Radiolabeled Glucose Derivatives for Tumor Imaging Using SPECT and PET

Liu, T.; Zhang, J.; Wang, X.; Yang, Ji Can; Tang, Zhigang; Lu, Jiaying

doi:10.2174/09298673113209990254

Cited by 24 publications

(10 citation statements)

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“…Both of the techniques are used widely for characterization and measurement of the biological properties at the cellular and molecular levels. 673 The azide−alkyne click reaction is an appropreate reaction and is far better than the conventional methodologies for the development of carbohydrate-based imaging probes for several reasons, such as higher decay-corrected radiochemical yield, higher specific activity, and shorter synthesis time. Synthesis of radiotracers must be rapid and selective and should preserve functional groups on the bioactive molecule.…”

Section: F-labeling In "Carbo-click"mentioning

confidence: 99%

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

et al. 2016

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Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC), popularly known as the "click reaction", serves as the most potent and highly dependable tool for facile construction of simple to complex architectures at the molecular level. Click-knitted threads of two exclusively different molecular entities have created some really interesting structures for more than 15 years with a broad spectrum of applicability, including in the fascinating fields of synthetic chemistry, medicinal science, biochemistry, pharmacology, material science, and catalysis. The unique properties of the carbohydrate moiety and the advantages of highly chemo- and regioselective click chemistry, such as mild reaction conditions, efficient performance with a wide range of solvents, and compatibility with different functionalities, together produce miraculous neoglycoconjugates and neoglycopolymers with various synthetic, biological, and pharmaceutical applications. In this review we highlight the successful advancement of Cu(I)-catalyzed click chemistry in glycoscience and its applications as well as future scope in different streams of applied sciences.

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Section: F-labeling In "Carbo-click"mentioning

confidence: 99%

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

et al. 2016

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“…However, aerobic glycolysis in tumor cells may be limited by glucose uptake . Glucose derivatives labeled with various radioactive isotopes and fluorescent dyes have been used to monitor increased glucose uptake associated with a high glycolytic rate in vivo . These include 2‐deoxy‐D‐[1,2‐ 3 H]‐glucose, 2‐deoxy‐D‐[1‐ 14 C]‐glucose, 2‐deoxy‐2‐( 18 F)‐fluoro‐D‐glucose ( 18 F‐FDG) and the fluorescent probe 2‐[N‐(7‐nitrobenz‐2‐oxa‐1,3‐diaxol‐4‐yl)amino]‐2‐deoxyglucose (2‐NBDG) .…”

Section: Conventional Assessment Of Glycolysismentioning

confidence: 99%

Probing carbohydrate metabolism using hyperpolarized ¹³C‐labeled molecules

et al. 2018

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Glycolysis is a fundamental metabolic process in all organisms. Anomalies in glucose metabolism are linked to various pathological conditions. In particular, elevated aerobic glycolysis is a characteristic feature of rapidly growing cells. Glycolysis and the closely related pentose phosphate pathway can be monitored in real time by hyperpolarized 13 C-labeled metabolic substrates such as 13 C-enriched, deuterated D-glucose derivatives, [2-13 C]-D-fructose, [2-13 C] dihydroxyacetone, [1-13 C]-Dglycerate, [1-13 C]-D-glucono-δ-lactone and [1-13 C] pyruvate in healthy and diseased tissues. Elevated glycolysis in tumors (the Warburg effect) was also successfully imaged using hyperpolarized [U-13 C 6 , U-2 H 7 ]-D-glucose, while the size of the preexisting lactate pool can be measured by 13 C MRS and/or MRI with hyperpolarized [1-13 C]pyruvate. This review summarizes the application of various hyperpolarized 13 C-labeled metabolites to the real-time monitoring of glycolysis and related metabolic processes in normal and diseased tissues. KEYWORDS dynamic nuclear polarization, glycolysis, hyperpolarized 13 C NMR, metabolic probes 1 | INTRODUCTION Glucose is a fundamental source of energy in living cells. It is present in all living organisms and utilized by both aerobic and anaerobic organisms. 1In eukaryotes, oxidation of glucose through glycolysis and the citric acid cycle (or tricarboxylic acid cycle, TCA cycle) yields energy in the form of ATP along with the release of carbon dioxide (CO 2 ) and water. Glycolysis, the breakdown of glucose, includes several reversible and three irreversible (committed) enzymatic reactions leading to the end-product pyruvate (Figure 1). 2,3 The enzymes of the three committed steps in glycolysis are allosterically controlled both positively and negatively. 4-8 Pyruvate is a key metabolic intermediate with many potential fates, including the production of carbohydrates through gluconeogenesis, fatty acids, amino acids or energy (ATP) via acetyl-CoA. Anomalies in glucose metabolism are linked to various pathological conditions, 9-11 so any method that could reliably monitor glucose metabolism in vivo not only would be valuable in fundamental studies of those diseases but could also be a valuable diagnostic biomarker. It has been widely documented that tumors and other rapidly proliferating cells have a dramatic increased rate of glucose uptake and lactate production even in the presence of adequate oxygen supply (the Warburg effect). 9,12,13 In addition, the expression levels of the mono-carboxylate transporters MCT1 and MCT4 are higher in cancer, and this facilitates the export of lactate from cancer cells. Although there is still an ongoing debate about why aerobic glycolysis is advantageous for tumor growth, in general cancer cells modulate glucose uptake as well as several glycolytic enzymes to match their energy demands by rapidly, albeit /journal/nbm 1 of 23 inefficiently, producing ATP in aerobic glycolysis, and to fulfill their increased demand for anabolic intermediates. [14][15]...

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“…Generator produced isotopes, such as 99mTc and 68Ga, are readily available and affordable. The availability of a generator and kit chemistry to prepare 99mTc and 68Ga-based molecular probes may have a significant impact on nuclear medicine (Liu et al, 2014 ). It has been shown that 99mTc-glucarate may behave as a suitable alternative to 18F-FDG as a promising breast tumor imaging agent and needs to be further investigated (Gambini et al, 2011 ).…”

Section: Perspectivesmentioning

confidence: 99%

Molecular imaging of breast cancer: present and future directions

et al. 2014

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Medical imaging technologies have undergone explosive growth over the past few decades and now play a central role in clinical oncology. But the truly transformative power of imaging in the clinical management of cancer patients lies ahead. Today, imaging is at a crossroads, with molecularly targeted imaging agents expected to broadly expand the capabilities of conventional anatomical imaging methods. Molecular imaging will allow clinicians to not only see where a tumor is located in the body, but also to visualize the expression and activity of specific molecules (e.g., proteases and protein kinases) and biological processes (e.g., apoptosis, angiogenesis, and metastasis) that influence tumor behavior and/or response to therapy. Breast cancer, the most common cancer among women and a research area where our group is actively involved, is a very heterogeneous disease with diverse patterns of development and response to treatment. Hence, molecular imaging is expected to have a major impact on this type of cancer, leading to important improvements in diagnosis, individualized treatment, and drug development, as well as our understanding of how breast cancer arises.

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Radiolabeled Glucose Derivatives for Tumor Imaging Using SPECT and PET

Cited by 24 publications

References 0 publications

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

Probing carbohydrate metabolism using hyperpolarized ¹³C‐labeled molecules

Molecular imaging of breast cancer: present and future directions

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Radiolabeled Glucose Derivatives for Tumor Imaging Using SPECT and PET

Cited by 24 publications

References 0 publications

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

Probing carbohydrate metabolism using hyperpolarized 13C‐labeled molecules

Molecular imaging of breast cancer: present and future directions

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Probing carbohydrate metabolism using hyperpolarized ¹³C‐labeled molecules