Targeting Mycobacterium tuberculosis Biotin Protein Ligase (MtBPL) with Nucleoside-Based Bisubstrate Adenylation Inhibitors

Bockman, Matthew R.; Kalinda, Alvin S.; Petrelli, Riccardo; De la Mora-Rey, Teresa; Tiwari, Divya; Liu, Feng; Dawadi, Surendra; Nandakumar, Madhumitha; Rhee, Kyu Y.; Schnappinger, Dirk; Finzel, Barry C.; Aldrich, Courtney C.

doi:10.1021/acs.jmedchem.5b00719

Title: Targeting Mycobacterium tuberculosis Biotin Protein Ligase (MtBPL) with Nucleoside-Based Bisubstrate Adenylation Inhibitors

Journal Article · Thu Sep 03 00:00:00 EDT 2015 · Journal of Medicinal Chemistry

DOI:https://doi.org/10.1021/acs.jmedchem.5b00719· OSTI ID:1241056

Bockman, Matthew R. ^[1]; Kalinda, Alvin S. ^[1]; Petrelli, Riccardo ^[1]; De la Mora-Rey, Teresa ^[1]; Tiwari, Divya ^[2]; Liu, Feng ^[1]; Dawadi, Surendra ^[1]; Nandakumar, Madhumitha ^[2]; Rhee, Kyu Y. ^[2]; Schnappinger, Dirk ^[2]; Finzel, Barry C. ^[1]; Aldrich, Courtney C. ^[1]

Univ. of Minnesota, Minneapolis, MN (United States)
Weill Cornell Medical College, New York, NY (United States)

Mycobacterium tuberculosis (Mtb), responsible for both latent and symptomatic tuberculosis (TB), remains the second leading cause of mortality among infectious diseases worldwide. Mycobacterial biotin protein ligase (MtBPL) is an essential enzyme in Mtb and regulates lipid metabolism through the post-translational biotinylation of acyl coenzyme A carboxylases. Herein, we report the synthesis and evaluation of a systematic series of potent nucleoside-based inhibitors of MtBPL that contain modifications to the ribofuranosyl ring of the nucleoside. All compounds were characterized by isothermal titration calorimetry (ITC) and shown to bind potently with K_Ds ≤ 2 nM. Additionally, we obtained high-resolution cocrystal structures for a majority of the compounds. Despite fairly uniform biochemical potency, the whole-cell Mtb activity varied greatly with minimum inhibitory concentrations (MIC) ranging from 0.78 to >100 μM. Cellular accumulation studies showed a nearly 10-fold enhancement in accumulation of a C-2'-α analogue over the corresponding C-2'-β analogue, consistent with their differential whole-cell activity.

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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: National Institutes of Health (NIH); Cancer Center Support Grant; Industrial Macromolecular Crystallography Association

Grant/Contract Number:: AI091790; S10-OD017982; CA-77598

OSTI ID:: 1241056

Journal Information:: Journal of Medicinal Chemistry, Vol. 58, Issue 18; ISSN 0022-2623

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: ENGLISH

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Cited by: 35 works

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References (62)

A new evolutionary scenario for the Mycobacterium tuberculosis complex Brosch, R.; Gordon, S. V.; Marmiesse, M. Proceedings of the National Academy of Sciences, Vol. 99, Issue 6 https://doi.org/10.1073/pnas.052548299	journal	March 2002
From Multidrug- to Extensively Drug-Resistant Tuberculosis: Upward Trends as Seen from a 15-Year Nationwide Study Stoffels, Karolien; Allix-Béguec, Caroline; Groenen, Guido PLoS ONE, Vol. 8, Issue 5 https://doi.org/10.1371/journal.pone.0063128	journal	May 2013
Mycobacterial outer membrane is a lipid bilayer and the inner membrane is unusually rich in diacyl phosphatidylinositol dimannosides Bansal-Mutalik, Ritu; Nikaido, Hiroshi Proceedings of the National Academy of Sciences, Vol. 111, Issue 13 https://doi.org/10.1073/pnas.1403078111	journal	March 2014
The Envelope of Mycobacteria Brennan, Patrick J.; Nikaido, Hiroshi Annual Review of Biochemistry, Vol. 64, Issue 1 https://doi.org/10.1146/annurev.bi.64.070195.000333	journal	June 1995
Mycolic acids: structure, biosynthesis and physiological functions Barry, Clifton E.; Lee, Richard E.; Mdluli, Khisimusi Progress in Lipid Research, Vol. 37, Issue 2-3 https://doi.org/10.1016/S0163-7827(98)00008-3	journal	July 1998
Towards understanding the functional diversity of cell wall mycolic acids of Mycobacterium tuberculosis Verschoor, Jan A.; Baird, Mark S.; Grooten, Johan Progress in Lipid Research, Vol. 51, Issue 4 https://doi.org/10.1016/j.plipres.2012.05.002	journal	October 2012
The dimycocerosate ester polyketide virulence factors of mycobacteria Onwueme, Kenolisa C.; Vos, Cheryl J.; Zurita, Juan Progress in Lipid Research, Vol. 44, Issue 5 https://doi.org/10.1016/j.plipres.2005.07.001	journal	September 2005
Long-chain multiple methyl-branched fatty acid-containing lipids of Mycobacterium tuberculosis: Biosynthesis, transport, regulation and biological activities Jackson, Mary; Stadthagen, Gustavo; Gicquel, Brigitte Tuberculosis, Vol. 87, Issue 2 https://doi.org/10.1016/j.tube.2006.05.003	journal	March 2007
Iron, mycobacteria and tuberculosis Ratledge, Colin Tuberculosis, Vol. 84, Issue 1-2 https://doi.org/10.1016/j.tube.2003.08.012	journal	January 2004
The Acyl-AMP Ligase FadD32 and AccD4-containing Acyl-CoA Carboxylase Are Required for the Synthesis of Mycolic Acids and Essential for Mycobacterial Growth: IDENTIFICATION OF THE CARBOXYLATION PRODUCT AND DETERMINATION OF THE ACYL-CoA CARBOXYLASE COMPONENTS Portevin, D.; de Sousa-D'Auria, C.; Montrozier, H. Journal of Biological Chemistry, Vol. 280, Issue 10 https://doi.org/10.1074/jbc.M408578200	journal	January 2005
Biochemical and Structural Characterization of an Essential Acyl Coenzyme A Carboxylase from Mycobacterium tuberculosis Gago, Gabriela; Kurth, Daniel; Diacovich, Lautaro Journal of Bacteriology, Vol. 188, Issue 2 https://doi.org/10.1128/JB.188.2.477-486.2006	journal	January 2006
ACCase 6 is the essential acetyl-CoA carboxylase involved in fatty acid and mycolic acid biosynthesis in mycobacteria Kurth, Daniel G.; Gago, Gabriela M.; de la Iglesia, Agustina Microbiology, Vol. 155, Issue 8 https://doi.org/10.1099/mic.0.027714-0	journal	August 2009
Ligand Specificity of Group I Biotin Protein Ligase of Mycobacterium tuberculosis Purushothaman, Sudha; Gupta, Garima; Srivastava, Richa PLoS ONE, Vol. 3, Issue 5 https://doi.org/10.1371/journal.pone.0002320	journal	May 2008
Bisubstrate Adenylation Inhibitors of Biotin Protein Ligase from Mycobacterium tuberculosis Duckworth, Benjamin P.; Geders, Todd W.; Tiwari, Divya Chemistry & Biology, Vol. 18, Issue 11 https://doi.org/10.1016/j.chembiol.2011.08.013	journal	November 2011
Structure Guided Design of Biotin Protein Ligase Inhibitors for Antibiotic Discovery Paparella, Ashleigh; Soares da Costa, Tatiana; Yap, Min Current Topics in Medicinal Chemistry, Vol. 14, Issue 1 https://doi.org/10.2174/1568026613666131111103149	journal	December 2013
Bisubstrate Inhibitors of Biotin Protein Ligase in Mycobacterium tuberculosis Resistant to Cyclonucleoside Formation Shi, Ce; Tiwari, Divya; Wilson, Daniel J. ACS Medicinal Chemistry Letters, Vol. 4, Issue 12 https://doi.org/10.1021/ml400328a	journal	October 2013
The Biotin Repressor: Modulation of Allostery by Corepressor Analogs Brown, Patrick H.; Cronan, John E.; Grøtli, Morten Journal of Molecular Biology, Vol. 337, Issue 4 https://doi.org/10.1016/j.jmb.2004.01.041	journal	April 2004
β-Keto and β-hydroxyphosphonate analogs of biotin-5′-AMP are inhibitors of holocarboxylase synthetase Sittiwong, Wantanee; Cordonier, Elizabeth L.; Zempleni, Janos Bioorganic & Medicinal Chemistry Letters, Vol. 24, Issue 24 https://doi.org/10.1016/j.bmcl.2014.11.010	journal	December 2014
Selective inhibition of Biotin Protein Ligase from Staphylococcus aureus Soares da Costa, Tatiana P.; Tieu, William; Yap, Min Y. Journal of Biological Chemistry, Vol. 287, Issue 21 https://doi.org/10.1074/jbc.M112.356576	journal	May 2012
Optimising in situ click chemistry: the screening and identification of biotin protein ligase inhibitors Tieu, William; Soares da Costa, Tatiana P.; Yap, Min Y. Chemical Science, Vol. 4, Issue 9 https://doi.org/10.1039/c3sc51127h	journal	January 2013
Heterocyclic acyl-phosphate bioisostere-based inhibitors of Staphylococcus aureus biotin protein ligase Tieu, William; Jarrad, Angie M.; Paparella, Ashleigh S. Bioorganic & Medicinal Chemistry Letters, Vol. 24, Issue 19 https://doi.org/10.1016/j.bmcl.2014.08.030	journal	October 2014
Biotin Analogues with Antibacterial Activity Are Potent Inhibitors of Biotin Protein Ligase Soares da Costa, Tatiana P.; Tieu, William; Yap, Min Y. ACS Medicinal Chemistry Letters, Vol. 3, Issue 6 https://doi.org/10.1021/ml300106p	journal	May 2012
Active site conformational changes upon reaction intermediate biotinyl-5'-AMP binding in biotin protein ligase from Mycobacterium tuberculosis: M. tuberculosis BPL Ma, Qingjun; Akhter, Yusuf; Wilmanns, Matthias Protein Science, Vol. 23, Issue 7 https://doi.org/10.1002/pro.2475	journal	April 2014
Synthesis of carbocyclic aminonucleosides Daluge, Susan; Vince, Robert The Journal of Organic Chemistry, Vol. 43, Issue 12 https://doi.org/10.1021/jo00406a002	journal	June 1978
2-Azabicyclo[2.2.1]hept-5-en-3-one: Chemical Profile of a Versatile Synthetic Building Block and its Impact on the Development of Therapeutics Singh, Rohit; Vince, Robert Chemical Reviews, Vol. 112, Issue 8 https://doi.org/10.1021/cr2004822	journal	May 2012
.pi.-Allylpalladium Formation from Allylic Amines via N,N-Ditosylimides and N-Tosylamides: Efficient Synthesis of the Antiviral Agent Carbovir Jung, Michael E.; Rhee, Hakjune The Journal of Organic Chemistry, Vol. 59, Issue 17 https://doi.org/10.1021/jo00096a006	journal	August 1994
Inhibition of Siderophore Biosynthesis in Mycobacterium tuberculosis with Nucleoside Bisubstrate Analogues: Structure−Activity Relationships of the Nucleobase Domain of 5′- O -[ N -(Salicyl)sulfamoyl]adenosine Neres, João; Labello, Nicholas P.; Somu, Ravindranadh V. Journal of Medicinal Chemistry, Vol. 51, Issue 17 https://doi.org/10.1021/jm800567v	journal	August 2008
Preparation of Carbocyclic S -Adenosylazamethionine Accompanied by a Practical Synthesis of (−)-Aristeromycin Yang, Minmin; Ye, Wei; Schneller, Stewart W. The Journal of Organic Chemistry, Vol. 69, Issue 11 https://doi.org/10.1021/jo040119g	journal	May 2004
Antitubercular Nucleosides That Inhibit Siderophore Biosynthesis: SAR of the Glycosyl Domain Somu, Ravindranadh V.; Wilson, Daniel J.; Bennett, Eric M. Journal of Medicinal Chemistry, Vol. 49, Issue 26 https://doi.org/10.1021/jm061068d	journal	December 2006
Highly Stereoselective Synthesis of Aristeromycin through Dihydroxylation of 4-Aryl-1-azido-2-cyclopentenes Ainai, Takauki; Wang, Yong-Gang; Tokoro, Yuko The Journal of Organic Chemistry, Vol. 69, Issue 3 https://doi.org/10.1021/jo034672u	journal	February 2004
A new type of silyl protecting groups in nucleoside chemistry Markiewicz, W. T.; Wiewiórowski, M. Nucleic Acids Research, Vol. 5, Issue suppl_1 https://doi.org/10.1093/nar/1.suppl_1.s185	journal	January 1978
Synthesis of 2′-([1,2,3]Triazol-1-yl)-2′-deoxyadenosines O′Mahony, Gavin; Svensson, Sara; Sundgren, Andreas Nucleosides, Nucleotides and Nucleic Acids, Vol. 27, Issue 5 https://doi.org/10.1080/15257770802086880	journal	April 2008
A critical electrostatic interaction mediates inhibitor recognition by human asparagine synthetase Ikeuchi, Hideyuki; Meyer, Megan E.; Ding, Yun Bioorganic & Medicinal Chemistry, Vol. 17, Issue 18 https://doi.org/10.1016/j.bmc.2009.07.071	journal	September 2009
Aqueous trifluoroacetic acid—an efficient reagent for exclusively cleaving the 5′-end of 3′,5′-TIPDS protected ribonucleosides Zhu, Xue-Feng; Williams, Howard J.; Scott, A. Ian Tetrahedron Letters, Vol. 41, Issue 49 https://doi.org/10.1016/S0040-4039(00)01685-3	journal	December 2000
CHEMICAL SYNTHESIS OF THE NOVEL CA ²⁺ MESSENGER NAADP Dowden, James; Brown, Richard S.; Moreau, Christelle Nucleosides, Nucleotides & Nucleic Acids, Vol. 24, Issue 5-7 https://doi.org/10.1081/NCN-200061786	journal	April 2005
Deoxyribosyl analogues of methionyl and isoleucyl sulfamate adenylates as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases Kim, Sung Eun; Kim, Su Yeon; Kim, Sunghoon Bioorganic & Medicinal Chemistry Letters, Vol. 15, Issue 14 https://doi.org/10.1016/j.bmcl.2005.05.035	journal	July 2005
Über neue organische Phosphorverbindungen III. Phosphinmethylenderivate und Phosphinimine Staudinger, H.; Meyer, Jules Helvetica Chimica Acta, Vol. 2, Issue 1, p. 635-646 https://doi.org/10.1002/hlca.19190020164	journal	January 1919
Sixty years of staudinger reaction Gololobov, Yu. G.; Zhmurova, I. N.; Kasukhin, L. F. Tetrahedron, Vol. 37, Issue 3 https://doi.org/10.1016/S0040-4020(01)92417-2	journal	January 1981
Efficient general method for sulfamoylation of a hydroxyl group Okada, Makoto; Iwashita, Shigeki; Koizumi, Naoyuki Tetrahedron Letters, Vol. 41, Issue 36 https://doi.org/10.1016/S0040-4039(00)01130-8	journal	September 2000
Fluorinated nucleosides Pankiewicz, Krzysztof W. Carbohydrate Research, Vol. 327, Issue 1-2 https://doi.org/10.1016/S0008-6215(00)00089-6	journal	July 2000
Recent advances in the synthesis of fluorinated nucleosides Qiu, Xiao-Long; Xu, Xiu-Hua; Qing, Feng-Ling Tetrahedron, Vol. 66, Issue 4 https://doi.org/10.1016/j.tet.2009.11.001	journal	January 2010
5′-Carbamoyl derivatives of 2′-C-methyl-purine nucleosides as selective A1 adenosine receptor agonists: Affinity, efficacy, and selectivity for A1 receptor from different species Cappellacci, Loredana; Franchetti, Palmarisa; Vita, Patrizia Bioorganic & Medicinal Chemistry, Vol. 16, Issue 1 https://doi.org/10.1016/j.bmc.2007.09.035	journal	January 2008
Improved Protocol for the Synthesis of Flexibly Protected Morpholino Monomers from Unprotected Ribonucleosides Pattanayak, Sankha; Paul, Sibasish; Nandi, Bappaditya Nucleosides, Nucleotides and Nucleic Acids, Vol. 31, Issue 11 https://doi.org/10.1080/15257770.2012.724491	journal	November 2012
A Non-Enzymatic, DNA Template-Directed Morpholino Primer Extension Approach Bell, Neil M.; Wong, Raymond; Micklefield, Jason Chemistry - A European Journal, Vol. 16, Issue 7 https://doi.org/10.1002/chem.200902237	journal	February 2010
New oligonucleotide analogues based on morpholine subunits joined by oxalyl diamide tether Abramova, Tatiana V.; Kassakin, Marat F.; Lomzov, Alexander A. Bioorganic Chemistry, Vol. 35, Issue 3 https://doi.org/10.1016/j.bioorg.2006.12.003	journal	June 2007
Conformational analysis in carbohydrate chemistry. I. Conformational free energies. The conformations and α : β ratios of aldopyranoses in aqueous solution Angyal, Sj Australian Journal of Chemistry, Vol. 21, Issue 11 https://doi.org/10.1071/CH9682737	journal	January 1968
Novel substrate of adenosine deaminase Schaeffer, Howard J.; Gurwara, S.; Vince, Robert Journal of Medicinal Chemistry, Vol. 14, Issue 4 https://doi.org/10.1021/jm00286a024	journal	April 1971
An Isothermal Titration Calorimeter Christensen, James J.; Johnston, H. Dee; Izatt, Reed M. Review of Scientific Instruments, Vol. 39, Issue 9 https://doi.org/10.1063/1.1683671	journal	September 1968
Some Binding-Related Drug Properties are Dependent on Thermodynamic Signature: Optimization of Drug Candidates Schön, Arne; Madani, Navid; Smith, Amos B. Chemical Biology & Drug Design, Vol. 77, Issue 3 https://doi.org/10.1111/j.1747-0285.2010.01075.x	journal	February 2011
Isothermal titration calorimetry to determine association constants for high-affinity ligands Velazquez-Campoy, Adrian; Freire, Ernesto Nature Protocols, Vol. 1, Issue 1 https://doi.org/10.1038/nprot.2006.28	journal	June 2006
The use of differential scanning fluorimetry to detect ligand interactions that promote protein stability Niesen, Frank H.; Berglund, Helena; Vedadi, Masoud Nature Protocols, Vol. 2, Issue 9 https://doi.org/10.1038/nprot.2007.321	journal	September 2007
Morpholino Antisense Oligomers: Design, Preparation, and Properties Summerton, James; Weller, Dwight Antisense and Nucleic Acid Drug Development, Vol. 7, Issue 3 https://doi.org/10.1089/oli.1.1997.7.187	journal	June 1997
Metabolomics of Mycobacterium tuberculosis Reveals Compartmentalized Co-Catabolism of Carbon Substrates de Carvalho, Luiz Pedro S.; Fischer, Steven M.; Marrero, Joeli Chemistry & Biology, Vol. 17, Issue 10 https://doi.org/10.1016/j.chembiol.2010.08.009	journal	October 2010
Lipoamide Channel-Binding Sulfonamides Selectively Inhibit Mycobacterial Lipoamide Dehydrogenase Bryk, Ruslana; Arango, Nancy; Maksymiuk, Christina Biochemistry, Vol. 52, Issue 51 https://doi.org/10.1021/bi401077f	journal	November 2013
Synthesis of 1,3-Diamines Through Rhodium-Catalyzed CH Insertion Kurokawa, Toshiki; Kim, Mihyong; Du Bois, J. Angewandte Chemie International Edition, Vol. 48, Issue 15 https://doi.org/10.1002/anie.200806192	journal	March 2009
Synthesis and Aminoacyl-tRNA Synthetase Inhibitory Activity of Prolyl Adenylate Analogs Heacock, Donald; Forsyth, Craig J.; Shiba, Kiyotaka Bioorganic Chemistry, Vol. 24, Issue 3 https://doi.org/10.1006/bioo.1996.0025	journal	September 1996
Enhancing the Stability and Biological Functionalities of Quantum Dots via Compact Multifunctional Ligands Susumu, Kimihiro; Uyeda, H. Tetsuo; Medintz, Igor L. Journal of the American Chemical Society, Vol. 129, Issue 45 https://doi.org/10.1021/ja0749744	journal	November 2007
2‘- C -Methyl Analogues of Selective Adenosine Receptor Agonists: Synthesis and Binding Studies ^† Franchetti, Palmarisa; Cappellacci, Loredana; Marchetti, Stefano Journal of Medicinal Chemistry, Vol. 41, Issue 10 https://doi.org/10.1021/jm9707737	journal	May 1998
Phaser crystallographic software McCoy, Airlie J.; Grosse-Kunstleve, Ralf W.; Adams, Paul D. Journal of Applied Crystallography, Vol. 40, Issue 4 https://doi.org/10.1107/S0021889807021206	journal	July 2007
PHENIX: a comprehensive Python-based system for macromolecular structure solution Adams, Paul D.; Afonine, Pavel V.; Bunkóczi, Gábor Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 2, p. 213-221 https://doi.org/10.1107/S0907444909052925	journal	January 2010
JLigand : a graphical tool for the CCP 4 template-restraint library Lebedev, Andrey A.; Young, Paul; Isupov, Michail N. Acta Crystallographica Section D Biological Crystallography, Vol. 68, Issue 4 https://doi.org/10.1107/S090744491200251X	journal	March 2012
Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays Mosmann, Tim Journal of Immunological Methods, Vol. 65, Issue 1-2 https://doi.org/10.1016/0022-1759(83)90303-4	journal	December 1983

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Title: Targeting Mycobacterium tuberculosis Biotin Protein Ligase (MtBPL) with Nucleoside-Based Bisubstrate Adenylation Inhibitors

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