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Journal of Enzyme Inhibition and Medicinal Chemistry Volume 32, 2017 - Issue 1
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Research Article

Design, synthesis and evaluation of 18F-labeled cationic carbonic anhydrase IX inhibitors for PET imaging

Zhengxing ZhangDepartment of Molecular Oncology, BC Cancer Agency, Vancouver, British Columbia, Canada; View further author information
,
Joseph LauDepartment of Molecular Oncology, BC Cancer Agency, Vancouver, British Columbia, Canada; View further author information
,
Chengcheng ZhangDepartment of Molecular Oncology, BC Cancer Agency, Vancouver, British Columbia, Canada; View further author information
,
Nadine ColpoDepartment of Molecular Oncology, BC Cancer Agency, Vancouver, British Columbia, Canada; View further author information
,
Alessio NocentiniDepartment of Neurofarba, Section of Pharmaceutical and Nutriceutical Sciences, Università Degli Studi Di Firenze, Florence, Italy; View further author information
,
Claudiu T. SupuranDepartment of Neurofarba, Section of Pharmaceutical and Nutriceutical Sciences, Università Degli Studi Di Firenze, Florence, Italy; View further author information
,
François BénardDepartment of Molecular Oncology, BC Cancer Agency, Vancouver, British Columbia, Canada; ;Department of Functional Imaging, BC Cancer Agency, Vancouver, British Columbia, Canada; ;Department of Radiology, University of British Columbia, Vancouver, British Columbia, CanadaView further author information
&
Kuo-Shyan LinDepartment of Molecular Oncology, BC Cancer Agency, Vancouver, British Columbia, Canada; ;Department of Functional Imaging, BC Cancer Agency, Vancouver, British Columbia, Canada; ;Department of Radiology, University of British Columbia, Vancouver, British Columbia, CanadaCorrespondence[email protected]
View further author information
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Pages 722-730 | Received 10 Mar 2017, Accepted 16 Mar 2017, Published online: 07 Apr 2017

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Mazin A. A. Najm, Walaa R. Mahmoud, Azza T. Taher, Safinaz E-S. Abbas, Fadi M. Awadallah, Heba Abdelrasheed Allam, Daniela Vullo & Claudiu T. Supuran. (2022) Design and synthesis of some new benzoylthioureido phenyl derivatives targeting carbonic anhydrase enzymes. Journal of Enzyme Inhibition and Medicinal Chemistry 37:1, pages 2702-2709.
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Claudiu T Supuran. (2020) Experimental Carbonic Anhydrase Inhibitors for the Treatment of Hypoxic Tumors. Journal of Experimental Pharmacology 12, pages 603-617.
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Siham A. Alissa, Hanan A. Alghulikah, Zeid A. Alothman, Sameh M. Osman, Sonia Del Prete, Clemente Capasso, Alessio Nocentini & Claudiu T. Supuran. (2020) Phosphonamidates are the first phosphorus-based zinc binding motif to show inhibition of β-class carbonic anhydrases from bacteria, fungi, and protozoa. Journal of Enzyme Inhibition and Medicinal Chemistry 35:1, pages 59-64.
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Alessio Nocentini & Claudiu T. Supuran. (2019) Advances in the structural annotation of human carbonic anhydrases and impact on future drug discovery. Expert Opinion on Drug Discovery 14:11, pages 1175-1197.
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Claudiu T. Supuran. (2018) Carbonic anhydrase inhibitors as emerging agents for the treatment and imaging of hypoxic tumors. Expert Opinion on Investigational Drugs 27:12, pages 963-970.
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Alessio Nocentini & Claudiu T. Supuran. (2018) Carbonic anhydrase inhibitors as antitumor/antimetastatic agents: a patent review (2008–2018). Expert Opinion on Therapeutic Patents 28:10, pages 729-740.
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Fadi M. Awadallah, Silvia Bua, Walaa R. Mahmoud, Hossam H. Nada, Alessio Nocentini & Claudiu T. Supuran. (2018) Inhibition studies on a panel of human carbonic anhydrases with N1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails. Journal of Enzyme Inhibition and Medicinal Chemistry 33:1, pages 629-638.
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Articles from other publishers (34)

Lizeth Y. F. Haveman, Danielle J. Vugts & Albert D. Windhorst. (2023) State of the art procedures towards reactive [18F]fluoride in PET tracer synthesis. EJNMMI Radiopharmacy and Chemistry 8:1.
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Sridhar Goud Nerella, Priti Singh, Pavitra S. Thacker, Mohammed Arifuddin & Claudiu T. Supuran. (2023) PET radiotracers and fluorescent probes for imaging human carbonic anhydrase IX and XII in hypoxic tumors. Bioorganic Chemistry 133, pages 106399.
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Arne Rotermund, Sarah Brandt, Martin S. Staege, Jana Luetzkendorf, Lutz P. Mueller & Thomas Mueller. (2023) Differential CMS-Related Expression of Cell Surface Carbonic Anhydrases IX and XII in Colorectal Cancer Models—Implications for Therapy. International Journal of Molecular Sciences 24:6, pages 5797.
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Xinlin Zhong, Junjie Yan, Xiang Ding, Chen Su, Yuping Xu & Min Yang. (2023) Recent Advances in Bioorthogonal Click Chemistry for Enhanced PET and SPECT Radiochemistry. Bioconjugate Chemistry 34:3, pages 457-476.
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Pierrick Gouel, Pierre Decazes, Pierre Vera, Isabelle Gardin, Sébastien Thureau & Pierre Bohn. (2023) Advances in PET and MRI imaging of tumor hypoxia. Frontiers in Medicine 10.
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Kuo-Ting Chen & Yann Seimbille. (2022) New Developments in Carbonic Anhydrase IX-Targeted Fluorescence and Nuclear Imaging Agents. International Journal of Molecular Sciences 23:11, pages 6125.
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Siao-Syun Guan, Cheng-Tien Wu, Tse-Zung Liao, Kun-Liang Lin, Cheng-Liang Peng, Ying-Hsia Shih, Mao-Feng Weng, Chun-Tang Chen, Chung-Hsin Yeh, Ying-Chieh Wang & Shing‑Hwa Liu. (2021) A novel 111indium-labeled dual carbonic anhydrase 9-targeted probe as a potential SPECT imaging radiotracer for detection of hypoxic colorectal cancer cells. European Journal of Pharmaceutics and Biopharmaceutics 168, pages 38-52.
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Valeria Burianova, Stanislav Kalinin, Claudiu T. Supuran & Mikhail Krasavin. (2021) Radiotracers for positron emission tomography (PET) targeting tumour-associated carbonic anhydrase isoforms. European Journal of Medicinal Chemistry 213, pages 113046.
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Yuan Zhu, Leyuan Chen, Wenbin Hou & Yiliang Li. (2021) Recent Progress in Nucleophilic Fluoride Mediated Fluorine-18 Labeling of Arenes and Heteroarenes. Chinese Journal of Organic Chemistry, pages 1774.
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Joseph Lau, Kuo-Shyan Lin & François Bénard. 2021. The Carbonic Anhydrases: Current and Emerging Therapeutic Targets. The Carbonic Anhydrases: Current and Emerging Therapeutic Targets 253 279 .
Sean W. Reilly & Robert H. Mach. 2020. Handbook of Radiopharmaceuticals. Handbook of Radiopharmaceuticals 325 341 .
Shimpei Iikuni, Hiroyuki Watanabe, Yoichi Shimizu, Yuji Nakamoto & Masahiro Ono. (2020) PET imaging and pharmacological therapy targeting carbonic anhydrase-IX high-expressing tumors using US2 platform based on bivalent ureidosulfonamide. PLOS ONE 15:12, pages e0243327.
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Shimpei Iikuni, Yuya Okada, Yoichi Shimizu, Hiroyuki Watanabe & Masahiro Ono. (2020) Synthesis and evaluation of indium-111-labeled imidazothiadiazole sulfonamide derivative for single photon emission computed tomography imaging targeting carbonic anhydrase-IX. Bioorganic & Medicinal Chemistry Letters 30:14, pages 127255.
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Jay S. Wright, Tanpreet Kaur, Sean Preshlock, Sean S. Tanzey, Wade P. Winton, Liam S. Sharninghausen, Nicholas Wiesner, Allen F. Brooks, Melanie S. Sanford & Peter J. H. Scott. (2020) Copper-mediated late-stage radiofluorination: five years of impact on preclinical and clinical PET imaging. Clinical and Translational Imaging 8:3, pages 167-206.
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Andrew V. Mossine, Sean S. Tanzey, Allen F. Brooks, Katarina J. Makaravage, Naoko Ichiishi, Jason M. Miller, Bradford D. Henderson, Thomas Erhard, Christian Bruetting, Marc B. Skaddan, Melanie S. Sanford & Peter J. H. Scott. (2020) Synthesis of high-molar-activity [18F]6-fluoro-l-DOPA suitable for human use via Cu-mediated fluorination of a BPin precursor. Nature Protocols 15:5, pages 1742-1759.
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Florian Guibbal, Patrick G. Isenegger, Thomas C. Wilson, Anna Pacelli, Damien Mahaut, Jeroen B. I. Sap, Nicholas J. Taylor, Stefan Verhoog, Sean Preshlock, Rebekka Hueting, Bart Cornelissen & Véronique Gouverneur. (2020) Manual and automated Cu-mediated radiosynthesis of the PARP inhibitor [18F]olaparib. Nature Protocols 15:4, pages 1525-1541.
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Nerella Sridhar Goud, Raman Kumar Joshi, Rose Dawn Bharath & Pardeep Kumar. (2020) Fluorine-18: A radionuclide with diverse range of radiochemistry and synthesis strategies for target based PET diagnosis. European Journal of Medicinal Chemistry 187, pages 111979.
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Javad Garousi, Fokko J. Huizing, Anzhelika Vorobyeva, Bogdan Mitran, Ken G. Andersson, Charles Dahlsson Leitao, Fredrik Y. Frejd, John Löfblom, Johan Bussink, Anna Orlova, Sandra Heskamp & Vladimir Tolmachev. (2019) Comparative evaluation of affibody- and antibody fragments-based CAIX imaging probes in mice bearing renal cell carcinoma xenografts. Scientific Reports 9:1.
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Shimpei Iikuni, Keiichi Tanimura, Hiroyuki Watanabe, Yoichi Shimizu, Hideo Saji & Masahiro Ono. (2019) Development of the 99m Tc-Hydroxamamide Complex as a Probe Targeting Carbonic Anhydrase IX . Molecular Pharmaceutics 16:4, pages 1489-1497.
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Jaime A Espinoza, Ismael Riquelme, Eduardo A Sagredo, Lorena Rosa, Patricia García, Carolina Bizama, María Apud-Bell, Pamela Leal, Helga Weber, Felipe Benavente, Sergio Vargas, Diego Romero, Alexis M Kalergis & Juan Carlos Roa. (2019) Mucin 5B, carbonic anhydrase 9 and claudin 18 are potential theranostic markers of gallbladder carcinoma. Histopathology 74:4, pages 597-607.
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Lina Jia, Xiao Li, Dengfeng Cheng & Lan Zhang. (2019) Fluorine-18 click radiosynthesis and microPET/CT evaluation of a small peptide-a potential PET probe for carbonic anhydrase IX. Bioorganic & Medicinal Chemistry 27:5, pages 785-789.
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Marc A. Ilies & Jean-Yves Winum. 2019. Carbonic Anhydrases. Carbonic Anhydrases 331 365 .
Alessio Nocentini, William A. Donald & Claudiu T. Supuran. 2019. Carbonic Anhydrases. Carbonic Anhydrases 151 185 .
Kuo-Ting Chen, Kevin Nguyen, Christian Ieritano, Feng Gao & Yann Seimbille. (2018) A Flexible Synthesis of 68Ga-Labeled Carbonic Anhydrase IX (CAIX)-Targeted Molecules via CBT/1,2-Aminothiol Click Reaction. Molecules 24:1, pages 23.
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Claudiu T. Supuran, Vincenzo Alterio, Anna Di Fiore, Katia D’ Ambrosio, Fabrizio Carta, Simona Maria Monti & Giuseppina De Simone. (2018) Inhibition of carbonic anhydrase IX targets primary tumors, metastases, and cancer stem cells: Three for the price of one. Medicinal Research Reviews 38:6, pages 1799-1836.
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Hany S. Ibrahim, Heba Abdelrasheed Allam, Walaa R. Mahmoud, Alessandro Bonardi, Alessio Nocentini, Paola Gratteri, Eslam S. Ibrahim, Hatem A. Abdel-Aziz & Claudiu T. Supuran. (2018) Dual-tail arylsulfone-based benzenesulfonamides differently match the hydrophobic and hydrophilic halves of human carbonic anhydrases active sites: Selective inhibitors for the tumor-associated hCA IX isoform. European Journal of Medicinal Chemistry 152, pages 1-9.
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Alessio Nocentini, Silvia Bua, Sonia Del Prete, Yeganeh Entezari Heravi, Ali A. Saboury, Anastasia Karioti, Anna Rita Bilia, Clemente Capasso, Paola Gratteri & Claudiu T. Supuran. (2018) Natural Polyphenols Selectively Inhibit β-Carbonic Anhydrase from the Dandruff-Producing Fungus Malassezia globosa : Activity and Modeling Studies . ChemMedChem 13:8, pages 816-823.
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Alessio Nocentini, Davide Moi, Gianfranco Balboni, Severo Salvadori, Valentina Onnis & Claudiu T. Supuran. (2018) Synthesis and biological evaluation of novel pyrazoline-based aromatic sulfamates with potent carbonic anhydrase isoforms II, IV and IX inhibitory efficacy. Bioorganic Chemistry 77, pages 633-639.
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Shams-ul Mahmood, Aamer Saeed, Sivia Bua, Alessio Nocentini, Paola Gratteri & Claudiu T. Supuran. (2018) Synthesis, biological evaluation and computational studies of novel iminothiazolidinone benzenesulfonamides as potent carbonic anhydrase II and IX inhibitors. Bioorganic Chemistry 77, pages 381-386.
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Alessio Nocentini, Davide Moi, Gianfranco Balboni, Valentina Onnis & Claudiu T. Supuran. (2018) Discovery of thiazolin-4-one-based aromatic sulfamates as a new class of carbonic anhydrase isoforms I, II, IV, and IX inhibitors. Bioorganic Chemistry 77, pages 293-299.
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Paulo Sérgio Gonçalves Nunes, Zhengxing Zhang, Hsiou-Ting Kuo, Chengcheng Zhang, Julie Rousseau, Etienne Rousseau, Joseph Lau, Daniel Kwon, Ivone Carvalho, François Bénard & Kuo-Shyan Lin. (2018) Synthesis and evaluation of an 18 F-labeled trifluoroborate derivative of 2-nitroimidazole for imaging tumor hypoxia with positron emission tomography . Journal of Labelled Compounds and Radiopharmaceuticals 61:4, pages 370-379.
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Andrew V. Mossine, Allen F. Brooks, Vadim Bernard-Gauthier, Justin J. Bailey, Naoko Ichiishi, Ralf Schirrmacher, Melanie S. Sanford & Peter J.H. Scott. (2018) Automated synthesis of PET radiotracers by copper-mediated 18 F-fluorination of organoborons: Importance of the order of addition and competing protodeborylation . Journal of Labelled Compounds and Radiopharmaceuticals 61:3, pages 228-236.
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Wagdy M. Eldehna, Mahmoud F. Abo-Ashour, Alessio Nocentini, Paola Gratteri, Ibrahim H. Eissa, Mohamed Fares, Omnia E. Ismael, Hazem A. Ghabbour, Mahmoud M. Elaasser, Hatem A. Abdel-Aziz & Claudiu T. Supuran. (2017) Novel 4/3-((4-oxo-5-(2-oxoindolin-3-ylidene)thiazolidin-2-ylidene)amino) benzenesulfonamides: Synthesis, carbonic anhydrase inhibitory activity, anticancer activity and molecular modelling studies. European Journal of Medicinal Chemistry 139, pages 250-262.
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Claudiu T. Supuran. (2017) Carbonic Anhydrase Inhibition and the Management of Hypoxic Tumors. Metabolites 7:3, pages 48.
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