GRK 1910 related publications of the research training group members

2016

NTS2-Selective Neurotensin Mimetics with Tetrahydrofuran Amino Acids

Nadja A. Simeth, Manuel Bause, Michael Dobmeier, Ralf C. Kling, Daniel Lachmann, Harald Huebner, Juergen Einsiedel, Peter Gmeiner, Burkhard Koenig

Bioorg. Med. Chem., 2016, in press

doi:10.1016/j.bmc.2016.10.039

Structure-based discovery of opioid analgesics with reduced side effects

Aashish Manglik, Henry Lin, Dipendra K. Aryal, John D. McCorvy, Daniela Dengler, Gregory Corder, Anat Levit, Ralf C. Kling, Viachaslau Bernat, Harald Hübner, Xi-Ping Huang, Maria F. Sassano, Patrick M. Giguère, Stefan Löber, Da Duan, Grégory Scherrer, Brian K. Kobilka, Peter Gmeiner, Bryan L. Roth, Brian K. Shoichet

Nature, 2016, 537, 185-190.

doi: 10.1038/nature19112

Label-free versus conventional cellular assays: functional investigations on the human histamine H1 receptor

S. Lieb, T. Littmann, N. Plank, J. Felixberger, M. Tanaka, T. Schäfer, S. Krief, S. Elz, K. Friedland, G. Bernhardt, J. Wegener, T. Ozawa, A. Buschauer

Pharmacol. Res., 2016, 114, 13-26.

doi: 10.1016/j.phrs.2016.10.010

Identification of two distinct sites for antagonist and biased agonist binding to the humane chemokine receptor CXCR3

Lampros Milanos, Noureldin Saleh, Ralf C. Kling, Jonas Kaindl, Nuska Tschammer, Timothy Clark

Angew. Chem. Int. Ed., 2016, accepted.

doi: 10.1002/anie.201607831R2

Dibenzo[b,f][1,4]oxazepines and dibenzo[b,e]oxepines: Influence of the chlorine substitution pattern on the pharmacology at the H1R, H4R, 5-HT2AR and other selected GPCRs

Franziska Naporra, Susanne Gobleder, Hans-Joachim Wittmann, Julia Spindler, Michael Bodensteiner, Günther Bernhardt, Harald Hübner, Peter Gmeiner, Sigurd Elz, Andrea Strasser

Pharmacol. Res., 2016, 113, 610-625.

doi: 10.1016/j.phrs.2016.09.042

Structure-guided development of heterodimer-selective GPCR ligands

H. Hübner, T. Schellhorn, M. Gienger, C. Schaab, J. Kaindl, L. Leeb, T. Clark, D. Möller, P. Gmeiner

Nature Communications, 2016, 7, 12298.

doi: 10.1038/ncomms12298

Multiple D2 heteroreceptor complexes: new targets for treatment of schizophrenia

Borroto-Escuela D. O., Pintsuk J., Schäfer T., Friedland K., Ferraro L., Tanganelli S., Fang L., Fuxe K.

Therapeutic Advances in Psychopharmacology, 2016, 6, 77-94.

doi: 10.1177/2045125316637570

A Three-Site Mechanism for Agonist/Antagonist Action on the Vasopressin Receptors

N. Saleh, E. Haensele, L. Banting, J. Sopkova-de Oliveira Santos, D. C. Whitley, G. Saldino, F. L. Gervasio, R. Bureau and T. Clark

Angew. Chemie Int. Ed., 2016, 128, 8140-8144

doi: 10.1002/anie.201602729

Discovery and Characterization of Biased Allosteric Agonists of the Chemokine Receptor CXCR3

L. Milanos, R. Brox, T. Frank, G. Poklukar, R. Palmisano, R. Waibel, J. Einsiedel, M. Dürr, I. Ivanović-Burmazović, O. Larsen, G. M. Hjortø, M. M. Rosenkilde, N. Tschammer

J. Med. Chem., 2016, 59, 2222-2243. 

doi: 1.1021/acs.jmedchem.5b01965

Biosensors

Hajek, K.; Schmittlein, C.; Oberleitner, M.; Shin, I.; Wegener, J.

Encyclopedia of Life Sciences, Wiley & Co. 2016

doi:10.1002/9780470015902.a0026401

Radical arylation of tyrosine residues in peptides

S. K. Fehler, G. Pratsch, C. Östreicher, M. C. D. Fürst, M. Pischetsrieder, M. R. Heinrich

Tetrahedron 2016, 72, 7888-789.

doi:10.1016/j.tet.2016.04.084

Hydrogen Peroxide Promoted Mizoroki–Heck Reactions of Phenyldiazenes with Acrylates, Acrylamides, and Styrenes

R. Lasch, S. K. Fehler, M. R. Heinrich

Org. Lett. 2016, 18(7), 1586-1589

doi: 10.1021/acs.orglett.6b00449.

Structure-guided development of dual β2 adrenergic/dopamine D2 receptor agonists

D. Weichert, M. Stanek, H. Hübner, P. Gmeiner

Bioorg. Med. Chem. 2016, 24, 2641–2653.

doi:10.1016/j.bmc.2016.04.028

18F- and 68Ga-Labeled Neurotensin Peptides for PET Imaging of Neurotensin Receptor 1

S. Maschauer, J. Einsiedel, H. Hübner, P. Gmeiner, O. Prante

J. Med. Chem. 2016, 59, in press.

doi: 10.1021/acs.jmedchem.6b00675

High affinity agonists of the neuropeptide Y (NPY) Y4 receptor derived from the C-terminal pentapeptide of human pancreatic polypeptide (hPP): synthesis, stereochemical discrimination and radiolabeling

K. K. Kuhn, T. Ertl, S. Dukorn, M. Keller, G. Bernhardt, O. Reiser, A. Buschauer

J. Med. Chem. 2016, 59, 6045–6058.

doi: 10.1021/acs.jmedchem.6b00309

Label-free analysis of GPCR-stimulation: The critical impact of cell adhesion

S. Lieb, S. Michaelis, N. Plank, G. Bernhardt, A. Buschauer, J. Wegener

Pharmacol. Res. 2016, 108, 65-74.

doi: 10.1016/j.phrs.2016.04.026

2,4-Diaminopyrimidines as dual ligands at the histamine H1 and H4 receptor - H1/H4-receptor selectivity

Hammer, Sebastian und Gobleder, Susanne und Naporra, Franziska und Wittmann, Hans-Joachim und Elz, Sigurd und Heinrich, Markus und Strasser, Andrea 

Bioorg. Med. Chem. Lett. 2016, 26, 292-300.

doi: 10.1016/j.bmcl.2015.12.035

Conformational restriction and enantioseparation increase potency and selectivity of cyanoguanidine-type histamine H4 receptor agonists

R. Geyer, U. Nordemann, A. Strasser, H.-J. Wittmann, A. Buschauer

J. Med. Chem. 2016, 59, 3452−3470.

doi: 10.1021/acs.jmedchem.6b00120

Synthetic Peptides as Protein Mimics

Groß, A., Hashimoto, C., Sticht, H. and Eichler, J.

Front. Bioeng. Biotechnol 2016, 3:211, 580-603.

doi: 10.3389/fbioe.2015.00211

Mimicking of arginine by functionalized Nω-carbamoylated arginine as a new broadly applicable approach to labeled bioactive peptides: high affinity angiotensin, neuropeptide Y, neuropeptide FF and neurotensin receptor ligands as examples

M. Keller, K. Kuhn, J. Einsiedel, H. Hübner, S. Biselli, C. Mollereau, D. Wifling, J. Svobodova, G. Bernhardt, C. Cabrele, P. Vanderheyden, P. Gmeiner, A. Buschauer,

J. Med. Chem. 2016, 59, 1925−1945.

doi: 10.1021/acs.jmedchem.5b01495

2015

Impedance Analysis of different cell monolayers grown on gold-film electrodes

Reiß, B.; Wegener, J.

IEEE Eng. Med. Biol. 2015, 7079-7082.

doi: 10.1109/EMBC.2015.7320023

Turning peptide ligands into small-molecule inhibitors of protein-protein interactions

Hashimoto, C. and Eichler, J.

ChemBioChem 2015, 16, 1855 – 1856.

doi: 10.1002/cbic.201500298

How the structural elucidation of the natural product stephanosporin led to new developments in aryl radical and medicinal chemistry

K. Fehler, M. R. Heinrich,

Synlett 2015, 580-603. (account article)

doi: 10.1055/s-0034-1378945

Cycloadditions to phenylazocarboxylic esters: a new access to highly substituted triazoles

R. Lasch, M. R. Heinrich,

Tetrahedron 2015, 71, 4282-4295.

doi: 10.1016/j.tet.2015.04.078

Monitoring the impact of Nanomaterials on animal cells by impedance analysis: a non-invasive, label-free and multi-modal approach

Sperber, M.; Hupf, C.; Lemberger, M.; Goricnik, B.; Hinterreiter, N.; Lukic, S.; Oberleitner, M.; Stolwijk, J.A.; Wegener, J.

Bioanalytical Reviews 2015, 5, 45-108.

doi: 10.1007/11663_2015_13

Zinc-mediated allylation and benzylation of phenylazocarboxylic esters

R. Lasch, M. R. Heinrich,

J. Org. Chem. 2015, 80, 10412–10420.

doi: 10.1021/acs.joc.5b01978

Nw-carbamoylation of the argininamide moiety: an avenue to insurmountable NPY Y1 receptor antagonists and a radiolabeled selective high affinity molecular tool ([3H]UR-MK299) with extended residence time

M. Keller, S. Weiss, C. Hutzler, K. Kuhn, C. Mollereau, S. Dukorn, L. Schindler, G. Bernhardt, B. König, A. Buschauer,

J. Med. Chem. 2015, 58, 8834–8849.

doi: 10.1021/acs.jmedchem.5b00925

Ligand selectivity of a synthetic CXCR4 mimetic peptide

Groß, A., Brox, R., Damm, D., Tschammer, N., Schmidt, B. and Eichler, J.

Bioorg. Med. Chem. , 2015, 23, 4050–4055.

doi:10.1016/j.bmc.2015.03.003

Functionalization of photochromic dithienylmaleimides

D. Wutz, C. Falenczyk, N. Kuzmanovic and B. König,

RSC Adv., 2015, 5, 18075-18086.

doi:10.1039/C5RA00015G

Arrestin-Bound Rhodopsin: A Molecular Structure and its Impact on the Development of Biased GPCR Ligands

Dorothee Moeller, Peter Gmeiner,

Angew. Chem. Int. Ed. 2015, 54, 13166-13168.

doi:10.1002/anie.201507724

1,4-Disubstituted aromatic piperazines with high 5-HT2A/D2selectivity: Quantitative structure-selectivity investigations, docking, synthesis and biological evaluation

Dorothee Moeller, Ismail Salama, Ralf C. Kling, Harald Huebner, Peter Gmeiner,

Bioorg. Med. Chem. 2015, 23, 6195-6209.

doi:10.1016/j.bmc.2015.07.050

Covalent Molecular Probes for Class A G Protein-Coupled Receptors: Advances and Applications

Dietmar Weichert and Peter Gmeiner,

ACS Chem. Biol.. 2015, 10, 1376-1386.

doi:10.1021/acschembio.5b00070

Molecular Determinants of Biased Agonism at the Dopamine D2 Receptor

Dietmar Weichert, Ashutosh Banerjee, Christine Hiller, Ralf C. Kling, Harald Huebner, and Peter Gmeiner,

J. Med. Chem. 2015, 58, 2703-2717.

doi:10.1021/jm501889t

Flow cytometric analysis with a fluorescent formyl peptide receptor ligand as a new method to study the pharmacological profile of the histamine H2-receptor

K. Werner, S. Kälble, S. Wolter, E. H. Schneider, A. Buschauer, D. Neumann, R. Seifert,

Naunyn Schmiedebergs Arch. Pharmacol. 2015, 388(10), 1039-1052.

doi: 10.1007/s00210-015-1133-2

Towards labeled argininamide-type NPY Y1 receptor antagonists: Identification of a favorable propionylation site in BIBO3304

M. Keller, L. Schindler, G. Bernhardt, A. Buschauer,

Arch. Pharm. (Weinheim). 2015, 348, 390–398.

doi: 10.1002/ardp.201400427

M2 subtype preferring dibenzodiazepinone-type muscarinic receptor ligands: effect of chemical homo-dimerization on orthosteric (and allosteric?) binding

M. Keller, C. Tränkle, X. She, A. Pegoli, G. Bernhardt, A. Buschauer, R. W. Read

Bioorg. Med. Chem. 2015, 23, 3970–3990.

doi: 10.1016/j.bmc.2015.01.015

Dimeric carbamoylguanidine-type histamine H2 receptor ligands: A new class of potent and selective agonists

N. Kagermeier, K. Werner, M. Keller, P. Baumeister, G. Bernhardt, R. Seifert, A. Buschauer

Bioorg. Med. Chem. 2015, 23, 3957–3969.

doi: 10.1016/j.bmc.2015.01.012

Fluoro-substituted phenylazocarboxamides: Dopaminergic behavior and N-arylating properties for irreversible binding

Amelie L. Bartuschat, Tamara Schellhorn, Harald Huebner, Peter Gmeiner and Markus R. Heinrich

Bioorg. Med. Chem. 2015, 23, 3938-3947.

doi:10.1016/j.bmc.2014.12.012]

Modulation of GPCRs by monovalent cations and anions.

Strasser, Andrea und Wittmann, Hans-Joachim und Schneider, Erich H. und Seifert, Roland.

Naunyn-Schmiedeberg's Archives of Pharmacology 2015, 388, 363-380.

doi:10.1007/s00210-014-1073-2

Binding pathway of histamine to the hH4R, observed by unconstrained molecular dynamics

Hans-Joachim Wittmann, Andrea Strasser.

Bioorg. Med. Chem. Lett. 2015, 25, 1259–1268.

doi:10.1016/j.bmcl.2015.01.052

Improved radiosynthesis and preliminary in vivo evaluation of a 18F-labeled glycopeptide-peptoid hybrid for PET imaging of neurotensin receptor 2.

S. Maschauer, C. Greff, J. Einsiedel, J. Ott, P. Tripal, H. Hübner, P. Gmeiner, O. Prante.

Bioorg. Med. Chem. 2015, 23, 4026-33.

doi: 10.1016/j.bmc.2015.01.053

Synthesis and in Vitro and in Vivo Evaluation of an 18F-Labeled Neuropeptide Y Analogue for Imaging of Breast Cancer by PET.

S. Hofmann, S. Maschauer, T. Kuwert, A. G. Beck-Sickinger, O. Prante

Mol. Pharm.  2015, 12, 1121-30.

doi: 10.1021/mp500601z

GPCR crystal structures: Medicinal chemistry in the pocket

Jeremy Shonberg, Ralf C. Kling, Peter Gmeiner, Stefan Löber 

Bioorg. Med. Chem. 2015, accepted.

doi:10.1016/j.bmc.2014.12.034

Targeted mass spectrometry for the analysis of nutritive modulation of catalase and heme oxygenase-1 expression

Nina Zaenglein, Joanna Tucher, Monika Pischetsrieder

Journal of Proteomics 2015, 117, 58-69.

doi: 10.1016/j.jprot.2015.01.010

The extracellular loop 2 (ECL2) of the human histamine H4 receptor substantially contributes to ligand binding and constitutive activity

D. Wifling, G. Bernhardt, S. Dove, A. Buschauer

PLoS ONE, 2015, 10, e0117185. 

doi: 10.1371/journal.pone.0117185

[3H]UR-DE257: Development of a Tritium-Labeled Squaramide-Type Selective Histamine H2 Receptor Antagonist

P. Baumeister, D. Erdmann, S. Biselli, N. Kagermeier, S. Elz, G. Bernhardt, A. Buschauer

ChemMedChem 2015, 10, 83-93.

DOI: 10.1002/cmdc.201402344.

Molecular determinants for the high constitutive activity of the human histamine H4 receptor: functional studies on orthologues and mutants

D. Wifling, K. Löffel, U. Nordemann, A. Strasser, G. Bernhardt, S. Dove, R. Seifert, A. Buschauer

Br. J. Pharmacol. 2015, , 172, 785–798.

DOI: 10.1111/bph.12801

2014

Identifying Modulators of CXC Receptors 3 and 4 with Tailored Selectivity using Multi-Target Docking

Denis Schmidt, Viachaslau Bernat, Regine Brox, Nuska Tschammer, and Peter Kolb

ACS Chem. Biol., 201410, 715-724.

DOI: 10.1021/cb500577j

Peptides Containing β-Amino Acid Patterns: Challenges and Successes in Medicinal Chemistry

Chiara Cabrele, Tamás A. Martinek, Oliver Reiser, and Łukasz Berlicki

J. Med. Chem. 201457, 9718–9739.

DOI: 10.1021/jm5010896

Synthesis of dibenzo[c,e][1,2]diazocines - a new group of eight-membered cyclic azo compounds

T. Nokubi, S. Kindt, T. Clark, A. Kamimura, M. R. Heinrich

Tetrahedron Lett. 2014, 56, 316-320 

DOI: 10.1016/j.tetlet.2014.11.064

Covalent agonists for studying G protein-coupled receptor activation

Dietmar Weichert, Andrew C. Kruse, Aashish Manglik, Christine Hiller, Cheng Zhang, Harald Huebner, Brian K. Kobilka, and Peter Gmeiner

Proc. Natl. Acad. Sci. USA, 2014, 111, 10744-10748.

DOI: 10.1073/pnas.1410415111

The trapping of phenyldiazene in cycloaddition reactions

Stefanie Fehler, Gerald Pratsch, Markus R. Heinrich

Angew. Chem. Int. Ed. 2014, 53, 11361-11365

DOI: 10.1002/anie.201406175

Chromo-pharmacophores: photochromic diarylmaleimide inhibitors for sirtuins

C. Falenczyk, M. Schiedel, B. Karaman, T. Rumpf, N. Kuzmanovic, M. Grøtli, W. Sippl, M. Jung, B. König

Chem. Sci2014, 5, 4794 - 4799

DOI: 10.1039/C4SC01346H

Versatile trivalent C3-symmetric scaffolds and their use for covalent stabilization of the foldon trimer

Berthelmann, A., Lach, J., Gräwert M.A., Groll, M. and Eichler, J.

Org. Biomol. Chem. 2014, 12, 2606-2614

DOI: 10.1039/C3OB42251H.

Synthesis and evaluation of fluoro substituted pyridinylcarboxamides and their phenylazo analogues as potential dopamine D3 receptor PET ligands

N. Nebel, S. Maschauer, A. Bartuschat, S. K. Fehler, H. Hübner, P. Gmeiner, T. Kuwert, M. R. Heinrich, O. Prante, C. Hocke

Bioorg. Med. Chem. Lett. 2014, 24, 5399–5403

DOI: 10.1016/j.bmcl.2014.10.043

Boronic acids as probes for investigation of allosteric regulation of the chemokine receptor CXCR3

Viachaslau Bernat, Regine Brox, Tizita Haimanot Admas, Nuska Tschammer 

ACS Chem. Biol., 2014, 9, 2664–2677. 

DOI: 10.1021/cb500678c

Functionally Selective Dopamine D2, D3 Receptor Partial Agonists

Dorothee Moeller, Ralf C. Kling, Marika Skultety, Kristina Leuner, Harald Huebner, and Peter Gmeiner

J. Med. Chem., 2014, 57, 4861-4875.

DOI: 10.1021/jm5004039

Active-State Model of a Dopamine D2 Receptor - Galphai Complex Stabilized by Aripiprazole-Type Partial Agonists

Ralf C. Kling, Nuska Tschammer, Harald Lanig, Timothy Clark, Peter Gmeiner

PLOS ONE 2014, 9, e100069. 

DOI: 10.1371/journal.pone.0100069

Fast and efficient 18F-labeling via [18F]fluorophenylazocarboxylic esters

Stefanie K. Fehler, Simone Maschauer, Sarah B. Hoefling, Amelie L. Bartuschat, Nuska Tschammer, Harald Huebner, Peter Gmeiner, Olaf Prante, Markus R. Heinrich

Chem. Eur. J. 2014, 20, 370-375

DOI: 10.1002/chem.201303409

No evidence for histamine H4-receptor in human monocytes

K. Werner, D. Neumann, A. Buschauer, R. Seifert

J. Pharmacol. Exp. Ther. 2014, 351, 519–526

DOI: 10.1124/jpet.114.218107

2013

Replacement of Thr32 and Gln34 in the C-Terminal Neuropeptide Y Fragment 25–36 by cis-Cyclobutane and cis-Cyclopentane β-Amino Acids Shifts Selectivity toward the Y4 Receptor

L. Berlicki, M. Kaske, R. Gutierrez-Abad, G. Bernhardt, O. Illa, R. Ortuño, C. Cabrele, A. Buschauer, O. Reiser

J. Med. Chem. 2013, 56, 8422−8431.

DOI: 10.1021/jm4008505

Dimeric argininamide-type neuropeptide Y receptor antagonists: Chiral discrimination between Y1 and Y4 receptors

M. Keller, M. Kaske, T. Holzammer, G. Bernhardt, A. Buschauer,

Bioorg. Med. Chem. 2013, 21, 6303-6322

DOI: 10.1016/j.bmc.2013.08.065