Synthesis, radiolabeling and in vivo evaluation of [C-11](R)-1-[4-[2-(4-methoxyphenyl)phenyl piperazin-1-yl]-3-(2-pyrazinyloxy)-2-propanol, a potential PET radioligand for the 5-HT7 receptor

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Synthesis, radiolabeling and in vivo evaluation of [C-11](R)-1-[4-[2-(4-methoxyphenyl)phenyl piperazin-1-yl]-3-(2-pyrazinyloxy)-2-propanol, a potential PET radioligand for the 5-HT7 receptor. / Hansen, Hanne D.; Lacivita, Enza; Di Pilato, Pantaleo; Herth, Matthias Manfred; Lehel, Szabolcs; Ettrup, Anders; Andersen, Valdemar L.; Dyssegaard, Agnete; De Giorgio, Paola; Perrone, Roberto; Berardi, Francesco; Colabufo, Nicola Antonio; Niso, Mauro; Knudsen, Gitte M.; Leopoldo, Marcello.

In: European Journal of Medicinal Chemistry, Vol. 79, 22.05.2014, p. 152-163.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Hansen, HD, Lacivita, E, Di Pilato, P, Herth, MM, Lehel, S, Ettrup, A, Andersen, VL, Dyssegaard, A, De Giorgio, P, Perrone, R, Berardi, F, Colabufo, NA, Niso, M, Knudsen, GM & Leopoldo, M 2014, 'Synthesis, radiolabeling and in vivo evaluation of [C-11](R)-1-[4-[2-(4-methoxyphenyl)phenyl piperazin-1-yl]-3-(2-pyrazinyloxy)-2-propanol, a potential PET radioligand for the 5-HT7 receptor', European Journal of Medicinal Chemistry, vol. 79, pp. 152-163. https://doi.org/10.1016/j.ejmech.2014.03.066

APA

Hansen, H. D., Lacivita, E., Di Pilato, P., Herth, M. M., Lehel, S., Ettrup, A., Andersen, V. L., Dyssegaard, A., De Giorgio, P., Perrone, R., Berardi, F., Colabufo, N. A., Niso, M., Knudsen, G. M., & Leopoldo, M. (2014). Synthesis, radiolabeling and in vivo evaluation of [C-11](R)-1-[4-[2-(4-methoxyphenyl)phenyl piperazin-1-yl]-3-(2-pyrazinyloxy)-2-propanol, a potential PET radioligand for the 5-HT7 receptor. European Journal of Medicinal Chemistry, 79, 152-163. https://doi.org/10.1016/j.ejmech.2014.03.066

Vancouver

Hansen HD, Lacivita E, Di Pilato P, Herth MM, Lehel S, Ettrup A et al. Synthesis, radiolabeling and in vivo evaluation of [C-11](R)-1-[4-[2-(4-methoxyphenyl)phenyl piperazin-1-yl]-3-(2-pyrazinyloxy)-2-propanol, a potential PET radioligand for the 5-HT7 receptor. European Journal of Medicinal Chemistry. 2014 May 22;79:152-163. https://doi.org/10.1016/j.ejmech.2014.03.066

Author

Hansen, Hanne D. ; Lacivita, Enza ; Di Pilato, Pantaleo ; Herth, Matthias Manfred ; Lehel, Szabolcs ; Ettrup, Anders ; Andersen, Valdemar L. ; Dyssegaard, Agnete ; De Giorgio, Paola ; Perrone, Roberto ; Berardi, Francesco ; Colabufo, Nicola Antonio ; Niso, Mauro ; Knudsen, Gitte M. ; Leopoldo, Marcello. / Synthesis, radiolabeling and in vivo evaluation of [C-11](R)-1-[4-[2-(4-methoxyphenyl)phenyl piperazin-1-yl]-3-(2-pyrazinyloxy)-2-propanol, a potential PET radioligand for the 5-HT7 receptor. In: European Journal of Medicinal Chemistry. 2014 ; Vol. 79. pp. 152-163.

Bibtex

@article{a0fd055f7b734b87bddea6466a55522a,
title = "Synthesis, radiolabeling and in vivo evaluation of [C-11](R)-1-[4-[2-(4-methoxyphenyl)phenyl piperazin-1-yl]-3-(2-pyrazinyloxy)-2-propanol, a potential PET radioligand for the 5-HT7 receptor",
abstract = "In the search for a novel serotonin 7 (5-HT7) receptor PET radioligand we synthesized and evaluated a new series of biphenylpiperazine derivatives in vitro. Among the studied compounds, (R)-1-[4-[2-(4-methoxyphenyl)phenyl]piperazin-1-yl]-3-(2-pyrazinyloxy)-2-propanol ((R)-16), showed the best combination of affinity, selectivity, and lipophilicity, and was thus chosen for carbon-11 labelling and evaluation in pigs. After intravenous injection, [11C](R)-16 entered the pig brain and displayed reversible tracer kinetics. Pretreatment with the 5-HT7 receptor selective antagonist SB-269970 (1) resulted in limited decrease in the binding of [11C](R)-16, suggesting that this radioligand is not optimal for imaging the brain 5-HT7 receptor in vivo but it may serve as a lead compound for the design of novel 5-HT7 receptor PET radioligands.",
keywords = "5-HT7 receptor, PET, Radioligand, Arylpiperazine, SB-269970",
author = "Hansen, {Hanne D.} and Enza Lacivita and {Di Pilato}, Pantaleo and Herth, {Matthias Manfred} and Szabolcs Lehel and Anders Ettrup and Andersen, {Valdemar L.} and Agnete Dyssegaard and {De Giorgio}, Paola and Roberto Perrone and Francesco Berardi and Colabufo, {Nicola Antonio} and Mauro Niso and Knudsen, {Gitte M.} and Marcello Leopoldo",
year = "2014",
month = may,
day = "22",
doi = "10.1016/j.ejmech.2014.03.066",
language = "English",
volume = "79",
pages = "152--163",
journal = "European Journal of Medicinal Chemistry",
issn = "0223-5234",
publisher = "Elsevier Masson",

}

RIS

TY - JOUR

T1 - Synthesis, radiolabeling and in vivo evaluation of [C-11](R)-1-[4-[2-(4-methoxyphenyl)phenyl piperazin-1-yl]-3-(2-pyrazinyloxy)-2-propanol, a potential PET radioligand for the 5-HT7 receptor

AU - Hansen, Hanne D.

AU - Lacivita, Enza

AU - Di Pilato, Pantaleo

AU - Herth, Matthias Manfred

AU - Lehel, Szabolcs

AU - Ettrup, Anders

AU - Andersen, Valdemar L.

AU - Dyssegaard, Agnete

AU - De Giorgio, Paola

AU - Perrone, Roberto

AU - Berardi, Francesco

AU - Colabufo, Nicola Antonio

AU - Niso, Mauro

AU - Knudsen, Gitte M.

AU - Leopoldo, Marcello

PY - 2014/5/22

Y1 - 2014/5/22

N2 - In the search for a novel serotonin 7 (5-HT7) receptor PET radioligand we synthesized and evaluated a new series of biphenylpiperazine derivatives in vitro. Among the studied compounds, (R)-1-[4-[2-(4-methoxyphenyl)phenyl]piperazin-1-yl]-3-(2-pyrazinyloxy)-2-propanol ((R)-16), showed the best combination of affinity, selectivity, and lipophilicity, and was thus chosen for carbon-11 labelling and evaluation in pigs. After intravenous injection, [11C](R)-16 entered the pig brain and displayed reversible tracer kinetics. Pretreatment with the 5-HT7 receptor selective antagonist SB-269970 (1) resulted in limited decrease in the binding of [11C](R)-16, suggesting that this radioligand is not optimal for imaging the brain 5-HT7 receptor in vivo but it may serve as a lead compound for the design of novel 5-HT7 receptor PET radioligands.

AB - In the search for a novel serotonin 7 (5-HT7) receptor PET radioligand we synthesized and evaluated a new series of biphenylpiperazine derivatives in vitro. Among the studied compounds, (R)-1-[4-[2-(4-methoxyphenyl)phenyl]piperazin-1-yl]-3-(2-pyrazinyloxy)-2-propanol ((R)-16), showed the best combination of affinity, selectivity, and lipophilicity, and was thus chosen for carbon-11 labelling and evaluation in pigs. After intravenous injection, [11C](R)-16 entered the pig brain and displayed reversible tracer kinetics. Pretreatment with the 5-HT7 receptor selective antagonist SB-269970 (1) resulted in limited decrease in the binding of [11C](R)-16, suggesting that this radioligand is not optimal for imaging the brain 5-HT7 receptor in vivo but it may serve as a lead compound for the design of novel 5-HT7 receptor PET radioligands.

KW - 5-HT7 receptor

KW - PET

KW - Radioligand

KW - Arylpiperazine

KW - SB-269970

U2 - 10.1016/j.ejmech.2014.03.066

DO - 10.1016/j.ejmech.2014.03.066

M3 - Journal article

C2 - 24732791

VL - 79

SP - 152

EP - 163

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

SN - 0223-5234

ER -

ID: 130891001