Evaluation of 4-[18F]fluoro-1-butyne as a radiolabeled synthon for click chemistry with azido compounds

Applied Radiation and Isotopes - Tập 68 - Trang 329-333 - 2010
Dong Hyun Kim1, Yearn Seong Choe1, Byung-Tae Kim1
1Department of Nuclear Medicine, Samsung Medical Center, Sungkyunkwan University School of Medicine, Center for Molecular and Cellular Imaging, Samsung Biomedical Research Institute, 50 Ilwon-dong, Kangnam-ku, Seoul 135-710, Republic of Korea

Tài liệu tham khảo

Bock, 2006, Cu(I)-catalyzed alkyne-azide “click” cycloaddition from a mechanistic and synthetic perspective, Eur. J. Org. Chem., 1, 51, 10.1002/ejoc.200500483

Eglinton, 1950, Researches on acetylenic compounds. Part XXVII. The preparation and properties of the toluene-p-sulphonates of acetylenic alcohols, J. Chem. Soc., 3650, 10.1039/jr9500003650

Glaser, 2007, “Click labeling” with 2-[18F]fluoroethylazide for positron emission tomography, Bioconjugate Chem., 18, 989, 10.1021/bc060301j

Hausner, 2008, In vivo positron emission tomography (PET) imaging with an avβ6 specific peptide radiolabeled using 18F-click chemistry: evaluation and comparison with the corresponding 4-[18F]fluorobenzoyl- and 2-[18F]fluoropropionyl-peptides, J. Med. Chem., 51, 5901, 10.1021/jm800608s

Hennion, 1954, The preparation of vinylacetylene, J. Am. Chem. Soc., 76, 5160, 10.1021/ja01649a054

Hotha, 2006, “Click chemistry” inspired synthesis of pseudo-oligosaccharides and amino acid glycoconjugates, J. Org. Chem., 71, 364, 10.1021/jo051731q

Huisgen, 1984, Historical note, general principle and mechanistic criteria, vol. 1, 1

Huisgen, 1963, Kinetics and mechanism of 1,3-dipolar cycloaddition, Angew. Chem. Int. Ed., 2, 633, 10.1002/anie.196306331

Job, 1962, Propargyl fluoride and its microwave spectrum, Nature, 193, 677, 10.1038/193677a0

Kim, 2009, Synthesis of 17-[4-(2-[18F]fluoroethyl)-1H-1,2,3-triazol-1-yl]-6-thia-heptadecanoic acid as a novel radiotracer for evaluation of myocardial fatty acid utilization, Bioconjugate Chem., 20, 1139, 10.1021/bc800472a

Kim, 2008, Facile nucleophilic fluorination reactions using tert-alcohols as a reaction medium: significantly enhanced reactivity of alkali metal fluorides and improved selectivity, J. Org. Chem., 73, 957, 10.1021/jo7021229

Kim, 2006, A new class of SN2 reactions catalyzed by protic solvents: facile fluorination for isotopic labeling of diagnostic molecules, J. Am. Chem. Soc., 128, 16394, 10.1021/ja0646895

Kolb, 2001, Click chemistry: diverse chemical function from a few good reactions, Angew. Chem. Int. Ed., 40, 2004, 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5

Li, 2007, Click chemistry for 18F-labeling of RGD peptides and microPET imaging of tumor integrin avβ3 expression, Bioconjugate Chem., 18, 1987, 10.1021/bc700226v

Link, 2003, Cell surface labeling of Escherichia coli via copper(I)-catalyzed [3+2] cycloaddition, J. Am. Chem. Soc., 125, 11164, 10.1021/ja036765z

Mindt, 2008, “Click-to-chelate”: In vitro and in vivo comparison of a 99mTc(CO)3-labeled N(τ)-histidine folate derivative with its isostructural, clicked 1,2,3-triazole analogue, Bioconjugate Chem., 19, 1689, 10.1021/bc800183r

Ross, 2008, Fluorine-18 click radiosynthesis and preclinical evaluation of a new F-labeled folic acid derivative, Bioconjugate Chem., 19, 2462, 10.1021/bc800356r

Rostovtsev, 2002, A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes, Angew. Chem. Int. Ed., 41, 2596, 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4

Speers, 2003, Activity-based protein profiling in vivo using a copper(I)-catalyzed azide-alkyne [3+2] cycloaddition, J. Am. Chem. Soc., 125, 4686, 10.1021/ja034490h

Tornoe, 2002, Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides, J. Org. Chem., 67, 3057, 10.1021/jo011148j

Wang, 2003, Bioconjugation by copper(I)-catalyzed azide-alkyne [3+2] cycloaddition, J. Am. Chem. Soc., 125, 3192, 10.1021/ja021381e