Research groups
- Bioresources and Pharmaceutical Chemistry
- Haug research group web pages
- TargetRNA MSCA Doctoral Network
- Norwegian Nuclear Medicine Consortium
Research
We are interested in research questions that lie on the interface of chemistry and biology. The research projects that we are involved in are rooted within medicinal chemistry and biological chemistry, and we apply synthetic organic chemistry to address our research questions. The group has been instrumental for the establishment of the Laboratory for High-throughput experimentation - HTE@UiB, which is lead by Professor Haug. Several of our projects require access to synthetic peptides, and the group has established and runs the Peptide synthesis laboratory at the Department of Chemistry.
The group is part of the research group on Bioresources and Pharmaceutical Chemistry.
Publications
Feature article
Academic article
- Gartan, Parveen; Khorsand, Fahimeh; Mizar, Pushpak et al. (2024). Investigating Polypharmacology through Targeting Known Human Neutrophil Elastase Inhibitors to Proteinase 3. (external link)
- Alsaker, Nicolai Etwin; Halskau, Øyvind; Haug, Bengt Erik et al. (2024). Phospholipid Membrane Interactions of Model Ac-WL-X-LL-OH Peptides Investigated by Solid-State Nuclear Magnetic Resonance. (external link)
- Khorsand, Fahimeh; Haug, Bengt Erik; Kursula, Inari Talvikki et al. (2024). Expression and purification of human neutrophil proteinase 3 from insect cells and characterization of ligand binding. (external link)
- Myklebust, Line Merethe; Baumann, Markus; Støve, Svein Isungset et al. (2023). Optimized bisubstrate inhibitors for the actin N-terminal acetyltransferase NAA80. (external link)
- Berge-Seidl, Sebastian; Nielsen, Nis Valentin; Alfonso, Armando A. Rodriguez et al. (2022). Identification of a phage display-derived peptide interacting with the N-terminal region of factor VII activating protease (FSAP) enables characterization of zymogen activation. (external link)
- Espeland, Ludvik Olai; Georgiou, Charis; Klein, Raphael et al. (2021). An Experimental Toolbox for Structure-Based Hit Discovery for P. aeruginosa FabF, a Promising Target for Antibiotics . (external link)
- García de Jalón , Elvira; Ruiz de Garibay, Gorka; Haug, Bengt Erik et al. (2021). CytoCy5S™, a compound of many structures. in vitro and in vivo evaluation of four near-infrared fluorescent substrates of nitroreductase (NTR). (external link)
- García de Jalón , Elvira; Kleinmanns, Katrin; Fosse, Vibeke Samuelsen et al. (2021). Comparison of Five Near-Infrared Fluorescent Folate Conjugates in an Ovarian Cancer Model. (external link)
- Ruiz de Garibay, Gorka; García de Jalón , Elvira; Stigen, Endre et al. (2021). Repurposing 18F-FMISO as a PET tracer for translational imaging of nitroreductase-based gene directed enzyme prodrug therapy. (external link)
- Guttormsen, Yngve; Fairhurst, Magnus John Espeland; Pandey, Sunil Kumar et al. (2020). Total synthesis of phorbazole B. (external link)
- Ndukwe, Ikenna E.; Lam, Yu-hong; Pandey, Sunil Kumar et al. (2020). Unequivocal structure confirmation of a breitfussin analog by anisotropic NMR measurements. (external link)
- Østnes Hansen, Kine; Andersen, Jeanette hammer; Bayer, Annette et al. (2019). Kinase chemodiversity from the Arctic: the breitfussins. (external link)
- Fairhurst, Magnus John E.; Muhammad, Zeeshan; Haug, Bengt Erik et al. (2018). Aldol condensations on a 3-alkylidene-2,5-diketopiperazine - synthesis of two marine natural products. (external link)
- Goris, Marianne; Magin, Robert S.; Foyn, Håvard et al. (2018). Structural determinants and cellular environment define processed actin as the sole substrate of the N-terminal acetyltransferase NAA80. (external link)
- Nestvold, Janne M.; Wang, Mengyu; Camilio, Ketil Andre et al. (2017). Oncolytic peptide LTX-315 induces an immune-mediated abscopal effect in a rat sarcoma model. (external link)
- Sveinbjørnsson, Baldur; Camilio, Ketil Andre; Haug, Bengt Erik et al. (2017). LTX-315: a first-in-class oncolytic peptide that reprograms the tumor microenvironment. (external link)
- Baumann, Markus; Nome, Lina Marie ; Zachariassen, Zack Georg et al. (2017). Synthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonism. (external link)
- Baumann, Markus; Hussain, Mohammad Musarraf; Henne, Nina et al. (2017). Influence of chain length on the activity of tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4). (external link)
- Haug, Bengt Erik; Camilio, Ketil Andre; Eliassen, liv tone et al. (2016). Discovery of a 9-mer cationic peptide (LTX-315) as a potential first in class oncolytic peptide. (external link)
- Støve, Svein Isungset; Magin, Robert S.; Foyn, Håvard et al. (2016). Crystal structure of the Golgi-associated human N-alpha acetyltransferase 60 (Naa60/NatF) reveals the molecular determinants for substrate-specific acetylation.. (external link)
- Pandey, Sunil Kumar; Guttormsen, Yngve; Haug, Bengt Erik et al. (2015). A concise total synthesis of breitfussin A and B. (external link)
- Aubi Catevilla, Oscar; Flydal, Marte Innselset; Zheng, Huaixin et al. (2015). Discovery of a Specific Inhibitor of Pyomelanin Synthesis in Legionella pneumophila. (external link)
- Zachariassen, Zack Georg; Karlshøj, Stefanie; Haug, Bengt Erik et al. (2015). Probing the molecular interactions between CXC chemokine receptor 4 (CXCR4) and an arginine-based tripeptidomimetic antagonist (KRH-1636). (external link)
- Liu, Liwei; Budnjo, Adnan; Jokela, Jouni et al. (2015). Pseudoaeruginosins, nonribosomal peptides in nodularia spumigena. (external link)
- Narawane, Shailesh; Budnjo, Adnan; Grauffel, Cédric et al. (2014). In silico design, synthesis, and assays of specific substrates for proteinase 3: Influence of fluorogenic and charged groups. (external link)
- Zachariassen, Zack Georg; Thiele, Stefanie; Berg, Erik et al. (2014). Design, synthesis, and biological evaluation of scaffold-based tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4). (external link)
- Budnjo, Adnan; Narawane, Shailesh; Grauffel, Cédric et al. (2014). Reversible ketomethylene-based inhibitors of human neutrophil proteinase 3. (external link)
- McCormack, Emmet ; Silden, Elisabeth; West, Richard M. et al. (2013). Nitroreductase, a near-infrared reporter platform for in vivo time-domain optical imaging of metastatic cancer. (external link)
- Harmsen, Rianne; Sivertsen, Annfrid; Michetti, Davide et al. (2013). Synthesis and docking of novel piperidine renin inhibitors. (external link)
- Rekdal, Øystein; Haug, Bengt Erik; Kalaaji, manar et al. (2012). The relative spatial positions of tryptophan and cationic residues in helical membrane-active peptides determines their cytotoxicity. (external link)
- Farooq, Tahir; Haug, Bengt Erik; Sydnes, Leiv Kristen et al. (2012). 1,3-Dipolar cycloaddition of benzyl azide to two highly functionalized alkynes. (external link)
- Farooq, Tahir; Sydnes, Leiv Kristen; Törnroos, Karl Wilhelm et al. (2012). Debenzylation of Functionalized 4-and 5-substituted 1,2,3-fTriazoles. (external link)
- Steinkopf, Signe; Hanekam, Linda; Schaathun, Marit et al. (2012). Interaction of local anaesthetic articaine enantiomers with brain lipids: A Langmuir monolayer study. (external link)
- Harmsen, Rianne; Sydnes, Leiv Kristen; Törnroos, Karl Wilhelm et al. (2011). Synthesis of trans-4-Triazolyl-Substituted 3-Hydroxypiperidines. (external link)
- Skjevik, Åge Aleksander; Haug, Bengt Erik; Lygre, Henning et al. (2011). Intramolecular hydrogen bonding in articaine can be related to superior bone tissue penetration: A molecular dynamics study. (external link)
- Haug, Bengt Erik; Stensen, Wenche; Kalaaji, manar et al. (2008). Synthetic antimicrobial peptidomimetics with therapeutic potential. (external link)
- Svenson, Johan Karl; Stensen, Wenche; Brandsdal, Bjørn Olav et al. (2008). Antimicrobial Peptides with Stability toward Tryptic Degradation. (external link)
- Haug, Bengt Erik; Stensen, Wenche; Svendsen, John Sigurd (2007). Application of the Suzuki-Miyaura cross-coupling to increase antimicrobial potency generates promising novel antibacterials. (external link)
- Haug, Bengt Erik; Brewer, M; Rich, DH (2005). Facile degradative lactonization of Gln-Arg and Gln-Phe hydroxyethylene dipeptide derivatives. (external link)
- Haug, Bengt Erik; Rich, Daniel H. (2004). Synthesis of a Gln-Phe hydroxyethylene dipeptide isostere. (external link)
- Haug, Bengt Erik; Stensen, Wenche; Stiberg, Trine et al. (2004). Bulky nonproteinogenic amino acids permit the design of very small and effective cationic antibacterial peptides. (external link)
- Eliassen, liv tone; Haug, Bengt Erik; Berge, Gerd et al. (2003). Enhanced antitumor activity of 15-residue bovine lactoferricin derivatives containing bulky aromatic amino acids and lipophilic N-terminal modifications. (external link)
- Strøm, M. B.; Haug, Bengt Erik; Skar, Merete L. et al. (2003). The Pharmacophore of Short Cationic Antibacterial Peptides. (external link)
- Lejon, Tore; Svendsen, John Sigurd; Haug, Bengt Erik (2002). Simple parameterization of non-proteinogenic amino acids for QSAR of antibacterial peptides. (external link)
- Haug, Bengt Erik; Andersen, Jill Mari; Rekdal, Øystein et al. (2002). Synthesis of a 2-arylsulphonylated tryptophan: the antibacterial activity of bovine lactoferricin peptides containing Trp(2-Pmc). (external link)
- Haug, Bengt Erik; Skar, Merete L.; Svendsen, John Sigurd (2001). Bulky Aromatic Amino Acids Increase the Antibacterial Activity of Bovine Lactoferricin Peptides. (external link)
- Haug, Bengt Erik; Svendsen, John Sigurd (2001). The Role of Tryptophan in the Antibacterial Activity of a 15-Residue Bovine Lactoferricin Peptide. (external link)
- Strøm, M. B.; Haug, Bengt Erik; Rekdal, Øystein et al. (2001). Important structural features of 15-residue lactoferricin derivatives and methods for improvement of antimicrobial activity. (external link)
- Haug, Bengt Erik; Skar, Merete L.; Svendsen, John Sigurd (2001). The effects of charge and lipophilicity on the antibacterial activity of undecapeptides derived from bovine lactoferricin. (external link)
- Lejon, Tore Sigvard; Haug, Bengt Erik (2000). Fargestoffer i Sopp. (external link)
Academic lecture
- Alsaker, Nicolai Etwin; Nerdal, Willy; Haug, Bengt Erik et al. (2023). Phospholipid membrane interactions of model peptides and depth of insertion investigated via solid-state NMR. (external link)
- Petit, Guillaume; Østnes Hansen, Kine; Andersen, Jeanette Hammer et al. (2023). A fragment to bind them all: Characterising phorbazole fragments as pan-kinase inhibitor. (external link)
- Herranz Carnero, Michel; Moldes-Anaya, Angel; Haug, Bengt Erik et al. (2022). Innovative molecular imaging technique for Granzyme-B characterization as an emerging biomarker for radio-immunotherapy combinations. (external link)
- Brenk, Ruth; Haug, Bengt Erik; Georgiou, Charis (2022). TARGETING A PSEUDOMONAS AERUGINOSA β-KETOACYL-(ACYL-CARRIER-PROTEIN) SYNTHASE WITH COVALENT INHIBITORS INSPIRED BY CERULENIN. (external link)
- Hegdahl, Stian Hersvik; Akervold, Kristine; Kongjampee, Usanee et al. (2022). Biogas Residues as Feedstock for Hydrothermal Conversion: Bio-Oil Yield Optimisation and Fate of Drugs. (external link)
- Brenk, Ruth; Haug, Bengt Erik; Underhaug, Jarl et al. (2021). Targeting Bacterial Fatty Acid Synthesis using Fragment-Based Drug Design. (external link)
- Haug, Bengt Erik (2020). Synthesis and Biological Activity of the Breitfussins. (external link)
- Haug, Bengt Erik (2016). Discovery of LTX-315 - A potential first-in-class oncolytic peptide. (external link)
- Haug, Bengt Erik (2016). BIOSNet - From marine natural products to commercial leads. (external link)
- Pandey, Sunil Kumar; Guttormsen, Yngve; Haug, Bengt Erik et al. (2015). Total synthesis of breitfussin A and B.. (external link)
- Haug, Bengt Erik (2014). Design and synthesis of substrates and inhibitors for Proteinase 3. (external link)
- Haug, Bengt Erik (2014). Design and synthesis of ketomethylene-based inhibitors of human neutrophil Proteinase 3. (external link)
- Haug, Bengt Erik (2012). Hvordan lager man et legemiddel?. (external link)
- Haug, Bengt Erik (2012). Novel Renin Inhibitors. (external link)
- Haug, Bengt Erik (2012). Synthesis of piperidine derivatives. (external link)
- Farooq, Tahir; Haug, Bengt Erik; Sydnes, Leiv Kristen (2010). [3+2] Cycloaddition of benzyl azide to two highly functionalized alkynes. (external link)
- Haug, Bengt Erik (2009). Synthesis of biologically active peptides and peptidomimetics. (external link)
- Haug, Bengt Erik (2006). Synthesis of a Gln-Phe hydroxyethylene dipeptide isostere. (external link)
- Haug, Bengt Erik; Svendsen, John Sigurd (2001). Antibacterial Activity of 15-Residues Bovine Lactoferricin Derivatives Employing non-coded Aromatic Amino Acids, Peptides 2000. (external link)
- Haug, Bengt Erik; Svendsen, John Sigurd (2000). Increased Antibacterial activity of 15-residues Bovine Lactoferricin Derivatives employing non-coded Aromatic Amino Acids,. (external link)
Poster
- Brenk, Ruth; Haug, Bengt Erik; Georgiou, Charis (2022). A P. AERUGINOSA FATTY ACID SYNTHESIS PROTEIN CRYSTALLOGRAPHIC FRAGMENT SCREEN AND ATTEMPTED OPTIMIZATION OF A HIT. (external link)
- Rekand, Illimar; Zeeshan, Muhammad; Mizar, Pushpak et al. (2022). Structure-based hit discovery for riboswitch ligands. (external link)
- Baumann, Markus; Myklebust, Line Merethe; Foyn, Håvard et al. (2020). Inhibition of the Actin N-terminal acetyltransferase NAA80. (external link)
- Ree, Rasmus Moen; Myklebust, Line Merethe; Foyn, Håvard et al. (2018). naa10 knockdown and NatA inhibition point to role for the NatA complex in zebrafish dorsoventral axis formation . (external link)
- Baumann, Markus; Myklebust, Line Merethe; Goris, Marianne et al. (2018). Inhibition of the Actin N-terminal acetyltransferase NAA80. (external link)
- Guttormsen, Yngve; Pandey, Sunil Kumar; Haug, Bengt Erik et al. (2017). Halogenation of electron rich heterocycles: Where does it go?. (external link)
- Fairhurst, Magnus John E.; Zeeshan, Muhammad; Bayer, Annette et al. (2017). Synthesis of the natural product (3Z,6Z)-3-((1H-imidazol-5-yl)methylene)-6-(2-methylpropylidene)-piperazine-2,5-dione. (external link)
- Rekand, Illimar Hugo; Haug, Bengt Erik (2016). Synthesis of a Challenging Amide. (external link)
- Haug, Bengt Erik; Baumann, Markus; Stefanie, Karlshøj et al. (2016). Scaffold-based tripeptidomimetic CXCR4 antagonists. (external link)
- Fairhurst, Magnus John E.; Bayer, Annette; Haug, Bengt Erik (2016). Synthesis of Analogues of the Bioactive Compound Barettin. (external link)
- Pandey, Sunil Kumar; Guttormsen, Yngve; Haug, Bengt Erik et al. (2016). Total Synthesis of Breitfussin A and B. (external link)
- Baumann, Markus; Våbenø, Jon; Haug, Bengt Erik (2015). Synthetic studies towards peptidomimetic CXCR4 antagonists. (external link)
- Baumann, Markus; Våbenø, Jon; Haug, Bengt Erik (2015). Synthetic studies towards CXCR4 antagonists. (external link)
- de Jalón, Elvira Garcia; Lund, Kjetil Børve; Stigen, Endre et al. (2015). Synthetic studies towards nitroreductase-activated fluorescent probes. (external link)
- Baumann, Markus; Våbenø, Jon; Haug, Bengt Erik (2014). Synthetic studies towards CXCR4 antagonists. (external link)
- Budnjo, Adnan; Narawane, Shailesh; Reuter, Nathalie et al. (2014). Synthesis and biological evaluation of pseudopeptide inhibitors of Proteinase 3. (external link)
- Henne, Nina; Våbenø, Jon; Haug, Bengt Erik (2014). Synthetic studies towards CXCR4 antagonists. (external link)
- Budnjo, Adnan; Haug, Bengt Erik (2012). Synthesis of a Ketomethylene Dipeptide Isostere. (external link)
- Harmsen, Rianne; Sivertsen, Annfrid; Michetti, Davide et al. (2012). Synthesis and docking of 4-triazolyl substituted piperidine derivatives as novel renin inhibitors. (external link)
- Steinkopf, Signe; Hanekam, Linda; Schaathun, Marit et al. (2012). Local Anesthetic Articaine Enantiomers interaction with Brain Lipids. (external link)
- Harmsen, Rianne; Sydnes, Leiv Kristen; Törnroos, Karl Wilhelm et al. (2011). Synthesis of 3,4-disubstituted piperidines. (external link)
- Harmsen, Rianne; Sydnes, Leiv Kristen; Haug, Bengt Erik (2011). Synthesis of 3,4-disubstituted piperidines. (external link)
- Farooq, Tahir; Haug, Bengt Erik; Sydnes, Leiv K. (2009). Cycloaddition with highly functionalized terminal alkynes. (external link)
- Haug, Bengt Erik (2006). Novel Antibacterial Tripeptides. (external link)
- Haug, Bengt Erik; Svendsen, John Sigurd (2001). Preparation of (2S)-3-amino-(2,2,5,7,8-pentamethyl-chroman-6-sulfonyl)-1H-indol-3-yl)-propionic acid and its incorporation into antibacterial lactoferricin peptides. (external link)
Doctoral dissertation
- Baumann, Markus; Haug, Bengt Erik; Våbenø, Jon (2016). Synthesis of Bicyclic CXCR4 Antagonists . (external link)
- Budnjo, Adnan; Haug, Bengt Erik (2014). Synthesis of serine protease inhibitors. (external link)
- Harmsen, Rianne; Haug, Bengt Erik; Sydnes, Leiv Kristen (2012). Synthesis of novel renin inhibitors. (external link)
- Farooq, Tahir; Haug, Bengt Erik; Sydnes, Leiv Kristen (2012). Synthesis of Some Nitrogen Heterocycles of Medicinal Relevance. (external link)
Popular scientific lecture
- Haug, Bengt Erik (2016). Peptider, peptidomimetika og legemiddelutvikling. (external link)
- Haug, Bengt Erik (2013). Hvordan lager man legemiddelmolekyler?. (external link)
- Haug, Bengt Erik (2012). Peptider og legemiddelutvikling. (external link)
- Haug, Bengt Erik (2012). The Nobel Prize in Chemistry 2012. (external link)
- Haug, Bengt Erik (2012). Hvordan lager man et legemiddel?. (external link)
- Haug, Bengt Erik (2007). Antimikrobielle peptider - En kilde til utvikling av fremtidenslegemidler mot mikrober og kreft?. (external link)
Academic literature review
- Våbenø, Jon; Haug, Bengt Erik; Rosenkilde, Mette M. (2015). Progress toward rationally designed small-molecule peptide and peptidomimetic CXCR4 antagonists. (external link)
- Haug, Bengt Erik; Strøm, Morten B.; Svendsen, John Sigurd (2007). The medicinal chemistry of short lactoferricin-based antibacterial peptides. (external link)
Abstract
- Harmsen, Rianne; Sivertsen, A; Michetti, Davide et al. (2012). Synthesis and docking of 4-triazolyl substituted piperidine derivatives as novel renin inhibitors. (external link)
- Zachariassen, Zack Georg; Thiele, S; Rosenkilde, MM et al. (2011). SAR and Binding Mode for CXCR4 Antagonists Based on an Arg-Arg-Nal Tripeptide Motif. (external link)
Popular scientific article
Other product
Projects
Addressing the need for new antibiotics through underexplored bacterial targets
The group in involved in several research projects where novel targets for future antibiotics are investigated. Our focus is on processes that are essential in bacteria and in our work, we address several different riboswitches, which are non-coding structural elements in mRNA that regulate gene expression by binding to small organic molecules, in addition to key enzymes within the fatty acid synthesis machinery in bacteria.
The group is a partner in the EU Horizon funded Marie Skłodowska-Curie Action (MSCA) doctoral training network TargetRNA.
Early drug discovery
The group is partner in the RESPOND3 project on responsible early digital drug discovery within the Centre for Digital Life Norway. This project focuses on developing better computational approaches and responsible innovation strategies in early drug discovery with applications to antibiotics targeting riboswitches and inflammatory lung diseases.
Molecular imaging
The group is part of the Tracer Development Center of the Norwegian Nuclear Medicine Consortium.
Inhibitors of N-terminal acetyl transferases
Proteins constitute an essential part of the machinery of life and display enormous variation in both structure and function. In addition to the diversity inferred by the 20 coded amino acids, proteins are often covalently modified during or after biosynthesis, which adds additional layers of complexity.
Acetylation is one of the most common co- or post-translational protein modifications and occurs either on the amino group of lysine side chains (K-acetylation) or on the alpha-amino group of N-terminal residues (Nt-acetylation).
Nt-acetylation of proteins is extremely common and occurs on more than 80% of all human proteins. Biochemically it consists of transfer of an acetyl group from acetyl coenzyme A (Ac-CoA) to the protein substrate and is catalyzed by the N-terminal acetyltransferase (NAT) group of enzymes.
Although our understanding of the NATs has increased in recent years, there are fundamental questions that remain unanswered in the field:- What are the cellular roles of NAT enzymes (and thus Nt-acetylation)?- Can NATs be targeted for therapeutic intervention in cancer and other diseases?
Access to specific and potent NAT inhibitors is a prerequisite to answer these questions, and we are working toward equipping the scientific community with these molecular tools in collaboration with the Arnesen group at UiB.