible and near-infrared wavelength-excitable fluorescent dyes for molecular imaging of cancer [J].
Adams, Kristen E. ;
Ke, Shi ;
Kwon, Sunkuk ;
Liang, Feng ;
Fan, Zhen ;
Lu, Yang ;
Hirschi, Karen ;
Mawad, Michel E. ;
Barry, Michael A. ;
Sevick-Muraca, Eva M. .
JOURNAL OF BIOMEDICAL OPTICS, 2007, 12 (02)
[3]   Self-Assembled Near-Infrared Dye Nanoparticles as a Selective Protein Sensor by Activation of a Dormant Fluorophore [J].
Anees, Palapuravan ;
Sreejith, Sivaramapanicker ;
Ajayaghosh, Ayyappanpillai .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (38) :13233-13239
[4]  
[Anonymous], 2012, ANGEW CHEM, V124, P6702
[5]  
[Anonymous], 2013, ANGEW CHEM
[6]  
Antaris AL, 2016, NAT MATER, V15, P235, DOI [10.1038/NMAT4476, 10.1038/nmat4476]
[7]   Virtual screening of 4-anilinoquinazoline analogues as EGFR kinase inhibitors: Importance of hydrogen bonds in the evaluation of poses and scoring functions [J].
Aparna, V ;
Rambabu, G ;
Panigrahi, SK ;
Sarma, JARP ;
Desiraju, GR .
JOURNAL OF CHEMICAL INFORMATION AND MODELING, 2005, 45 (03) :725-738
[8]   Potential 18F-labeled biomarkers for epidermal growth factor receptor tyrosine kinase [J].
Bonasera, TA ;
Ortu, G ;
Rozen, Y ;
Krais, R ;
Freedman, NMT ;
Chisin, R ;
Gazit, A ;
Levitzki, A ;
Mishani, E .
NUCLEAR MEDICINE AND BIOLOGY, 2001, 28 (04) :359-374
[9]   BODIPY-Tetrazine Derivatives as Superbright Bioorthogonal Turn-on Probes [J].
Carlson, Jonathan C. T. ;
Meimetis, Labros G. ;
Hilderbrand, Scott A. ;
Weissleder, Ralph .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (27) :6917-6920
[10]   Computational study of the binding mode of epidermal growth factor receptor kinase inhibitors [J].
Chen, Hai-Feng .
CHEMICAL BIOLOGY & DRUG DESIGN, 2008, 71 (05) :434-446