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Literature DB >> 30655934

The ProTide Prodrug Technology: Where Next?

Ashwag S Alanazi¹, Edward James¹, Youcef Mehellou¹.

Abstract

The ProTide prodrug technology has proved very useful in the discovery of nucleotide therapeutics and has successfully led to two FDA-approved drugs. However, with the extensive application of this prodrug approach to nucleotides for nearly three decades, the intellectual property (IP) landscape is becoming congested and, to overcome this, new inventive applications of the ProTide prodrug technology are emerging.

Year: 2018 PMID： 30655934 PMCID： PMC6331162 DOI： 10.1021/acsmedchemlett.8b00586

Source DB: PubMed Journal: ACS Med Chem Lett ISSN： 1948-5875 Impact factor: 4.345

9 in total

1. Phosphotyrosine prodrugs: design, synthesis and anti-STAT3 activity of ISS-610 aryloxy triester phosphoramidate prodrugs.

Authors: Ageo Miccoli; Binar A Dhiani; Youcef Mehellou
Journal: Medchemcomm Date: 2018-11-07 Impact factor: 3.597

2. Phosphonamidate Prodrugs of a Butyrophilin Ligand Display Plasma Stability and Potent Vγ9 Vδ2 T Cell Stimulation.

Authors: Nicholas A Lentini; Benjamin J Foust; Chia-Hung Christine Hsiao; Andrew J Wiemer; David F Wiemer
Journal: J Med Chem Date: 2018-09-26 Impact factor: 7.446

Review 3. Approved Antiviral Drugs over the Past 50 Years.

Authors: Erik De Clercq; Guangdi Li
Journal: Clin Microbiol Rev Date: 2016-07 Impact factor: 26.132

4. Novel phosphoramidate prodrugs of N-acetyl-(D)-glucosamine with antidegenerative activity on bovine and human cartilage explants.

Authors: Michaela Serpi; Rita Bibbo; Stephanie Rat; Helen Roberts; Claire Hughes; Bruce Caterson; María José Alcaraz; Anna Torrent Gibert; Carlos Raul Alaez Verson; Christopher McGuigan
Journal: J Med Chem Date: 2012-05-11 Impact factor: 7.446

5. Kinase-independent phosphoramidate S1P₁ receptor agonist benzyl ether derivatives.

Authors: Edward James; Fabrizio Pertusati; Andrea Brancale; Chris McGuigan
Journal: Bioorg Med Chem Lett Date: 2017-02-09 Impact factor: 2.823

6. Fosmetpantotenate (RE-024), a phosphopantothenate replacement therapy for pantothenate kinase-associated neurodegeneration: Mechanism of action and efficacy in nonclinical models.

Authors: Daniel Elbaum; Maria G Beconi; Edith Monteagudo; Annalise Di Marco; Maria S Quinton; Kathryn A Lyons; Andrew Vaino; Steven Harper
Journal: PLoS One Date: 2018-03-09 Impact factor: 3.240

Review 7. The ProTide Prodrug Technology: From the Concept to the Clinic.

Authors: Youcef Mehellou; Hardeep S Rattan; Jan Balzarini
Journal: J Med Chem Date: 2017-08-24 Impact factor: 7.446

8. Synthesis and biological evaluation of phosphate prodrugs of 4-phospho-D-erythronohydroxamic acid, an inhibitor of 6-phosphogluconate dehydrogenase.

Authors: Gian Filippo Ruda; Vincent P Alibu; Christos Mitsos; Olivier Bidet; Marcel Kaiser; Reto Brun; Michael P Barrett; Ian H Gilbert
Journal: ChemMedChem Date: 2007-08 Impact factor: 3.466

9. Synthesis and Biological Evaluation of ( E)-4-Hydroxy-3-methylbut-2-enyl Phosphate (HMBP) Aryloxy Triester Phosphoramidate Prodrugs as Activators of Vγ9/Vδ2 T-Cell Immune Responses.

Authors: Martin S Davey; Roshni Malde; Rory C Mykura; Alfie T Baker; Taher E Taher; Cécile S Le Duff; Benjamin E Willcox; Youcef Mehellou
Journal: J Med Chem Date: 2018-02-23 Impact factor: 7.446

9 in total

10 in total

1. A Chemical Strategy for Intracellular Arming of an Endogenous Broad-Spectrum Antiviral Nucleotide.

Authors: Kellan T Passow; Haley S Caldwell; Kiet A Ngo; Jamie J Arnold; Nicole M Antczak; Anoop Narayanan; Joyce Jose; Shana J Sturla; Craig E Cameron; Alexander T Ciota; Daniel A Harki
Journal: J Med Chem Date: 2021-10-18 Impact factor: 7.446

2. A mild and concise synthesis of aryloxy phosphoramidate prodrug of alcohols via transesterification reaction.

Authors: Hanglu Ying; Jie Yao; Fan Wu; Yufen Zhao; Feng Ni
Journal: RSC Adv Date: 2022-04-29 Impact factor: 4.036

3. Tissue-Specific Proteomics Analysis of Anti-COVID-19 Nucleoside and Nucleotide Prodrug-Activating Enzymes Provides Insights into the Optimization of Prodrug Design and Pharmacotherapy Strategy.

Authors: Jiapeng Li; Shuhan Liu; Jian Shi; Xinwen Wang; Yanling Xue; Hao-Jie Zhu
Journal: ACS Pharmacol Transl Sci Date: 2021-04-01

The ProTide Prodrug Technology: Where Next?

1. Phosphotyrosine prodrugs: design, synthesis and anti-STAT3 activity of ISS-610 aryloxy triester phosphoramidate prodrugs.

2. Phosphonamidate Prodrugs of a Butyrophilin Ligand Display Plasma Stability and Potent Vγ9 Vδ2 T Cell Stimulation.

Review 3. Approved Antiviral Drugs over the Past 50 Years.

4. Novel phosphoramidate prodrugs of N-acetyl-(D)-glucosamine with antidegenerative activity on bovine and human cartilage explants.

5. Kinase-independent phosphoramidate S1P₁ receptor agonist benzyl ether derivatives.

6. Fosmetpantotenate (RE-024), a phosphopantothenate replacement therapy for pantothenate kinase-associated neurodegeneration: Mechanism of action and efficacy in nonclinical models.

Review 7. The ProTide Prodrug Technology: From the Concept to the Clinic.

8. Synthesis and biological evaluation of phosphate prodrugs of 4-phospho-D-erythronohydroxamic acid, an inhibitor of 6-phosphogluconate dehydrogenase.

9. Synthesis and Biological Evaluation of ( E)-4-Hydroxy-3-methylbut-2-enyl Phosphate (HMBP) Aryloxy Triester Phosphoramidate Prodrugs as Activators of Vγ9/Vδ2 T-Cell Immune Responses.

1. A Chemical Strategy for Intracellular Arming of an Endogenous Broad-Spectrum Antiviral Nucleotide.

2. A mild and concise synthesis of aryloxy phosphoramidate prodrug of alcohols via transesterification reaction.

3. Tissue-Specific Proteomics Analysis of Anti-COVID-19 Nucleoside and Nucleotide Prodrug-Activating Enzymes Provides Insights into the Optimization of Prodrug Design and Pharmacotherapy Strategy.

4. In vivo pharmacokinetic study of remdesivir dry powder for inhalation in hamsters.

5. Synthesis and Anti-Hepatitis B Activities of 3'-Fluoro-2'-Substituted Apionucleosides.

6. Nucleotide Analogues as Inhibitors of SARS-CoV-2 Polymerase.

7. Nucleotide Analogues as Inhibitors of SARS-CoV-2 Polymerase, a Key Drug Target for COVID-19.

8. Sofosbuvir terminated RNA is more resistant to SARS-CoV-2 proofreader than RNA terminated by Remdesivir.

9. A Simple and Effective "Elimination" Approach for Selective Cancer Therapy to Reveal the Role of H₂O₂.

10. Nucleotide analogues as inhibitors of SARS-CoV Polymerase.