Significance of nitroimidazole compounds and hypoxia‐inducible factor‐1 for imaging tumor hypoxia

Kizaka‐Kondoh, Shinae; Konse-Nagasawa, Hideko

doi:10.1111/j.1349-7006.2009.01195.x

Cited by 213 publications

(192 citation statements)

References 73 publications

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“…Radiolabeled nitroimidazole derivatives are used for imaging hypoxic tissue because the nitroimidazole residue is reduced to reactive chemical species that can bind to intracellular components in the absence of sufficient oxygen [1][2][3][4][5].…”

Section: Introductionmentioning

confidence: 99%

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

Seelam

Lee

et al. 2015

Bioorganic & Medicinal Chemistry

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Section: Introductionmentioning

confidence: 99%

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

Seelam

Lee

et al. 2015

Bioorganic & Medicinal Chemistry

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“…4). Quantifying the extent of hypoxia requires that nitroimidazole binding be primarily dependent on oxygen concentration (PO 2 <5 mmHg) as well as nitroreductase levels in the tumor cells [89]. 18 F-FMISO is a well-studied hypoxia marker in humans and animals and widely tested.…”

Section: Hypoxia Pet Imagingmentioning

confidence: 99%

Current Molecular Imaging Positron Emitting Radiotracers in Oncology

Zhu

Shim

2011

Nucl Med Mol Imaging

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Molecular imaging is one of the fastest growing areas of medical imaging. Positron emission tomography (PET) has been widely used in the clinical management of patients with cancer. Nuclear imaging provides biological information at the cellular, subcellular, and molecular level in living subjects with noninvasive procedures. In particular, PET imaging takes advantage of traditional diagnostic imaging techniques and introduces positron-emitting probes to determine the expression of indicative molecular targets at different stages of cancer. 18 F-fluorodeoxyglucose ( 18 F-FDG), the only FDA approved oncological PET tracer, has been widely utilized in cancer diagnosis, staging, restaging, and even monitoring response to therapy; however, 18 F-FDG is not a tumor-specific PET tracer. Over the last decade, many promising tumor-specific PET tracers have been developed and evaluated in preclinical and clinical studies. This review provides an overview of the current non-18 F-FDG PET tracers in oncology that have been developed based on tumor characteristics such as increased metabolism, hyperproliferation, angiogenesis, hypoxia, apoptosis, and tumor-specific antigens and surface receptors.

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confidence: 99%

“…2,3) Therefore, there has been a growing impetus to develop non-invasive imaging methods to detect and assess tumor hypoxia. 4,5) In the development of imaging probes for tumor hypoxia, nitroimidazoles have received particular attention as exogenous markers because of their unique behavior in hypoxic environments owing to their high electron affinity. 4) Nitroimidazole compounds undergo selective bioreduction in hypoxic cells to form reactive species that irreversibly bind to cellular macromolecules.…”

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confidence: 99%

“…4,5) In the development of imaging probes for tumor hypoxia, nitroimidazoles have received particular attention as exogenous markers because of their unique behavior in hypoxic environments owing to their high electron affinity. 4) Nitroimidazole compounds undergo selective bioreduction in hypoxic cells to form reactive species that irreversibly bind to cellular macromolecules. 6) Currently, positron emission tomography using nitroimidazole tracers is the most advanced technique to achieve non-invasive in vivo mapping of tumor hypoxia with anatomical resolution.…”

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confidence: 99%

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Development of a Hypoxia-Selective Near-Infrared Fluorescent Probe for Non-invasive Tumor Imaging

Youssif

Okuda

Kadonosono

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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A near-infrared fluorochrome, GPU-311, was designed, synthesized and evaluated for its application in non-invasive imaging of tumor hypoxia. Efficient synthesis was achieved by nucleophilic substitution and click chemistry ring using the bifunctional tetraethylene glycol linker 2 containing thiol and azide groups for the conjugation of the propargylated nitroimidazole 1 and the heptamethine cyanine dye 3 bearing a 2-chloro-1-cyclohexenyl ring. GPU-311 exhibited long excitation and emission wavelength (Ex/Em 785/802 nm) and a decent quantum yield (0.05). The water solubility and hydrophilicity of GPU-311 increased. After in vitro treatment of SUIT-2/HRE-Luc pancreatic cancer cells with GPU-311, a higher level of fluorescence was observed selectively in hypoxia than in normoxia. However, in vivo fluorescence imaging of a mouse xenograft model after GPU-311 administration revealed inadequate accumulation of GPU-311 in tumors due to its rapid elimination through the liver.Key words near-infrared fluorescence; tumor hypoxia; 2-nitroimidazole; in vivo imaging Tumor hypoxia is now known as one of the most prominent features of malignant neoplasias, distinguishing them from normal tissues.1) The hypoxic status of various solid tumors can markedly influence the therapeutic response of malignant tumors to conventional irradiation, chemotherapy and other nonsurgical treatment modalities.2,3) Therefore, there has been a growing impetus to develop non-invasive imaging methods to detect and assess tumor hypoxia. 4,5) In the development of imaging probes for tumor hypoxia, nitroimidazoles have received particular attention as exogenous markers because of their unique behavior in hypoxic environments owing to their high electron affinity. 4)Nitroimidazole compounds undergo selective bioreduction in hypoxic cells to form reactive species that irreversibly bind to cellular macromolecules. 6) Currently, positron emission tomography using nitroimidazole tracers is the most advanced technique to achieve non-invasive in vivo mapping of tumor hypoxia with anatomical resolution. 7) However, radionuclide imaging requires radioactive compounds which have an intrinsically limited half-life and expose the patient and practitioner to ionizing radiation, and are therefore subject to a variety of stringent safety regulations that limit their repeated use.In contrast, optical imaging has comparable sensitivity to radionuclide imaging, and it can be "targeted" if the emitting fluorophore is conjugated to a targeting ligand. 8) That is safer and easier to perform than nuclear imaging. Optical imaging in the near-infrared (NIR) region (700-900 nm) has a low absorption by intrinsic photoactive biomolecules and allows light to penetrate several centimeters into the tissue, a depth sufficient for imaging practically all small animal models. 9)Therefore, NIR fluorescence imaging, a less expensive and non-invasive technique, may be a powerful tool for imaging tumor hypoxia. Recently, we developed an NIR hypoxia probe, GPU-167 (Fig. 1), comprising 2-ni...

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Significance of nitroimidazole compounds and hypoxia‐inducible factor‐1 for imaging tumor hypoxia

Abstract: A tumor-specific microenvironment is characterized by hypoxia, in which oxygen tension is considerably lower than in normal tissues.

Cited by 213 publications

References 73 publications

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

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

Current Molecular Imaging Positron Emitting Radiotracers in Oncology

Development of a Hypoxia-Selective Near-Infrared Fluorescent Probe for Non-invasive Tumor Imaging

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