Design and synthesis of novel 18F-radiolabelled glucosamine derivatives for cancer imaging

Carroll, Laurence; Witney, Timothy H.; Aboagye, Eric O.

doi:10.1039/c3md00023k

Cited by 12 publications

(16 citation statements)

References 18 publications

(22 reference statements)

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“…We synthesized 18 F-NFTG by a copper-catalyzed 1,3-dipolar cycloaddition reaction (22). For in vivo PET studies injection-ready 18 F-NFTG was obtained from 18 F-fluoride with a radiochemical yield of 15%±5% (non-decay-corrected) (22).…”

Section: Resultsmentioning

confidence: 99%

“…For in vivo PET studies injection-ready 18 F-NFTG was obtained from 18 F-fluoride with a radiochemical yield of 15%±5% (non-decay-corrected) (22). The radiochemical purity was >98% from n =12 individual syntheses.…”

Section: Resultsmentioning

confidence: 99%

“…18 F-NFTG synthesis and radiolabeling was performed according to previously described methodology (22). …”

Section: Methodsmentioning

confidence: 99%

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A Novel Radiotracer to Image Glycogen Metabolism in Tumors by Positron Emission Tomography

et al. 2014

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The high rate of glucose uptake to fuel the bioenergetic and anabolic demands of proliferating cancer cells is well recognized, and exploited with 18F-2-fluoro-2-deoxyglucose positron emission tomography (18F-FDG-PET) to image tumors clinically. In contrast, enhanced glucose storage as glycogen (glycogenesis) in cancer is less well understood and the availability of a non-invasive method to image glycogen in vivo could provide important biologic insights. Here, we demonstrate that 18F-N-(methyl-(2-fluoroethyl)-1H-[1,2,3]triazole-4-yl)glucosamine (18F-NFTG) annotates glycogenesis in cancer cells and tumors in vivo, measured by PET. Specificity of glycogen labeling was demonstrated by isolating 18F-NFTG-associated glycogen and with stable knockdown of glycogen synthase 1, which inhibited 18F-NFTG uptake, while oncogene (Rab25) activation-associated glycogen synthesis led to increased uptake. We further show that the rate of glycogenesis is cell cycle-regulated, enhanced during the non-proliferative state of cancer cells. We demonstrate that glycogen levels, 18F-NFTG, but not 18F-FDG uptake, increase proportionally with cell density and G1/G0 arrest with potential application in the assessment of activation of oncogenic pathways related to glycogenesis and the detection of post treatment tumor quiescence.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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A Novel Radiotracer to Image Glycogen Metabolism in Tumors by Positron Emission Tomography

et al. 2014

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“…Glucosamine (2-amino-2-deoxyglucose), an FDG derivative, also binds to glucose transporters overexpressed by cancer cells and glucosamine derivatives have shown potential as a cancer imaging agent in preclinical studies [43–45]. Several studies have demonstrated that functionalization of nanoparticles with glucosamine or other glucose derivatives can be used as a strategy to increase the cell uptake or alter the biodistribution of the glyconanoparticles as compared with nonglycoparticles [46–50].…”

Section: Introductionmentioning

confidence: 99%

Targeting Breast Cancer with Sugar-Coated Carbon Nanotubes

Fahrenholtz

Hadimani

King

et al. 2015

Nanomedicine (Lond.)

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Aims To evaluate the use of glucosamine functionalized multiwalled carbon nanotubes (glyco-MWCNTs) for breast cancer targeting. Materials & methods Two types of glucosamine functionalized MWCNTs were developed (covalently linked glucosamine and non-covalently phospholipid-glucosamine coated) and evaluated for their potential to bind and target breast cancer cells in vitro and in vivo. Results & conclusion Binding of glyco-MWCNTs in breast cancer cells is mediated by specific interaction with glucose transporters. Glyco-MWCNTs prepared by non-covalent coating with phospholipid-glucosamine displayed an extended blood circulation time, delayed urinary clearance, low tissue retention and increased breast cancer tumor accumulation in vivo. These studies lay the foundation for development of a cancer diagnostic agent based upon glyco-MWCNTs with the potential for superior accuracy over current radiopharmaceuticals.

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“…Using the conditions of Smith and co-workers, [ 18 F]fluoromethyl glucosamine derivative 23 could be obtained in a radiochemical yield of 8 AE 2% (n = 15, ndc). 55 Two successful [ 18 F]fluoromethylations of secondary amines with [ 18 F]fluoromethyl tosylate (Scheme 13) are (1) the synthesis of [ 18 F]fluoro-d 2 -methylflumazenil 25 for imaging benzodiazepine receptors and (2) the synthesis of the progesterone receptor agonist 27. Very different reaction conditions were applied in each reaction.…”

Section: [ 18 F]fluoromethyl Halides and Sulfonatesmentioning

confidence: 99%

Fluorine-18 labelled building blocks for PET tracer synthesis

et al. 2017

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Positron emission tomography (PET) is an important driver for present day healthcare. Fluorine-18 is the most widely used radioisotope for PET imaging and a thorough overview of the available radiochemistry methodology is a prerequisite for selection of a synthetic approach for new fluorine-18 labelled PET tracers. These PET tracers can be synthesised either by late-stage radiofluorination, introducing fluorine-18 in the last step of the synthesis, or by a building block approach (also called modular build-up approach), introducing fluorine-18 in a fast and efficient manner in a building block, which is reacted further in one or multiple reaction steps to form the PET tracer. This review presents a comprehensive overview of the synthesis and application of fluorine-18 labelled building blocks since 2010.

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Design and synthesis of novel 18F-radiolabelled glucosamine derivatives for cancer imaging

Cited by 12 publications

References 18 publications

A Novel Radiotracer to Image Glycogen Metabolism in Tumors by Positron Emission Tomography

A Novel Radiotracer to Image Glycogen Metabolism in Tumors by Positron Emission Tomography

Targeting Breast Cancer with Sugar-Coated Carbon Nanotubes

Fluorine-18 labelled building blocks for PET tracer synthesis

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