Bengt Erik Haug
Stilling
Professor
Tilhørighet
Forskergrupper
Forskning
Vi er interessert i forskningsspørsmål som ligger på grensesnittet mellom kjemi og biologi. Forskningsprosjektene vi er involvert i er forankret i legemiddelkjemi og biologisk kjemi, og vi bruker syntetisk organisk kjemi som metode for å addressere våre forskningsspørsmål. Gruppen har hatt en viktig rolle i etableringen av Laboratory for high-throughput experimentation - HTE@UiB, som professor Haug leder. Flere av prosjektene vi jobber med krever også tilgang til syntetiske peptider, og gruppen har etablert og driver Laboratorium for peptidsyntese ved Kjemisk institutt.
Gruppen er del av forskningsgruppen for Bioressurser og farmasøytisk kjemi.
Publikasjoner
Kronikk
Vitenskapelig artikkel
- Gartan, Parveen; Khorsand, Fahimeh; Mizar, Pushpak et al. (2024). Investigating Polypharmacology through Targeting Known Human Neutrophil Elastase Inhibitors to Proteinase 3. (ekstern lenke)
- 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. (ekstern lenke)
- 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. (ekstern lenke)
- Myklebust, Line Merethe; Baumann, Markus; Støve, Svein Isungset et al. (2023). Optimized bisubstrate inhibitors for the actin N-terminal acetyltransferase NAA80. (ekstern lenke)
- 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. (ekstern lenke)
- 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. (ekstern lenke)
- 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 . (ekstern lenke)
- 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. (ekstern lenke)
- 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). (ekstern lenke)
- Guttormsen, Yngve; Fairhurst, Magnus John Espeland; Pandey, Sunil Kumar et al. (2020). Total synthesis of phorbazole B. (ekstern lenke)
- Ndukwe, Ikenna E.; Lam, Yu-hong; Pandey, Sunil Kumar et al. (2020). Unequivocal structure confirmation of a breitfussin analog by anisotropic NMR measurements. (ekstern lenke)
- Østnes Hansen, Kine; Andersen, Jeanette hammer; Bayer, Annette et al. (2019). Kinase chemodiversity from the Arctic: the breitfussins. (ekstern lenke)
- 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. (ekstern lenke)
- 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. (ekstern lenke)
- 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. (ekstern lenke)
- Sveinbjørnsson, Baldur; Camilio, Ketil Andre; Haug, Bengt Erik et al. (2017). LTX-315: a first-in-class oncolytic peptide that reprograms the tumor microenvironment. (ekstern lenke)
- 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. (ekstern lenke)
- 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). (ekstern lenke)
- 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.. (ekstern lenke)
- 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. (ekstern lenke)
- Pandey, Sunil Kumar; Guttormsen, Yngve; Haug, Bengt Erik et al. (2015). A concise total synthesis of breitfussin A and B. (ekstern lenke)
- Liu, Liwei; Budnjo, Adnan; Jokela, Jouni et al. (2015). Pseudoaeruginosins, nonribosomal peptides in nodularia spumigena. (ekstern lenke)
- Aubi Catevilla, Oscar; Flydal, Marte Innselset; Zheng, Huaixin et al. (2015). Discovery of a Specific Inhibitor of Pyomelanin Synthesis in Legionella pneumophila. (ekstern lenke)
- 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). (ekstern lenke)
- 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. (ekstern lenke)
- 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). (ekstern lenke)
- Budnjo, Adnan; Narawane, Shailesh; Grauffel, Cédric et al. (2014). Reversible ketomethylene-based inhibitors of human neutrophil proteinase 3. (ekstern lenke)
- Harmsen, Rianne; Sivertsen, Annfrid; Michetti, Davide et al. (2013). Synthesis and docking of novel piperidine renin inhibitors. (ekstern lenke)
- 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. (ekstern lenke)
- Farooq, Tahir; Sydnes, Leiv Kristen; Törnroos, Karl Wilhelm et al. (2012). Debenzylation of Functionalized 4-and 5-substituted 1,2,3-fTriazoles. (ekstern lenke)
- Steinkopf, Signe; Hanekam, Linda; Schaathun, Marit et al. (2012). Interaction of local anaesthetic articaine enantiomers with brain lipids: A Langmuir monolayer study. (ekstern lenke)
- 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. (ekstern lenke)
- Farooq, Tahir; Haug, Bengt Erik; Sydnes, Leiv Kristen et al. (2012). 1,3-Dipolar cycloaddition of benzyl azide to two highly functionalized alkynes. (ekstern lenke)
- Harmsen, Rianne; Sydnes, Leiv Kristen; Törnroos, Karl Wilhelm et al. (2011). Synthesis of trans-4-Triazolyl-Substituted 3-Hydroxypiperidines. (ekstern lenke)
- 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. (ekstern lenke)
- Haug, Bengt Erik; Stensen, Wenche; Kalaaji, manar et al. (2008). Synthetic antimicrobial peptidomimetics with therapeutic potential. (ekstern lenke)
- Svenson, Johan Karl; Stensen, Wenche; Brandsdal, Bjørn Olav et al. (2008). Antimicrobial Peptides with Stability toward Tryptic Degradation. (ekstern lenke)
- Haug, Bengt Erik; Stensen, Wenche; Svendsen, John Sigurd (2007). Application of the Suzuki-Miyaura cross-coupling to increase antimicrobial potency generates promising novel antibacterials. (ekstern lenke)
- Haug, Bengt Erik; Brewer, M; Rich, DH (2005). Facile degradative lactonization of Gln-Arg and Gln-Phe hydroxyethylene dipeptide derivatives. (ekstern lenke)
- Haug, Bengt Erik; Rich, Daniel H. (2004). Synthesis of a Gln-Phe hydroxyethylene dipeptide isostere. (ekstern lenke)
- 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. (ekstern lenke)
- Strøm, M. B.; Haug, Bengt Erik; Skar, Merete L. et al. (2003). The Pharmacophore of Short Cationic Antibacterial Peptides. (ekstern lenke)
- 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. (ekstern lenke)
- Lejon, Tore; Svendsen, John Sigurd; Haug, Bengt Erik (2002). Simple parameterization of non-proteinogenic amino acids for QSAR of antibacterial peptides. (ekstern lenke)
- 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). (ekstern lenke)
- 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. (ekstern lenke)
- Haug, Bengt Erik; Skar, Merete L.; Svendsen, John Sigurd (2001). Bulky Aromatic Amino Acids Increase the Antibacterial Activity of Bovine Lactoferricin Peptides. (ekstern lenke)
- 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. (ekstern lenke)
- Haug, Bengt Erik; Svendsen, John Sigurd (2001). The Role of Tryptophan in the Antibacterial Activity of a 15-Residue Bovine Lactoferricin Peptide. (ekstern lenke)
- Lejon, Tore Sigvard; Haug, Bengt Erik (2000). Fargestoffer i Sopp. (ekstern lenke)
Vitenskapelig foredrag
- Petit, Guillaume; Østnes Hansen, Kine; Andersen, Jeanette Hammer et al. (2023). A fragment to bind them all: Characterising phorbazole fragments as pan-kinase inhibitor. (ekstern lenke)
- 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. (ekstern lenke)
- Brenk, Ruth; Haug, Bengt Erik; Georgiou, Charis (2022). TARGETING A PSEUDOMONAS AERUGINOSA β-KETOACYL-(ACYL-CARRIER-PROTEIN) SYNTHASE WITH COVALENT INHIBITORS INSPIRED BY CERULENIN. (ekstern lenke)
- 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. (ekstern lenke)
- 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. (ekstern lenke)
- Brenk, Ruth; Haug, Bengt Erik; Underhaug, Jarl et al. (2021). Targeting Bacterial Fatty Acid Synthesis using Fragment-Based Drug Design. (ekstern lenke)
- Haug, Bengt Erik (2020). Synthesis and Biological Activity of the Breitfussins. (ekstern lenke)
- Haug, Bengt Erik (2016). BIOSNet - From marine natural products to commercial leads. (ekstern lenke)
- Haug, Bengt Erik (2016). Discovery of LTX-315 - A potential first-in-class oncolytic peptide. (ekstern lenke)
- Pandey, Sunil Kumar; Guttormsen, Yngve; Haug, Bengt Erik et al. (2015). Total synthesis of breitfussin A and B.. (ekstern lenke)
- Haug, Bengt Erik (2014). Design and synthesis of substrates and inhibitors for Proteinase 3. (ekstern lenke)
- Haug, Bengt Erik (2014). Design and synthesis of ketomethylene-based inhibitors of human neutrophil Proteinase 3. (ekstern lenke)
- Haug, Bengt Erik (2012). Synthesis of piperidine derivatives. (ekstern lenke)
- Haug, Bengt Erik (2012). Hvordan lager man et legemiddel?. (ekstern lenke)
- Haug, Bengt Erik (2012). Novel Renin Inhibitors. (ekstern lenke)
- Farooq, Tahir; Haug, Bengt Erik; Sydnes, Leiv Kristen (2010). [3+2] Cycloaddition of benzyl azide to two highly functionalized alkynes. (ekstern lenke)
- Haug, Bengt Erik (2009). Synthesis of biologically active peptides and peptidomimetics. (ekstern lenke)
- Haug, Bengt Erik (2006). Synthesis of a Gln-Phe hydroxyethylene dipeptide isostere. (ekstern lenke)
- Haug, Bengt Erik; Svendsen, John Sigurd (2001). Antibacterial Activity of 15-Residues Bovine Lactoferricin Derivatives Employing non-coded Aromatic Amino Acids, Peptides 2000. (ekstern lenke)
- Haug, Bengt Erik; Svendsen, John Sigurd (2000). Increased Antibacterial activity of 15-residues Bovine Lactoferricin Derivatives employing non-coded Aromatic Amino Acids,. (ekstern lenke)
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. (ekstern lenke)
- Rekand, Illimar; Zeeshan, Muhammad; Mizar, Pushpak et al. (2022). Structure-based hit discovery for riboswitch ligands. (ekstern lenke)
- Baumann, Markus; Myklebust, Line Merethe; Foyn, Håvard et al. (2020). Inhibition of the Actin N-terminal acetyltransferase NAA80. (ekstern lenke)
- Baumann, Markus; Myklebust, Line Merethe; Goris, Marianne et al. (2018). Inhibition of the Actin N-terminal acetyltransferase NAA80. (ekstern lenke)
- 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 . (ekstern lenke)
- 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. (ekstern lenke)
- Guttormsen, Yngve; Pandey, Sunil Kumar; Haug, Bengt Erik et al. (2017). Halogenation of electron rich heterocycles: Where does it go?. (ekstern lenke)
- Rekand, Illimar Hugo; Haug, Bengt Erik (2016). Synthesis of a Challenging Amide. (ekstern lenke)
- Pandey, Sunil Kumar; Guttormsen, Yngve; Haug, Bengt Erik et al. (2016). Total Synthesis of Breitfussin A and B. (ekstern lenke)
- Fairhurst, Magnus John E.; Bayer, Annette; Haug, Bengt Erik (2016). Synthesis of Analogues of the Bioactive Compound Barettin. (ekstern lenke)
- Haug, Bengt Erik; Baumann, Markus; Stefanie, Karlshøj et al. (2016). Scaffold-based tripeptidomimetic CXCR4 antagonists. (ekstern lenke)
- Baumann, Markus; Våbenø, Jon; Haug, Bengt Erik (2015). Synthetic studies towards CXCR4 antagonists. (ekstern lenke)
- de Jalón, Elvira Garcia; Lund, Kjetil Børve; Stigen, Endre et al. (2015). Synthetic studies towards nitroreductase-activated fluorescent probes. (ekstern lenke)
- Baumann, Markus; Våbenø, Jon; Haug, Bengt Erik (2015). Synthetic studies towards peptidomimetic CXCR4 antagonists. (ekstern lenke)
- Budnjo, Adnan; Narawane, Shailesh; Reuter, Nathalie et al. (2014). Synthesis and biological evaluation of pseudopeptide inhibitors of Proteinase 3. (ekstern lenke)
- Henne, Nina; Våbenø, Jon; Haug, Bengt Erik (2014). Synthetic studies towards CXCR4 antagonists. (ekstern lenke)
- Baumann, Markus; Våbenø, Jon; Haug, Bengt Erik (2014). Synthetic studies towards CXCR4 antagonists. (ekstern lenke)
- Harmsen, Rianne; Sivertsen, Annfrid; Michetti, Davide et al. (2012). Synthesis and docking of 4-triazolyl substituted piperidine derivatives as novel renin inhibitors. (ekstern lenke)
- Steinkopf, Signe; Hanekam, Linda; Schaathun, Marit et al. (2012). Local Anesthetic Articaine Enantiomers interaction with Brain Lipids. (ekstern lenke)
- Budnjo, Adnan; Haug, Bengt Erik (2012). Synthesis of a Ketomethylene Dipeptide Isostere. (ekstern lenke)
- Harmsen, Rianne; Sydnes, Leiv Kristen; Haug, Bengt Erik (2011). Synthesis of 3,4-disubstituted piperidines. (ekstern lenke)
- Harmsen, Rianne; Sydnes, Leiv Kristen; Törnroos, Karl Wilhelm et al. (2011). Synthesis of 3,4-disubstituted piperidines. (ekstern lenke)
- Farooq, Tahir; Haug, Bengt Erik; Sydnes, Leiv K. (2009). Cycloaddition with highly functionalized terminal alkynes. (ekstern lenke)
- Haug, Bengt Erik (2006). Novel Antibacterial Tripeptides. (ekstern lenke)
- 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. (ekstern lenke)
Doktorgradsavhandling
- Baumann, Markus; Haug, Bengt Erik; Våbenø, Jon (2016). Synthesis of Bicyclic CXCR4 Antagonists . (ekstern lenke)
- Budnjo, Adnan; Haug, Bengt Erik (2014). Synthesis of serine protease inhibitors. (ekstern lenke)
- Farooq, Tahir; Haug, Bengt Erik; Sydnes, Leiv Kristen (2012). Synthesis of Some Nitrogen Heterocycles of Medicinal Relevance. (ekstern lenke)
- Harmsen, Rianne; Haug, Bengt Erik; Sydnes, Leiv Kristen (2012). Synthesis of novel renin inhibitors. (ekstern lenke)
Populærvitenskapelig foredrag
- Haug, Bengt Erik (2016). Peptider, peptidomimetika og legemiddelutvikling. (ekstern lenke)
- Haug, Bengt Erik (2013). Hvordan lager man legemiddelmolekyler?. (ekstern lenke)
- Haug, Bengt Erik (2012). Peptider og legemiddelutvikling. (ekstern lenke)
- Haug, Bengt Erik (2012). Hvordan lager man et legemiddel?. (ekstern lenke)
- Haug, Bengt Erik (2012). The Nobel Prize in Chemistry 2012. (ekstern lenke)
- Haug, Bengt Erik (2007). Antimikrobielle peptider - En kilde til utvikling av fremtidenslegemidler mot mikrober og kreft?. (ekstern lenke)
Vitenskapelig oversiktsartikkel/review
- Våbenø, Jon; Haug, Bengt Erik; Rosenkilde, Mette M. (2015). Progress toward rationally designed small-molecule peptide and peptidomimetic CXCR4 antagonists. (ekstern lenke)
- Haug, Bengt Erik; Strøm, Morten B.; Svendsen, John Sigurd (2007). The medicinal chemistry of short lactoferricin-based antibacterial peptides. (ekstern lenke)
Sammendrag/abstract
- Harmsen, Rianne; Sivertsen, A; Michetti, Davide et al. (2012). Synthesis and docking of 4-triazolyl substituted piperidine derivatives as novel renin inhibitors. (ekstern lenke)
- 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. (ekstern lenke)
Populærvitenskapelig artikkel
Annet produkt
Prosjekter
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.