Synthesis of a potent and selective (18)F-labeled delta-opioid receptor antagonist derived from the Dmt-Tic pharmacophore for positron emission tomography imaging.

PubWeight™: 0.79‹?›

🔗 View Article (PMC 2667121)

Published in J Med Chem on March 01, 2008

Authors

Eun Kyoung Ryu1, Zhanhong Wu, Kai Chen, Lawrence H Lazarus, Ewa D Marczak, Yusuke Sasaki, Akihiro Ambo, Severo Salvadori, Chuancheng Ren, Heng Zhao, Gianfranco Balboni, Xiaoyuan Chen

Author Affiliations

1: Molecular Imaging Program at Stanford, Department of Radiology and Bio-X Program, Stanford University School of Medicine, Stanford, CA 94305, USA.

Articles cited by this

Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol (1973) 47.81

Some quantitative uses of drug antagonists. Br J Pharmacol Chemother (1959) 41.90

Kinetic parameters of narcotic agonists and antagonists, with particular reference to N-allylnoroxymorphone (naloxone). Br J Pharmacol Chemother (1968) 5.00

Attacking pain at its source: new perspectives on opioids. Nat Med (2003) 2.53

18F-labeled RGD peptide: initial evaluation for imaging brain tumor angiogenesis. Nucl Med Biol (2004) 1.99

18F-labeled mini-PEG spacered RGD dimer (18F-FPRGD2): synthesis and microPET imaging of alphavbeta3 integrin expression. Eur J Nucl Med Mol Imaging (2007) 1.49

microPET of tumor integrin alphavbeta3 expression using 18F-labeled PEGylated tetrameric RGD peptide (18F-FPRGD4). J Nucl Med (2007) 1.46

Opioids as modulators of cell death and survival--unraveling mechanisms and revealing new indications. Pharmacol Rev (2004) 1.40

Evaluation of the Dmt-Tic pharmacophore: conversion of a potent delta-opioid receptor antagonist into a potent delta agonist and ligands with mixed properties. J Med Chem (2002) 1.40

The delta-opioid receptor: molecular pharmacology, signal transduction, and the determination of drug efficacy. Pharmacol Rev (1999) 1.33

The antidepressant -like effects of delta-opioid receptor agonists. Mol Interv (2006) 1.26

PET imaging of opioid receptors in pain: progress and new directions. Curr Pharm Des (2004) 1.17

Mu-, delta- and kappa-opioid receptor populations are differentially altered in distinct areas of postmortem brains of Alzheimer's disease patients. Brain Res (2001) 1.15

Opioid receptor genes inactivated in mice: the highlights. Neuropeptides (2002) 1.13

Dermorphin gene sequence peptide with high affinity and selectivity for delta-opioid receptors. J Biol Chem (1989) 1.07

Anxiolytic- and antidepressant-like activities of H-Dmt-Tic-NH-CH(CH2-COOH)-Bid (UFP-512), a novel selective delta opioid receptor agonist. Peptides (2007) 1.05

Function of negative charge in the "address domain" of deltorphins. J Med Chem (1991) 1.02

6-N,N-dimethylamino-2,3-naphthalimide: a new environment-sensitive fluorescent probe in delta- and mu-selective opioid peptides. J Med Chem (2006) 1.02

Imaging delta- and mu-opioid receptors by PET in lung carcinoma patients. J Nucl Med (2007) 1.00

Non-invasive radiotracer imaging as a tool for drug development. Curr Pharm Des (2000) 0.99

Effect of lysine at C-terminus of the Dmt-Tic opioid pharmacophore. J Med Chem (2006) 0.97

Endomorphin 2 analogues containing Dmp residue as an aromatic amino acid surrogate with high mu-opioid receptor affinity and selectivity. Bioorg Med Chem (2003) 0.97

Interaction of deltorphin with opioid receptors: molecular determinants for affinity and selectivity. Peptides (1993) 0.95

Inverse agonism and neutral antagonism at wild-type and constitutively active mutant delta opioid receptors. J Pharmacol Exp Ther (2004) 0.93

The expression of delta- and kappa-opioid receptor is enhanced during intestinal inflammation in mice. J Pharmacol Exp Ther (2003) 0.91

In vitro and in vivo pharmacological profile of UFP-512, a novel selective delta-opioid receptor agonist; correlations between desensitization and tolerance. Br J Pharmacol (2007) 0.91

Antiparkinson potential of delta-opioid receptor agonists. Eur J Pharmacol (2000) 0.86

Quantification of delta-opioid receptors in human brain with N1'-([11C]methyl) naltrindole and positron emission tomography. J Cereb Blood Flow Metab (1999) 0.84

Indium-labeled macrocyclic conjugates of naltrindole: high-affinity radioligands for in vivo studies of peripheral delta opioid receptors. J Med Chem (2007) 0.82

From the potent and selective mu opioid receptor agonist H-Dmt-d-Arg-Phe-Lys-NH(2) to the potent delta antagonist H-Dmt-Tic-Phe-Lys(Z)-OH. J Med Chem (2005) 0.82

Further studies on the effect of lysine at the C-terminus of the Dmt-Tic opioid pharmacophore. Bioorg Med Chem (2007) 0.82

PET imaging of human cardiac opioid receptors. Eur J Nucl Med Mol Imaging (2002) 0.81

ARD-353 [4-((2R,5S)-4-(R)-(4-diethylcarbamoylphenyl)(3-hydroxyphenyl)methyl)-2,5-dimethylpiperazin-1-ylmethyl)benzoic acid], a novel nonpeptide delta receptor agonist, reduces myocardial infarct size without central effects. J Pharmacol Exp Ther (2005) 0.79

Selective delta-opioid receptor ligands: potential PET ligands based on naltrindole. Bioorg Med Chem Lett (2001) 0.79

Characterization of N,N(Me)2-Dmt-Tic-OH, a delta selective opioid dipeptide antagonist. Neuroreport (2000) 0.77

Articles by these authors

Ferroelectric metal-organic framework with a high dielectric constant. J Am Chem Soc (2006) 9.51

High-thermoelectric performance of nanostructured bismuth antimony telluride bulk alloys. Science (2008) 7.34

In vivo biodistribution and highly efficient tumour targeting of carbon nanotubes in mice. Nat Nanotechnol (2006) 6.93

Carbon nanotubes as photoacoustic molecular imaging agents in living mice. Nat Nanotechnol (2008) 6.41

Peptide-labeled near-infrared quantum dots for imaging tumor vasculature in living subjects. Nano Lett (2006) 5.63

Circulation and long-term fate of functionalized, biocompatible single-walled carbon nanotubes in mice probed by Raman spectroscopy. Proc Natl Acad Sci U S A (2008) 4.89

In vivo visualization of embryonic stem cell survival, proliferation, and migration after cardiac delivery. Circulation (2006) 4.48

Multimodality molecular imaging of tumor angiogenesis. J Nucl Med (2008) 3.99

Drug delivery with carbon nanotubes for in vivo cancer treatment. Cancer Res (2008) 3.47

US imaging of tumor angiogenesis with microbubbles targeted to vascular endothelial growth factor receptor type 2 in mice. Radiology (2008) 3.15

Nitrolinoleic acid: an endogenous peroxisome proliferator-activated receptor gamma ligand. Proc Natl Acad Sci U S A (2005) 3.03

microPET imaging of glioma integrin {alpha}v{beta}3 expression using (64)Cu-labeled tetrameric RGD peptide. J Nucl Med (2005) 2.96

Nanoparticle-based theranostic agents. Adv Drug Deliv Rev (2010) 2.86

Dual-function probe for PET and near-infrared fluorescence imaging of tumor vasculature. J Nucl Med (2007) 2.86

Decoy state quantum key distribution. Phys Rev Lett (2005) 2.77

PET/MRI dual-modality tumor imaging using arginine-glycine-aspartic (RGD)-conjugated radiolabeled iron oxide nanoparticles. J Nucl Med (2008) 2.77

microPET-based biodistribution of quantum dots in living mice. J Nucl Med (2007) 2.76

Nanoplatforms for targeted molecular imaging in living subjects. Small (2007) 2.69

Quantitative PET imaging of tumor integrin alphavbeta3 expression with 18F-FRGD2. J Nucl Med (2006) 2.65

Particle size, surface coating, and PEGylation influence the biodistribution of quantum dots in living mice. Small (2009) 2.59

(64)Cu-labeled tetrameric and octameric RGD peptides for small-animal PET of tumor alpha(v)beta(3) integrin expression. J Nucl Med (2007) 2.50

Paused Pol II coordinates tissue morphogenesis in the Drosophila embryo. Cell (2013) 2.42

Activation of the hedgehog pathway in advanced prostate cancer. Mol Cancer (2004) 2.32

PET/NIRF/MRI triple functional iron oxide nanoparticles. Biomaterials (2010) 2.31

Quantitative PET of EGFR expression in xenograft-bearing mice using 64Cu-labeled cetuximab, a chimeric anti-EGFR monoclonal antibody. Eur J Nucl Med Mol Imaging (2007) 2.31

Nitrated fatty acids: Endogenous anti-inflammatory signaling mediators. J Biol Chem (2006) 2.31

PET imaging of colorectal cancer in xenograft-bearing mice by use of an 18F-labeled T84.66 anti-carcinoembryonic antigen diabody. J Nucl Med (2007) 2.28

PET of vascular endothelial growth factor receptor expression. J Nucl Med (2006) 2.18

The nanostructured origin of deformation twinning. Nano Lett (2012) 2.13

Clinical outcomes of thoracoscopic lobectomy for patients with clinical N0 and pathologic N2 non-small cell lung cancer. Ann Thorac Surg (2012) 2.12

Loss of insulin signaling in vascular endothelial cells accelerates atherosclerosis in apolipoprotein E null mice. Cell Metab (2010) 2.09

In vitro and in vivo characterization of 64Cu-labeled Abegrin, a humanized monoclonal antibody against integrin alpha v beta 3. Cancer Res (2006) 2.09

Imaging of integrins as biomarkers for tumor angiogenesis. Curr Pharm Des (2008) 2.04

Near-infrared fluorescent RGD peptides for optical imaging of integrin alphavbeta3 expression in living mice. Bioconjug Chem (2005) 2.01

Ultrahigh sensitivity carbon nanotube agents for photoacoustic molecular imaging in living mice. Nano Lett (2010) 2.00

Hydrogen peroxide activates endothelial nitric-oxide synthase through coordinated phosphorylation and dephosphorylation via a phosphoinositide 3-kinase-dependent signaling pathway. J Biol Chem (2001) 1.99

Solution structure of the Alzheimer amyloid beta-peptide (1-42) in an apolar microenvironment. Similarity with a virus fusion domain. Eur J Biochem (2002) 1.99

Altered mitochondrial dynamics contributes to endothelial dysfunction in diabetes mellitus. Circulation (2011) 1.95

Molecular evolution analysis and geographic investigation of severe acute respiratory syndrome coronavirus-like virus in palm civets at an animal market and on farms. J Virol (2005) 1.93

(68)Ga-labeled multimeric RGD peptides for microPET imaging of integrin alpha(v)beta (3) expression. Eur J Nucl Med Mol Imaging (2008) 1.91

18F-labeled galacto and PEGylated RGD dimers for PET imaging of αvβ3 integrin expression. Mol Imaging Biol (2009) 1.90

Ultrasmall c(RGDyK)-coated Fe3O4 nanoparticles and their specific targeting to integrin alpha(v)beta3-rich tumor cells. J Am Chem Soc (2008) 1.89

Preparation of peptide-conjugated quantum dots for tumor vasculature-targeted imaging. Nat Protoc (2008) 1.87

A thiol-reactive 18F-labeling agent, N-[2-(4-18F-fluorobenzamido)ethyl]maleimide, and synthesis of RGD peptide-based tracer for PET imaging of alpha v beta 3 integrin expression. J Nucl Med (2006) 1.83

A dedicated superbend x-ray microdiffraction beamline for materials, geo-, and environmental sciences at the advanced light source. Rev Sci Instrum (2009) 1.82

The tachykinin peptide family. Pharmacol Rev (2002) 1.82

How molecular imaging is speeding up antiangiogenic drug development. Mol Cancer Ther (2006) 1.81

Pulse accumulation, radial heat conduction, and anisotropic thermal conductivity in pump-probe transient thermoreflectance. Rev Sci Instrum (2008) 1.80

64Cu-labeled alpha-melanocyte-stimulating hormone analog for microPET imaging of melanocortin 1 receptor expression. Bioconjug Chem (2007) 1.79

Unusual magnetic properties of one-dimensional molecule-based magnets associated with a structural phase transition. Inorg Chem (2002) 1.78

Frequent activation of the hedgehog pathway in advanced gastric adenocarcinomas. Carcinogenesis (2005) 1.77

Parkinson's disease in China: prevalence in Beijing, Xian, and Shanghai. Lancet (2005) 1.75

Near-infrared fluorescent deoxyglucose analogue for tumor optical imaging in cell culture and living mice. Bioconjug Chem (2006) 1.75

(68)Ga-labeled cyclic RGD dimers with Gly3 and PEG4 linkers: promising agents for tumor integrin alphavbeta3 PET imaging. Eur J Nucl Med Mol Imaging (2009) 1.69

Cytokine-stimulated GTP cyclohydrolase I expression in endothelial cells requires coordinated activation of nuclear factor-kappaB and Stat1/Stat3. Circ Res (2004) 1.69

Surface-engineered magnetic nanoparticle platforms for cancer imaging and therapy. Acc Chem Res (2011) 1.69

NADPH oxidase 4 promotes endothelial angiogenesis through endothelial nitric oxide synthase activation. Circulation (2011) 1.68

Upconversion nanoparticles: design, nanochemistry, and applications in theranostics. Chem Rev (2014) 1.68

Anti-angiogenic cancer therapy based on integrin alphavbeta3 antagonism. Anticancer Agents Med Chem (2006) 1.64

Click chemistry for (18)F-labeling of RGD peptides and microPET imaging of tumor integrin alphavbeta3 expression. Bioconjug Chem (2007) 1.64

Peptides and peptide hormones for molecular imaging and disease diagnosis. Chem Rev (2010) 1.63

Why integrin as a primary target for imaging and therapy. Theranostics (2011) 1.61

Clinicopathological and prognostic significance of serum and tissue Dickkopf-1 levels in human hepatocellular carcinoma. Liver Int (2011) 1.60

High-affinity peptide against MT1-MMP for in vivo tumor imaging. J Control Release (2011) 1.59

Pilot pharmacokinetic and dosimetric studies of (18)F-FPPRGD2: a PET radiopharmaceutical agent for imaging α(v)β(3) integrin levels. Radiology (2011) 1.59

Trafficking mesenchymal stem cell engraftment and differentiation in tumor-bearing mice by bioluminescence imaging. Stem Cells (2009) 1.58

Comparison study of [18F]FAl-NOTA-PRGD2, [18F]FPPRGD2, and [68Ga]Ga-NOTA-PRGD2 for PET imaging of U87MG tumors in mice. Bioconjug Chem (2011) 1.56

Oxorhenium(V) complexes containing tridentate Schiff-base and monothiol coligands. Inorganica Chim Acta (2000) 1.56

Light-triggered theranostics based on photosensitizer-conjugated carbon dots for simultaneous enhanced-fluorescence imaging and photodynamic therapy. Adv Mater (2012) 1.56

Dual-modality optical and positron emission tomography imaging of vascular endothelial growth factor receptor on tumor vasculature using quantum dots. Eur J Nucl Med Mol Imaging (2008) 1.55

The Akt signaling pathway contributes to postconditioning's protection against stroke; the protection is associated with the MAPK and PKC pathways. J Neurochem (2008) 1.54

Scientometric trends and knowledge maps of global health systems research. Health Res Policy Syst (2014) 1.51

Liquid-liquid separation in solutions of normal and sickle cell hemoglobin. Proc Natl Acad Sci U S A (2002) 1.50

Suppression of the JNK pathway by induction of a metabolic stress response prevents vascular injury and dysfunction. Circulation (2008) 1.50

Intracellular delivery of an anionic antisense oligonucleotide via receptor-mediated endocytosis. Nucleic Acids Res (2008) 1.49

Characterizing breast cancer xenograft epidermal growth factor receptor expression by using near-infrared optical imaging. Acta Radiol (2009) 1.49

Uncoupling protein 2 impacts endothelial phenotype via p53-mediated control of mitochondrial dynamics. Circ Res (2013) 1.48

Integrin targeting for tumor optical imaging. Theranostics (2011) 1.47

Dual roles of the MAPK/ERK1/2 cell signaling pathway after stroke. J Neurosci Res (2008) 1.47

Effects of nanoparticle size on cellular uptake and liver MRI with polyvinylpyrrolidone-coated iron oxide nanoparticles. ACS Nano (2010) 1.46

microPET of tumor integrin alphavbeta3 expression using 18F-labeled PEGylated tetrameric RGD peptide (18F-FPRGD4). J Nucl Med (2007) 1.46