Purdue University
Mark S. Cushman, Ph.D.
Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, 575 Stadium Mall Drive, West Lafayette, IN 47907, USA
Publications
O-Nucleoside, S-Nucleoside, and N-Nucleoside Probes of Lumazine Synthase and Riboflavin Synthase
Arindam Talukdar, Yujie Zhao, Wei Lv, Adelbert Bacher, Boris A. Illarionov, Markus Fischer, Mark Cushman
Journal of Organic Chemistry 77, 6239-6261 (2012)
Structural study and thermodynamic characterization of inhibitor binding to lumazine synthase from Bacillus anthracis
Ekaterina Morgunova; Boris Illarionov; Sabine Saller; Aleksander Popov; Thota Sambaiah; Adelbert Bacher; Mark Cushman; Markus Fischer; Rudolf Ladenstein
Acta Crystallographica, Section D: Biological Crystallography D66, 1001-1011 (2010)
Virtual screening, selection and development of a benzindolone structural scaffold for inhibition of lumazine synthase
Arindam Talukdar; Ekaterina Morgunova; Jianxin Duan; Winfried Meining; Nicolas Foloppe; Lennart Nilsson; Adelbert Bacher; Boris Illarionov; Markus Fischer; Rudolf Ladenstein; Mark Cushman
Bioorganic & Medicinal Chemistry 18, 3518-3534 (2010)
Mechanistic Insights on Riboflavin Synthase Inspired by Selective Binding of the 6,7-Dimethyl-8-ribityllumazine Exomethylene Anion
Ryu-Ryun Kim; Boris Illarionov; Monika Joshi; Mark Cushman; Chan Yong Lee; Wolfgang Eisenreich; Markus Fischer; Adelbert Bacher
Journal of the American Chemical Society 132, 2983-2990 (2010)
Discovery and Development of a Small Molecule Library with Lumazine Synthase Inhibitory Activity
Arindam Talukdar; Meghan Breen; Adelbert Bacher; Boris Illarionov; Markus Fischer; Gunda Georg; Qi-Zhuang Ye; Mark Cushman
Journal of Organic Chemistry 74, 5123-5134 (2009)
Discovery and Development of the Covalent Hydrates of Trifluoromethylated Pyrazoles as Riboflavin Synthase Inhibitors with Antibiotic Activity Against Mycobacterium tuberculosis
Yujie Zhao; Adelbert Bacher; Boris Illarionov; Markus Fischer; Gunda Georg; Qi-Zhuang Ye; Phillip E. Fanwick; Scott G. Franzblau; Baojie Wan; Mark Cushman
Journal of Organic Chemistry 74, 5297-5303 (2009)
15N{31P} REDOR NMR Studies of the Binding of Phosphonate Reaction Intermediate Analogues to Saccharomyces cerevisiae Lumazine Synthase
Tsyr-Yan Yu; Robert D. O'Connor; Astrid C. Sivertsen; Colby Chiauzzi; Barbara Poliks; Markus Fischer; Adelbert Bacher; Ilka Haase; Mark Cushman; Jacob Schaefer
Biochemistry 47, 13942-13951 (2008)
A New Series of N-[2,4-Dioxo-6-D-ribitylamino-1,2,3,4-tetrahydropyrimidin-5-yl]oxalamic Acid Derivatives as Inhibitors of Lumazine Synthase and Riboflavin Synthase: Design, Synthesis, Biochemical Evaluation, Crystallography, and Mechanistic Implications
Yanlei Zhang; Boris Illarionov; Ekaterina Morgunova; Guangyi Jin; Adelbert Bacher; Markus Fischer; Rudolf Ladenstein; Mark Cushman
Journal of Organic Chemistry 73, 2715-2724 (2008)
A high-throughput screening platform for inhibitors of the riboflavin biosynthesis pathway
Johannes Kaiser; Boris Illarionov; Felix Rohdich; Wolfgang Eisenreich; Sabine Saller; Jan van den Brulle; Mark Cushman; Adelbert Bacher; Markus Fischer
Analytical Biochemistry 365, 52-61 (2007)
Ligand binding properties of the N-terminal domain of riboflavin synthase from Escherichia coli
Chan Yong Lee; Boris Illarionov; Young-Eun Woo; Kristina Kemter; Ryu-Ryun Kim; Sabine Eberhardt; Mark Cushman; Wolfgang Eisenreich; Markus Fischer; Adelbert Bacher
Journal of Biochemistry and Molecular Biology 40, 239-246 (2007)
Lumazine Synthase from Candida albicans as an Anti-fungal Target Enzyme: Structural and Biochemical Basis for Drug Design
Ekaterina Morgunova; Sabine Saller; Ilka Haase; Mark Cushman; Adelbert Bacher; Markus Fischer; Rudolf Ladenstein
Journal of Biological Chemistry 282, 17231-17241 (2007)
A Novel Lumazine Synthase Inhibitor Derived from Oxidation of 1,3,6,8-Tetrahydroxy-2,7-naphthyridine to a Tetraazaperylenehexaone Derivative
Yanlei Zhang; Boris Illarionov; Adelbert Bacher; Markus Fischer; Gunda I. Georg; Qi-Zhuang Ye; David Vander Velde; Phillip E. Fanwick; Yunlong Song; Mark Cushman
Journal of Organic Chemistry 72, 2769-2776 (2007)
Synthesis and enzyme inhibitory activity of the S-nucleoside analogue of the tibitylaminopyrimidine substrate of lumazine synthase and product of riboflavin synthase
Arindam Talukdar; Boris Illarionov; Adelbert Bacher; Markus Fischer; Mark Cushman
Journal of Organic Chemistry 72, 7167-7175 (2007)
A new series of 3-alkyl phosphate derivatives of 4,5,6,7-tetrahydro-1-D-ribityl-1H-pyrazolo[3,4-d]pyrimidinedione as inhibitors of lumazine synthase: design, synthesis, and evaluation
Yanlei Zhang; Guangyi Jin; Boris Illarionov; Adelbert Bacher; Markus Fischer; Mark Cushman
Journal of Organic Chemistry 72, 7176-7184 (2007)
Structural and thermodynamic insights into the binding mode of five novel inhibitors of lumazine synthase from Mycobacterium tuberculosis
Ekaterina Morgunova; Boris Illarionov; Thota Sambaiah; Ilka Haase; Adelbert Bacher; Mark Cushman; Markus Fischer; Rudolf Ladenstein
FEBS Journal 273, 4790-4804 (2006)
Crystal Structure of an Archaeal Pentameric Riboflavin Synthase in Complex with a Substrate Analog Inhibitor: stereochemical implications
Arne Ramsperger; Martin Augustin; Ann-Kathrin Schott; Stefan Gerhardt; Tobias Krojer; Wolfgang Eisenreich; Boris Illarionov; Mark Cushman; Adelbert Bacher; Robert Huber; Markus Fischer
Journal of Biological Chemistry 281, 1224-1232 (2006)
A high-throughput screen utilizing the fluorescence of riboflavin for identification of lumazine synthase inhibitors
Jinhua Chen; Boris Illarionov; Adelbert Bacher; Markus Fischer; Ilka Haase; Gunda Georg; Qi-Zhuang Ye; Zeqiang Ma; Mark Cushman
Analytical Biochemistry 338, 124-130 (2005)
Crystal Structure of Lumazine Synthase from Mycobacterium tuberculosis as a Target for Rational Drug Design: Binding Mode of a New Class of Purinetrione Inhibitors
Ekaterina Morgunova; Winfried Meining; Boris Illarionov; Ilka Haase; Guangyi Jin; Adelbert Bacher; Mark Cushman; Markus Fischer; Rudolf Ladenstein
Biochemistry 44, 2746-2758 (2005)
Design, synthesis, and biochemical evaluation of 1,5,6,7-tetrahydro-6,7-dioxo-9-D-ribitylaminolumazines bearing alkyl phosphate substituents as inhibitors of lumazine synthase and riboflavin synthase
Mark Cushman; Guangyi Jin; Boris Illarionov; Markus Fischer; Rudolf Ladenstein; Adelbert Bacher
Journal of Organic Chemistry 70, 8162-8170 (2005)
Erratum: Journal of Organic Chemistry 70, 9092-9092 (2005)
Structural basis of charge transfer complex formation by riboflavin bound to 6,7-dimethyl-8-ribityllumazine synthase
M ichael Koch; Constanze Breithaupt; Stefan Gerhardt; Ilka Haase; Stefan Weber; Mark Cushman; Robert Huber; Adelbert Bacher; Markus Fischer
European Journal of Biochemistry 271, 3208-3214 (2004)
Design, Synthesis, and Evaluation of 9-D-Ribitylamino-1,3,7,9-tetrahydro-2,6,8-purinetriones Bearing Alkyl Phosphate and α,α-Difluorophosphonate Substituents as Inhibitors of Riboflavin Synthase and Lumazine Synthase
Mark Cushman; Thota Sambaiah; Guangyi Jin; Boris Illarionov; Markus Fischer; Adelbert Bacher
Journal of Organic Chemistry 69, 601-612 (2004)
Design, Synthesis, and Evaluation of Acyclic C-Nucleoside and N-Methylated Derivatives of the Ribitylaminopyrimidine Substrate of Lumazine Synthase as Potential Enzyme Inhibitors and Mechanistic Probes
Jinhua Chen; Thota Sambaiah; Boris Illarionov; Markus Fischer; Adelbert Bacher; Mark Cushman
Journal of Organic Chemistry 69, 6996-7003 (2004)
Riboflavin synthase of Schizosaccharomyces pombe. Protein dynamics revealed by 19F NMR protein perturbation experiments
Markus Fischer; Ann-Kathrin Schott; Kristina Kemter; Richard Feicht; Gerald Richter; Boris Illarionov; Wolfgang Eisenreich; Stefan Gerhardt; Mark Cushman; Stefan Steinbacher; Robert Huber; Adelbert Bacher
BMC Biochemistry 4, 18-18 (2003)
Enzyme catalysis via control of activation entropy: site-directed mutagenesis of 6,7-dimethyl-8-ribityllumazine synthase
Markus Fischer; Ilka Haase; Klaus Kis; Winfried Meining; Rudolf Ladenstein; Mark Cushman; Nicholas Schramek; Robert Huber; Adelbert Bacher
Journal of Molecular Biology 326, 783-793 (2003)
A Structure-based Model of the Reaction Catalyzed by Lumazine Synthase from Aquifex aeolicus
Xiaofeng Zhang; Winfried Meining; Mark Cushman; Ilka Haase; Markus Fischer; Adelbert Bacher; Rudolf Ladenstein
Journal of Molecular Biology 328, 167-182 (2003)
Investigation of the binding of epimer A of the covalent hydrate of 6,7-bis(trifluoromethyl)-8-D-ribityllumazine to a recombinant F22W Bacillus subtilis lumazine synthase mutant by 15N{19F} REDOR NMR
Anil K. Mehta; Daniel R. Studelska; Markus Fischer; Andreas Gießauf; Kristina Kemter; Adelbert Bacher; Mark Cushman; Jacob Schaefer
Journal of Organic Chemistry 67, 2087-2092 (2002)
Design, synthesis, and evaluation of 6-carboxyalkyl and 6-Phosphonoxyalkyl derivatives of 7-oxo-8-ribitylaminolumazines as inhibitors of riboflavin synthase and lumazine synthase
Mark Cushman; Donglai Yang; Stefan Gerhardt; Robert Huber; Markus Fischer; Klaus Kis; Adelbert Bacher
Journal of Organic Chemistry 67, 5807-5816 (2002)
Incorporation of an Amide into 5-Phosphonoalkyl-6-D-ribitylaminopyrimidinedione Lumazine synthase Inhibitors results in an unexpected reversal of selectivity for riboflavin synthase vs. lumazine synthase
Mark Cushman; Donglai Yang; Jeffrey T. Mihalic; Jinhua Chen; Stefan Gerhardt; Robert Huber; Markus Fischer; Klaus Kis; Adelbert Bacher
Journal of Organic Chemistry 67, 6871-6877 (2002)
Studies on the Reaction Mechanism of Riboflavin Synthase. X-Ray Crystal Structure of a Complex with 6-Carboxyethyl-7-Oxo-8-Ribityllumazine
Stefan Gerhardt; Ann-Kathrin Schott; Norman Kairies; Mark Cushman; Boris Illarionov; Wolfgang Eisenreich; Adelbert Bacher; Robert Huber; Stefan Steinbacher; Markus Fischer
Structure 10, 1371-1381 (2002)
The crystal structure of riboflavin synthase of Schizosaccharomyces pombe in complex with 6-carboxyethyl-7-oxo-8-ribityllumazine reveals insights into the reaction mechanism
Stefan Gerhardt; Stefan Steinbacher; N. Kairies; Robert Huber; A.-K. Schott; Boris Illarionov; Wolfgang Eisenreich; Adelbert Bacher; Markus Fischer; Mark Cushman -/- Editors: Stephen Chapman; Richard Perham; Nigel Scrutton
Flavins and Flavoproteins 2002, Proceedings of the International Symposium, 14th, Cambridge, United Kingdom, July 14-18, 2002 45-50 (2002)
19F NMR ligand perturbation studies on the riboflavin synthase of Schizosaccharomyces pombe
Markus Fischer; A.-K. Schott; K. Kemter; Richard Feicht; Gerald Richter; Boris Illarionov; Wolfgang Eisenreich; Adelbert Bacher; Stefan Gerhardt; Stefan Steinbacher; Robert Huber; Mark Cushman -/- Editors: Stephen Chapman; Richard Perham; Nigel Scrutton
Flavins and Flavoproteins 2002, Proceedings of the International Symposium, 14th, Cambridge, United Kingdom, July 14-18, 2002 161-166 (2002)
The crystal structure of lumazine synthase from Schizosaccharomyces pombe reveals its binding mode to riboflavin
Stefan Gerhardt; Stefan Steinbacher; Jens T. Kaiser; Robert Huber; Ilka Haase; Adelbert Bacher; Markus Fischer; Mark Cushman -/- Editors: Stephen Chapman; Richard Perham; Nigel Scrutton
Flavins and Flavoproteins 2002, Proceedings of the International Symposium, 14th, Cambridge, United Kingdom, July 14-18, 2002 857-862 (2002)
19F NMR ligand perturbation studies on 6,7-bis(trifluoromethyl)-8-ribityllumazine-7-hydrates and the lumazine synthase complex of Bacillus subtilis. Site-directed mutagenesis changes the mechanism and the stereoselectivity of the catalysed haloform-type reaction
Johannes Scheuring; Karl Kugelbrey; Sevil Weinkauf; Mark Cushman; Adelbert Bacher; Markus Fischer
Journal of Organic Chemistry 66, 3811-3819 (2001)
The atomic structure of the pentameric lumazine synthase from Saccharomyces cerevisiae at 1.85 Å resolution reveals the binding mode of a phosphonate intermediate analogue
Winfried Meining; Simone Mörtl; Markus Fischer; Mark Cushman; Adelbert Bacher; Rudolf Ladenstein
Journal of Molecular Biology 299, 181-197 (2000)
Investigation of the binding of fluorolumazines to the 1-MDa capsid of lumazine synthase by 15N{19F} REDOR NMR
Jon M. Goetz; Barbara Poliks; Barbara Studelska; Markus Fischer; Karl Kugelbrey; Adelbert Bacher; Mark Cushman; Jacob Schaefer
Journal of the American Chemical Society 121, 7500-7508 (1999)
19F NMR studies on lumazine synthase from Bacillus subtilis
Markus Fischer; Karl Kugelbrey; Johannes Scheuring; Mark Cushman
Flavins and Flavoproteins 1999, Proceedings of the International Symposium, 13th, Konstanz, Germany, Aug. 29-Sept. 4, 1999 809-812 (1999)
Investigation of the binding of 6,7-bis(trifluoromethyl)-8-ribityllumazines to 15N-labeled lumazine synthase by REDOR-NMR
Markus Fischer; Jon M. Goetz; Barbara Poliks; Daniel R. Studelska; Andreas Gießauf; Karl Kugelbrey; Mark Cushman; Jacob Schaefer -/- Editor: Sandro Ghisla
Flavins and Flavoproteins 1999, Proceedings of the International Symposium, 13th, Konstanz, Germany, Aug. 29-Sept. 4, 1999 829-832 (1999)
Biosynthesis of riboflavin. Structure and mechanism of lumazine synthase
Adelbert Bacher; Markus Fischer; Klaus Kis; Karl Kugelbrey; Simone Mörtl; Johannes Scheuring; Sevil Weinkauf; Sabine Eberhardt; K. Schmidt-Bäse; Robert Huber; K. Ritsert; Mark Cushman; Rudolf Ladenstein
Biochemical Society Transactions 24, 89-94 (1996)
NMR analysis of site-specific binding in oligomeric proteins. Dynamic studies on the interaction of riboflavin synthase with trifluoromethyl-substituted intermediates
Johannes Scheuring; Markus Fischer; Mark Cushman; J. Lee; Adelbert Bacher; H. Oschkinat
Biochemistry 35, 9637-9646 (1996)
