Medicinal chemistry

Publications

2020

Bodart L, Derlet A, Buol X, Leyssens T, Tumanov N, Wouters J. Combining two antitubercular drugs, clofazimine and 4-aminosalicylic acid, in order to improve clofazimine aqueous solubility and 4-aminosalicylic acid thermal stability. J Pharm Sci. 2020 Sep 22:S0022-3549(20)30552-9.

Maurya B, Pochet L, Wouters J, Colaço M, Misquith S. MetA (Rv3341) from Mycobacterium tuberculosis H37Rv strain exhibits substrate dependent dual role of transferase and hydrolase activity. Biochimie. 2020 Sep 22:S0300-9084(20)30219-4.

Yang J, Petitjean SJL, Koehler M, Zhang Q, Dumitru AC, Chen W, Derclaye S, Vincent SP, Soumillion P, Alsteens D. Molecular interaction and inhibition of SARS-CoV-2 binding to the ACE2 receptor. Nat Commun. 2020 Sep 11;11(1):4541.

Davoine C, Bouckaert C, Fillet M, Pochet L. Factor XII/XIIa inhibitors: Their discovery, development, and potential indications. Eur J Med Chem. 2020 Aug 20;208:112753.

Pierson E, Wouters J. Biochemical characterization of phosphoserine phosphatase SerB2 from Mycobacterium marinum. Biochem Biophys Res Commun. 2020 Oct 1;530(4):739-744.

Buol X, Robeyns K, Caro Garrido C, Tumanov N, Collard L, Wouters J, Leyssens T. Improving Nefiracetam Dissolution and Solubility Behavior Using a Cocrystallization Approach. Pharmaceutics. 2020 Jul 9;12(7):E653.

Maaliki C, Fu J, Villaume S, Viljoen A, Raynaud C, Hammoud S, Thibonnet J, Kremer L, Vincent SP, Thiery E. Synthesis and evaluation of heterocycle structures as potential inhibitors of Mycobacterium tuberculosis UGM. Bioorg Med Chem. 2020 Jul 1;28(13):115579.

Linclau B, Ardá A, Reichardt NC, Sollogoub M, Unione L, Vincent SP, Jiménez-Barbero J. Fluorinated carbohydrates as chemical probes for molecular recognition studies. Current status and perspectives. Chem Soc Rev. 2020 Jun 10.

Ameryckx A, Pochet L, Wang G, Yildiz E, Saadi BE, Wouters J, Van Bambeke F, Frédérick R. Pharmacomodulations of the benzoyl-thiosemicarbazide scaffold reveal antimicrobial agents targeting d-alanyl-d-alanine ligase in bacterio. Eur J Med Chem. 2020 May 18;200:112444.

Liang L, Wei TW, Wu PY, Herrebout W, Tsai MD, Vincent S. Non-hydrolyzable heptose bis- and monophosphate analogues modulate the pro-inflammatory TIFA- NF-κB signalling. Chembiochem. 2020 May 26.

Leherte L, Haufroid M, Mirgaux M, Wouters J. Investigation of bound and unbound phosphoserine phosphatase conformations through Elastic Network Models and Molecular Dynamics simulations. J Biomol Struct Dyn. 2020 Jun 4:1-17.

Mambourg K, Bodart L, Tumanov N, Lanners S, Wouters J. Synthesis, crystal structure and conformational analysis of an unexpected [1,5]dithiocine product of aminopyridine and thiovanillin. Acta Crystallogr C Struct Chem. 2020 Mar 1;76(Pt3):205-211.

Pierson E, Haufroid M, Gosain TP, Chopra P, Singh R, Wouters J. Identification and Repurposing of Trisubstituted Harmine Derivatives as Novel Inhibitors of Mycobacterium tuberculosis Phosphoserine Phosphatase. Molecules. 2020 Jan 19;25(2):415.

2019

Carvalho A, Viaene J, Vandenbussche G, De Braekeleer K, Masereel B, Wouters J, Souard F, Vander Heyden Y, Van Antwerpen P, Delporte C, Mathieu V. A new potential anti-cancer beta-carboline derivative decreases the expression levels of key proteins involved in glioma aggressiveness: A proteomic investigation. Drug Dev Res. 2019 Sep 9.

Bodart L, Tumanov N and Wouters J. Structural variety of clofaziminium salts: effect of the counter-ion on clofaziminium conformation and crystal packing. Acta Crystallographica Section B 2019;75(4):674-686.

Delbrouck JA, Bochatay VN, Tikad A, Vincent SP. Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification. Org Lett. 2019 Jul 19;21(14):5562-5566.

Leoni L, Carletta A, Fusaro L, Dubois J, Tumanov NA, Aprile C, Wouters J, Dalla Cort A. A Simple and Efficient Mechanochemical Route for the Synthesis of Salophen Ligands and of the Corresponding Zn, Ni, and Pd Complexes. Molecules. 2019 Jun 22;24(12).

Haufroid M, Mirgaux M, Leherte L, Wouters J. Crystal structures and snapshots along the reaction pathway of human phosphoserine phosphatase. Acta Crystallogr D Struct Biol. 2019 Jun 1;75(Pt 6):592-604.

Haufroid M, Wouters J. Targeting the Serine Pathway: A Promising Approach against Tuberculosis? Pharmaceuticals (Basel). 2019 Apr 30;12(2).

Marx S, Bodart L, Tumanov N, Wouters J. Design and Synthesis of a New Soluble Natural β-Carboline Derivative for Preclinical Study by Intravenous Injection. Int J Mol Sci. 2019 Mar 25;20(6).

Spillier Q, Vertommen D, Ravez S, Marteau R, Thémans Q, Corbet C, Feron O, Wouters J, Frédérick R. Anti-alcohol abuse drug disulfiram inhibits human PHGDH via disruption of its active tetrameric form through a specific cysteine oxidation. Sci Rep. 2019 Mar 18;9(1):4737.

Angladon MA, Fossépré M, Leherte L, Vercauteren DP. Interaction of POPC, DPPC, and POPE with the μ opioid receptor: A coarse-grained molecular dynamics study. PLoS One. 2019 Mar 14;14(3):e0213646.

Marx S, Van Gysel M, Breuer A, Dal Maso T, Michiels C, Wouters J, Le Calvé B. Potentialization of anticancer agents by identification of new chemosensitizers active under hypoxia. Biochem Pharmacol. 2019 Apr;162:224-236.

Michaux C, Pepete E. Unravelling the refolding of membrane proteins, one of the most challenging therapeutic targets Med Clin Sci. 2019;1(2):1-3.

2018

Prevost J, Kozlova A, Es Saadi B, Yildiz E, Modaffari S, Lambert D, Pochet L, Wouters J, Dolušić E, Frédérick R. Convenient one-pot formation of highly functionalized 5-bromo-2-aminothiazoles, potential endocannabinoid hydrolase MAGL inhibitors. Tetrahedron Letters. 2018.

Ameryckx A, Thabault L, Pochet L, Leimanis S, Poupaert JH, Wouters J, Joris B, Van Bambeke F, Frédérick R. 1-(2-Hydroxybenzoyl)-thiosemicarbazides are promising antimicrobial agents targeting d-alanine-d-alanine ligase in bacterio. Eur J Med Chem. 2018 Nov 5;159:324-338.

Farcaş E, Hanson J, Pochet L, Fillet M. Capillary electrophoretic mobility shift displacement assay for the assessment of weak drug-protein interactions. Anal Chim Acta. 2018 Nov 30;1034:214-222.

Farcaş E, Pochet L, Fillet M. Transverse diffusion of laminar flow profiles as a generic capillary electrophoresis method for in-line nanoreactor mixing: Application to the investigation of antithrombotic activity. Talanta. 2018 Oct 1;188:516-521.

Jaunet-Lahary T, Vercauteren DP, Fleury F, Laurent AD. Computational simulations determining disulfonic stilbene derivative bioavailability within human serum albumin. Phys Chem Chem Phys. 2018 Jul 4;20(26):18020-18030.

Colaço M, Carletta A, Van Gysel M, Robeyns K, Tumanov N, Wouters J. Direct Access by Mechanochemistry or Sonochemistry to Protonated Merocyanines: Components of a Four-State Molecular Switch. ChemistryOpen. 2018 Jul 2;7(7):520-526.

Drapier T, Geubelle P, Bouckaert C, Nielsen L, Laulumaa S, Goffin E, Dilly S, Francotte P, Hanson J, Pochet L, Kastrup JS, Pirotte B. Enhancing action of positive allosteric modulators through the design of dimeric compounds. J Med Chem. 2018 Jun 28;61(12):5279-5291.

Carletta A, Colaço M, Mouchet S, Plas A, Tumanov N, Fusaro L, Champagne B, Lanners S, and Wouters J. Tetraphenylborate Anion Induces Photochromism in N-Salicylideneamino-1-alkylpyridinium Derivatives Through Formation of Tetra-Aryl Boxes. 2018 J Phys Chem C.

2017

Liang L, Vincent SP. Synthesis of D-glycero-D-manno-heptose 1,7-bisphosphate (HBP) featuring a β-stereoselective bis-phosphorylation. 2017 Tetrahedron Letters. 58, 37, p. 3631-3633.

Fu J, Fu H, Dieu M, Halloum I, Kremer L, Xia Y, Pan W, Vincent SP. Identification of inhibitors targeting Mycobacterium tuberculosis cell wall biosynthesis via dynamic combinatorial chemistry. Chem Commun (Camb). 2017 Sep 26;53(77):10632-10635.

Hinz T, Kallen K, Britten CM, Flamion B, Granzer U, Hoos A, Huber C, Khleif S, Kreiter S, Rammensee HG, Sahin U, Singh-Jasuja H, Türeci Ö, Kalinke U. The European Regulatory Environment of RNA-Based Vaccines. Methods Mol Biol. 2017;1499:203-222.

Frédérick R, Pochet L, De Tullio P, Dufrasne F. 31ièmes Journées Franco-Belges de Pharmacochimie: Meeting Report. Pharmaceuticals (Basel). 2017 Dec 4;10(4).

Nitelet A, Wouters J, Dewez DF, Evano G. Copper-Catalyzed Alkenylation of Cyanamides. Org Lett. 2017 Nov 14.

Leherte L, Vercauteren DP. Reduced Point Charge Models of Proteins: Effect of Protein-Water Interactions in Molecular Dynamics Simulations of Ubiquitin Systems. J Phys Chem B. 2017 Oct 26;121(42):9771-9784.

Villaume SA, Fu J, N'Go I, Liang H, Lou H, Kremer L, Pan W, Vincent SP. Natural and Synthetic Flavonoids as Potent Mycobacterium tuberculosis UGM Inhibitors. Chemistry. 2017 Aug 1;23(43):10423-10429.

Maignen F, Hauben M, Dogné JM. A mathematical framework to quantify the masking effect associated with the confidence intervals of measures of disproportionality. Ther Adv Drug Saf. 2017 Jul;8(7):231-244.

Farcaş E, Bouckaert C, Servais AC, Hanson J, Pochet L, Fillet M. Partial filling affinity capillary electrophoresis as a useful tool for fragment-based drug discovery: A proof of concept on thrombin. Anal Chim Acta. 2017 Sep 1;984:211-222.

Rondelet G, Fleury L, Faux C, Masson V, Dubois J, Arimondo PB, Willems L, Wouters J. Inhibition studies of DNA methyltransferases by maleimide derivatives of RG108 as non-nucleoside inhibitors. Future Med Chem. 2017 Sep;9(13):1465-1481.

Bouckaert C, Zhu S, Govers-Riemslag JWP, Depoorter M, Diamond SL, Pochet L. Discovery and assessment of water soluble coumarins as inhibitors of the coagulation contact pathway. Thromb Res. 2017 Jul 19;157:126-133.

Balti M, Plas A, Meinguet C, Haufroid M, Thémans Q, Efrit ML, Wouters J, Lanners S. Synthesis of 4- and 5-arylthiazolinethiones as inhibitors of indoleamine 2,3-dioxygenase. Bioorg Med Chem Lett. 2016 Jun 18.

Rondelet G, Wouters J. Human DNA (cytosine-5)-methyltransferases: A functional and structural perspective for epigenetic cancer therapy. Biochimie. 2017 Aug;139:137-147.

Farcaş E, Pochet L, Crommen J, Servais AC, Fillet M. Capillary electrophoresis in the context of drug discovery. J Pharm Biomed Anal. 2017 Sep 10;144:195-212.

Harmsen B, Robeyns K, Wouters J, Leyssens T. A study of Fasoracetam's solid state forms: A potential anti-Alzheimer pharmaceutical. J Pharm Sci. 2017 May;106(5):1317-1321.

Carvalho A, Chu J, Meinguet C, Kiss R, Vandenbussche G, Masereel B, Wouters J, Kornienko A, Pelletier J, Mathieu V. Data in support of a harmine-derived beta-carboline in vitro effects in cancer cells through protein synthesis. Data Brief. 2017 May 5;12:546-551.

Carvalho A, Chu J, Meinguet C, Kiss R, Vandenbussche G, Masereel B, Wouters J, Kornienko A, Pelletier J, Mathieu V. A harmine-derived beta-carboline displays anti-cancer effects in vitro by targeting protein synthesis. Eur J Pharmacol. 2017 Jun 15;805:25-35.

2016

Dubois J, Colaço M, Rondelet G, Wouters J. Synthesis and Crystallographic Characterization of a Maleimide Derivative of Tryptamine. 2016 Crystals, 6.

Carletta A, Buol X, Leyssens T, Champagne B, Wouters J. Polymorphic and Isomorphic Cocrystals of a N-Salicylidene-3-aminopyridine with Dicarboxylic Acids: Tuning of Solid-State Photo- and Thermochromism. 2016 J. Phys. Chem. C, 120 (18), 10001.

Fossépré M, Leherte L, Laaksonen A, Vercauteren DP. Multiscale design of coarse-grained elastic network-based potentials for the μ opioid receptor. J Mol Model. 2016 Sep;22(9):227.

Leherte, L. Reduced point charge models of proteins: Assessment based on molecular dynamics simulations (2016) Molecular Simulation, 42 (4), pp. 289-304.

Hanquet G, Salom-Roig X, Lanners S. New Insights into the Synthesis and Biological Activity of the Pamamycin Macrodiolides. Chimia (Aarau). 2016;70(1):20-8.

Bouckaert C, Serra S, Rondelet G, Dolušić E, Wouters J, Dogné JM, Frédérick R, Pochet L. Synthesis, evaluation and structure-activity relationship of new 3-carboxamide coumarins as FXIIa inhibitors. Eur J Med Chem. 2016 Jan 16;110:181-194.

Farcas E, Servais AC, Lamalle C, Chiap P, Pochet L, Fillet M. Fully automated electrophoretically mediated microanalysis for CYP1A1 activity monitoring optimized by multivariate approach. Electrophoresis. 2016 Jan;37(2):248-55.

Leclere L., Fransolet M., Cambier P., El Bkassiny S., Tikad A., Dieu M., Vincent S.P., Van Cutsem P., Michiels C. Identification of a cytotoxic molecule in heat-modified citrus pectin (2016) Carbohydrate Polymers, 137, pp. 39-51.

Rondelet G, Dal Maso T, Willems L, Wouters J. Structural basis for recognition of histone H3K36me3 nucleosome by human de novo DNA methyltransferases 3A and 3B. J Struct Biol. 2016 Jun;194(3):357-67.

2015

The Members of the Organizing Committee. 29ièmes Journées Franco-Belges de Pharmacochimie: Meeting Report. Pharmaceuticals (Basel). 2015 Nov 17;8(4):758-777.

Carletta A, Tilborg A, Moineaux L, de Ruyck J, Basile L, Salerno L, Romeo G, Wouters J, Guccione S. How does binding of imidazole-based inhibitors to heme oxygenase-1 influence their conformation? Insights combining crystal structures and molecular modelling. Acta Crystallogr B Struct Sci Cryst Eng Mater. 2015 Aug 1;71(Pt 4):447-54.

Meinguet C, Masereel B, Wouters J. Preparation and characterization of a new harmine-based antiproliferative compound in complex with cyclodextrin: Increasing solubility while maintaining biological activity. Eur J Pharm Sci. 2015 Sep 18;77:135-40.

Meinguet C, Bruyère C, Frédérick R, Mathieu V, Vancraeynest C, Pochet L, Laloy J, Mortier J, Wolber G, Kiss R, Masereel B, Wouters J. 3D-QSAR, design, synthesis and characterization of trisubstituted harmine derivatives with in vitro antiproliferative properties. Eur J Med Chem. 2015 Apr 13;94:45-55.

Naoîmé, A., Laaksonen, A., Vercauteren, D.P. A Coarse-Grained Simulation Study of the Structures, Energetics, and Dynamics of Linear and Circular DNA with Its Ions (2015) Journal of Chemical Theory and Computation, 11 (6), pp. 2813-2826.

2014

Fossépré M, Leherte L, Laaksonen A, Vercauteren DP. On the modularity of the intrinsic flexibility of the µ opioid receptor: a computational study. PLoS One. 2014 Dec 30;9(12):e115856.

Serra S, Moineaux L, Vancraeynest C, Masereel B, Wouters J, Pochet L, Frederick R Thiosemicarbazide, a fragment with promising indolamine-2,3-dioxygenase (IDO) inhibition properties. European journal of medicinal chemistry 2014, 82:96-105.

Maignen F, Hauben M, Hung E, Holle LV, Dogne JM. A conceptual approach to the masking effect of measures of disproportionality. Pharmacoepidemiol Drug Saf. 2014 Feb;23(2):208-17.

Maignen F, Hauben M, Hung E, Van Holle L, Dogne JM. Assessing the extent and impact of the masking effect of disproportionality analyses on two spontaneous reporting systems databases. Pharmacoepidemiol Drug Saf. 2014 Feb;23(2):195-207.

2013

Britten CM, Singh-Jasuja H, Flamion B, Hoos A, Huber C, Kallen KJ, Khleif SN, Kreiter S, Nielsen M, Rammensee HG, Sahin U, Hinz T, Kalinke U. The regulatory landscape for actively personalized cancer immunotherapies. Nature biotechnology 2013, 31:880-882.

Leclere L, Cutsem PV, Michiels C Anti-cancer activities of pH- or heat-modified pectin. Frontiers in pharmacology 2013, 4:128.

2012

Frederick R, Bruyere C, Vancraeynest C, Reniers J, Meinguet C, Pochet L, Backlund A, Masereel B, Kiss R, Wouters J Novel trisubstituted harmine derivatives with original in vitro anticancer activity Journal of medicinal chemistry 2012, 55:6489-6501.

Moineaux L, Laurent S, Reniers J, Dolusic E, Galleni M, Frere JM, Masereel B, Frederick R, Wouters J Synthesis, crystal structures and electronic properties of isomers of chloro-pyridinylvinyl-1H-indoles European journal of medicinal chemistry 2012, 54:95-102.

Pilotte L, Larrieu P, Stroobant V, Colau D, Dolusic E, Frédérick R, De Plaen E, Uyttenhove C, Wouters J, Masereel B, Van den Eynde BJ. Reversal of tumoral immune resistance by inhibition of tryptophan 2,3-dioxygenase Proceedings of the National Academy of Sciences of the United States of America 2012, 109:2497-2502.

2011

J. Reniers, C. Meinguet, L. Moineaux, B. Masereel, S.P. Vincent, R. Frederick, J. Wouters. Synthesis and inhibition study of monoamine oxidase, indoleamine 2,3-dioxygenase and tryptophan 2,3-dioxygenase by 3,8-substituted 5H-indeno[1,2-c]pyridazin-5-one derivatives. European Journal of Medicinal Chemistry, Volume 46, Issue 12, December 2011, Pages 6104-6111.

Eduard Dolusic, Pierre Larrieu, Laurence Moineaux, Vincent Stroobant, Luc Pilotte, Didier Colau, Lionel Pochet, Benoît Van den Eynde, Bernard Masereel, Johan Wouters, and Raphaël Frédérick. Tryptophan 2,3-Dioxygenase (TDO) Inhibitors. 3-(2-(Pyridyl)ethenyl)indoles as Potential Anticancer Immunomodulators. J. Med. Chem., 2011, 54 (15), pp 5320–5334