Hjem
Bengt Erik Haugs bilde
Foto:
UiB
  • E-postBengt-Erik.Haug@uib.no
  • Telefon+47 55 58 34 68
  • Besøksadresse
    Allégaten 41
    Realfagbygget
    5007 Bergen
    Rom 
    4055a
  • Postadresse
    Postboks 7803
    5020 Bergen

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. 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.

Vitenskapelig artikkel
  • Vis forfatter(e) (2024). Investigating Polypharmacology through Targeting Known Human Neutrophil Elastase Inhibitors to Proteinase 3. Journal of Chemical Information and Modeling. 621-626.
  • Vis forfatter(e) (2023). Optimized bisubstrate inhibitors for the actin N-terminal acetyltransferase NAA80. Frontiers in Chemistry.
  • Vis forfatter(e) (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. ACS Chemical Biology. 2631-2642.
  • Vis forfatter(e) (2021). Repurposing 18F-FMISO as a PET tracer for translational imaging of nitroreductase-based gene directed enzyme prodrug therapy. Theranostics. 6044-6057.
  • Vis forfatter(e) (2021). CytoCy5S™, a compound of many structures. in vitro and in vivo evaluation of four near-infrared fluorescent substrates of nitroreductase (NTR). Dyes and pigments. 1-11.
  • Vis forfatter(e) (2021). Comparison of Five Near-Infrared Fluorescent Folate Conjugates in an Ovarian Cancer Model. Molecular Imaging and Biology. 144-155.
  • Vis forfatter(e) (2021). An Experimental Toolbox for Structure-Based Hit Discovery for P. aeruginosa FabF, a Promising Target for Antibiotics . ChemMedChem. 2715.
  • Vis forfatter(e) (2020). Unequivocal structure confirmation of a breitfussin analog by anisotropic NMR measurements. Chemical Science. 12081-12088.
  • Vis forfatter(e) (2020). Total synthesis of phorbazole B. Molecules. 1-10.
  • Vis forfatter(e) (2019). Kinase chemodiversity from the Arctic: the breitfussins. Journal of Medicinal Chemistry. 10167-10181.
  • Vis forfatter(e) (2018). Structural determinants and cellular environment define processed actin as the sole substrate of the N-terminal acetyltransferase NAA80. Proceedings of the National Academy of Sciences of the United States of America. 4405-4410.
  • Vis forfatter(e) (2018). Aldol condensations on a 3-alkylidene-2,5-diketopiperazine - synthesis of two marine natural products. Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry. 1303-1306.
  • Vis forfatter(e) (2017). Synthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonism. Tetrahedron. 3866-3877.
  • Vis forfatter(e) (2017). Oncolytic peptide LTX-315 induces an immune-mediated abscopal effect in a rat sarcoma model. Oncoimmunology. 1-13.
  • Vis forfatter(e) (2017). LTX-315: a first-in-class oncolytic peptide that reprograms the tumor microenvironment. Future Medicinal Chemistry. 1339-1344.
  • Vis forfatter(e) (2017). Influence of chain length on the activity of tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4). Bioorganic & Medicinal Chemistry. 646-657.
  • Vis forfatter(e) (2016). Discovery of a 9-mer cationic peptide (LTX-315) as a potential first in class oncolytic peptide. Journal of Medicinal Chemistry. 2918-2927.
  • Vis forfatter(e) (2016). Crystal structure of the Golgi-associated human N-alpha acetyltransferase 60 (Naa60/NatF) reveals the molecular determinants for substrate-specific acetylation. Structure. 1044-1056.
  • Vis forfatter(e) (2015). Pseudoaeruginosins, nonribosomal peptides in nodularia spumigena. ACS Chemical Biology. 725-733.
  • Vis forfatter(e) (2015). Probing the molecular interactions between CXC chemokine receptor 4 (CXCR4) and an arginine-based tripeptidomimetic antagonist (KRH-1636). Journal of Medicinal Chemistry. 8141-8153.
  • Vis forfatter(e) (2015). Discovery of a Specific Inhibitor of Pyomelanin Synthesis in Legionella pneumophila. Journal of Medicinal Chemistry. 8402-8412.
  • Vis forfatter(e) (2015). A concise total synthesis of breitfussin A and B. Organic Letters. 122-125.
  • Vis forfatter(e) (2014). Reversible ketomethylene-based inhibitors of human neutrophil proteinase 3. Journal of Medicinal Chemistry. 9396-9408.
  • Vis forfatter(e) (2014). In silico design, synthesis, and assays of specific substrates for proteinase 3: Influence of fluorogenic and charged groups. Journal of Medicinal Chemistry. 1111-1115.
  • Vis forfatter(e) (2014). Design, synthesis, and biological evaluation of scaffold-based tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4). Bioorganic & Medicinal Chemistry. 4759-4769.
  • Vis forfatter(e) (2013). Synthesis and docking of novel piperidine renin inhibitors. Monatshefte für Chemie. 479-494.
  • Vis forfatter(e) (2013). Nitroreductase, a near-infrared reporter platform for in vivo time-domain optical imaging of metastatic cancer. Cancer Research. 1276-1286.
  • Vis forfatter(e) (2012). The relative spatial positions of tryptophan and cationic residues in helical membrane-active peptides determines their cytotoxicity. Journal of Biological Chemistry. 233-244.
  • Vis forfatter(e) (2012). Interaction of local anaesthetic articaine enantiomers with brain lipids: A Langmuir monolayer study. European Journal of Pharmaceutical Sciences. 394-401.
  • Vis forfatter(e) (2012). Debenzylation of Functionalized 4-and 5-substituted 1,2,3-fTriazoles. Synthesis (Stuttgart). 2070-2078.
  • Vis forfatter(e) (2012). 1,3-Dipolar cycloaddition of benzyl azide to two highly functionalized alkynes. Monatshefte für Chemie. 505-512.
  • Vis forfatter(e) (2011). Synthesis of trans-4-Triazolyl-Substituted 3-Hydroxypiperidines. Synthesis (Stuttgart). 749-754.
  • Vis forfatter(e) (2011). Intramolecular hydrogen bonding in articaine can be related to superior bone tissue penetration: A molecular dynamics study. Biophysical Chemistry. 18-25.
  • Vis forfatter(e) (2008). Synthetic antimicrobial peptidomimetics with therapeutic potential. Journal of Medicinal Chemistry. 4306-4314.
  • Vis forfatter(e) (2008). Antimicrobial Peptides with Stability toward Tryptic Degradation. Biochemistry. 3777-3788.
  • Vis forfatter(e) (2007). Application of the Suzuki-Miyaura cross-coupling to increase antimicrobial potency generates promising novel antibacterials. Bioorganic & Medicinal Chemistry Letters.
  • Vis forfatter(e) (2005). Facile degradative lactonization of Gln-Arg and Gln-Phe hydroxyethylene dipeptide derivatives. Journal of Peptide Research.
  • Vis forfatter(e) (2004). Synthesis of a Gln-Phe hydroxyethylene dipeptide isostere. Organic Letters. 4783-4786.
  • Vis forfatter(e) (2004). Bulky nonproteinogenic amino acids permit the design of very small and effective cationic antibacterial peptides. Journal of Medicinal Chemistry. 4159-4162.
  • Vis forfatter(e) (2003). The Pharmacophore of Short Cationic Antibacterial Peptides. Journal of Medicinal Chemistry. 1567-1570.
  • Vis forfatter(e) (2003). Enhanced antitumor activity of 15-residue bovine lactoferricin derivatives containing bulky aromatic amino acids and lipophilic N-terminal modifications. Journal of Peptide Science. 510-517.
  • Vis forfatter(e) (2002). Synthesis of a 2-arylsulphonylated tryptophan: the antibacterial activity of bovine lactoferricin peptides containing Trp(2-Pmc). Journal of Peptide Science. 307-313.
  • Vis forfatter(e) (2002). Simple parameterization of non-proteinogenic amino acids for QSAR of antibacterial peptides. Journal of Peptide Science. 302-306.
  • Vis forfatter(e) (2001). The effects of charge and lipophilicity on the antibacterial activity of undecapeptides derived from bovine lactoferricin. Journal of Peptide Science. 425-432.
  • Vis forfatter(e) (2001). The Role of Tryptophan in the Antibacterial Activity of a 15-Residue Bovine Lactoferricin Peptide. Journal of Peptide Science. 190-196.
  • Vis forfatter(e) (2001). Important structural features of 15-residue lactoferricin derivatives and methods for improvement of antimicrobial activity. International Journal of Biochemistry and Cell Biology.
  • Vis forfatter(e) (2001). Bulky Aromatic Amino Acids Increase the Antibacterial Activity of Bovine Lactoferricin Peptides. Journal of Peptide Science. 425-432.
  • Vis forfatter(e) (2000). Fargestoffer i Sopp. Kjemi.
Faglig foredrag
  • Vis forfatter(e) (2014). Havet - vårt nye medisinskap?
Populærvitenskapelig foredrag
  • Vis forfatter(e) (2016). Peptider, peptidomimetika og legemiddelutvikling.
  • Vis forfatter(e) (2013). Hvordan lager man legemiddelmolekyler?
  • Vis forfatter(e) (2012). The Nobel Prize in Chemistry 2012.
  • Vis forfatter(e) (2012). Peptider og legemiddelutvikling.
  • Vis forfatter(e) (2012). Hvordan lager man et legemiddel?
  • Vis forfatter(e) (2007). Antimikrobielle peptider - En kilde til utvikling av fremtidenslegemidler mot mikrober og kreft?
Vitenskapelig foredrag
  • Vis forfatter(e) (2023). Phospholipid membrane interactions of model peptides and depth of insertion investigated via solid-state NMR.
  • Vis forfatter(e) (2023). A fragment to bind them all: Characterising phorbazole fragments as pan-kinase inhibitor.
  • Vis forfatter(e) (2022). TARGETING A PSEUDOMONAS AERUGINOSA β-KETOACYL-(ACYL-CARRIER-PROTEIN) SYNTHASE WITH COVALENT INHIBITORS INSPIRED BY CERULENIN.
  • Vis forfatter(e) (2022). Innovative molecular imaging technique for Granzyme-B characterization as an emerging biomarker for radio-immunotherapy combinations.
  • Vis forfatter(e) (2022). Biogas Residues as Feedstock for Hydrothermal Conversion: Bio-Oil Yield Optimisation and Fate of Drugs.
  • Vis forfatter(e) (2021). Targeting Bacterial Fatty Acid Synthesis using Fragment-Based Drug Design.
  • Vis forfatter(e) (2020). Synthesis and Biological Activity of the Breitfussins.
  • Vis forfatter(e) (2016). Discovery of LTX-315 - A potential first-in-class oncolytic peptide.
  • Vis forfatter(e) (2016). BIOSNet - From marine natural products to commercial leads.
  • Vis forfatter(e) (2015). Total synthesis of breitfussin A and B.
  • Vis forfatter(e) (2014). Design and synthesis of substrates and inhibitors for Proteinase 3.
  • Vis forfatter(e) (2014). Design and synthesis of ketomethylene-based inhibitors of human neutrophil Proteinase 3.
  • Vis forfatter(e) (2012). Synthesis of piperidine derivatives.
  • Vis forfatter(e) (2012). Novel Renin Inhibitors.
  • Vis forfatter(e) (2012). Hvordan lager man et legemiddel?
  • Vis forfatter(e) (2010). [3+2] Cycloaddition of benzyl azide to two highly functionalized alkynes.
  • Vis forfatter(e) (2009). Synthesis of biologically active peptides and peptidomimetics.
  • Vis forfatter(e) (2006). Synthesis of a Gln-Phe hydroxyethylene dipeptide isostere.
  • Vis forfatter(e) (2001). Antibacterial Activity of 15-Residues Bovine Lactoferricin Derivatives Employing non-coded Aromatic Amino Acids, Peptides 2000.
  • Vis forfatter(e) (2000). Increased Antibacterial activity of 15-residues Bovine Lactoferricin Derivatives employing non-coded Aromatic Amino Acids,.
Annet produkt
  • Vis forfatter(e) (2001). Antimicrobial compounds and formulations.
Kompendium
  • Vis forfatter(e) (2010). IUPAC ICOS-18 Proceedings.
Populærvitenskapelig artikkel
  • Vis forfatter(e) (2001). FARGESTOFFER I SOPP. Blekksoppen. 16-19.
Kronikk
  • Vis forfatter(e) (2024). Kjemi og beredskap. Stavanger Aftenblad. 52-52.
Doktorgradsavhandling
  • Vis forfatter(e) (2016). Synthesis of Bicyclic CXCR4 Antagonists .
  • Vis forfatter(e) (2014). Synthesis of serine protease inhibitors.
  • Vis forfatter(e) (2012). Synthesis of novel renin inhibitors.
  • Vis forfatter(e) (2012). Synthesis of Some Nitrogen Heterocycles of Medicinal Relevance.
Sammendrag/abstract
  • Vis forfatter(e) (2012). Synthesis and docking of 4-triazolyl substituted piperidine derivatives as novel renin inhibitors. Journal of Peptide Science. S125-S125.
  • Vis forfatter(e) (2011). SAR and Binding Mode for CXCR4 Antagonists Based on an Arg-Arg-Nal Tripeptide Motif. Biopolymers. 492-492.
Poster
  • Vis forfatter(e) (2022). Structure-based hit discovery for riboswitch ligands.
  • Vis forfatter(e) (2022). A P. AERUGINOSA FATTY ACID SYNTHESIS PROTEIN CRYSTALLOGRAPHIC FRAGMENT SCREEN AND ATTEMPTED OPTIMIZATION OF A HIT.
  • Vis forfatter(e) (2020). Inhibition of the Actin N-terminal acetyltransferase NAA80.
  • Vis forfatter(e) (2018). naa10 knockdown and NatA inhibition point to role for the NatA complex in zebrafish dorsoventral axis formation .
  • Vis forfatter(e) (2018). Inhibition of the Actin N-terminal acetyltransferase NAA80.
  • Vis forfatter(e) (2017). Synthesis of the natural product (3Z,6Z)-3-((1H-imidazol-5-yl)methylene)-6-(2-methylpropylidene)-piperazine-2,5-dione.
  • Vis forfatter(e) (2017). Halogenation of electron rich heterocycles: Where does it go?
  • Vis forfatter(e) (2016). Total Synthesis of Breitfussin A and B.
  • Vis forfatter(e) (2016). Synthesis of a Challenging Amide.
  • Vis forfatter(e) (2016). Synthesis of Analogues of the Bioactive Compound Barettin.
  • Vis forfatter(e) (2016). Scaffold-based tripeptidomimetic CXCR4 antagonists.
  • Vis forfatter(e) (2015). Synthetic studies towards peptidomimetic CXCR4 antagonists.
  • Vis forfatter(e) (2015). Synthetic studies towards nitroreductase-activated fluorescent probes.
  • Vis forfatter(e) (2015). Synthetic studies towards CXCR4 antagonists.
  • Vis forfatter(e) (2014). Synthetic studies towards CXCR4 antagonists.
  • Vis forfatter(e) (2014). Synthetic studies towards CXCR4 antagonists.
  • Vis forfatter(e) (2014). Synthesis and biological evaluation of pseudopeptide inhibitors of Proteinase 3.
  • Vis forfatter(e) (2012). Synthesis of a Ketomethylene Dipeptide Isostere.
  • Vis forfatter(e) (2012). Synthesis and docking of 4-triazolyl substituted piperidine derivatives as novel renin inhibitors.
  • Vis forfatter(e) (2012). Local Anesthetic Articaine Enantiomers interaction with Brain Lipids.
  • Vis forfatter(e) (2011). Synthesis of 3,4-disubstituted piperidines.
  • Vis forfatter(e) (2011). Synthesis of 3,4-disubstituted piperidines.
  • Vis forfatter(e) (2009). Cycloaddition with highly functionalized terminal alkynes.
  • Vis forfatter(e) (2006). Novel Antibacterial Tripeptides.
  • Vis forfatter(e) (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.
Vitenskapelig oversiktsartikkel/review
  • Vis forfatter(e) (2015). Progress toward rationally designed small-molecule peptide and peptidomimetic CXCR4 antagonists. Future Medicinal Chemistry. 1261-1283.
  • Vis forfatter(e) (2007). The medicinal chemistry of short lactoferricin-based antibacterial peptides. Current Medicinal Chemistry. 1-18.

Se fullstendig oversikt over publikasjoner i CRIStin.

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.

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.