schliessen

Filtern

 

Bibliotheken

N-(3,4-Dimethylisoxazol-5-yl)piperazine-4-[4-(2-fluoro-4-[(11)C]methylphenyl)thiazol-2-yl]-1-carboxamide: A promising positron emission tomography ligand for fatty acid amide hydrolase.

To visualize fatty acid amide hydrolase (FAAH) in brain in vivo, we developed a novel positron emission tomography (PET) ligand N-(3,4-dimethylisoxazol-5-yl)piperazine-4-[4-(2-fluoro-4-[(11)C]methylphenyl)thiazol-2-yl]-1-carboxamide ([(11)C]DFMC, [(11)C]1). DFMC (1) was shown to have high binding af... Full description

Journal Title: Bioorganic & medicinal chemistry February 15, 2016, Vol.24(4), pp.627-634
Main Author: Shimoda, Yoko
Other Authors: Fujinaga, Masayuki , Hatori, Akiko , Yui, Joji , Zhang, Yiding , Nengaki, Nobuki , Kurihara, Yusuke , Yamasaki, Tomoteru , Xie, Lin , Kumata, Katsushi , Ishii, Hideki , Zhang, Ming-Rong
Format: Electronic Article Electronic Article
Language: English
Subjects:
Pet
ID: E-ISSN: 1464-3391 ; DOI: 10.1016/j.bmc.2015.12.026
Link: http://search.proquest.com/docview/1762343294/?pq-origsite=primo
Zum Text:
SendSend as email Add to Book BagAdd to Book Bag
Staff View
recordid: proquest1762343294
title: N-(3,4-Dimethylisoxazol-5-yl)piperazine-4-[4-(2-fluoro-4-[(11)C]methylphenyl)thiazol-2-yl]-1-carboxamide: A promising positron emission tomography ligand for fatty acid amide hydrolase.
format: Article
creator:
  • Shimoda, Yoko
  • Fujinaga, Masayuki
  • Hatori, Akiko
  • Yui, Joji
  • Zhang, Yiding
  • Nengaki, Nobuki
  • Kurihara, Yusuke
  • Yamasaki, Tomoteru
  • Xie, Lin
  • Kumata, Katsushi
  • Ishii, Hideki
  • Zhang, Ming-Rong
subjects:
  • Amidohydrolases–Antagonists & Inhibitors
  • Animals–Metabolism
  • Benzamides–Pharmacology
  • Brain–Drug Effects
  • Carbamates–Metabolism
  • Carbon Radioisotopes–Pharmacology
  • Humans–Chemical Synthesis
  • Ligands–Chemistry
  • Mice–Pharmacology
  • Molecular Structure–Methods
  • Piperazines–Administration & Dosage
  • Positron-Emission Tomography–Analysis
  • Radiopharmaceuticals–Chemistry
  • Rats–Chemical Synthesis
  • Thiazoles–Chemistry
  • Tissue Distribution–Pharmacology
  • Benzamides
  • Carbamates
  • Carbon Radioisotopes
  • Ligands
  • N-(3,4-Dimethylisoxazol-5-Yl)Piperazine-4-(4-(2-Fluoro-4-((11)C)Methylphenyl)Thiazol-2-Yl)1-Carboxamide
  • Piperazines
  • Radiopharmaceuticals
  • Thiazoles
  • Cyclohexyl Carbamic Acid 3'-Carbamoylbiphenyl-3-Yl Ester
  • Amidohydrolases
  • Fatty-Acid Amide Hydrolase
  • Fatty Acid Amide Hydrolase
  • Irreversible Specific Binding
  • Pet
  • [(11)C]Methyl Iodide
ispartof: Bioorganic & medicinal chemistry, February 15, 2016, Vol.24(4), pp.627-634
description: To visualize fatty acid amide hydrolase (FAAH) in brain in vivo, we developed a novel positron emission tomography (PET) ligand N-(3,4-dimethylisoxazol-5-yl)piperazine-4-[4-(2-fluoro-4-[(11)C]methylphenyl)thiazol-2-yl]-1-carboxamide ([(11)C]DFMC, [(11)C]1). DFMC (1) was shown to have high binding affinity (IC50: 6.1nM) for FAAH. [(11)C]1 was synthesized by C-(11)C coupling reaction of arylboronic ester 2 with [(11)C]methyl iodide in the presence of Pd catalyst. At the end of synthesis, [(11)C]1 was obtained with a radiochemical yield of 20±10% (based on [(11)C]CO2, decay-corrected, n=5) and specific activity of 48-166GBq/μmol. After the injection of [(11)C]1 in mice, high uptake of radioactivity (>2% ID/g) was distributed in the lung, liver, kidney, and brain, organs with high FAAH expression. PET images of rat brains for [(11)C]1 revealed high uptakes in the cerebellar nucleus (SUV=2.4) and frontal cortex (SUV=2.0), two known brain regions with high FAAH expression. Pretreatment with the FAAH-selective inhibitor URB597 reduced the brain uptake. Higher than 90% of the total radioactivity in the rat brain was irreversible at 30min after the radioligand injection. The present results indicate that [(11)C]1 is a promising PET ligand for imaging of FAAH in living brain.
language: eng
source:
identifier: E-ISSN: 1464-3391 ; DOI: 10.1016/j.bmc.2015.12.026
fulltext: fulltext
issn:
  • 14643391
  • 1464-3391
url: Link


@attributes
ID1375619504
RANK0.07
NO1
SEARCH_ENGINEprimo_central_multiple_fe
SEARCH_ENGINE_TYPEPrimo Central Search Engine
LOCALfalse
PrimoNMBib
record
control
sourcerecordid1762343294
sourceidproquest
recordidTN_proquest1762343294
sourcesystemPC
pqid1762343294
galeid451360788
display
typearticle
titleN-(3,4-Dimethylisoxazol-5-yl)piperazine-4-[4-(2-fluoro-4-[(11)C]methylphenyl)thiazol-2-yl]-1-carboxamide: A promising positron emission tomography ligand for fatty acid amide hydrolase.
creatorShimoda, Yoko ; Fujinaga, Masayuki ; Hatori, Akiko ; Yui, Joji ; Zhang, Yiding ; Nengaki, Nobuki ; Kurihara, Yusuke ; Yamasaki, Tomoteru ; Xie, Lin ; Kumata, Katsushi ; Ishii, Hideki ; Zhang, Ming-Rong
contributorShimoda, Yoko (correspondence author) ; Shimoda, Yoko (record owner)
ispartofBioorganic & medicinal chemistry, February 15, 2016, Vol.24(4), pp.627-634
identifierE-ISSN: 1464-3391 ; DOI: 10.1016/j.bmc.2015.12.026
subjectAmidohydrolases–Antagonists & Inhibitors ; Animals–Metabolism ; Benzamides–Pharmacology ; Brain–Drug Effects ; Carbamates–Metabolism ; Carbon Radioisotopes–Pharmacology ; Humans–Chemical Synthesis ; Ligands–Chemistry ; Mice–Pharmacology ; Molecular Structure–Methods ; Piperazines–Administration & Dosage ; Positron-Emission Tomography–Analysis ; Radiopharmaceuticals–Chemistry ; Rats–Chemical Synthesis ; Thiazoles–Chemistry ; Tissue Distribution–Pharmacology ; Benzamides ; Carbamates ; Carbon Radioisotopes ; Ligands ; N-(3,4-Dimethylisoxazol-5-Yl)Piperazine-4-(4-(2-Fluoro-4-((11)C)Methylphenyl)Thiazol-2-Yl)1-Carboxamide ; Piperazines ; Radiopharmaceuticals ; Thiazoles ; Cyclohexyl Carbamic Acid 3'-Carbamoylbiphenyl-3-Yl Ester ; Amidohydrolases ; Fatty-Acid Amide Hydrolase ; Fatty Acid Amide Hydrolase ; Irreversible Specific Binding ; Pet ; [(11)C]Methyl Iodide
languageeng
source
descriptionTo visualize fatty acid amide hydrolase (FAAH) in brain in vivo, we developed a novel positron emission tomography (PET) ligand N-(3,4-dimethylisoxazol-5-yl)piperazine-4-[4-(2-fluoro-4-[(11)C]methylphenyl)thiazol-2-yl]-1-carboxamide ([(11)C]DFMC, [(11)C]1). DFMC (1) was shown to have high binding affinity (IC50: 6.1nM) for FAAH. [(11)C]1 was synthesized by C-(11)C coupling reaction of arylboronic ester 2 with [(11)C]methyl iodide in the presence of Pd catalyst. At the end of synthesis, [(11)C]1 was obtained with a radiochemical yield of 20±10% (based on [(11)C]CO2, decay-corrected, n=5) and specific activity of 48-166GBq/μmol. After the injection of [(11)C]1 in mice, high uptake of radioactivity (>2% ID/g) was distributed in the lung, liver, kidney, and brain, organs with high FAAH expression. PET images of rat brains for [(11)C]1 revealed high uptakes in the cerebellar nucleus (SUV=2.4) and frontal cortex (SUV=2.0), two known brain regions with high FAAH expression. Pretreatment with the FAAH-selective inhibitor URB597 reduced the brain uptake. Higher than 90% of the total radioactivity in the rat brain was irreversible at 30min after the radioligand injection. The present results indicate that [(11)C]1 is a promising PET ligand for imaging of FAAH in living brain.
version6
lds50peer_reviewed
links
openurl$$Topenurl_article
openurlfulltext$$Topenurlfull_article
backlink$$Uhttp://search.proquest.com/docview/1762343294/?pq-origsite=primo$$EView_record_in_ProQuest_(subscribers_only)
search
creatorcontrib
0Shimoda, Yoko
1Fujinaga, Masayuki
2Hatori, Akiko
3Yui, Joji
4Zhang, Yiding
5Nengaki, Nobuki
6Kurihara, Yusuke
7Yamasaki, Tomoteru
8Xie, Lin
9Kumata, Katsushi
10Ishii, Hideki
11Zhang, Ming-Rong
titleN-(3,4-Dimethylisoxazol-5-yl)piperazine-4-[4-(2-fluoro-4-[(11)C]methylphenyl)thiazol-2-yl]-1-carboxamide: A promising positron emission tomography ligand for fatty acid amide hydrolase.
subject
0Amidohydrolases–Antagonists & Inhibitors
1Animals–Metabolism
2Benzamides–Pharmacology
3Brain–Drug Effects
4Carbamates–Metabolism
5Carbon Radioisotopes–Pharmacology
6Humans–Chemical Synthesis
7Ligands–Chemistry
8Mice–Pharmacology
9Molecular Structure–Methods
10Piperazines–Administration & Dosage...
11Fatty acid amide hydrolase
12Irreversible specific binding
13PET
14[(11)C]methyl iodide
general
0English
110.1016/j.bmc.2015.12.026
2MEDLINE (ProQuest)
3ProQuest Biological Science Collection
4ProQuest Natural Science Collection
5ProQuest SciTech Collection
6Biological Science Database
7Natural Science Collection
8SciTech Premium Collection
9Health Research Premium Collection
10Health Research Premium Collection (Alumni edition)
11Biological Science Index (ProQuest)
sourceidproquest
recordidproquest1762343294
issn
014643391
11464-3391
rsrctypearticle
creationdate2016
addtitleBioorganic & medicinal chemistry
searchscope
01007527
11007944
21009130
310000004
410000038
510000050
610000120
710000159
810000238
910000253
1010000260
1110000270
1210000271
1310000302
1410000350
15proquest
scope
01007527
11007944
21009130
310000004
410000038
510000050
610000120
710000159
810000238
910000253
1010000260
1110000270
1210000271
1310000302
1410000350
15proquest
lsr43
01007527false
11007944false
21009130false
310000004false
410000038false
510000050false
610000120false
710000159false
810000238false
910000253false
1010000260false
1110000270false
1210000271false
1310000302false
1410000350false
contributorShimoda, Yoko
startdate20160215
enddate20160215
citationpf 627 pt 634 vol 24 issue 4
lsr30VSR-Enriched:[description, issn, pqid, galeid]
sort
titleN-(3,4-Dimethylisoxazol-5-yl)piperazine-4-[4-(2-fluoro-4-[(11)C]methylphenyl)thiazol-2-yl]-1-carboxamide: A promising positron emission tomography ligand for fatty acid amide hydrolase.
authorShimoda, Yoko ; Fujinaga, Masayuki ; Hatori, Akiko ; Yui, Joji ; Zhang, Yiding ; Nengaki, Nobuki ; Kurihara, Yusuke ; Yamasaki, Tomoteru ; Xie, Lin ; Kumata, Katsushi ; Ishii, Hideki ; Zhang, Ming-Rong
creationdate20160215
lso0120160215
facets
frbrgroupid5298208780728402221
frbrtype5
newrecords20181218
languageeng
creationdate2016
topic
0Amidohydrolases–Antagonists & Inhibitors
1Animals–Metabolism
2Benzamides–Pharmacology
3Brain–Drug Effects
4Carbamates–Metabolism
5Carbon Radioisotopes–Pharmacology
6Humans–Chemical Synthesis
7Ligands–Chemistry
8Mice–Pharmacology
9Molecular Structure–Methods
10Piperazines–Administration & Dosage...
collection
0MEDLINE (ProQuest)
1ProQuest Biological Science Collection
2ProQuest Natural Science Collection
3ProQuest SciTech Collection
4Biological Science Database
5Natural Science Collection
6SciTech Premium Collection
7Health Research Premium Collection
8Health Research Premium Collection (Alumni edition)
9Biological Science Index (ProQuest)
prefilterarticles
rsrctypearticles
creatorcontrib
0Shimoda, Yoko
1Fujinaga, Masayuki
2Hatori, Akiko
3Yui, Joji
4Zhang, Yiding
5Nengaki, Nobuki
6Kurihara, Yusuke
7Yamasaki, Tomoteru
8Xie, Lin
9Kumata, Katsushi
10Ishii, Hideki
11Zhang, Ming-Rong
jtitleBioorganic & medicinal chemistry
toplevelpeer_reviewed
delivery
delcategoryRemote Search Resource
fulltextfulltext
addata
aulast
0Shimoda
1Fujinaga
2Hatori
3Yui
4Zhang
5Nengaki
6Kurihara
7Yamasaki
8Xie
9Kumata
10Ishii
aufirst
0Yoko
1Masayuki
2Akiko
3Joji
4Yiding
5Nobuki
6Yusuke
7Tomoteru
8Lin
9Katsushi
10Hideki
11Ming-Rong
au
0Shimoda, Yoko
1Fujinaga, Masayuki
2Hatori, Akiko
3Yui, Joji
4Zhang, Yiding
5Nengaki, Nobuki
6Kurihara, Yusuke
7Yamasaki, Tomoteru
8Xie, Lin
9Kumata, Katsushi
10Ishii, Hideki
11Zhang, Ming-Rong
addauShimoda, Yoko
atitleN-(3,4-Dimethylisoxazol-5-yl)piperazine-4-[4-(2-fluoro-4-[(11)C]methylphenyl)thiazol-2-yl]-1-carboxamide: A promising positron emission tomography ligand for fatty acid amide hydrolase.
jtitleBioorganic & medicinal chemistry
risdate20160215
volume24
issue4
spage627
epage634
pages627-634
eissn1464-3391
formatjournal
genrearticle
ristypeJOUR
doi10.1016/j.bmc.2015.12.026
urlhttp://search.proquest.com/docview/1762343294/
issn09680896
date2016-02-15