Synthesis and Characterization of Radioiodinated (S)-5-Iodonicotine : A New Ligand for Potential Imaging of Brain Nicotinic Cholinergic Receptors by Single Photon Emission Computed Tomography

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概要

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• (S)-5-Iodonicotine (4a), an (S)-nicotine analog iodinated at the 5-position of the pyridine ring, was synthesized and evaluated as a potential radiopharmaceutical for investigating brain nicotine receptors by single photon emission computerized tomography (SPECT). [^<125>I]-(S)-5-Iodonicotine ([^<125>I]-4a) was synthesized by the iododestannylation reaction under no-carrier-added conditions and purified by high-performance liquid chromatography (HPLC). The binding affinity of 4a for brain nicotine receptors was measured in terms of displacement of [^3H]cytisine from binding sites in rat cortical membranes. The binding data revealed that the affinity of 4a was the same as that of (S)-nicotine and 80-fold higher than that of the (R)-enantiomer (4b). Biodistribution studies in mice disclosed that the brain uptake of [^<125;>I]-4a was rapid and profound. Regional cerebral distribution studies in rats by autoradiography disclosed that the accumulation of [^<125>I]-4a was dense in the thalamus, intermediate in the cortex and striatum, and less marked in the cerebellum. Furthermore, the administration of (S)-nicotine reduced the uptake of [^<125>I]-4a in the thalamus and resulted in a nearly identifal level of radioactivity in the cerebellum. [^<125>I]-(R)-5-Iodonicotine ([^<125>I]-4b) showed more rapid washout from the brain and a less extensive regional cerebral distribution than the (S)-enantiomer ([^<125>I]-4a). Thus, 4a bound to brain nicotine receptors in vivo, and therefore iodine-123-labeled 4a may be a potential radioligand for use in in vivo cerebral nicotinic receptor studies by SPECT.

• 公益社団法人日本薬学会の論文
• 1997-02-15

著者

• Saji Hideo

  茨城県立医療大学 放射線技術科学

• Magata Y

  Photon Medical Research Center Hamamatsu University School Of Medicine:molecular Imaging Frontier Re

• Magata Yasuhiro

  京都大学 医学研究科心臓血管外科学

• Magata Yasuhiro

  浜松医科大学附属光量子医学研究センター

• Kiyono Yasushi

  Department Of Radioisotope Laboratory Graduate School Of Medicine Kyoto University

• Kiyono Yasushi

  京都大学 薬研究 病態機能分析

• Kiyono Yasushi

  Faculty Of Pharmaceutical Sciences Kyoto University

• Magata Y

  Laboratory Of Genome-bio Photonics Photon Medical Research Center Hamamatsu University School Of Med

• Yasuhiro Magata

  Photon Medical Research Center Hamamatsu University School Of Medicine:molecular Imaging Frontier Re

• YOSHIDA AKIRA

  Mitsubishi Kyoto Hospital

• Konishi Junji

  京都大学 医学研究科心臓血管外科学

• Konishi Junji

  京都大学 院循環病態学

• Konishi J

  Department Of Nuclear Medicine And Diagnostic Imaging

• SAJI Hideo

  Faculty of Pharmaceutical Sciences, Kyoto University

• YOKOYAMA Akira

  Faculty of Pharmaceutical Sciences, Kyoto University

• YONEKURA Yoshiharu

  School of Medicine, Kyoto University

• KONISHI Junji

  School of Medicine, Kyoto University

• Ida Yuko

  Department Of Applied Pharmacology Graduate School Of Medicine And Pharmaceutical Sciences Universit

• Ishii Yasushi

  Third Division Dept. Of Internal Medicine And Nuclear Medicine

• Iida Y

  Department Of Bioimaging Medical Sciences Gunma University

• Iida Yasuhiko

  Department Of Bioimaging Medical Sciences Gunma University

• Iida Yasuhiko

  Department Of Radiopharmaceutical Chemistry Faculty Of Pharmaceutical Sciences Kyoto University

• Yokoyama A

  Biomedical Imaging Research Center Fukui Medical School

• WATANABE Akira

  Faculty of Pharmaceutical Sciences, Kyoto University

• MAGATA Yasuhiro

  School of Medicine, Kyoto University

• YAMADA Yoshihisa

  Faculty of Pharmaceutical Sciences, Kyoto University

• IIDA Yasuhiko

  School of Medicine, Kyoto University

• Miyake Yoshinori

  Department Of Radiology And Nuclear Medicine National Cardiovascular Center

• Yamamuro Masaki

  Department Of Diagnostic Imaging And Nuclear Medicine Kyoto University Graduate School Of Medicine

• Saji Hideo

  Dep. Of Patho-functional Bioanalysis Graduate School Of Pharmaceutical Sciences Kyoto Univ.

• Yokoyama Akira

  Biomedical Imaging Research Center Fukui Medical School

• Sakahara H

  Kyoto Univ. School Of Medicine

• Ishii Yasushi

  Department Of Radiology Kyoto University School Of Medicine

• Watanabe A

  Faculty Of Pharmaceutical Sciences Kyoto University

• Yamada Yoshihisa

  Faculty Of Pharmaceutical Sciences Kyoto University

• Ishii Yasushi

  Department Of Patho-functional Bioanalysis Graduate School Of Pharmaceutical Sciences Kyoto Universi

• Watanabe Akira

  Faculty Of Liberal Arts And Science Yamagata University

• YOKOYAMA AKIRA

  Faculty of Agriculture, Nagoya University

• Yamada Yoshihisa

  Faculty of Engineering, University of Yamanashi, 4-3-11 Takeda, Kofu, Yamanashi 400-8511, Japan

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