Literature DB >> 33604284

Synthesis and Preliminary Evaluation of a Novel 18F-Labeled 2-Nitroimidazole Derivative for Hypoxia Imaging.

Jing Lu1,2, Chi Zhang1, Xi Yang3,4, Xi-Juan Yao1, Qun Zhang2, Xin-Chen Sun1.   

Abstract

OBJECTIVE: Hypoxia is prevalent in tumors and plays a pivotal role in resistance to chemoradiotherapy. 18F-MISO (18F-labeled fluoromisonidazole) is currently the preferred choice of PET hypoxia tracers in clinical practice, but has severe disadvantages involving complex labeling methods and low efficient imaging due to lipophilicity. We aimed to design a novel nitroimidazole derivative labeled by 18F via a chelation technique to detect hypoxic regions and provide a basis for planning radiotherapy.
MATERIALS AND METHODS: First, we synthesized a 2-nitroimidazole precursor, 2-[4-(carboxymethyl)-7-[2-(2-(2-nitro-1H-imidazol-1-yl)acetamido)ethyl]-1,4,7-triazanonan-1-yl]acetic acid (NOTA-NI). For 18F-labeling, a 18F solution was reacted with a mixture of AlCl3 and NOTA-NI at pH 3.5 and 100°C for 20 min, and the radiochemical purity and stability were evaluated. Biological behaviors of Al18F-NOTA-NI were analyzed by an uptake study in ECA109 normoxic and hypoxic cells, and a biodistribution study and microPET imaging in ECA109 xenografted mice.
RESULTS: Al18F-NOTA-NI required a straightforward and efficient labeling procedure compared with 18F-MISO. The uptake values were distinctly higher in hypoxic tumor cells. Animal studies revealed that the imaging agent was principally excreted via the kidneys. Due to hydrophilicity, the radioactivities in blood and muscle were decreased, and we could clearly distinguish xenografted tumors from para-carcinoma tissue by PET imaging.
CONCLUSIONS: The nitroimidazole tracer Al18F-NOTA-NI steadily accumulated in hypoxic areas in tumors and was rapidly eliminated from normal tissue. It appears to be a promising candidate for hypoxia imaging with high sensitivity and resolution.
Copyright © 2021 Lu, Zhang, Yang, Yao, Zhang and Sun.

Entities:  

Keywords:  18F; 2-nitroimidazole; PET tracer; chemoradiotherapy resistance; hypoxia

Year:  2021        PMID: 33604284      PMCID: PMC7884749          DOI: 10.3389/fonc.2020.572097

Source DB:  PubMed          Journal:  Front Oncol        ISSN: 2234-943X            Impact factor:   6.244


  31 in total

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Review 2.  Imaging hypoxia to improve radiotherapy outcome.

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Journal:  Nat Rev Clin Oncol       Date:  2012-11-13       Impact factor: 66.675

3.  18F-Flortanidazole Hypoxia PET Holds Promise as a Prognostic and Predictive Imaging Biomarker in a Lung Cancer Xenograft Model Treated with Metformin and Radiotherapy.

Authors:  Sven De Bruycker; Christel Vangestel; Tim Van den Wyngaert; Patrick Pauwels; Leonie Wyffels; Steven Staelens; Sigrid Stroobants
Journal:  J Nucl Med       Date:  2018-07-06       Impact factor: 10.057

Review 4.  Hypoxia and hypoxia-inducible factors: master regulators of metastasis.

Authors:  Xin Lu; Yibin Kang
Journal:  Clin Cancer Res       Date:  2010-10-20       Impact factor: 12.531

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Authors:  Gaber Komar; Marko Seppänen; Olli Eskola; Paula Lindholm; Tove J Grönroos; Sarita Forsback; Hannu Sipilä; Sydney M Evans; Olof Solin; Heikki Minn
Journal:  J Nucl Med       Date:  2008-11-07       Impact factor: 10.057

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Authors:  William J McBride; Robert M Sharkey; Habibe Karacay; Christopher A D'Souza; Edmund A Rossi; Peter Laverman; Chien-Hsing Chang; Otto C Boerman; David M Goldenberg
Journal:  J Nucl Med       Date:  2009-05-14       Impact factor: 10.057

7.  Synthesis, in vitro and in vivo characterization of two novel 68Ga-labelled 5-nitroimidazole derivatives as potential agents for imaging hypoxia.

Authors:  Soledad Fernández; Sylvia Dematteis; Javier Giglio; Hugo Cerecetto; Ana Rey
Journal:  Nucl Med Biol       Date:  2012-12-05       Impact factor: 2.408

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Journal:  Eur J Nucl Med Mol Imaging       Date:  2009-05-09       Impact factor: 9.236

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Journal:  Br J Cancer       Date:  2003-09-15       Impact factor: 7.640

10.  Repeatability of tumour hypoxia imaging using [18F]EF5 PET/CT in head and neck cancer.

Authors:  Antti Silvoniemi; Sami Suilamo; Timo Laitinen; Sarita Forsback; Eliisa Löyttyniemi; Samuli Vaittinen; Virva Saunavaara; Olof Solin; Tove J Grönroos; Heikki Minn
Journal:  Eur J Nucl Med Mol Imaging       Date:  2017-10-26       Impact factor: 9.236

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  1 in total

1.  Pre-Clinical Study of the [18F]AlF-Labeled HER2 Affibody for Non-Invasive HER2 Detection in Gastric Cancer.

Authors:  Jingya Han; Yang Chen; Yan Zhao; Xinming Zhao; Jingmian Zhang; Jianfang Wang; Zhaoqi Zhang
Journal:  Front Med (Lausanne)       Date:  2022-02-16
  1 in total

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