The University of Queensland

Chemical synthesis of grafted cyclotides using a “plug and play” approach

Koehbach, Johannes, Muratspahić, Edin, Ahmed, Zakaria M, White, Andrew M, Tomašević, Nataša, Durek, Thomas, Clark, Richard J, Gruber, Christian W and Craik, David J (2024). Chemical synthesis of grafted cyclotides using a “plug and play” approach. RSC Chemical Biology. doi: 10.1039/d4cb00008k

Design and structural validation of peptide–drug conjugate ligands of the kappa-opioid receptor

Muratspahić, Edin, Deibler, Kristine, Han, Jianming, Tomašević, Nataša, Jadhav, Kirtikumar B., Olivé-Marti, Aina-Leonor, Hochrainer, Nadine, Hellinger, Roland, Koehbach, Johannes, Fay, Jonathan F., Rahman, Mohammad Homaidur, Hegazy, Lamees, Craven, Timothy W., Varga, Balazs R., Bhardwaj, Gaurav, Appourchaux, Kevin, Majumdar, Susruta, Muttenthaler, Markus, Hosseinzadeh, Parisa, Craik, David J., Spetea, Mariana, Che, Tao, Baker, David and Gruber, Christian W. (2023). Design and structural validation of peptide–drug conjugate ligands of the kappa-opioid receptor. Nature Communications, 14 (1) 8064, 1-17. doi: 10.1038/s41467-023-43718-w

Development of a selective peptide κ-opioid receptor antagonist by late-stage functionalization with cysteine staples

Muratspahić, Edin, White, Andrew M., Ciotu, Cosmin I., Hochrainer, Nadine, Tomašević, Nataša, Koehbach, Johannes, Lewis, Richard J., Spetea, Mariana, Fischer, Michael J. M., Craik, David J. and Gruber, Christian W. (2023). Development of a selective peptide κ-opioid receptor antagonist by late-stage functionalization with cysteine staples. Journal of Medicinal Chemistry, 66 (17), 11843-11854. doi: 10.1021/acs.jmedchem.3c00426

Exploring the therapeutic potential of an antinociceptive and anti-inflammatory peptide from wasp venom

Galante, Priscilla, Campos, Gabriel A. A., Moser, Jacqueline C. G., Martins, Danubia B., Dos Santos Cabrera, Marcia P., Rangel, Marisa, Coelho, Luiza C., Simon, Karina S., Amado, Veronica M., de A. I. Muller, Jessica, Koehbach, Johannes, Lohman, Rink-Jan, Cabot, Peter J., Vetter, Irina, Craik, David J., Toffoli-Kadri, Monica C., Monge-Fuentes, Victoria, Goulart, Jair T., Schwartz, Elisabeth F., Silva, Luciano P., Bocca, Anamelia L. and Mortari, Márcia R (2023). Exploring the therapeutic potential of an antinociceptive and anti-inflammatory peptide from wasp venom. Scientific Reports, 13 (1) 12491, 1-15. doi: 10.1038/s41598-023-38828-w

A chemoenzymatic approach to produce a cyclic analogue of the analgesic drug MVIIA (Ziconotide)

Zhou, Yan, Harvey, Peta J., Koehbach, Johannes, Chan, Lai Yue, Jones, Alun, Andersson, Åsa, Vetter, Irina, Durek, Thomas and Craik, David J. (2023). A chemoenzymatic approach to produce a cyclic analogue of the analgesic drug MVIIA (Ziconotide). Angewandte Chemie, 135 (29) e202302812, 1-5. doi: 10.1002/ange.202302812

A chemo-enzymatic approach to produce a cyclic analogue of the analgesic drug MVIIA (Ziconotide)

Zhou, Yan, Harvey, Peta J., Koehbach, Johannes, Chan, Lai Yue, Jones, Alun, Andersson, Åsa, Vetter, Irina, Durek, Thomas and Craik, David J. (2023). A chemo-enzymatic approach to produce a cyclic analogue of the analgesic drug MVIIA (Ziconotide). Angewandte Chemie, 62 (29) e202302812, e202302812. doi: 10.1002/anie.202302812

Author Correction: Tick holocyclotoxins trigger host paralysis by presynaptic inhibition

Chand, Kirat K., Lee, Kah Meng, Lavidis, Nickolas A., Rodriguez-Valle, Manuel, Ijaz, Hina, Koehbach, Johannes, Clark, Richard J., Lew-Tabor, Ala and Noakes, Peter G. (2022). Author Correction: Tick holocyclotoxins trigger host paralysis by presynaptic inhibition. Scientific Reports, 12 (1) 20636, 1-1. doi: 10.1038/s41598-022-24528-4

Antinociceptive peptides from venomous arthropods

Muller, Jessica A. I., Chan, Lai Y., Toffoli-Kadri, Monica C., Mortari, Marcia R., Craik, David J. and Koehbach, Johannes (2022). Antinociceptive peptides from venomous arthropods. Toxin Reviews, 42 (1), 1-20. doi: 10.1080/15569543.2022.2065510

Importance of the cyclic cystine knot structural motif for immunosuppressive effects of cyclotides

Hellinger, Roland, Muratspahić, Edin, Devi, Seema, Koehbach, Johannes, Vasileva, Mina, Harvey, Peta J., Craik, David J., Gründemann, Carsten and Gruber, Christian W. (2021). Importance of the cyclic cystine knot structural motif for immunosuppressive effects of cyclotides. ACS Chemical Biology, 16 (11) acschembio.1c00524, 2373-2386. doi: 10.1021/acschembio.1c00524

Design of a stable cyclic peptide analgesic derived from sunflower seeds that targets the κ-opioid receptor for the treatment of chronic abdominal pain

Muratspahić, Edin, Tomašević, Nataša, Koehbach, Johannes, Duerrauer, Leopold, Hadžić, Seid, Castro, Joel, Schober, Gudrun, Sideromenos, Spyridon, Clark, Richard J., Brierley, Stuart M., Craik, David J. and Gruber, Christian W. (2021). Design of a stable cyclic peptide analgesic derived from sunflower seeds that targets the κ-opioid receptor for the treatment of chronic abdominal pain. Journal of Medicinal Chemistry, 64 (13) acs.jmedchem.1c00158, 9042-9055. doi: 10.1021/acs.jmedchem.1c00158

Comparison of a short linear antimicrobial peptide with its disulfide-cyclized and cyclotide-grafted variants against clinically relevant pathogens

Koehbach, Johannes, Gani, Jurnorain, Hilpert, Kai and Craik, David J. (2021). Comparison of a short linear antimicrobial peptide with its disulfide-cyclized and cyclotide-grafted variants against clinically relevant pathogens. Microorganisms, 9 (6) 1249, 1249. doi: 10.3390/microorganisms9061249

Antimicrobial and anticancer properties of synthetic peptides derived from the wasp Parachartergus fraternus

Muller, Jessica A. I., Lawrence, Nicole, Chan, Lai Yue, Harvey, Peta J., Elliott, Alysha G., Blaskovich, Mark A. T., Gonçalves, Jacqueline C., Galante, Priscilla, Mortari, Marcia R., Toffoli-Kadri, Mônica C., Koehbach, Johannes and Craik, David (2021). Antimicrobial and anticancer properties of synthetic peptides derived from the wasp Parachartergus fraternus. Chembiochem , 22 (8) cbic.202000716, 1415-1423. doi: 10.1002/cbic.202000716

Cyclotides from Brazilian Palicourea sessilis and their effects on human lymphocytes

Pinto, Meri Emili F., Chan, Lai Yue, Koehbach, Johannes, Devi, Seema, Gründemann, Carsten, Gruber, Christian W., Gomes, Mario, Bolzani, Vanderlan S., Cilli, Eduardo Maffud and Craik, David J. (2021). Cyclotides from Brazilian Palicourea sessilis and their effects on human lymphocytes. Journal of Natural Products, 84 (1) acs.jnatprod.0c01069, 81-90. doi: 10.1021/acs.jnatprod.0c01069

Harnessing cyclotides to design and develop novel peptide GPCR ligands

Muratspahić, Edin, Koehbach, Johannes, Gruber, Christian W. and Craik, David J. (2020). Harnessing cyclotides to design and develop novel peptide GPCR ligands. RSC Chemical Biology, 1 (4), 177-191. doi: 10.1039/d0cb00062k

The vast structural diversity of antimicrobial peptides

Koehbach, Johannes and Craik, David J. (2019). The vast structural diversity of antimicrobial peptides. Trends in Pharmacological Sciences, 40 (7), 517-528. doi: 10.1016/j.tips.2019.04.012

Inhibition of breast cancer cell migration by cyclotides isolated from Pombalia calceolaria

Pinto, Meri Emili F., Najas, Jhenny Z. G., Magalhães, Luma G., Bobey, Antonio F., Mendonça, Jacqueline N., Lopes, Norberto P., Leme, Flávia M., Teixeira, Simone P., Trovó, Marcelo, Andricopulo, Adriano D., Koehbach, Johannes, Gruber, Christian W., Cilli, Eduardo Maffud and Bolzani, Vanderlan S. (2018). Inhibition of breast cancer cell migration by cyclotides isolated from Pombalia calceolaria. Journal of Natural Products, 81 (5), 1203-1208. doi: 10.1021/acs.jnatprod.7b00969

Transcriptome and toxin family analysis of the paralysis tick, Ixodes holocyclus

Rodriguez-Valle, Manuel, Moolhuijzen, Paula, Barrero, Roberto A., Ong, Chian Teng, Busch, Greta, Karbanowicz, Thomas, Booth, Mitchell, Clark, Richard, Koehbach, Johannes, Ijaz, Hina, Broady, Kevin, Agnew, Kim, Knowles, Aleta G., Bellgard, Matthew I. and Tabor, Ala E. (2018). Transcriptome and toxin family analysis of the paralysis tick, Ixodes holocyclus. International Journal for Parasitology, 48 (1), 71-82. doi: 10.1016/j.ijpara.2017.07.007

Structure-activity relationships of insect defensins

Koehbach, Johannes (2017). Structure-activity relationships of insect defensins. Frontiers in Chemistry, 5 (JUL) 45. doi: 10.3389/fchem.2017.00045

Global map of oxytocin/vasopressin-like neuropeptide signalling in insects

Liutkeviciute, Zita, Koehbach, Johannes, Eder, Thomas, Gil-Mansilla, Esther and Gruber, Christian W. (2016). Global map of oxytocin/vasopressin-like neuropeptide signalling in insects. Scientific Reports, 6 (1) 39177, 55-61. doi: 10.1038/srep39177

Unveiling the diversity of cyclotides by combining peptidome and transcriptome analysis

Koehbach, Johannes and Clark, Richard J. (2016). Unveiling the diversity of cyclotides by combining peptidome and transcriptome analysis. Biopolymers, 106 (6), 774-783. doi: 10.1002/bip.22858

Tick holocyclotoxins trigger host paralysis by presynaptic inhibition

Chand, Kirat K., Lee, Kah Meng, Lavidis, Nickolas A., Rodriguez-Valle, Manuel, Ijaz, Hina, Koehbach, Johannes, Clark, Richard J., Lew-Tabor, Ala and Noakes, Peter G. (2016). Tick holocyclotoxins trigger host paralysis by presynaptic inhibition. Scientific Reports, 6 (1) 29446, 29446. doi: 10.1038/srep29446

MALDI TOF/TOF-based approach for the identification of d-amino acids in biologically active peptides and proteins

Koehbach, Johannes, Gruber, Christian W., Becker, Christian, Kreil, David P. and Jilek, Alexander (2016). MALDI TOF/TOF-based approach for the identification of d-amino acids in biologically active peptides and proteins. Journal of Proteome Research, 15 (5), 1487-1496. doi: 10.1021/acs.jproteome.5b01067

Peptidomics of circular cysteine-rich plant peptides: Analysis of the diversity of cyclotides from viola tricolor by transcriptome and proteome mining

Hellinger, Roland, Koehbach, Johannes, Soltis, Douglas E., Carpenter, Eric J., Wong, Gane Ka-Shu and Gruber, Christian W. (2015). Peptidomics of circular cysteine-rich plant peptides: Analysis of the diversity of cyclotides from viola tricolor by transcriptome and proteome mining. Journal of Proteome Research, 14 (11), 4851-4862. doi: 10.1021/acs.jproteome.5b00681

Inhibition of human prolyl oligopeptidase activity by the cyclotide psysol 2 isolated from Psychotria solitudinum

Hellinger, Roland, Koehbach, Johannes, Puigpinos, Albert, Clark, Richard J., Tarrago, Teresa, Giralt, Ernest and Gruber, Christian W. (2015). Inhibition of human prolyl oligopeptidase activity by the cyclotide psysol 2 isolated from Psychotria solitudinum. Journal of Natural Products, 78 (5), 1073-1082. doi: 10.1021/np501061t

Unravelling peptidomes by in silico mining

Koehbach, Johannes and Jackson, Kathryn A. V. (2015). Unravelling peptidomes by in silico mining. Peptidomics, 2 (1), 17-25. doi: 10.1515/ped-2015-0002

Ribifolin, an orbitide from jatropha ribifolia, and its potential antimalarial activity

Pinto, Meri Emili F., Batista, Joao M., Koehbach, Johannes, Gaur, Pratibha, Sharma, Abhinay, Nakabashi, Myna, Cilli, Eduardo Maffud, Giesel, Guilherme M., Verli, Hugo, Gruber, Christian W., Blanch, Ewan W., Tavares, Joseam F., da Silva, Marcelo S., Garcia, Celia R. S. and Bolzani, Vanderlan S. (2015). Ribifolin, an orbitide from jatropha ribifolia, and its potential antimalarial activity. Journal of Natural Products, 78 (3), 374-380. doi: 10.1021/np5007668

Cyclotides in the Rubiaceae

Koehbach, Johannes and Gruber, Christian W. (2015). Cyclotides in the Rubiaceae. Advances in Botanical Research, 76, 51-78. doi: 10.1016/bs.abr.2015.09.002

MUW resarcher of the month MUW resarcher of the month

Koehbach, Johannes (2014). MUW resarcher of the month MUW resarcher of the month. Wiener klinische Wochenschrift, 126 (17-18), 555-556. doi: 10.1007/s00508-014-0615-4

Immunosuppressive activity of an aqueous Viola tricolor herbal extract

Hellinger, Roland, Koehbach, Johannes, Fedchuk, Halyna, Sauer, Barbara, Huber, Roman, Gruber, Christian W. and Gruendemann, Carsten (2014). Immunosuppressive activity of an aqueous Viola tricolor herbal extract. Journal of Ethnopharmacology, 151 (1), 299-306. doi: 10.1016/j.jep.2013.10.044

Biosynthese und molekulare Wirkung von zyklischen Pflanzenpeptiden

Koehbach, Johannes and Gruber, Christian W. (2014). Biosynthese und molekulare Wirkung von zyklischen Pflanzenpeptiden. BioSpektrum, 20 (7), 741-743. doi: 10.1007/s12268-014-0511-5

From ethnopharmacology to drug design

Koehbach, Johannes and Gruber, Christian W. (2013). From ethnopharmacology to drug design. Communicative and Integrative Biology, 6 (6) e27583. doi: 10.4161/cib.27583

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

Cyclotide discovery in Gentianales revisited—identification and characterization of cyclic cystine-knot peptides and their phylogenetic distribution in Rubiaceae plants

Koehbach, Johannes, Attah, Alfred F., Berger, Andreas, Hellinger, Roland, Kutchan, Toni M., Carpenter, Eric J., Rolf, Megan, Sonibare, Mubo A., Moody, Jones O., Wong, Gane Ka-Shu, Dessein, Steven, Greger, Harald and Gruber, Christian W. (2013). Cyclotide discovery in Gentianales revisited—identification and characterization of cyclic cystine-knot peptides and their phylogenetic distribution in Rubiaceae plants. Biopolymers, 100 (5), 438-452. doi: 10.1002/bip.22328

Characterizing circular peptides in mixtures: sequence fragment assembly of cyclotides from a violet plant by MALDI-TOF/TOF mass spectrometry

Hashempour, Hossein, Koehbach, Johannes, Daly, Norelle L., Ghassempour, Alireza and Gruber, Christian W. (2013). Characterizing circular peptides in mixtures: sequence fragment assembly of cyclotides from a violet plant by MALDI-TOF/TOF mass spectrometry. Amino Acids, 44 (2), 581-595. doi: 10.1007/s00726-012-1376-x

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

Uterine contractility of plants used to facilitate childbirth in Nigerian ethnomedicine

Attah, Alfred F., O'Brien, Margaret, Koehbach, Johannes, Sonibare, Mubo A., Moody, Jones O., Smith, Terry J. and Gruber, Christian W. (2012). Uterine contractility of plants used to facilitate childbirth in Nigerian ethnomedicine. Journal of Ethnopharmacology, 143 (1), 377-382. doi: 10.1016/j.jep.2012.06.042

The nonpeptide oxytocin receptor agonist WAY 267,464: receptor-binding profile, prosocial effects and distribution of c-Fos expression in adolescent rats

Hicks, C., Jorgensen, W., Brown, C., Fardell, J., Koehbach, J., Gruber, C. W., Kassiou, M., Hunt, G. E. and McGregor, I. S. (2012). The nonpeptide oxytocin receptor agonist WAY 267,464: receptor-binding profile, prosocial effects and distribution of c-Fos expression in adolescent rats. Journal of Neuroendocrinology, 24 (7), 1012-1029. doi: 10.1111/j.1365-2826.2012.02311.x

Do plant cyclotides have potential as immunosuppressant peptides?

Gruendemann, Carsten, Koehbach, Johannes, Huber, Roman and Gruber, Christian W. (2012). Do plant cyclotides have potential as immunosuppressant peptides?. Journal of Natural Products, 75 (2), 167-174. doi: 10.1021/np200722w

Discovery of Novel Oxytocin-Like Neuropeptides in Insects

Liutkeviciute, Z., Koehbach, J., Gil-Mansilla, E., Eder, T. and Gruber, C. W. (2016). Discovery of Novel Oxytocin-Like Neuropeptides in Insects. HOBOKEN: WILEY.

Discovery, Synthesis and Characterization of Novel Cysteine-Rich Peptides From Insects

Koehbach, J. and Clark, R. J. (2016). Discovery, Synthesis and Characterization of Novel Cysteine-Rich Peptides From Insects. HOBOKEN: WILEY.

Exploring the chemistry and pharmacological potential of bioactive peptides from insects

Koehbach, Johannes and Clark, Richard J. (2015). Exploring the chemistry and pharmacological potential of bioactive peptides from insects. 14th International Congress on Amino Acids, Peptides and Proteins, Vienna, Austria, August 3–7, 2015. Wien, Austria: Springer Wien. doi: 10.1007/s00726-015-2016-z

Exploring Bioactive Peptides as Pharmacological Tools for Oxytocin and Vasopressin Ligand Design

Gruber, C., Koehbach, J. and Freissmuth, M. (2014). Exploring Bioactive Peptides as Pharmacological Tools for Oxytocin and Vasopressin Ligand Design. WILEY-BLACKWELL.

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. London, United Kingdom: Portland Press. doi: 10.1042/BST20120256

Characterizing circular peptides in mixtures: sequence fragment assembly of cyclotides from a violet plant by MALDI-TOF/TOF mass spectrometry

Hashempour, H., Koehbach, J., Ghassempour, A. and Gruber, C. W. (2012). Characterizing circular peptides in mixtures: sequence fragment assembly of cyclotides from a violet plant by MALDI-TOF/TOF mass spectrometry. WILEY-BLACKWELL.

Combinatorial library of natural cyclic peptides with immunosuppressive properties

Gruber, C. W., Gruendemann, C., Koehbach, J. and Huber, R. (2012). Combinatorial library of natural cyclic peptides with immunosuppressive properties. WILEY-BLACKWELL.

Pharmacological applications of natural peptide libraries

Koehbach, Johannes, Muttenthaler, Markus, Gründemann, Carsten and Gruber, Christian W (2012). Pharmacological applications of natural peptide libraries. 18th Scientific Symposium of the Austrian Pharmacological Society (APHAR), Graz, Austria, 20-21 September, 2012. London, United Kingdom: Springer Nature. doi: 10.1186/2050-6511-13-s1-a31

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. 32nd European Peptide Symposium "Peptides 2012", Athens, Greece, 02-07 September 2012. West Sussex, United Kingdom: John Wiley and Sons. doi: 10.1002/psc.2449

Improved peptidomics screening protocol for the identification of cyclotide-containing plants

Koehbach, J., Dessein, S., Greger, H. and Gruber, C. W. (2011). Improved peptidomics screening protocol for the identification of cyclotide-containing plants. 59th International Congress and Annual Meeting of the Society-for-Medicinal-Plant-and-Natural-Product-Research, Antalya Turkey, Sep 04-09, 2011. GEORG THIEME VERLAG KG.

Modulation of Myometrial Smooth Muscle Cell Contractility by Plant Cyclotides

Kinsella, Marie, Koehbach, Johannes, Smith, Terry J., Gruber, Christian W. and O'Brien, Margaret (2011). Modulation of Myometrial Smooth Muscle Cell Contractility by Plant Cyclotides. SAGE PUBLICATIONS INC.

Discovery of circular disulfide-rich peptides in plants with oxytocin-like activity

Gruber, Christian W., Koehbach, Johannes and O'Brien, Margaret (2011). Discovery of circular disulfide-rich peptides in plants with oxytocin-like activity. 22nd American Peptide Symposium, San Diego Ca, Jun 25-30, 2011. WILEY-BLACKWELL.