Dirk Tourwe

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Dirk Tourwe

Publications by authors named "Dirk Tourwe"

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100Publications

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Synthesis and Evaluation of Stabilized and Selective Neuromedin U-1 Receptor Agonists.

ACS Med Chem Lett 2018 May 23;9(5):496-501. Epub 2018 Apr 23.

Research Group of Organic Chemistry, Departments of Chemistry and Bioengineering Sciences, Vrije Universiteit Brussel, Pleinlaan 2, 1050 Brussels, Belgium.

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May 2018

Indoloazepinone-Constrained Oligomers as Cell-Penetrating and Blood-Brain-Barrier-Permeating Compounds.

Chembiochem 2018 Apr 28;19(7):696-705. Epub 2018 Feb 28.

Research Group of Organic Chemistry, Departments of Chemistry and Bioengineering Sciences, Vrije Universiteit Brussel, Pleinlaan 2, 1050, Brussels, Belgium.

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April 2018

Efficient One-Pot Access to Trisubstituted 2-Benzazepin-3-ones as Constrained Pseudopeptide Analogues and Privileged Scaffolds.

Med Chem 2018 ;14(4):400-408

Research Group of Organic Chemistry, Departments of Chemistry and Bioengineering Sciences, Vrije Universiteit Brussel, Pleinlaan 2, B-1050, Brussels, Belgium.

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January 2018

Development of potent and proteolytically stable human neuromedin U receptor agonists.

Eur J Med Chem 2018 Jan 14;144:887-897. Epub 2017 Dec 14.

Research Group of Organic Chemistry, Departments of Chemistry and Bioengineering Sciences, Vrije Universiteit Brussel, Pleinlaan 2, 1050, Brussels, Belgium. Electronic address:

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January 2018

χ-Space Screening of Dermorphin-Based Tetrapeptides through Use of Constrained Arylazepinone and Quinolinone Scaffolds.

ACS Med Chem Lett 2017 Nov 4;8(11):1177-1182. Epub 2017 Oct 4.

Research Group of Organic Chemistry, Departments of Chemistry and Bioengineering Sciences, Vrije Universiteit Brussel, Pleinlaan 2, 1050 Brussels, Belgium.

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November 2017

Hydrazone Linker as a Useful Tool for Preparing Chimeric Peptide/Nonpeptide Bifunctional Compounds.

ACS Med Chem Lett 2017 Jan 1;8(1):73-77. Epub 2016 Nov 1.

Department of Neuropeptides, Mossakowski Medical Research Centre Polish Academy of Sciences , 5 Pawińskiego Str., 02-106 Warsaw, Poland.

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January 2017

Side Chain Cyclized Aromatic Amino Acids: Great Tools as Local Constraints in Peptide and Peptidomimetic Design.

J Med Chem 2016 Dec 12;59(24):10865-10890. Epub 2016 Oct 12.

Research Group of Organic Chemistry, Departments of Chemistry and Bio-Engineering Sciences, Vrije Universiteit Brussel , Pleinlaan 2, 1050 Brussels, Belgium.

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December 2016

Synthesis and binding characteristics of [(3)H]neuromedin N, a NTS2 receptor ligand.

Neuropeptides 2016 Jun 8;57:15-20. Epub 2015 Dec 8.

Department of Neuropeptides, Mossakowski Medical Research Centre, Polish Academy of Sciences, 5 Pawinskiego Street, 02106 Warsaw, Poland; Department of Pharmacodynamics, Centre for Preclinical Research and Technology, Medical University of Warsaw, 1B Banacha Str., 02-106 Warsaw, Poland. Electronic address:

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June 2016

T3P-Promoted, Mild, One-Pot Syntheses of Constrained Polycyclic Lactam Dipeptide Analogues via Stereoselective Pictet-Spengler and Meyers Lactamization Reactions.

Org Lett 2015 Sep 31;17(18):4482-5. Epub 2015 Aug 31.

Research Group of Organic Chemistry, Departments of Chemistry and Bio-Engineering Sciences, Vrije Universiteit Brussel , Pleinlaan 2, B-1050 Brussels, Belgium.

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September 2015

Neuropeptide FF receptors as novel targets for limbic seizure attenuation.

Neuropharmacology 2015 Aug 9;95:415-23. Epub 2015 May 9.

Center for Neurosciences, Department of Pharmaceutical Chemistry, Drug Analysis and Drug Information, Vrije Universiteit Brussel, Laarbeeklaan 103, 1090 Brussels, Belgium. Electronic address:

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August 2015

Azepinone-Containing Tetrapeptide Analogues of Melanotropin Lead to Selective hMC4R Agonists and hMC5R Antagonist.

ACS Med Chem Lett 2015 Feb 3;6(2):192-7. Epub 2014 Dec 3.

Research Group of Organic Chemistry, Vrije Universiteit Brussel , Pleinlaan 2, B-1050 Brussels, Belgium.

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February 2015

Presence and regulation of insulin-regulated aminopeptidase in mouse macrophages.

J Renin Angiotensin Aldosterone Syst 2014 Dec 14;15(4):466-79. Epub 2014 Feb 14.

Myeloid Cell Immunology Laboratory, VIB, Belgium Cellular and Molecular Immunology Unit, Vrije Universiteit Brussel, Belgium.

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December 2014

Hybrid opioid/non-opioid ligands in pain research.

Curr Pharm Des 2013 ;19(42):7435-50

Department of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium.

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September 2014

One-pot isomerization-cross metathesis-reduction (ICMR) synthesis of lipophilic tetrapeptides.

ACS Comb Sci 2014 Jul 18;16(7):342-51. Epub 2014 Jun 18.

Department of Organic Chemistry, Vrije Universiteit Brussel , Pleinlaan 2, B-1050 Brussels, Belgium.

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July 2014

Synthesis of fused 3-aminoazepinones via trapping of a new class of cyclic seven-membered allenamides with furan.

Org Lett 2014 Jul 9;16(14):3712-5. Epub 2014 Jul 9.

Research Group of Organic Chemistry, Department of Chemistry and Department of Bio-engineering Sciences, Faculty of Science and Bio-engineering Sciences and ‡Department of General Chemistry, Vrije Universiteit Brussel , Pleinlaan 2, B-1050 Brussels, Belgium.

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July 2014

Development and pharmacological characterization of conformationally constrained urotensin II-related peptide agonists.

J Med Chem 2013 Dec 26;56(23):9612-22. Epub 2013 Nov 26.

INRS-Institut Armand-Frappier, Institut national de la recherche scientifique, Université du Québec , Ville de Laval, Québec, QC H7V 1B7, Canada.

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December 2013

Highly diastereoselective synthesis of 1-carbamoyl-4-aminoindoloazepinone derivatives via the Ugi reaction.

Org Lett 2013 Nov 25;15(22):5866-9. Epub 2013 Oct 25.

Department of Organic Chemistry, Vrije Universiteit Brussel , Pleinlaan 2, B-1050 Brussels, Belgium , and Institute of Organic Chemistry , Polish Academy of Sciences, Kasprzaka Str. 44/52, 01-224 Warsaw, Poland.

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November 2013

Stabilisation of a short α-helical VIP fragment by side chain to side chain cyclisation: a comparison of common cyclisation motifs by circular dichroism.

J Pept Sci 2013 Jul 27;19(7):423-32. Epub 2013 May 27.

Department of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, B-1050, Brussels, Belgium.

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July 2013

[3H]IVDE77, a novel radioligand with high affinity and selectivity for the insulin-regulated aminopeptidase.

Eur J Pharmacol 2013 Feb 31;702(1-3):93-102. Epub 2013 Jan 31.

Molecular and Biochemical Pharmacology, Vrije Universiteit Brussel, Building E, Pleinlaan 2, B-1050 Brussels, Belgium.

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February 2013

Synergetic effects of DNA demethylation and histone deacetylase inhibition in primary rat hepatocytes.

Invest New Drugs 2012 Aug 29;30(4):1715-24. Epub 2011 Mar 29.

Department of Toxicology, Center for Pharmaceutical Research, Faculty of Medicine and Pharmacy, Vrije Universiteit Brussel, Laarbeeklaan 103, 1090 Brussels, Belgium.

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August 2012

Angiotensin IV displays only low affinity for native insulin-regulated aminopeptidase (IRAP).

Fundam Clin Pharmacol 2012 Apr 11;26(2):194-7. Epub 2011 Apr 11.

Research Group of Experimental Pharmacology, Department of Molecular and Biochemical Pharmacology, Vrije Universiteit Brussel, Pleinlaan 2, 1050 Brussels, Belgium.

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April 2012

Amino triazolo diazepines (Ata) as constrained histidine mimics.

Org Lett 2011 Dec 16;13(24):6468-71. Epub 2011 Nov 16.

Laboratory of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium.

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December 2011

PEGylation of (99m)Tc-labeled bombesin analogues improves their pharmacokinetic properties.

Nucl Med Biol 2011 Oct 21;38(7):997-1009. Epub 2011 Apr 21.

Paul Scherrer Institute, Center for Radiopharmaceutical Sciences ETH-PSI-USZ, CH-5232 Villigen-PSI, Switzerland.

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October 2011

Conformational constraints in angiotensin IV to probe the role of Tyr², Pro⁵ and Phe⁶.

J Pept Sci 2011 Aug 28;17(8):545-53. Epub 2011 Apr 28.

Department of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, 1050 Brussels, Belgium.

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August 2011

Binding of "AT4 receptor" ligands to insulin regulated aminopeptidase (IRAP) in intact Chinese hamster ovary cells.

Mol Cell Endocrinol 2011 Jun 30;339(1-2):34-44. Epub 2011 Mar 30.

Department of Molecular and Biochemical Pharmacology, Research Group of Experimental Pharmacology, Vrije Universiteit Brussel, Pleinlaan 2, 1050 Brussels, Belgium.

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June 2011

Design, synthesis, pharmacological evaluation, and structure-activity study of novel endomorphin analogues with multiple structural modifications.

J Med Chem 2011 Mar 2;54(5):1462-72. Epub 2011 Feb 2.

Institute of Biochemistry , Biological Research Center, Hungarian Academy of Sciences, PO Box 521, H-6701 Szeged, Hungary.

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March 2011

Molecular assembly of multifunctional ⁹⁹(m)Tc radiopharmaceuticals using "clickable" amino acid derivatives.

ChemMedChem 2010 Dec;5(12):2026-38

Department of Radiology and Nuclear Medicine, University Hospital Basel, Switzerland.

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December 2010

PK20, a new opioid-neurotensin hybrid peptide that exhibits central and peripheral antinociceptive effects.

Mol Pain 2010 Dec 6;6:86. Epub 2010 Dec 6.

Mossakowski Medical Research Centre, Polish Academy of Sciences, Pawinskiego Street 5, 02106 Warsaw, Poland.

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December 2010

Radical stability directs electron capture and transfer dissociation of β-amino acids in peptides.

Chemistry 2010 Apr 16;16(15):4612-22. Epub 2010 Mar 16.

Biomolecular Mass Spectrometry Laboratory, Ecole Polytechnique Fédérale de Lausanne, 1015 Lausanne (Switzerland), Fax: (+41) 21-693-9700.

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April 2010

Bis(thiosemicarbazones) as bifunctional chelators for the room temperature 64-copper labeling of peptides.

Dalton Trans 2010 Apr 3;39(15):3620-32. Epub 2010 Mar 3.

Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, United Kingdom.

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April 2010

Novel multiple opioid ligands based on 4-aminobenzazepinone (Aba), azepinoindole (Aia) and tetrahydroisoquinoline (Tic) scaffolds.

Bioorg Med Chem Lett 2010 Mar 20;20(5):1610-3. Epub 2010 Jan 20.

Department of Organic Chemistry, Vrije Universiteit Brussel, B-1050 Brussels, Belgium.

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March 2010

New tetracyclic tetrahydro-beta-carbolines as tryptophan-derived peptidomimetics.

Mol Divers 2010 Feb 16;14(1):97-108. Epub 2009 Jun 16.

Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093, Warsaw, Poland.

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February 2010

Development of a new microwave-assisted cleavable backbone amide linker (BAL): a comparative study.

Org Biomol Chem 2010 Jan 19;8(1):60-5. Epub 2009 Nov 19.

Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium.

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January 2010

Selective labeling of IRAP by the tritiated AT(4) receptor ligand [3H]Angiotensin IV and its stable analog [3H]AL-11.

Mol Cell Endocrinol 2009 Nov 28;311(1-2):77-86. Epub 2009 Jul 28.

Research Group of Experimental Pharmacology, Department of Molecular and Biochemical Pharmacology, Vrije Universiteit Brussel, Pleinlaan 2, 1050 Brussels, Belgium.

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November 2009

The replacement of His(4) in angiotensin IV by conformationally constrained residues provides highly potent and selective analogues.

J Med Chem 2009 Sep;52(18):5612-8

Department of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, 1050 Brussels, Belgium.

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September 2009

Carbohydrated [99mTc(CO)3](NalphaHis)Ac-bombesin(7-14) analogs.

Adv Exp Med Biol 2009 ;611:409-10

Vrije Universiteit Brussel, Department of Organic Chemistry, Pleinlaan 2, 1050 Brussels, Belgium.

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June 2009

A click approach to structurally diverse conjugates containing a central di-1,2,3-triazole metal chelate.

ChemMedChem 2009 Apr;4(4):529-39

Department of Chemistry and Applied Biosciences, Institute of Pharmaceutical Sciences, Zurich, Switzerland.

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April 2009

A stable neurotensin-based radiopharmaceutical for targeted imaging and therapy of neurotensin receptor-positive tumours.

Eur J Nucl Med Mol Imaging 2009 Jan 9;36(1):37-47. Epub 2008 Aug 9.

Paul Scherrer Institute, Center for Radiopharmaceutical Science, CH-5232, Villigen PSI, Switzerland.

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January 2009

A novel solid phase approach to Aia-containing peptides.

J Pept Sci 2009 Jan;15(1):16-22

Department of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium.

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January 2009

Conformationally constrained opioid ligands: the Dmt-Aba and Dmt-Aia versus Dmt-Tic scaffold.

Bioorg Med Chem Lett 2009 Jan 19;19(2):433-7. Epub 2008 Nov 19.

Department of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium.

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January 2009

Highly potent 4-amino-indolo[2,3-c]azepin-3-one-containing somatostatin mimetics with a range of sst receptor selectivities.

J Med Chem 2009 Jan;52(1):95-104

Department of Organic Chemistry, Vrije Universiteit Brussel, Brussels, Belgium.

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January 2009

Influence of the molecular charge on the biodistribution of bombesin analogues labeled with the [99mTc(CO)3]-core.

Bioconjug Chem 2008 Dec;19(12):2409-16

Paul Scherrer Institute, Centre for Radiopharmaceutical Science, CH-5232 Villigen PSI, Switzerland.

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December 2008

Glycation methods for bombesin analogs containing the (NalphaHis)Ac chelator for 99mTc(CO)3 radiolabeling.

Chem Biol Drug Des 2008 Dec 5;72(6):496-506. Epub 2008 Nov 5.

Department of Organic Chemistry, Vrije Universiteit Brussel, Brussels, Belgium.

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December 2008

Differential effects of hydroxamate histone deacetylase inhibitors on cellular functionality and gap junctions in primary cultures of mitogen-stimulated hepatocytes.

Toxicol Lett 2008 Apr 15;178(1):37-43. Epub 2008 Feb 15.

Department of Toxicology, Vrije Universiteit Brussel (VUB), Laarbeeklaan 103, B-1090 Brussels, Belgium.

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April 2008

Blood-brain barrier penetration by two dermorphin tetrapeptide analogues: role of lipophilicity vs structural flexibility.

J Med Chem 2008 Apr 28;51(8):2571-4. Epub 2008 Mar 28.

Organic Chemistry Department, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium.

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April 2008

Beta-homo-amino acid scan of angiotensin IV.

J Med Chem 2008 Apr 15;51(7):2291-6. Epub 2008 Mar 15.

Department of Organic Chemistry, Department of Molecular and Biochemical Pharmacology, Vrije Universiteit Brussel, Pleinlaan 2, 1050 Brussels, Belgium.

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April 2008

Endomorphin-2 with a beta-turn backbone constraint retains the potent micro-opioid receptor agonist properties.

J Med Chem 2008 Jan 7;51(1):173-7. Epub 2007 Dec 7.

Institute of Biochemistry, Biological Research Center of the Hungarian Academy of Sciences, Temesvári krt. 62., H-6726 Szeged, Hungary.

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January 2008

Novel diastereomeric opioid tetrapeptides exhibit differing pharmacological activity profiles.

Brain Res Bull 2007 Sep 8;74(1-3):119-29. Epub 2007 Jun 8.

Institute of Biochemistry, Biological Research Center, Hungarian Academy of Sciences, Temesvari krt. 62, H-6726 Szeged, Hungary.

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September 2007

High-performance liquid chromatographic separation of stereoisomers of N-phthaloyl-protected amino acids and dipeptidomimetics.

J Sep Sci 2007 Aug;30(12):1881-7

Department of Inorganic and Analytical Chemistry, University of Szeged, H-6720 Szeged, Dóm tér 7, Hungary.

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August 2007

The novel histone deacetylase inhibitor 4-Me2N-BAVAH differentially affects cell junctions between primary hepatocytes.

Toxicology 2007 Jul 7;236(1-2):92-102. Epub 2007 Apr 7.

Department of Toxicology, Vrije Universiteit Brussel, Laarbeeklaan 103, B-1090 Brussels, Belgium.

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July 2007

New sst4/5-selective somatostatin peptidomimetics based on a constrained tryptophan scaffold.

J Med Chem 2007 Jul 9;50(14):3397-401. Epub 2007 Jun 9.

Department of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, B-1050, Brussels, Belgium.

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July 2007

Chemical and biological characterization of new Re(CO)3/[99mTc](CO)3 bombesin analogues.

Nucl Med Biol 2007 Jan 28;34(1):17-28. Epub 2006 Nov 28.

Paul Scherrer Institute, Centre for Radiopharmaceutical Science, CH-5232 Villigen PSI, Switzerland.

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January 2007

Beta-methyl substitution of cyclohexylalanine in Dmt-Tic-Cha-Phe peptides results in highly potent delta opioid antagonists.

J Med Chem 2007 Jan;50(2):328-33

Institute of Biochemistry, Biological Research Center, Hungarian Academy of Sciences, Post Office Box 521, H-6701 Szeged, Hungary.

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January 2007

"Click to chelate": synthesis and installation of metal chelates into biomolecules in a single step.

J Am Chem Soc 2006 Nov;128(47):15096-7

Department of Chemistry and Applied Biosciences, ETH Zurich, 8093 Zurich, Switzerland.

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November 2006

High-performance liquid chromatographic enantioseparation of unusual secondary amino acids on a D-penicillamine-based chiral ligand exchange column.

Chirality 2006 Aug;18(7):539-43

University of Szeged, Department of Inorganic and Analytical Chemistry, Szeged, Hungary.

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August 2006

Fluorescein-labeled stable neurotensin derivatives.

J Pept Sci 2006 Aug;12(8):505-8

Organic Chemistry Department, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium.

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August 2006

Opioid receptor binding characteristics and structure-activity studies of novel tetrapeptides in the TIPP (Tyr-Tic-Phe-Phe) series.

Neurosignals 2005 ;14(6):317-28

Institute of Biochemistry, Biological Research Center, Hungarian Academy of Sciences, Szeged, Hungary.

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August 2006

Toward stable N4-modified neurotensins for NTS1-receptor-targeted tumor imaging with 99mTc.

J Med Chem 2006 Jul;49(15):4767-76

Institute of Radioisotopes - Radiodiagnostic Products, National Center for Scientific Research Demokritos, 15310 Athens, Greece.

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July 2006

Double-stabilized neurotensin analogues as potential radiopharmaceuticals for NTR-positive tumors.

Nucl Med Biol 2006 May 2;33(4):495-503. Epub 2006 May 2.

Center for Radiopharmaceutical Science, Paul Scherrer Institute, CH-5232 Villigen PSI, Switzerland.

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May 2006

Novel 99mTc-labeled neurotensin analogues with optimized biodistribution properties.

J Med Chem 2006 Mar;49(5):1833-6

Department of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium.

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March 2006

Solid-supported solution-phase synthesis of 4-amino-1,2,4,5-tetrahydro-2-benzazepine-3-ones.

J Comb Chem 2004 Jul-Aug;6(4):468-73

Organic Chemistry Department, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium.

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May 2005

A new structural motif for mu-opioid antagonists.

J Med Chem 2005 May;48(10):3644-8

Eenheid Organische Chemie, Vrije Universiteit Brussel, 2, Pleinlaan, B-1050 Brussels, Belgium.

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May 2005

Improving the tumor uptake of 99mTc-labeled neuropeptides using stabilized peptide analogues.

Cancer Biother Radiopharm 2004 Apr;19(2):181-8

Center for Radiopharmaceutical Science, Paul Scherrer Institut, Villigen, Switzerland.

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April 2004

Structure-activity study of the ORL1 antagonist Ac-Arg-D-Cha-Qaa-D-Arg-D-p-ClPhe-NH2.

J Med Chem 2004 Mar;47(7):1864-7

Eenheid Organische Chemie, Vrije Universiteit Brussel, 2, Pleinlaan, B-1050, Brussels, Belgium.

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March 2004

Comparison of the separation efficiencies of chirobiotic T and TAG columns in the separation of unusual amino acids.

J Chromatogr A 2004 Mar;1031(1-2):159-70

Department of Inorganic and Analytical Chemistry, University of Szeged, Dómtér 7, H-6720 Szeged, Hungary.

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March 2004

Direct and indirect high-performance liquid chromatographic enantioseparation of beta-amino acids.

J Chromatogr A 2004 Mar;1031(1-2):171-8

Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary.

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March 2004

Structure-activity study on the Phe side chain arrangement of endomorphins using conformationally constrained analogues.

J Med Chem 2004 Jan;47(3):735-43

Institute of Biochemistry, Biological Research Center of the Hungarian Academy of Sciences, 6701 Szeged, P.O. Box 521, Hungary.

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January 2004

Ab initio study of the binding of Trichostatin A (TSA) in the active site of histone deacetylase like protein (HDLP).

Org Biomol Chem 2003 Aug;1(16):2951-7

Vrije Universiteit Brussel, Organic Chemistry Group, Pleinlaan 2, B-1050 Brussel, Belgium.

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August 2003

Probing opioid receptor interactions with azacycloalkane amino acids. Synthesis of a potent and selective ORL1 antagonist.

J Med Chem 2002 Nov;45(24):5353-7

Département de Chimie, Université de Montréal, C. P. 6128, Succursale Centre Ville, Montréal, Québec, Canada H3C 3J7.

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November 2002

Synthesis of 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylic acid derivatives, doubly constrained ACC derivatives, by a remarkable cyclopropanation process.

J Org Chem 2002 Apr;67(7):2192-6

Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.

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April 2002

Application of a new chiral derivatizing agent to the enantioseparation of secondary amino acids.

J Chromatogr A 2002 Mar;948(1-2):283-94

Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6720, Szeged, Hungary.

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March 2002