Efficient method for iodine radioisotope labeling of cyclooctyne-containing molecules using strain-promoted copper-free click reaction

Jeon, Jongho; Kang, Jung Ae; Shim, Hyung Jin; Nam, You Ree; Yoon, Seonhye; Kim, Hye Rim; Lee, Dong Eun; Park, Sang Hyun

doi:10.1016/j.bmc.2015.04.045

Cited by 27 publications

(29 citation statements)

References 34 publications

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“…In general, the labeling procedure of radioactive iodine is significantly simpler than that of 14 C labeling. However, it is often difficult to accurately quantify 125 I-labeled analogs in animal models due to the low in vivo stability of the C-I bond and high accumulation of radioactive iodine in the thyroid [ 56 , 57 , 58 , 59 , 60 ].…”

Section: In Vivo Assessment Of Hazardous Substances Using Radioanamentioning

confidence: 99%

Radioanalytical Techniques to Quantitatively Assess the Biological Uptake and In Vivo Behavior of Hazardous Substances

et al. 2020

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Concern about environmental exposure to hazardous substances has grown over the past several decades, because these substances have adverse effects on human health. Methods used to monitor the biological uptake of hazardous substances and their spatiotemporal behavior in vivo must be accurate and reliable. Recent advances in radiolabeling chemistry and radioanalytical methodologies have facilitated the quantitative analysis of toxic substances, and whole-body imaging can be achieved using nuclear imaging instruments. Herein, we review recent literature on the radioanalytical methods used to study the biological distribution, changes in the uptake and accumulation of hazardous substances, including industrial chemicals, nanomaterials, and microorganisms. We begin with an overview of the radioisotopes used to prepare radiotracers for in vivo experiments. We then summarize the results of molecular imaging studies involving radiolabeled toxins and their quantitative assessment. We conclude the review with perspectives on the use of radioanalytical methods for future environmental research.

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Section: In Vivo Assessment Of Hazardous Substances Using Radioanamentioning

confidence: 99%

Radioanalytical Techniques to Quantitatively Assess the Biological Uptake and In Vivo Behavior of Hazardous Substances

et al. 2020

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“…The primary drawback of this technique is that the catalysts (usually Cu) are required, which can affect the biocompatibility of the materials [36]. To overcome this issue, significant amount of work has been performed to develop the metal‐free click reaction [37]. Our group prepared hydrogels via in situ Diels–Alder reaction, which could proceed in water without the use of any initiator or catalysts [38].…”

Section: Introductionmentioning

confidence: 99%

Preparation and Characterization of Thermal and pH Dual Sensitive Hydrogel Based on 1,3‐Dipole Cycloaddition Reaction

Wei

Liu

Zhu

et al. 2020

Polymer Engineering & Sci

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In this study, thermal and pH dual sensitive hydrogels were prepared via Cu-free 1,3-dipole cycloaddition between two copolymers which were modified by azide and maleimide functional groups, respectively. First, the thermally sensitive terpolymers were fabricated via conventional free-radical polymerization of N-isopropylacrylamide, hydroxyethyl methacrylate (HEMA), and N,N-dimethylacrylamide (DMA). Then, polymeric dipolarophiles were synthesized via the esterification between the above terpolymers and N-maleoyl alanine. Similarly, the pH-sensitive terpolymers were also fabricated via conventional free-radical polymerization of 4-vinylpyridine, HEMA, and DMA, and then, polymeric dipoles were acquired via the decoration of the as-prepared terpolymers with 2-azidoacetic acid. Afterward, the smart hydrogels were fabricated via the aqueous 1,3-dipole cycloaddition reaction between the as-prepared polymeric dipolarophiles and dipoles without the use of catalysts. The results of swelling measurements confirm that the hydrogels possessed thermal and pH dual sensitivity. Moreover, the investigation of the behavior of oscillatory swelling shrinking indicates their sensitivity to temperature and pH was reversible and repeatable, which is of great significance for the repeated use of the prepared hydrogels. The proposed strategy demonstrates a great application prospects in the preparation of hydrogels as there were no catalysts and organic solvents employed. POLYM. ENG. SCI., 60:917-924, 2020.

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“…Click ligation of radioactive tags on various biomolecules are also the object of an important research effort to provide new strategies for labeling with radioisotopes that require fast, simple and efficient procedures that are difficult to reach by conventional chemistry. 12 Recent reports have proposed the use of bioorthogonal chemistry for radioiodination of peptides or proteins with clickable prosthetic groups including the strain-promoted alkyneazide cycloaddition (SPAAC) 13,14 and the inverse electron demand Diels Alder cycloaddition (IEDDA) reactions, 15,16 but to our knowledge, such strategy has not yet been reported for astatination. Yet, the necessity of fast, simple and quantitative yielding labeling procedure is even more essential for astatination with 211 At because of its availability in low amounts, its shorter physical half-life compared to relevant iodine radioisotopes, and the marked radiolysis issues due to the astatine decay limiting the starting activity that can be engaged in a radiolabeling procedure, 17 for the preparation of radiopharmaceuticals for clinical use, or even for animal studies.…”

Section: Introductionmentioning

confidence: 99%

“…Hz) /13 C NMR (100 MHz, CDCl 3 ): δ 169.2, 168.1, 82.7, 70.0, 29.8, 25.7, 23.5, 17.7 / ESI: not Reagent available commercially from Click Chemistry Tools. The reaction mixture was extracted with CH 2 Cl 2 (2x30 mL).…”

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confidence: 99%

Prosthetic groups for radioiodination and astatination of peptides and proteins: A comparative study of five potential bioorthogonal labeling strategies

Navarro

Berdal

Chérel

et al. 2019

Bioorganic & Medicinal Chemistry

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Efficient method for iodine radioisotope labeling of cyclooctyne-containing molecules using strain-promoted copper-free click reaction

Cited by 27 publications

References 34 publications

Radioanalytical Techniques to Quantitatively Assess the Biological Uptake and In Vivo Behavior of Hazardous Substances

Radioanalytical Techniques to Quantitatively Assess the Biological Uptake and In Vivo Behavior of Hazardous Substances

Preparation and Characterization of Thermal and pH Dual Sensitive Hydrogel Based on 1,3‐Dipole Cycloaddition Reaction

Prosthetic groups for radioiodination and astatination of peptides and proteins: A comparative study of five potential bioorthogonal labeling strategies

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