Development of 68Ga-labeled multivalent nitroimidazole derivatives for hypoxia imaging

Seelam, Sudhakara Reddy; Lee, Ji Youn; Lee, Yun Sang; Hong, Mineui; Kim, Young Joo; Banka, Vinay Kumar; Lee, Dong Hoon; Chung, June Key; Jeong, Jae Min

doi:10.1016/j.bmc.2015.11.024

Cited by 20 publications

(28 citation statements)

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“…HBED-CC has been successfully applied in the theranostics of prostate cancer when conjugated to the prostate-specific membrane antigen (PSMA) (Virgolini et al, 2017 ) but the combination with oxygen sensitive groups is yet to been investigated. Gallium-68 labeled nitroimidazole complexes were studied in mice models with induced (xenografted) tumors for CT26 (colon cancer) (Seelam et al, 2015 ), A549 (Wu et al, 2015 ) or 3LL (Fernández et al, 2013 ) (lung cancer cell lines). The comparison with [ 18 F]F-FMISO revealed successful hypoxia imaging and improved clearance properties.…”

Section: Preclinical and Clinical Imaging Of Hypoxiamentioning

confidence: 99%

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Oxygen Sensing, Hypoxia Tracing and in Vivo Imaging with Functional Metalloprobes for the Early Detection of Non-communicable Diseases

2018

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Hypoxia has been identified as one of the hallmarks of tumor environments and a prognosis factor in many cancers. The development of ideal chemical probes for imaging and sensing of hypoxia remains elusive. Crucial characteristics would include a measurable response to subtle variations of pO2 in living systems and an ability to accumulate only in the areas of interest (e.g., targeting hypoxia tissues) whilst exhibiting kinetic stabilities in vitro and in vivo. A sensitive probe would comprise platforms for applications in imaging and therapy for non-communicable diseases (NCDs) relying on sensitive detection of pO2. Just a handful of probes for the in vivo imaging of hypoxia [mainly using positron emission tomography (PET)] have reached the clinical research stage. Many chemical compounds, whilst presenting promising in vitro results as oxygen-sensing probes, are facing considerable disadvantages regarding their general application in vivo. The mechanisms of action of many hypoxia tracers have not been entirely rationalized, especially in the case of metallo-probes. An insight into the hypoxia selectivity mechanisms can allow an optimization of current imaging probes candidates and this will be explored hereby. The mechanistic understanding of the modes of action of coordination compounds under oxygen concentration gradients in living cells allows an expansion of the scope of compounds toward in vivo applications which, in turn, would help translate these into clinical applications. We summarize hereby some of the recent research efforts made toward the discovery of new oxygen sensing molecules having a metal-ligand core. We discuss their applications in vitro and/or in vivo, with an appreciation of a plethora of molecular imaging techniques (mainly reliant on nuclear medicine techniques) currently applied in the detection and tracing of hypoxia in the preclinical and clinical setups. The design of imaging/sensing probe for early-stage diagnosis would longer term avoid invasive procedures providing platforms for therapy monitoring in a variety of NCDs and, particularly, in cancers.

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Section: Preclinical and Clinical Imaging Of Hypoxiamentioning

confidence: 99%

“… Diagrammatic representation of structures of [ 68 Ga]Ga NOTA and DOTA radiotracer bearing nitroimidazole units (Seelam et al, 2015 ). …”

Section: Preclinical and Clinical Imaging Of Hypoxiamentioning

confidence: 99%

Oxygen Sensing, Hypoxia Tracing and in Vivo Imaging with Functional Metalloprobes for the Early Detection of Non-communicable Diseases

2018

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“…developed 68 Ga-labeled agents based on mono-, bis-, and tris-nitroimidazole conjugates with the chelating agent 1,4,7-triazacyclononane-1,4,7-tris[methyl(2-carboxyethyl)phosphinic acid] (TRAP), to obtain a series of 68 Ga-labeled compounds. The radiochemical yields were extremely high and the uptake of tumor models in in vivo experiments revealed its remarkable ability to target hypoxic areas ( 194 ). Recently, Yoichi Shimizu et al.…”

Section: Existing Researchmentioning

confidence: 99%

Imaging of Tumor Hypoxia With Radionuclide-Labeled Tracers for PET

Huang

Fan

et al. 2021

Front. Oncol.

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The hypoxic state in a solid tumor refers to the internal hypoxic environment that appears as the tumor volume increases (the maximum radius exceeds 180-200 microns). This state can promote angiogenesis, destroy the balance of the cell’s internal environment, and lead to resistance to radiotherapy and chemotherapy, as well as poor prognostic factors such as metastasis and recurrence. Therefore, accurate quantification, mapping, and monitoring of hypoxia, targeted therapy, and improvement of tumor hypoxia are of great significance for tumor treatment and improving patient survival. Despite many years of development, PET-based hypoxia imaging is still the most widely used evaluation method. This article provides a comprehensive overview of tumor hypoxia imaging using radionuclide-labeled PET tracers. We introduced the mechanism of tumor hypoxia and the reasons leading to the poor prognosis, and more comprehensively included the past, recent and ongoing studies of PET radiotracers for tumor hypoxia imaging. At the same time, the advantages and disadvantages of mainstream methods for detecting tumor hypoxia are summarized.

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“…It has been mentioned 2010 by Notni et al 120 and many articles have been published about this topic during the past 5 years. 140,[158][159][160][161][162][163] TRAP has good labeling conditions (RT, 10 minutes), a good stability with gallium (log K GaL ¼ 26.2) 120 and it is very robust against impurities of the gallium generator. 159,164 TRAP has been applied to the following target vectors: bisphosphonates, 165 cyclo-RGDfk, 160 and nitroimidazoles.…”

Section: Deferiprone (Hpo-ligands)mentioning

confidence: 99%

“…159,164 TRAP has been applied to the following target vectors: bisphosphonates, 165 cyclo-RGDfk, 160 and nitroimidazoles. 162 Because trimerization was not always the best option, NOPO had been developed. 122 NOPO has a smaller stability constant (log K GaL ¼ 25.0) 121 than TRAP, but the stability is still high enough.…”

Section: Deferiprone (Hpo-ligands)mentioning

confidence: 99%