Detecting hypoxia in vitro using 18F-pretargeted IEDDA "click" chemistry in live cells

被引:7
作者
Allott, Louis [1 ,2 ]
Chen, Cen [1 ]
Braga, Marta [1 ]
Leung, Sau Fung Jacob [1 ]
Wang, Ning [1 ]
Barnes, Chris [1 ]
Brickute, Diana [1 ]
Carroll, Laurence [1 ,3 ]
Aboagye, Eric O. [1 ]
机构
[1] Imperial Coll London, Hammersmith Hosp, Dept Surg & Canc, Comprehens Canc Imaging Ctr,Fac Med, Du Cane Rd, London W12 0NN, England
[2] Univ Hull, Fac Hlth Sci, Positron Emiss Tomog Res Ctr, Cottingham Rd, Kingston Upon Hull HU6 7RX, Yorks, England
[3] Johns Hopkins Med Inst, Russell H Morgan Dept Radiol & Radiol Sci, Baltimore, MD 21205 USA
基金
英国工程与自然科学研究理事会; 英国医学研究理事会;
关键词
PET; AGENT; FMISO;
D O I
10.1039/d1ra02482e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We have exemplified a pretargeted approach to interrogate hypoxia in live cells using radioactive bioorthogonal inverse electron demand Diels-Alder (IEDDA) "click" chemistry. Our novel F-18-tetrazine probe ([F-18]FB-Tz) and 2-nitroimidazole-based TCO targeting molecule (8) showed statistically significant (P < 0.0001) uptake in hypoxic cells (ca. 90 %ID per mg) vs. normoxic cells (<10 %ID per mg) in a 60 min incubation of [F-18]FB-Tz. This is the first time that an intracellularly targeted small-molecule for IEDDA "click" has been used in conjunction with a radioactive reporter molecule in live cells and may be a useful tool with far-reaching applicability for a variety of applications.
引用
收藏
页码:20335 / 20341
页数:7
相关论文
共 29 条
[1]   Solid-supported cyanoborohydride cartridges for automation of reductive amination radiochemistry [J].
Allott, Louis ;
Barnes, Chris ;
Brickute, Diana ;
Leung, Sau Fung Jacob ;
Aboagye, Eric O. .
REACTION CHEMISTRY & ENGINEERING, 2019, 4 (10) :1748-1751
[2]   Rapid synthesis of maleimide functionalized fluorine-18 labeled prosthetic group using "radio-fluorination on the Sep-Pak" method [J].
Basuli, Falguni ;
Zhang, Xiang ;
Jagoda, Elaine M. ;
Choyke, Peter L. ;
Swenson, Rolf E. .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2018, 61 (08) :599-605
[3]   Pretargeted PET Imaging Using a Bioorthogonal 18F-Labeled trans-Cyclooctene in an Ovarian Carcinoma Model [J].
Billaud, Emilie M. F. ;
Belderbos, Sarah ;
Cleeren, Frederik ;
Maest, Wim ;
Van de Wouwer, Marlies ;
Koole, Michel ;
Verbruggen, Alfons ;
Hirnmelreich, Uwe ;
Geukens, Nick ;
Bormans, Guy .
BIOCONJUGATE CHEMISTRY, 2017, 28 (12) :2915-2920
[4]   Genetic Encoding of a Bicyclo[6.1.0]nonyne-Charged Amino Acid Enables Fast Cellular Protein Imaging by Metal-Free Ligation [J].
Borrmann, Annika ;
Milles, Sigrid ;
Plass, Tilman ;
Dommerholt, Jan ;
Verkade, Jorge M. M. ;
Wiessler, Manfred ;
Schultz, Carsten ;
van Hest, Jan C. M. ;
van Delft, Floris L. ;
Lemke, Edward A. .
CHEMBIOCHEM, 2012, 13 (14) :2094-2099
[5]  
Bruehlmeier M, 2004, J NUCL MED, V45, P1851
[6]   A bioorthogonal 68Ga-labelling strategy for rapid in vivo imaging [J].
Evans, Helen L. ;
Quang-De Nguyen ;
Carroll, Laurence S. ;
Kaliszczak, Maciej ;
Twyman, Frazer J. ;
Spivey, Alan C. ;
Aboagye, Eric O. .
CHEMICAL COMMUNICATIONS, 2014, 50 (67) :9557-9560
[7]   A Hitchhiker's Guide to Click-Chemistry with Nucleic Acids [J].
Fantoni, Nicolo Zuin ;
El-Sagheer, Afaf H. ;
Brown, Tom .
CHEMICAL REVIEWS, 2021, 121 (12) :7122-7154
[8]   'Click labelling' in PET radiochemistry [J].
Glaser, Matthias ;
Robins, Edward G. .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2009, 52 (9-10) :407-414
[9]   NONINVASIVE ASSESSMENT OF TUMOR MICROENVIRONMENT USING DYNAMIC CONTRAST-ENHANCED MAGNETIC RESONANCE IMAGING AND 18F-FLUOROMISONIDAZOLE POSITRON EMISSION TOMOGRAPHY IMAGING IN NECK NODAL METASTASES [J].
Jansen, Jacobus F. A. ;
Schoeder, Heiko ;
Lee, Nancy Y. ;
Wang, Ya ;
Pfister, David. G. ;
Fury, Matthew G. ;
Stambuk, Hilda E. ;
Humm, John L. ;
Koutcher, Jason A. ;
Shukla-Dave, Amita .
INTERNATIONAL JOURNAL OF RADIATION ONCOLOGY BIOLOGY PHYSICS, 2010, 77 (05) :1403-1410
[10]  
Kolb HC, 2001, ANGEW CHEM INT EDIT, V40, P2004, DOI 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.3.CO