publication . Article . Other literature type . 2018

Identification of the allosteric P2X7 receptor antagonist [11C]SMW139 as a PET tracer of microglial activation

Janssen, Bieneke; Vugts, Danielle J.; Wilkinson, Shane M.; Ory, Dieter; Chalon, Sylvie; Hoozemans, Jeroen J. M.; Schuit, Robert C.; Beaino, Wissam; Kooijman, Esther J. M.; van den Hoek, Johan; ...
Open Access English
  • Published: 26 Apr 2018
Abstract
Abstract The P2X7 receptor plays a significant role in microglial activation, and as a potential drug target, the P2X7 receptor is also an interesting target in positron emission tomography. The current study aimed at the development and evaluation of a potent tracer targeting the P2X7 receptor, to which end four adamantanyl benzamide analogues with high affinity for the human P2X7 receptor were labelled with carbon-11. All four analogues could be obtained in excellent radiochemical yield and high radiochemical purity and molar activity, and all analogues entered the rat brain. [11C]SMW139 showed the highest metabolic stability in rat plasma, and showed high bin...
Subjects
free text keywords: General, Settore BIO/14 - Farmacologia, Settore BIO/12 - Biochimica Clinica e Biologia Molecolare Clinica, Settore MED/37 - Neuroradiologia, Article, R, Science, Q, Multidisciplinary, In vitro, Receptor expression, Receptor, Pharmacology, Receptor antagonist, medicine.drug_class, medicine, Benzamide, chemistry.chemical_compound, chemistry, Allosteric regulation, In vivo, Ligand (biochemistry)
Funded by
EC| INMIND
Project
INMIND
Imaging of Neuroinflammation in Neurodegenerative Diseases
  • Funder: European Commission (EC)
  • Project Code: 278850
  • Funding stream: FP7 | SP1 | HEALTH
21 references, page 1 of 2

Beamer, E. Purinergic mechanisms in neuroinflammation: An update from molecules to behaviour. Neuropharmacology. 2016; 104: 94-104 [OpenAIRE] [PubMed] [DOI]

Bhattacharya, A, Biber, K. The Microglial ATP-Gated Ion Channel P2X7 As a CNS Drug Target. GLIA. 2016; 64: 1772-1787 [OpenAIRE] [PubMed] [DOI]

Burnstock, G. P2X ion channel receptors and inflammation. Purinergic Signalling. 2016; 12: 59-67 [OpenAIRE] [PubMed] [DOI]

Janssen, B. Synthesis and initial preclinical evaluation of the P2X7 receptor antagonist [11C]A-740003 as a novel tracer of neuroinflammation. J. Labelled Compd. Radiopharm.. 2014; 57: 509-516 [OpenAIRE] [DOI]

Gao, M, Wang, M, Green, MA, Hutchins, GD, Zheng, Q-H. Synthesis of [11C]GSK1482160 as a new PET agent for targeting P2X7 receptor. Bioorg. Med. Chem. Lett.. 2016; 25: 1965-1970 [OpenAIRE] [DOI]

Ory, D. Preclinical evaluation of a P2X7 receptor selective radiotracer: positron emission tomography studies in a rat model with local overexpression of the human P2X7 receptor and in non-human primates. J. Nucl. Med.. 2016; 57: 1436-1441 [OpenAIRE] [PubMed] [DOI]

Territo, PR. Characterization of C-11-GSK1482160 for Targeting the P2X7 Receptor as a Biomarker for Neuroinflammation. J. Nucl. Med.. 2017; 58: 458-465 [OpenAIRE] [PubMed] [DOI]

Fantoni, ER. Design, synthesis and evaluation in an LPS rodent model of neuroinflammation of a novel 18F-labelled PET tracer targeting P2X7. EJNMMI Res.. 2017; 2017: 7:31 [OpenAIRE]

Han, J. Pharmacologic characterizations of a P2X7 receptor-specific radioligand, [11C]GSK1482160 for neuroinflammatory response. Nucl. Med. Commun.. 2017; 38: 372-382 [OpenAIRE] [PubMed] [DOI]

Wilkinson, SM. Pharmacological evaluation of novel bioisosteres of an adamantanyl benzamide P2X7 receptor antagonist. ACS Chem. Neurosci.. 2017: 2374-2380

Baxter, A. Hit-to-Lead Studies: The Discovery of Potent Adamantane Amide P2X7 Receptor Antagonists. Bioorg. Med. Chem. Lett.. 2003; 13: 4047-4050 [OpenAIRE] [PubMed] [DOI]

Honore, P. A-740003 [N-(1-{[(Cyanoimino)(5-quinolinylamino)methyl]amino}-2,2-dimethylpropyl)-2-(3,4-dimethoxyphenyl)acetamide], a Novel and Selective P2X7 Receptor Antagonist, Dose-Dependently Reduces Neuropathic Pain in the Rat. J. Pharmacol. Exp. Ther.. 2006; 319: 1376-1385 [OpenAIRE] [PubMed] [DOI]

Perez-Medrano, A. Discovery and Biological Evaluation of Novel Cyanoguanidine P2X7 Antagonists with Analgesic Activity in a Rat Model of Neuropathic Pain. J. Med. Chem.. 2009; 52: 3366-3376 [OpenAIRE] [PubMed] [DOI]

Letavic, MA. Synthesis and Pharmacological Characterization of Two Novel, Brain Penetrating P2X7 Antagonists. ACS Med. Chem. Lett.. 2013; 4: 419-422 [OpenAIRE] [PubMed] [DOI]

Bhattacharya, A. Pharmacological characterization of a novel centrally permeable P2X7 receptor antagonist: JNJ-47965567. Br. J. Pharmacol.. 2013; 170: 624-640 [OpenAIRE] [PubMed] [DOI]

21 references, page 1 of 2
Abstract
Abstract The P2X7 receptor plays a significant role in microglial activation, and as a potential drug target, the P2X7 receptor is also an interesting target in positron emission tomography. The current study aimed at the development and evaluation of a potent tracer targeting the P2X7 receptor, to which end four adamantanyl benzamide analogues with high affinity for the human P2X7 receptor were labelled with carbon-11. All four analogues could be obtained in excellent radiochemical yield and high radiochemical purity and molar activity, and all analogues entered the rat brain. [11C]SMW139 showed the highest metabolic stability in rat plasma, and showed high bin...
Subjects
free text keywords: General, Settore BIO/14 - Farmacologia, Settore BIO/12 - Biochimica Clinica e Biologia Molecolare Clinica, Settore MED/37 - Neuroradiologia, Article, R, Science, Q, Multidisciplinary, In vitro, Receptor expression, Receptor, Pharmacology, Receptor antagonist, medicine.drug_class, medicine, Benzamide, chemistry.chemical_compound, chemistry, Allosteric regulation, In vivo, Ligand (biochemistry)
Funded by
EC| INMIND
Project
INMIND
Imaging of Neuroinflammation in Neurodegenerative Diseases
  • Funder: European Commission (EC)
  • Project Code: 278850
  • Funding stream: FP7 | SP1 | HEALTH
21 references, page 1 of 2

Beamer, E. Purinergic mechanisms in neuroinflammation: An update from molecules to behaviour. Neuropharmacology. 2016; 104: 94-104 [OpenAIRE] [PubMed] [DOI]

Bhattacharya, A, Biber, K. The Microglial ATP-Gated Ion Channel P2X7 As a CNS Drug Target. GLIA. 2016; 64: 1772-1787 [OpenAIRE] [PubMed] [DOI]

Burnstock, G. P2X ion channel receptors and inflammation. Purinergic Signalling. 2016; 12: 59-67 [OpenAIRE] [PubMed] [DOI]

Janssen, B. Synthesis and initial preclinical evaluation of the P2X7 receptor antagonist [11C]A-740003 as a novel tracer of neuroinflammation. J. Labelled Compd. Radiopharm.. 2014; 57: 509-516 [OpenAIRE] [DOI]

Gao, M, Wang, M, Green, MA, Hutchins, GD, Zheng, Q-H. Synthesis of [11C]GSK1482160 as a new PET agent for targeting P2X7 receptor. Bioorg. Med. Chem. Lett.. 2016; 25: 1965-1970 [OpenAIRE] [DOI]

Ory, D. Preclinical evaluation of a P2X7 receptor selective radiotracer: positron emission tomography studies in a rat model with local overexpression of the human P2X7 receptor and in non-human primates. J. Nucl. Med.. 2016; 57: 1436-1441 [OpenAIRE] [PubMed] [DOI]

Territo, PR. Characterization of C-11-GSK1482160 for Targeting the P2X7 Receptor as a Biomarker for Neuroinflammation. J. Nucl. Med.. 2017; 58: 458-465 [OpenAIRE] [PubMed] [DOI]

Fantoni, ER. Design, synthesis and evaluation in an LPS rodent model of neuroinflammation of a novel 18F-labelled PET tracer targeting P2X7. EJNMMI Res.. 2017; 2017: 7:31 [OpenAIRE]

Han, J. Pharmacologic characterizations of a P2X7 receptor-specific radioligand, [11C]GSK1482160 for neuroinflammatory response. Nucl. Med. Commun.. 2017; 38: 372-382 [OpenAIRE] [PubMed] [DOI]

Wilkinson, SM. Pharmacological evaluation of novel bioisosteres of an adamantanyl benzamide P2X7 receptor antagonist. ACS Chem. Neurosci.. 2017: 2374-2380

Baxter, A. Hit-to-Lead Studies: The Discovery of Potent Adamantane Amide P2X7 Receptor Antagonists. Bioorg. Med. Chem. Lett.. 2003; 13: 4047-4050 [OpenAIRE] [PubMed] [DOI]

Honore, P. A-740003 [N-(1-{[(Cyanoimino)(5-quinolinylamino)methyl]amino}-2,2-dimethylpropyl)-2-(3,4-dimethoxyphenyl)acetamide], a Novel and Selective P2X7 Receptor Antagonist, Dose-Dependently Reduces Neuropathic Pain in the Rat. J. Pharmacol. Exp. Ther.. 2006; 319: 1376-1385 [OpenAIRE] [PubMed] [DOI]

Perez-Medrano, A. Discovery and Biological Evaluation of Novel Cyanoguanidine P2X7 Antagonists with Analgesic Activity in a Rat Model of Neuropathic Pain. J. Med. Chem.. 2009; 52: 3366-3376 [OpenAIRE] [PubMed] [DOI]

Letavic, MA. Synthesis and Pharmacological Characterization of Two Novel, Brain Penetrating P2X7 Antagonists. ACS Med. Chem. Lett.. 2013; 4: 419-422 [OpenAIRE] [PubMed] [DOI]

Bhattacharya, A. Pharmacological characterization of a novel centrally permeable P2X7 receptor antagonist: JNJ-47965567. Br. J. Pharmacol.. 2013; 170: 624-640 [OpenAIRE] [PubMed] [DOI]

21 references, page 1 of 2
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