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

Abstract

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.

Authors:

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)

Publication Date:: Thu Sep 03 00:00:00 EDT 2015

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

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

OSTI Identifier:: 1241056

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

Resource Type:: Accepted Manuscript

Journal Name:: Journal of Medicinal Chemistry

Additional Journal Information:: Journal Volume: 58; Journal Issue: 18; Journal ID: ISSN 0022-2623

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: ENGLISH

Subject:: 60 APPLIED LIFE SCIENCES; Nutrition; Inhibitors; Lipids; Organic compounds; Ligands

Citation Formats


                    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., and Aldrich, Courtney C. Targeting Mycobacterium tuberculosis Biotin Protein Ligase (MtBPL) with Nucleoside-Based Bisubstrate Adenylation Inhibitors.  United States: N. p., 2015. 
Web.  doi:10.1021/acs.jmedchem.5b00719.

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                    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. Targeting Mycobacterium tuberculosis Biotin Protein Ligase (MtBPL) with Nucleoside-Based Bisubstrate Adenylation Inhibitors.  United States.  https://doi.org/10.1021/acs.jmedchem.5b00719

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                    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., and Aldrich, Courtney C. Thu .  
"Targeting Mycobacterium tuberculosis Biotin Protein Ligase (MtBPL) with Nucleoside-Based Bisubstrate Adenylation Inhibitors".  United States.  https://doi.org/10.1021/acs.jmedchem.5b00719.  https://www.osti.gov/servlets/purl/1241056.

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@article{osti_1241056,

  title        = {Targeting Mycobacterium tuberculosis Biotin Protein Ligase (MtBPL) with Nucleoside-Based Bisubstrate Adenylation Inhibitors},

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

  abstractNote = {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 KDs ≤ 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.},

  doi          = {10.1021/acs.jmedchem.5b00719},

  journal      = {Journal of Medicinal Chemistry},

  number       = 18,

  volume       = 58,

  place        = {United States},

  year         = {Thu Sep 03 00:00:00 EDT 2015},

  month        = {Thu Sep 03 00:00:00 EDT 2015}

}

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Trypanosoma brucei Inhibition by Essential Oils from Medicinal and Aromatic Plants Traditionally Used in Cameroon (Azadirachta indica, Aframomum melegueta, Aframomum daniellii, Clausena anisata, Dichrostachys cinerea and Echinops giganteus)
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Youssefi, Mohammad Reza; Moghaddas, Elham; Tabari, Mohaddeseh Abouhosseini
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DOI: 10.3390/molecules24112072

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

Abstract

Citation Formats

A new evolutionary scenario for the Mycobacterium tuberculosis complex journal, March 2002

From Multidrug- to Extensively Drug-Resistant Tuberculosis: Upward Trends as Seen from a 15-Year Nationwide Study journal, May 2013

Mycobacterial outer membrane is a lipid bilayer and the inner membrane is unusually rich in diacyl phosphatidylinositol dimannosides journal, March 2014

The Envelope of Mycobacteria journal, June 1995

Mycolic acids: structure, biosynthesis and physiological functions journal, July 1998

Towards understanding the functional diversity of cell wall mycolic acids of Mycobacterium tuberculosis journal, October 2012

The dimycocerosate ester polyketide virulence factors of mycobacteria journal, September 2005

Long-chain multiple methyl-branched fatty acid-containing lipids of Mycobacterium tuberculosis: Biosynthesis, transport, regulation and biological activities journal, March 2007

Iron, mycobacteria and tuberculosis 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 journal, January 2005

Biochemical and Structural Characterization of an Essential Acyl Coenzyme A Carboxylase from Mycobacterium tuberculosis journal, January 2006

ACCase 6 is the essential acetyl-CoA carboxylase involved in fatty acid and mycolic acid biosynthesis in mycobacteria journal, August 2009

Ligand Specificity of Group I Biotin Protein Ligase of Mycobacterium tuberculosis journal, May 2008

Bisubstrate Adenylation Inhibitors of Biotin Protein Ligase from Mycobacterium tuberculosis journal, November 2011

Structure Guided Design of Biotin Protein Ligase Inhibitors for Antibiotic Discovery journal, December 2013

Bisubstrate Inhibitors of Biotin Protein Ligase in Mycobacterium tuberculosis Resistant to Cyclonucleoside Formation journal, October 2013

The Biotin Repressor: Modulation of Allostery by Corepressor Analogs journal, April 2004

β-Keto and β-hydroxyphosphonate analogs of biotin-5′-AMP are inhibitors of holocarboxylase synthetase journal, December 2014

Selective inhibition of Biotin Protein Ligase from Staphylococcus aureus journal, May 2012

Optimising in situ click chemistry: the screening and identification of biotin protein ligase inhibitors journal, January 2013

Heterocyclic acyl-phosphate bioisostere-based inhibitors of Staphylococcus aureus biotin protein ligase journal, October 2014

Biotin Analogues with Antibacterial Activity Are Potent Inhibitors of Biotin Protein Ligase journal, May 2012

Active site conformational changes upon reaction intermediate biotinyl-5'-AMP binding in biotin protein ligase from Mycobacterium tuberculosis: M. tuberculosis BPL journal, April 2014

Synthesis of carbocyclic aminonucleosides 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 journal, May 2012

.pi.-Allylpalladium Formation from Allylic Amines via N,N-Ditosylimides and N-Tosylamides: Efficient Synthesis of the Antiviral Agent Carbovir 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 journal, August 2008

Preparation of Carbocyclic S -Adenosylazamethionine Accompanied by a Practical Synthesis of (−)-Aristeromycin journal, May 2004

Antitubercular Nucleosides That Inhibit Siderophore Biosynthesis: SAR of the Glycosyl Domain journal, December 2006

Highly Stereoselective Synthesis of Aristeromycin through Dihydroxylation of 4-Aryl-1-azido-2-cyclopentenes journal, February 2004

A new type of silyl protecting groups in nucleoside chemistry journal, January 1978

Synthesis of 2′-([1,2,3]Triazol-1-yl)-2′-deoxyadenosines journal, April 2008

A critical electrostatic interaction mediates inhibitor recognition by human asparagine synthetase journal, September 2009

Aqueous trifluoroacetic acid—an efficient reagent for exclusively cleaving the 5′-end of 3′,5′-TIPDS protected ribonucleosides journal, December 2000

CHEMICAL SYNTHESIS OF THE NOVEL CA 2+ MESSENGER NAADP journal, April 2005

Deoxyribosyl analogues of methionyl and isoleucyl sulfamate adenylates as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases journal, July 2005

Über neue organische Phosphorverbindungen III. Phosphinmethylenderivate und Phosphinimine journal, January 1919

Sixty years of staudinger reaction journal, January 1981

Efficient general method for sulfamoylation of a hydroxyl group journal, September 2000

Fluorinated nucleosides journal, July 2000

Recent advances in the synthesis of fluorinated nucleosides 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 journal, January 2008

Improved Protocol for the Synthesis of Flexibly Protected Morpholino Monomers from Unprotected Ribonucleosides journal, November 2012

A Non-Enzymatic, DNA Template-Directed Morpholino Primer Extension Approach journal, February 2010

New oligonucleotide analogues based on morpholine subunits joined by oxalyl diamide tether journal, June 2007

Conformational analysis in carbohydrate chemistry. I. Conformational free energies. The conformations and α : β ratios of aldopyranoses in aqueous solution journal, January 1968

Novel substrate of adenosine deaminase journal, April 1971

An Isothermal Titration Calorimeter journal, September 1968

Some Binding-Related Drug Properties are Dependent on Thermodynamic Signature: Optimization of Drug Candidates journal, February 2011

Isothermal titration calorimetry to determine association constants for high-affinity ligands journal, June 2006

The use of differential scanning fluorimetry to detect ligand interactions that promote protein stability journal, September 2007

Morpholino Antisense Oligomers: Design, Preparation, and Properties journal, June 1997

Metabolomics of Mycobacterium tuberculosis Reveals Compartmentalized Co-Catabolism of Carbon Substrates journal, October 2010

Lipoamide Channel-Binding Sulfonamides Selectively Inhibit Mycobacterial Lipoamide Dehydrogenase journal, November 2013

Synthesis of 1,3-Diamines Through Rhodium-Catalyzed CH Insertion journal, March 2009

Synthesis and Aminoacyl-tRNA Synthetase Inhibitory Activity of Prolyl Adenylate Analogs journal, September 1996

Enhancing the Stability and Biological Functionalities of Quantum Dots via Compact Multifunctional Ligands journal, November 2007

2‘- C -Methyl Analogues of Selective Adenosine Receptor Agonists: Synthesis and Binding Studies † journal, May 1998

Phaser crystallographic software journal, July 2007

PHENIX: a comprehensive Python-based system for macromolecular structure solution journal, January 2010

JLigand : a graphical tool for the CCP 4 template-restraint library journal, March 2012

Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays journal, December 1983

Targeting adenylate-forming enzymes with designed sulfonyladenosine inhibitors journal, April 2019

Active Essential Oils and Their Components in Use against Neglected Diseases and Arboviruses journal, February 2019

In Vitro and In Vivo Effectiveness of Carvacrol, Thymol and Linalool against Leishmania infantum journal, May 2019

Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents journal, November 2018

A single regulator NrtR controls bacterial NAD+ homeostasis via its acetylation journal, October 2019

Targeting protein biotinylation enhances tuberculosis chemotherapy journal, April 2018

Synthesis of Cyclic and Acyclic Nucleoside Phosphonates and Sulfonamides Derived from 6-(Thiophen-2-yl)-7-fluoro-7-deazapurine: Synthesis of Cyclic and Acyclic Nucleoside Phosphonates and Sulfonamides Derived from 6-(Thiophen-2-yl)-7-fluoro-7-deazapurine journal, May 2019

Trypanosoma brucei Inhibition by Essential Oils from Medicinal and Aromatic Plants Traditionally Used in Cameroon (Azadirachta indica, Aframomum melegueta, Aframomum daniellii, Clausena anisata, Dichrostachys cinerea and Echinops giganteus) journal, July 2017

Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents collection, January 2018

Targeting adenylate-forming enzymes with designed sulfonyladenosine inhibitors journal, April 2019

Targeting protein biotinylation enhances tuberculosis chemotherapy journal, April 2018

Active Essential Oils and Their Components in Use against Neglected Diseases and Arboviruses journal, February 2019

Advanced Resistance Studies Identify Two Discrete Mechanisms in Staphylococcus aureus to Overcome Antibacterial Compounds that Target Biotin Protein Ligase journal, April 2020

Trypanosoma brucei Inhibition by Essential Oils from Medicinal and Aromatic Plants Traditionally Used in Cameroon (Azadirachta indica, Aframomum melegueta, Aframomum daniellii, Clausena anisata, Dichrostachys cinerea and Echinops giganteus) journal, July 2017

Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents journal, November 2018

A new evolutionary scenario for the Mycobacterium tuberculosis complex
journal, March 2002

From Multidrug- to Extensively Drug-Resistant Tuberculosis: Upward Trends as Seen from a 15-Year Nationwide Study
journal, May 2013

Mycobacterial outer membrane is a lipid bilayer and the inner membrane is unusually rich in diacyl phosphatidylinositol dimannosides
journal, March 2014

The Envelope of Mycobacteria
journal, June 1995

Mycolic acids: structure, biosynthesis and physiological functions
journal, July 1998

Towards understanding the functional diversity of cell wall mycolic acids of Mycobacterium tuberculosis
journal, October 2012

The dimycocerosate ester polyketide virulence factors of mycobacteria
journal, September 2005

Long-chain multiple methyl-branched fatty acid-containing lipids of Mycobacterium tuberculosis: Biosynthesis, transport, regulation and biological activities
journal, March 2007

Iron, mycobacteria and tuberculosis
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
journal, January 2005

Biochemical and Structural Characterization of an Essential Acyl Coenzyme A Carboxylase from Mycobacterium tuberculosis
journal, January 2006

ACCase 6 is the essential acetyl-CoA carboxylase involved in fatty acid and mycolic acid biosynthesis in mycobacteria
journal, August 2009

Ligand Specificity of Group I Biotin Protein Ligase of Mycobacterium tuberculosis
journal, May 2008

Bisubstrate Adenylation Inhibitors of Biotin Protein Ligase from Mycobacterium tuberculosis
journal, November 2011

Structure Guided Design of Biotin Protein Ligase Inhibitors for Antibiotic Discovery
journal, December 2013

Bisubstrate Inhibitors of Biotin Protein Ligase in Mycobacterium tuberculosis Resistant to Cyclonucleoside Formation
journal, October 2013

The Biotin Repressor: Modulation of Allostery by Corepressor Analogs
journal, April 2004

β-Keto and β-hydroxyphosphonate analogs of biotin-5′-AMP are inhibitors of holocarboxylase synthetase
journal, December 2014

Selective inhibition of Biotin Protein Ligase from Staphylococcus aureus
journal, May 2012

Optimising in situ click chemistry: the screening and identification of biotin protein ligase inhibitors
journal, January 2013

Heterocyclic acyl-phosphate bioisostere-based inhibitors of Staphylococcus aureus biotin protein ligase
journal, October 2014

Biotin Analogues with Antibacterial Activity Are Potent Inhibitors of Biotin Protein Ligase
journal, May 2012

Active site conformational changes upon reaction intermediate biotinyl-5'-AMP binding in biotin protein ligase from Mycobacterium tuberculosis: M. tuberculosis BPL
journal, April 2014

Synthesis of carbocyclic aminonucleosides
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
journal, May 2012

.pi.-Allylpalladium Formation from Allylic Amines via N,N-Ditosylimides and N-Tosylamides: Efficient Synthesis of the Antiviral Agent Carbovir
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
journal, August 2008

Preparation of Carbocyclic S -Adenosylazamethionine Accompanied by a Practical Synthesis of (−)-Aristeromycin
journal, May 2004

Antitubercular Nucleosides That Inhibit Siderophore Biosynthesis: SAR of the Glycosyl Domain
journal, December 2006

Highly Stereoselective Synthesis of Aristeromycin through Dihydroxylation of 4-Aryl-1-azido-2-cyclopentenes
journal, February 2004

A new type of silyl protecting groups in nucleoside chemistry
journal, January 1978

Synthesis of 2′-([1,2,3]Triazol-1-yl)-2′-deoxyadenosines
journal, April 2008

A critical electrostatic interaction mediates inhibitor recognition by human asparagine synthetase
journal, September 2009

Aqueous trifluoroacetic acid—an efficient reagent for exclusively cleaving the 5′-end of 3′,5′-TIPDS protected ribonucleosides
journal, December 2000

CHEMICAL SYNTHESIS OF THE NOVEL CA ²⁺ MESSENGER NAADP
journal, April 2005

Deoxyribosyl analogues of methionyl and isoleucyl sulfamate adenylates as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases
journal, July 2005

Über neue organische Phosphorverbindungen III. Phosphinmethylenderivate und Phosphinimine
journal, January 1919

Sixty years of staudinger reaction
journal, January 1981

Efficient general method for sulfamoylation of a hydroxyl group
journal, September 2000

Fluorinated nucleosides
journal, July 2000

Recent advances in the synthesis of fluorinated nucleosides
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
journal, January 2008

Improved Protocol for the Synthesis of Flexibly Protected Morpholino Monomers from Unprotected Ribonucleosides
journal, November 2012

A Non-Enzymatic, DNA Template-Directed Morpholino Primer Extension Approach
journal, February 2010

New oligonucleotide analogues based on morpholine subunits joined by oxalyl diamide tether
journal, June 2007

Conformational analysis in carbohydrate chemistry. I. Conformational free energies. The conformations and α : β ratios of aldopyranoses in aqueous solution
journal, January 1968

Novel substrate of adenosine deaminase
journal, April 1971

An Isothermal Titration Calorimeter
journal, September 1968

Some Binding-Related Drug Properties are Dependent on Thermodynamic Signature: Optimization of Drug Candidates
journal, February 2011

Isothermal titration calorimetry to determine association constants for high-affinity ligands
journal, June 2006

The use of differential scanning fluorimetry to detect ligand interactions that promote protein stability
journal, September 2007

Morpholino Antisense Oligomers: Design, Preparation, and Properties
journal, June 1997

Metabolomics of Mycobacterium tuberculosis Reveals Compartmentalized Co-Catabolism of Carbon Substrates
journal, October 2010

Lipoamide Channel-Binding Sulfonamides Selectively Inhibit Mycobacterial Lipoamide Dehydrogenase
journal, November 2013

Synthesis of 1,3-Diamines Through Rhodium-Catalyzed CH Insertion
journal, March 2009

Synthesis and Aminoacyl-tRNA Synthetase Inhibitory Activity of Prolyl Adenylate Analogs
journal, September 1996

Enhancing the Stability and Biological Functionalities of Quantum Dots via Compact Multifunctional Ligands
journal, November 2007

2‘- C -Methyl Analogues of Selective Adenosine Receptor Agonists: Synthesis and Binding Studies ^†
journal, May 1998

Phaser crystallographic software
journal, July 2007

PHENIX: a comprehensive Python-based system for macromolecular structure solution
journal, January 2010

JLigand : a graphical tool for the CCP 4 template-restraint library
journal, March 2012

Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays
journal, December 1983

Targeting adenylate-forming enzymes with designed sulfonyladenosine inhibitors
journal, April 2019

Active Essential Oils and Their Components in Use against Neglected Diseases and Arboviruses
journal, February 2019

In Vitro and In Vivo Effectiveness of Carvacrol, Thymol and Linalool against Leishmania infantum
journal, May 2019

Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents
journal, November 2018

A single regulator NrtR controls bacterial NAD+ homeostasis via its acetylation
journal, October 2019

Targeting protein biotinylation enhances tuberculosis chemotherapy
journal, April 2018

Synthesis of Cyclic and Acyclic Nucleoside Phosphonates and Sulfonamides Derived from 6-(Thiophen-2-yl)-7-fluoro-7-deazapurine: Synthesis of Cyclic and Acyclic Nucleoside Phosphonates and Sulfonamides Derived from 6-(Thiophen-2-yl)-7-fluoro-7-deazapurine
journal, May 2019

Trypanosoma brucei Inhibition by Essential Oils from Medicinal and Aromatic Plants Traditionally Used in Cameroon (Azadirachta indica, Aframomum melegueta, Aframomum daniellii, Clausena anisata, Dichrostachys cinerea and Echinops giganteus)
journal, July 2017

Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents
collection, January 2018

Targeting adenylate-forming enzymes with designed sulfonyladenosine inhibitors
journal, April 2019

Targeting protein biotinylation enhances tuberculosis chemotherapy
journal, April 2018

Active Essential Oils and Their Components in Use against Neglected Diseases and Arboviruses
journal, February 2019

Advanced Resistance Studies Identify Two Discrete Mechanisms in Staphylococcus aureus to Overcome Antibacterial Compounds that Target Biotin Protein Ligase
journal, April 2020

Trypanosoma brucei Inhibition by Essential Oils from Medicinal and Aromatic Plants Traditionally Used in Cameroon (Azadirachta indica, Aframomum melegueta, Aframomum daniellii, Clausena anisata, Dichrostachys cinerea and Echinops giganteus)
journal, July 2017

Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents
journal, November 2018

In Vitro and In Vivo Effectiveness of Carvacrol, Thymol and Linalool against Leishmania infantum
journal, May 2019