title: Synthesis and evaluation of an (125)I-labeled azide prosthetic group for efficient and bioorthogonal radiolabeling of cyclooctyne-group containing molecules using copper-free click reaction.
abstract: Herein we report the radiosynthesis of a pyridine derived azide prosthetic group for iodine radioisotope labeling of dibenzocyclooctyne (DBCO) conjugated molecules. The radiolabeling of the stannylated precursor 2 was conducted using [(125)I]NaI and chloramine-T to give (125)I-labeled azide ([(125)I]1) with high radiochemical yield (72±8%, n=4) and radiochemical purity (>99%). Using (125)I-labeled azide ([(125)I]1), cyclic RGD peptide and near infrared fluorescent molecule were efficiently labeled with modest to good radiochemical yields. The biodistribution study and SPECT/CT images showed that [(125)I]1 underwent rapid renal clearance. These results clearly demonstrated that [(125)I]1 could be used as an useful radiotracer for in vivo pre-targeted imaging as well as efficient in vitro radiolabeling of DBCO containing molecules.
authors.affiliation: Advanced Radiation Technology Institute, Korea Atomic Energy Research Institute, Jeongeup, Jeonbuk 580-185, Republic of Korea.
authors.forename: Mi Hee
authors.initials: MH
authors.lastname: Choi
authors.affiliation: Advanced Radiation Technology Institute, Korea Atomic Energy Research Institute, Jeongeup, Jeonbuk 580-185, Republic of Korea.
authors.forename: Ha Eun
authors.initials: HE
authors.lastname: Shim
authors.affiliation: Advanced Radiation Technology Institute, Korea Atomic Energy Research Institute, Jeongeup, Jeonbuk 580-185, Republic of Korea.
authors.forename: You Ree
authors.initials: YR
authors.lastname: Nam
authors.affiliation: Advanced Radiation Technology Institute, Korea Atomic Energy Research Institute, Jeongeup, Jeonbuk 580-185, Republic of Korea.
authors.forename: Hye Rim
authors.initials: HR
authors.lastname: Kim
authors.affiliation: Advanced Radiation Technology Institute, Korea Atomic Energy Research Institute, Jeongeup, Jeonbuk 580-185, Republic of Korea.
authors.forename: Jung Ae
authors.initials: JA
authors.lastname: Kang
authors.affiliation: Advanced Radiation Technology Institute, Korea Atomic Energy Research Institute, Jeongeup, Jeonbuk 580-185, Republic of Korea.
authors.forename: Dong-Eun
authors.initials: DE
authors.lastname: Lee
authors.affiliation: Advanced Radiation Technology Institute, Korea Atomic Energy Research Institute, Jeongeup, Jeonbuk 580-185, Republic of Korea; Department of Radiation Biotechnology and Applied Radioisotope Science, Korea University of Science and Technology, Daejeon 305-350, Republic of Korea.
authors.forename: Sang Hyun
authors.initials: SH
authors.lastname: Park
authors.affiliation: Advanced Radiation Technology Institute, Korea Atomic Energy Research Institute, Jeongeup, Jeonbuk 580-185, Republic of Korea.
authors.forename: Dae Seong
authors.initials: DS
authors.lastname: Choi
authors.affiliation: Advanced Radiation Technology Institute, Korea Atomic Energy Research Institute, Jeongeup, Jeonbuk 580-185, Republic of Korea; Department of Radiation Biotechnology and Applied Radioisotope Science, Korea University of Science and Technology, Daejeon 305-350, Republic of Korea. Electronic address: jangbs@kaeri.re.kr.
authors.forename: Beom-Su
authors.initials: BS
authors.lastname: Jang
authors.affiliation: Advanced Radiation Technology Institute, Korea Atomic Energy Research Institute, Jeongeup, Jeonbuk 580-185, Republic of Korea; Department of Radiation Biotechnology and Applied Radioisotope Science, Korea University of Science and Technology, Daejeon 305-350, Republic of Korea. Electronic address: jeonj@kaeri.re.kr.
authors.forename: Jongho
authors.initials: J
authors.lastname: Jeon
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000818:Animals; D001386:Azides / Q000737:chemistry*; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry; D007457:Iodine Radioisotopes / Q000737:chemistry; D007553:Isotope Labeling; D051379:Mice; D008813:Mice, Inbred ICR; D009842:Oligopeptides / Q000737:chemistry; D019275:Radiopharmaceuticals / Q000138:chemical synthesis / Q000737:chemistry*; D014018:Tissue Distribution; D015899:Tomography, Emission-Computed, Single-Photon
chemical_list: D000480:Alkynes; D001386:Azides; D007457:Iodine Radioisotopes; D009842:Oligopeptides; D019275:Radiopharmaceuticals; D003300:Copper; C047981:arginyl-glycyl-aspartic acid
keywords: Biodistribution; Copper-free click reaction; In vivo imaging; Iodine radioisotope; Radiolabeling