The University of Queensland

Selenocystine peptides - synthesis, folding and applications

Muttenthaler, M. and Alewood, P. F. (2009). Selenocystine peptides - synthesis, folding and applications. In Johannes Buchner (Ed.), Oxidative folding of peptides and proteins (pp. 396-418) Cambridge , U.K.: Royal Society of Chemistry.

Oxytocin-like signaling in ants influences metabolic gene expression and locomotor activity

Liutkevičiūtė, Zita, Gil-Mansilla, Esther, Eder, Thomas, Casillas-Pérez, Barbara, Di Giglio, Maria Giulia, Muratspahić, Edin, Grebien, Florian, Rattei, Thomas, Muttenthaler, Markus, Cremer, Sylvia and Gruber, Christian W. (2018) Oxytocin-like signaling in ants influences metabolic gene expression and locomotor activity. The FASEB Journal, fj201800443. doi:10.1096/fj.201800443

Contractility measurements of human uterine smooth muscle to aid drug development

Arrowsmith, Sarah, Keov, Peter, Muttenthaler, Markus and Gruber, Christian W. (2018) Contractility measurements of human uterine smooth muscle to aid drug development. Journal of Visualized Experiments, 2018 131: . doi:10.3791/56639

Subtle modifications to oxytocin produce ligands that retain potency and improved selectivity across species

Muttenthaler, Markus, Andersson, Asa, Vetter, Irina, Menon, Rohit, Busnelli, Marta, Ragnarsson, Lotten, Bergmayr, Christian, Arrowsmith, Sarah, Deuis, Jennifer R., Chiu, Han Sheng, Palpant, Nathan J., O'Brien, Margaret, Smith, Terry J., Wray, Susan, Neumann, Inga D., Gruber, Christian W., Lewis, Richard J. and Alewood, Paul F. (2017) Subtle modifications to oxytocin produce ligands that retain potency and improved selectivity across species. Science Signaling, 10 508: 1-13. doi:10.1126/scisignal.aan3398

Nanoparticle cellular uptake by dendritic wedge peptides: achieving single peptide facilitated delivery

Breger, Joyce C., Muttenthaler, Markus, Delehanty, James B., Thompson, Darren A., Oh, Eunkeu, Susumu, Kimihiro, Deschamps, Jeffrey R., Anderson, George P., Field, Lauren D., Walper, Scott A., Dawson, Philip E. and Medintz, Igor L. (2017) Nanoparticle cellular uptake by dendritic wedge peptides: achieving single peptide facilitated delivery. Nanoscale, 9 29: 10447-10464. doi:10.1039/c7nr03362a

Development of a human vasopressin V1a-receptor antagonist from an evolutionary-related insect neuropeptide

Di Giglio, Maria Giulia , Muttenthaler, Markus, Harpsoe, Kasper, Liutkeviciute, Zita, Keov, Peter, Eder, Thomas, Rattei, Thomas, Arrowsmith, Sarah, Wray, Susan, Marek, Ales, Elbert, Tomas, Alewood, Paul F. , Gloriam, David E. and Gruber, Christian W. (2017) Development of a human vasopressin V1a-receptor antagonist from an evolutionary-related insect neuropeptide. Scientific Reports, 7 1: 41002. doi:10.1038/srep41002

Synthesis of multivalent [Lys8]-oxytocin dendrimers that inhibit visceral nociceptive responses

Wan, Jingjing, Mobli, Mehdi, Brust, Andreas, Muttenthaler, Markus, Andersson, Asa, Ragnarsson, Lotten, Castro, Joel, Vetter, Irina, Huang, Johnny X., Nilsson, Mathias, Brierley, Stuart M., Cooper, Matthew A., Lewis, Richard J. and Alewood, Paul F. (2017) Synthesis of multivalent [Lys8]-oxytocin dendrimers that inhibit visceral nociceptive responses. Australian Journal of Chemistry, 70 2: 162-171. doi:10.1071/CH16407

Design and characterization of superpotent bivalent ligands targeting oxytocin receptor dimers via a channel-like structure

Busnelli, Marta, Kleinau, Gunnar, Muttenthaler, Markus, Stoev, Stoytcho, Manning, Maurice, Bibic, Lucka, Howell, Lesley A., McCormick, Peter J., Di Lascio, Simona, Braida, Daniela, Sala, Mariaelvina, Rovati, G. Enrico, Bellini, Tommaso and Chini, Bice (2016) Design and characterization of superpotent bivalent ligands targeting oxytocin receptor dimers via a channel-like structure. Journal of Medicinal Chemistry, 59 15: 7152-7166. doi:10.1021/acs.jmedchem.6b00564

Methods, setup and safe handling for anhydrous hydrogen fluoride cleavage in Boc solid-phase peptide synthesis

Muttenthaler, Markus, Albericio, Fernando and Dawson, Philip E. (2015) Methods, setup and safe handling for anhydrous hydrogen fluoride cleavage in Boc solid-phase peptide synthesis. Nature Protocols, 10 7: 1067-1083. doi:10.1038/nprot.2015.061

Lipid bilayer crossing-the gate of symmetry. Water-soluble phenylproline-based blood-brain barrier shuttles

Arranz-Gibert, Pol, Guixer, Bernat, Malakoutikhah, Morteza, Muttenthaler, Markus, Guzman, Fanny, Teixido, Meritxell and Giralt, Ernest (2015) Lipid bilayer crossing-the gate of symmetry. Water-soluble phenylproline-based blood-brain barrier shuttles. Journal of the American Chemical Society, 137 23: 7357-7364. doi:10.1021/jacs.5b02050

Discovery, synthesis, and structure: activity relationships of conotoxins

Akondi, Kalyana, Muttenthaler, Markus, Dutertre, Sébastien, Kaas, Quentin, Craik, David J., Lewis, Richard J. and Alewood, Paul F. (2014) Discovery, synthesis, and structure: activity relationships of conotoxins. Chemical Reviews, Articles ASAP 11: 1-33. doi:10.1021/cr400401e

Selenoether oxytocin analogues have analgesic properties in a mouse model of chronic abdominal pain

Dantas De Araujo, Aline, Mobli, Mehdi, Castro, Joel, Harrington, Andrea M., Vetter, Irina, Dekan, Zoltan, Muttenthale, Markus, Wan, JingJing, Lewis, Richard J., King, Glenn F., Brierley, Stuart M. and Alewood, Paul F. (2014) Selenoether oxytocin analogues have analgesic properties in a mouse model of chronic abdominal pain. Nature Communications, 5 1: 3165.1-3165.12. doi:10.1038/ncomms4165

Oxytocic plant cyclotides as templates for peptide G protein-coupled receptor ligand design

Koehbach, Johannes, O'Brien, Margaret, Muttenthaler, Markus, Miazzo, Marion, Akcan, Muharrem, Elliott, Alysha G., Daly, Norelle L., Harvey, Peta J., Arrowsmith, Sarah, Gunasekera, Sunithi, Smith, Terry J., Wray, Susan, Göransson, Ulf, Dawson, Philip E., Craik, David J., Freissmuth, Michael and Gruber, Christian W. (2013) Oxytocic plant cyclotides as templates for peptide G protein-coupled receptor ligand design. Proceedings of the National Academy of Sciences of the United States of America, 110 52: 21183-21188. doi:10.1073/pnas.1311183110

Evaluation of diverse peptidyl motifs for cellular delivery of semiconductor quantum dots Optical Nanosensing in Cells

Gemmill, Kelly Boeneman, Muttenthaler, Markus, Delehanty, James B., Stewart, Michael H., Susumu, Kimihiro, Dawson, Philip E. and Medintz, Igor L. (2013) Evaluation of diverse peptidyl motifs for cellular delivery of semiconductor quantum dots Optical Nanosensing in Cells. Analytical and Bioanalytical Chemistry, 405 19: 6145-6154. doi:10.1007/s00216-013-6982-2

Exploring bioactive peptides from natural sources for oxytocin and vasopressin drug discovery

Gruber, Christian W., Koehbach, Johannes and Muttenthaler, Markus (2012) Exploring bioactive peptides from natural sources for oxytocin and vasopressin drug discovery. Future Medicinal Chemistry, 4 14: 1791-1798. doi:10.4155/FMC.12.108

Abundance and diversity of Conus species (Gastropoda: Conidae) at the northern tip of New Ireland province of Papua New Guinea

Muttenthaler, Markus, Dutertre, Sebastien, Wingerd, Joshua S., Aini, John W., Walton, Hugh, Alewood, Paul F. and Lewis, Richard J. (2012) Abundance and diversity of Conus species (Gastropoda: Conidae) at the northern tip of New Ireland province of Papua New Guinea. Nautilus, 126 2: 47-56.

Discovery of defense- and neuropeptides in social ants by genome-mining

Gruber, Christian W. and Muttenthaler, Markus (2012) Discovery of defense- and neuropeptides in social ants by genome-mining. PloS One, 7 3: e32559. doi:10.1371/journal.pone.0032559

Site-specific pKa determination of selenocysteine residues in selenovasopressin using 77Se NMR

Mobli, Mehdi, Morgenstern, David, King, Glenn F., Alewood, Paul F. and Muttenthaler, Markus (2011) Site-specific pKa determination of selenocysteine residues in selenovasopressin using 77Se NMR. Angewandte Chemie (International Edition), 50 50: 11952-11955. doi:10.1002/anie.201104169

Structure-activity studies on alpha-conotoxins

Muttenthaler, Markus, Akondi, Kalyana B. and Alewood, Paul F. (2011) Structure-activity studies on alpha-conotoxins. Current Pharmaceutical Design, 17 38: 4226-4241. doi:10.2174/138161211798999384

Modulating oxytocin activity and plasma stability by disulfide bond engineering

Muttenthaler, Markus, Andersson, Asa, Dantas de Araujo, Aline, Dekan, Zoltan, Lewis, Richard J. and Alewood, Paul F. (2010) Modulating oxytocin activity and plasma stability by disulfide bond engineering. Journal of Medicinal Chemistry, 53 24: 8585-8596. doi:10.1021/jm100989w

Ligand-based peptide design and combinatorial peptide libraries to target G protein-coupled receptors

Gruber, Christian W., Muttenthaler, Markus and Freissmuth, Michael (2010) Ligand-based peptide design and combinatorial peptide libraries to target G protein-coupled receptors. Current Pharmaceutical Design, 16 28: 3071-3088. doi:10.2174/138161210793292474

α-Conotoxin AuIB isomers exhibit distinct inhibitory mechanisms and differential sensitivity to stoichiometry of α3β4 nicotinic acetylcholine receptors

Grishin, Anton, Wang, Ching-I. A., Muttenthaler, Markus, Alewood, Paul F., Lewis, Richard J. and Adams, David J. (2010) α-Conotoxin AuIB isomers exhibit distinct inhibitory mechanisms and differential sensitivity to stoichiometry of α3β4 nicotinic acetylcholine receptors. Journal of Biological Chemistry, 285 29: 22254-22263. doi:10.1074/jbc.M110.111880

Solving the alpha-conotoxin folding problem: Efficient selenium-directed on-resin generation of more potent and stable nicotinic acetylcholine receptor antaqonists

Muttenthaler, Marcus, Nevin, Simon T., Grishin, Anton A., Ngo, Shyuan T., Choy, Peng T., Daly, Norelle L., Hu, Shu-Hong, Armishaw, Christopher J., Wang, Ching-I. A., Lewis, Richard J., Martin, Jennifer L., Noakes, Peter G., Craik, David J., Adams, David J. and Alewood, Paul F. (2010) Solving the alpha-conotoxin folding problem: Efficient selenium-directed on-resin generation of more potent and stable nicotinic acetylcholine receptor antaqonists. Journal of the American Chemical Society, 132 10: 3514-3522. doi:10.1021/ja910602h

p-Nitrobenzyl protection for cysteine and selenocysteine: A more stable alternative to the acetamidomethyl group

Muttenthaler, Markus, Ramos, Yesica Garcia, Feytens, Debby, Dantas de Araujo, Aline and Alewood, Paul F. (2010) p-Nitrobenzyl protection for cysteine and selenocysteine: A more stable alternative to the acetamidomethyl group. Biopolymers, 94 4: 423-432. doi:10.1002/bip.21502

Selenopeptide chemistry

Muttenthaler, Markus and Alewood, Paul F. (2008) Selenopeptide chemistry. Journal of Peptide Science, 14 12: 1223-1239. doi:10.1002/psc.1075

Conopressin-T from Conus tulipa reveals an antagonist switch in vasopressin-like peptide

Dutertre, Sébastien, Croker, Daniel, Daly, Norelle L., Andersson, Åsa, Muttenthaler, Markus, Lumsden, Natalie G., Craik, David J., Alewood, Paul F., Guillon, Gilles and Lewis, Richard J. (2008) Conopressin-T from Conus tulipa reveals an antagonist switch in vasopressin-like peptide. Journal of Biological Chemistry, 283 11: 7100-7108. doi:10.1074/jbc.M706477200

Synthesis and characterisation of new ditetrazole-ligands as more rigid building blocks of envisaged iron(II) spin-crossover coordination polymers

Muttenthaler M., Bartel M., Weinberger P., Hilscher G. and Linert W. (2005) Synthesis and characterisation of new ditetrazole-ligands as more rigid building blocks of envisaged iron(II) spin-crossover coordination polymers. Journal of Molecular Structure, 741 1-3: 159-169. doi:10.1016/j.molstruc.2005.02.007

Advancing the frontiers of chemical protein synthesis - the 7CPS meeting, Haifa, Israel

Conibear, Anne C. and Muttenthaler, Markus (2018) Advancing the frontiers of chemical protein synthesis - the 7CPS meeting, Haifa, Israel. Cell Chemical Biology, 25 3: 247-254. doi:10.1016/j.chembiol.2018.03.001

Expression and function of vasopressin receptor subtypes in human myometrium: implications for effective tocolysis

Arrowsmith, Sarah, Taylor, Olayisade, Muttenthaler, Markus and Wray, Susan (2016). Expression and function of vasopressin receptor subtypes in human myometrium: implications for effective tocolysis. In: Acta Physiologica. , , (21-22). .

Miklos Bodanszky Award Lecture Probing the Functional Complexity of Ancient Oxytocin in Health and Disease

Muttenthaler, Markus, Andersson, Asa, Ragnarsson, Lotten, Vetter, Irina, Busnelli, Marta, Chini, Bice, Arrowsmith, Sarah, Wray, Susan, de Araujo, Aline Dantas, Dutertre, Sebastien, Mobli, Mehdi, Lewis, Richard J., Gruber, Christian W. and Alewood, Paul F. (2016). Miklos Bodanszky Award Lecture Probing the Functional Complexity of Ancient Oxytocin in Health and Disease. In: Journal of Peptide Science. 34th European Peptide Symposium , Leipzig, Germany, (S7-S8). 4‐9 September 2016.

New pharmacological tools to investigate oxytocin receptors in neurodevelopmental brain disorders

Busnelli, M., Leonzino, M., Silva, B., Dona, E., Manning, M., Muttenthaler, M. and Chini, B. (2015). New pharmacological tools to investigate oxytocin receptors in neurodevelopmental brain disorders. In: Journal of Neurochemistry. 25th Biennial Meeting of the International-Society-for-Neurochemistry Jointly with the 13th Meeting of the Asian-Pacific-Society-for-Neurochemistry in Conjunction with the 35th Meeting of the Australasian-Neuroscience-Society, Cairns Australia, (168-168). Aug 23-27, 2015.

Re-Examining the Importance of Vasopressin Receptors in Myometrial Contraction.

Arrowsmith, Sarah, Wray, Susan and Muttenthaler, Markus (2015). Re-Examining the Importance of Vasopressin Receptors in Myometrial Contraction.. In: Reproductive Sciences. , , (332A-332A). .

Insights into the molecular evolution of oxytocin receptor ligand binding

Koehbach, Johannes, Stockner, Thomas, Bergmayr, Christian, Muttenthaler, Markus and Gruber, Christian W. (2013) Insights into the molecular evolution of oxytocin receptor ligand binding. Biochemical Society Transactions, 41 1: 197-204. doi:10.1042/BST20120256

Peptide-mediated cellular delivery of semiconductor quantum dots

Gemmill, K.B., Muttenthaler, M., Delehanty, J., Deschamps, J., Susumu, K., Stewart, M., Dawson, P., Huston, A. and Medintz, I. (2013). Peptide-mediated cellular delivery of semiconductor quantum dots. In: Šárka O. Southern, Conference on Sensing Technologies for Global Health, Military Medicine, and Environmental Monitoring III, Baltimore, United States, (). Apr 29-May 01, 2013. doi:10.1117/12.2015446

Novel sources for potent and selective GPCR modulators

Muttenthaler, M., Dawson, P. E., Gruber, C. W., Bergmayr, C., Freissmuth, M., Andersson, A., Vetter, I., Dutertre, S., Lewis, R. J. and Alewood, P. F. (2012). Novel sources for potent and selective GPCR modulators. In: unknown, unknown, (S26-S26). unknown. doi:10.1002/psc.2447

Pharmacological characterization of circular plant peptides with oxytocin-like activity

Koehbach, J., O'Brien, M., Miazzo, M., Muttenthaler, M., Akcan, M., Smith, T. J., Craik, D. J., Freissmuth, M. and Gruber, C. W. (2012). Pharmacological characterization of circular plant peptides with oxytocin-like activity. In: Proceedings of the 32nd European Peptide Symposium. 32nd European Peptide Symposium "Peptides 2012", Athens, Greece, (S98-S98). 02-07 September 2012. doi:10.1002/psc.2449

Conotoxins - blueprints for GPCR drug discovery?

Muttenthaler, M., Gruber, C. W., Andersson, A., Vetter, I., Nevin, S. T., Grishin, A. A., Dutertre, S., Daly, N. L., Craik, D. J., Adams, D. J., Lewis, R. J. and Alewood, P. F. (2011). Conotoxins - blueprints for GPCR drug discovery?. In: 22nd American Peptide Symposium, San Diego, CA, United States, (422-422). 25-30 June 2011.

Oxytocin agonist design - A selenocysteine mimetic reveals a functional selectivity switch for the human oxytocin receptor

Muttenthaler, M. M., de Araujo, A. D., Andersson, A., Vetter, I., Gruber, C., Ramos, Y. Garcia, Feytens, D., Bergmayr, C., Freissmuth, M., Lewis, R. and Alewood, P. (2010). Oxytocin agonist design - A selenocysteine mimetic reveals a functional selectivity switch for the human oxytocin receptor. In: Journal of Peptide Science. 31st European Peptide Symposium, Copenhagen, Denmark, (161-161). 5-9 September 2010. doi:10.1002/psc.1303

Selenocysteine in peptide drug design

Adams, D. J., Alewood, P. F., Choy, P. T., Craik, D. J., Daly, N. L., Grishin, A. A., Hu, S-H., Martin, J. L., Muttenthaler, M., Nevin, S. T., Ngo, S. T. and Noakes, P. G. (2008). Selenocysteine in peptide drug design. In: Royal Australian Chemical Institute (RACI) Annual Scientific Meeting: Drug Discovery and Development, Couran Cove Island Resort, Queensland, Australia, (). 13 - 17 July 2008.

Selenocysteine in peptide folding and drug design

Muttenthaler, M., Nevin, S. T., Grishin, A. A., Ngo, S. T., Choy, P. T., Daly, N. L., Hu, S-H., Martin, J. L., Noakes, P. G., Craik, D. J., Adams, D. J. and Alewood, P. F. (2008). Selenocysteine in peptide folding and drug design. In: XXth International Symposium on Medicinal Chemistry (EFMC-ISMC 2008), Vienna, Austria, (). 31 August - 4 September 2008.

Directed folding of alpha-conotoxins using selenocysteine

Muttenthaler, M. and Alewood, P. F. (2006). Directed folding of alpha-conotoxins using selenocysteine. In: Journal Of Peptide Science. 29th European Peptide Symposium. 29th European Peptide Symposium, Gdansk, Poland, (87-87). 3-8 September 2006. doi:10.1002/psc.796