Synthesis and preclinical evaluation of 2-(2-furanyl)-7-[2-[4-[4-(2-[11C]methoxyethoxy)phenyl]-1-piperazinyl]ethyl]7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5-amine ([11C]Preladenant) as a PET tracer for the imaging of cerebral adenosine A2A receptors

Xiaoyun Zhou; Shivashankar Khanapur; Anja P. Huizing; Rolf Zijlma; Marianne Schepers; Rudi A. J. O. Dierckx; Aren van Waarde; Erik de Vries; Philippus Elsinga

doi:10.1021/jm501065t

Synthesis and preclinical evaluation of 2-(2-furanyl)-7-[2-[4-[4-(2-[11C]methoxyethoxy)phenyl]-1-piperazinyl]ethyl]7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5-amine ([11C]Preladenant) as a PET tracer for the imaging of cerebral adenosine A2A receptors

Xiaoyun Zhou, Shivashankar Khanapur, Anja P. Huizing, Rolf Zijlma, Marianne Schepers, Rudi A. J. O. Dierckx, Aren van Waarde, Erik de Vries, Philippus Elsinga^*

^*Corresponding author for this work

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

28 Citations (Scopus)

Abstract

2-(2-Furanyl)-7-[2-[4-[4-(2-[C-11]methoxyethoxy)phenyl]-1-piperazinyl]ethyl]7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5-amine [(11)C]-3 ([C-11]Preladenant) was developed for mapping cerebral adenosine A2A receptors (A2ARs) with PET. The tracer was synthesized in high specific activity and purity. Tissue distribution was studied by PET imaging, ex vivo biodistribution (BD), and in vitro autoradiography (ARG) experiments. Regional brain uptake of [C-11]-3 was consistent with known A(2A)Rs distribution, with highest uptake in striatum. The results indicate that [C-11]-3 has favorable brain kinetics and exhibits suitable characteristics as an A(2A)R PET tracer.

Original language	English
Pages (from-to)	9204-9210
Number of pages	7
Journal	Journal of Medicinal Chemistry
Volume	57
Issue number	21
DOIs	https://doi.org/10.1021/jm501065t
Publication status	Published - 13-Nov-2014

Keywords

POSITRON-EMISSION-TOMOGRAPHY
PARKINSONS-DISEASE
BASAL GANGLIA
LIGAND
RAT
ISTRADEFYLLINE
ANTAGONISTS
POTENT
BRAIN

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Zhou, X., Khanapur, S., Huizing, A. P., Zijlma, R., Schepers, M., Dierckx, R. A. J. O., van Waarde, A., de Vries, E., & Elsinga, P. (2014). Synthesis and preclinical evaluation of 2-(2-furanyl)-7-[2-[4-[4-(2-[11C]methoxyethoxy)phenyl]-1-piperazinyl]ethyl]7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5-amine ([11C]Preladenant) as a PET tracer for the imaging of cerebral adenosine A2A receptors. Journal of Medicinal Chemistry, 57(21), 9204-9210. https://doi.org/10.1021/jm501065t

Zhou, Xiaoyun ; Khanapur, Shivashankar ; Huizing, Anja P. et al. / Synthesis and preclinical evaluation of 2-(2-furanyl)-7-[2-[4-[4-(2-[11C]methoxyethoxy)phenyl]-1-piperazinyl]ethyl]7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5-amine ([11C]Preladenant) as a PET tracer for the imaging of cerebral adenosine A2A receptors. In: Journal of Medicinal Chemistry. 2014 ; Vol. 57, No. 21. pp. 9204-9210.

@article{69afd17b4bca49bf89de7e1a88779336,

title = "Synthesis and preclinical evaluation of 2-(2-furanyl)-7-[2-[4-[4-(2-[11C]methoxyethoxy)phenyl]-1-piperazinyl]ethyl]7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5-amine ([11C]Preladenant) as a PET tracer for the imaging of cerebral adenosine A2A receptors",

abstract = "2-(2-Furanyl)-7-[2-[4-[4-(2-[C-11]methoxyethoxy)phenyl]-1-piperazinyl]ethyl]7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5-amine [(11)C]-3 ([C-11]Preladenant) was developed for mapping cerebral adenosine A2A receptors (A2ARs) with PET. The tracer was synthesized in high specific activity and purity. Tissue distribution was studied by PET imaging, ex vivo biodistribution (BD), and in vitro autoradiography (ARG) experiments. Regional brain uptake of [C-11]-3 was consistent with known A(2A)Rs distribution, with highest uptake in striatum. The results indicate that [C-11]-3 has favorable brain kinetics and exhibits suitable characteristics as an A(2A)R PET tracer.",

keywords = "POSITRON-EMISSION-TOMOGRAPHY, PARKINSONS-DISEASE, BASAL GANGLIA, LIGAND, RAT, ISTRADEFYLLINE, ANTAGONISTS, POTENT, BRAIN",

author = "Xiaoyun Zhou and Shivashankar Khanapur and Huizing, {Anja P.} and Rolf Zijlma and Marianne Schepers and Dierckx, {Rudi A. J. O.} and {van Waarde}, Aren and {de Vries}, Erik and Philippus Elsinga",

year = "2014",

month = nov,

day = "13",

doi = "10.1021/jm501065t",

language = "English",

volume = "57",

pages = "9204--9210",

journal = "Journal of Medicinal Chemistry",

issn = "0022-2623",

publisher = "AMER CHEMICAL SOC",

number = "21",

}

Zhou, X, Khanapur, S, Huizing, AP, Zijlma, R , Schepers, M , Dierckx, RAJO, van Waarde, A, de Vries, E & Elsinga, P 2014, 'Synthesis and preclinical evaluation of 2-(2-furanyl)-7-[2-[4-[4-(2-[11C]methoxyethoxy)phenyl]-1-piperazinyl]ethyl]7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5-amine ([11C]Preladenant) as a PET tracer for the imaging of cerebral adenosine A2A receptors', Journal of Medicinal Chemistry, vol. 57, no. 21, pp. 9204-9210. https://doi.org/10.1021/jm501065t

Synthesis and preclinical evaluation of 2-(2-furanyl)-7-[2-[4-[4-(2-[11C]methoxyethoxy)phenyl]-1-piperazinyl]ethyl]7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5-amine ([11C]Preladenant) as a PET tracer for the imaging of cerebral adenosine A2A receptors. / Zhou, Xiaoyun; Khanapur, Shivashankar; Huizing, Anja P. et al.
In: Journal of Medicinal Chemistry, Vol. 57, No. 21, 13.11.2014, p. 9204-9210.

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

TY - JOUR

T1 - Synthesis and preclinical evaluation of 2-(2-furanyl)-7-[2-[4-[4-(2-[11C]methoxyethoxy)phenyl]-1-piperazinyl]ethyl]7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5-amine ([11C]Preladenant) as a PET tracer for the imaging of cerebral adenosine A2A receptors

AU - Zhou, Xiaoyun

AU - Khanapur, Shivashankar

AU - Huizing, Anja P.

AU - Zijlma, Rolf

AU - Schepers, Marianne

AU - Dierckx, Rudi A. J. O.

AU - van Waarde, Aren

AU - de Vries, Erik

AU - Elsinga, Philippus

PY - 2014/11/13

Y1 - 2014/11/13

N2 - 2-(2-Furanyl)-7-[2-[4-[4-(2-[C-11]methoxyethoxy)phenyl]-1-piperazinyl]ethyl]7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5-amine [(11)C]-3 ([C-11]Preladenant) was developed for mapping cerebral adenosine A2A receptors (A2ARs) with PET. The tracer was synthesized in high specific activity and purity. Tissue distribution was studied by PET imaging, ex vivo biodistribution (BD), and in vitro autoradiography (ARG) experiments. Regional brain uptake of [C-11]-3 was consistent with known A(2A)Rs distribution, with highest uptake in striatum. The results indicate that [C-11]-3 has favorable brain kinetics and exhibits suitable characteristics as an A(2A)R PET tracer.

AB - 2-(2-Furanyl)-7-[2-[4-[4-(2-[C-11]methoxyethoxy)phenyl]-1-piperazinyl]ethyl]7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5-amine [(11)C]-3 ([C-11]Preladenant) was developed for mapping cerebral adenosine A2A receptors (A2ARs) with PET. The tracer was synthesized in high specific activity and purity. Tissue distribution was studied by PET imaging, ex vivo biodistribution (BD), and in vitro autoradiography (ARG) experiments. Regional brain uptake of [C-11]-3 was consistent with known A(2A)Rs distribution, with highest uptake in striatum. The results indicate that [C-11]-3 has favorable brain kinetics and exhibits suitable characteristics as an A(2A)R PET tracer.

KW - POSITRON-EMISSION-TOMOGRAPHY

KW - PARKINSONS-DISEASE

KW - BASAL GANGLIA

KW - LIGAND

KW - RAT

KW - ISTRADEFYLLINE

KW - ANTAGONISTS

KW - POTENT

KW - BRAIN

U2 - 10.1021/jm501065t

DO - 10.1021/jm501065t

M3 - Article

C2 - 25279444

SN - 0022-2623

VL - 57

SP - 9204

EP - 9210

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 21

ER -

Zhou X, Khanapur S, Huizing AP, Zijlma R , Schepers M , Dierckx RAJO et al. Synthesis and preclinical evaluation of 2-(2-furanyl)-7-[2-[4-[4-(2-[11C]methoxyethoxy)phenyl]-1-piperazinyl]ethyl]7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5-amine ([11C]Preladenant) as a PET tracer for the imaging of cerebral adenosine A2A receptors. Journal of Medicinal Chemistry. 2014 Nov 13;57(21):9204-9210. doi: 10.1021/jm501065t