Synthesis and evaluation of 18F- and 11C-labelled 9,10-ethanobenzo[b]quinolizinium derivatives for imaging of the NMDA receptor at the TCP-binding site

Nobuyasu Ishibashi; Tsuneo Kuwamura; Hiromi Sano; Fumihiko Yamamoto; Terushi Haradahira; Kazutoshi Suzuki; Tetsuya Suhara; Shigeki Sasaki; Minoru Maeda

doi:10.1002/(SICI)1099-1344(20000330)43:4<375::AID-JLCR324>3.0.CO;2-Q

Synthesis and evaluation of ¹⁸F- and ¹¹C-labelled 9,10-ethanobenzo[b]quinolizinium derivatives for imaging of the NMDA receptor at the TCP-binding site

Nobuyasu Ishibashi, Tsuneo Kuwamura, Hiromi Sano, Fumihiko Yamamoto, Terushi Haradahira, Kazutoshi Suzuki, Tetsuya Suhara, Shigeki Sasaki, Minoru Maeda

Chemo-Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

Derivatives of 9,10-ethanobenzo[b]quinolizinium are potent antagonists for the TCP-site of the NMDA receptor. Two fluoroethyl-substituted analogues were labelled with fluorine-18 by displacement of the tosylate with [¹⁸F]fluoride, followed by a Diels-Alder reaction. A methoxy-substituted analogue labelled with carbon-11 was obtained by O-methylation of the corresponding hydroxy precursor with [¹¹C]iodomethane. In biodistribution studies in mice with these three radioligands, it was found that they have little ability to penetrate the blood-brain barrier.

Original language	English
Pages (from-to)	375-383
Number of pages	9
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	43
Issue number	4
DOIs	https://doi.org/10.1002/(SICI)1099-1344(20000330)43:4<375::AID-JLCR324>3.0.CO;2-Q
Publication status	Published - Mar 30 2000

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Biochemistry
Radiology Nuclear Medicine and imaging
Drug Discovery
Spectroscopy
Organic Chemistry

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10.1002/(SICI)1099-1344(20000330)43:4<375::AID-JLCR324>3.0.CO;2-Q

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Ishibashi, N., Kuwamura, T., Sano, H., Yamamoto, F., Haradahira, T., Suzuki, K., Suhara, T., Sasaki, S., & Maeda, M. (2000). Synthesis and evaluation of ¹⁸F- and ¹¹C-labelled 9,10-ethanobenzo[b]quinolizinium derivatives for imaging of the NMDA receptor at the TCP-binding site. Journal of Labelled Compounds and Radiopharmaceuticals, 43(4), 375-383. https://doi.org/10.1002/(SICI)1099-1344(20000330)43:4<375::AID-JLCR324>3.0.CO;2-Q

Synthesis and evaluation of ¹⁸F- and ¹¹C-labelled 9,10-ethanobenzo[b]quinolizinium derivatives for imaging of the NMDA receptor at the TCP-binding site. / Ishibashi, Nobuyasu; Kuwamura, Tsuneo; Sano, Hiromi et al.
In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 43, No. 4, 30.03.2000, p. 375-383.

Research output: Contribution to journal › Article › peer-review

Ishibashi, N, Kuwamura, T, Sano, H, Yamamoto, F, Haradahira, T, Suzuki, K, Suhara, T, Sasaki, S & Maeda, M 2000, 'Synthesis and evaluation of ¹⁸F- and ¹¹C-labelled 9,10-ethanobenzo[b]quinolizinium derivatives for imaging of the NMDA receptor at the TCP-binding site', Journal of Labelled Compounds and Radiopharmaceuticals, vol. 43, no. 4, pp. 375-383. https://doi.org/10.1002/(SICI)1099-1344(20000330)43:4<375::AID-JLCR324>3.0.CO;2-Q

Ishibashi N, Kuwamura T, Sano H, Yamamoto F, Haradahira T, Suzuki K et al. Synthesis and evaluation of ¹⁸F- and ¹¹C-labelled 9,10-ethanobenzo[b]quinolizinium derivatives for imaging of the NMDA receptor at the TCP-binding site. Journal of Labelled Compounds and Radiopharmaceuticals. 2000 Mar 30;43(4):375-383. doi: 10.1002/(SICI)1099-1344(20000330)43:4<375::AID-JLCR324>3.0.CO;2-Q

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abstract = "Derivatives of 9,10-ethanobenzo[b]quinolizinium are potent antagonists for the TCP-site of the NMDA receptor. Two fluoroethyl-substituted analogues were labelled with fluorine-18 by displacement of the tosylate with [18F]fluoride, followed by a Diels-Alder reaction. A methoxy-substituted analogue labelled with carbon-11 was obtained by O-methylation of the corresponding hydroxy precursor with [11C]iodomethane. In biodistribution studies in mice with these three radioligands, it was found that they have little ability to penetrate the blood-brain barrier.",

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AU - Kuwamura, Tsuneo

AU - Sano, Hiromi

AU - Yamamoto, Fumihiko

AU - Haradahira, Terushi

AU - Suzuki, Kazutoshi

AU - Suhara, Tetsuya

AU - Sasaki, Shigeki

AU - Maeda, Minoru

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AB - Derivatives of 9,10-ethanobenzo[b]quinolizinium are potent antagonists for the TCP-site of the NMDA receptor. Two fluoroethyl-substituted analogues were labelled with fluorine-18 by displacement of the tosylate with [18F]fluoride, followed by a Diels-Alder reaction. A methoxy-substituted analogue labelled with carbon-11 was obtained by O-methylation of the corresponding hydroxy precursor with [11C]iodomethane. In biodistribution studies in mice with these three radioligands, it was found that they have little ability to penetrate the blood-brain barrier.

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Synthesis and evaluation of ¹⁸F- and ¹¹C-labelled 9,10-ethanobenzo[b]quinolizinium derivatives for imaging of the NMDA receptor at the TCP-binding site

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