Literature DB >> 19382883

Prodrug approaches to improving the oral absorption of antiviral nucleotide analogues.

Larryn W Peterson1, Charles E McKenna.   

Abstract

Nucleotide analogues have been well accepted as therapeutic agents active against a number of viruses. However, their use as antiviral agents is limited by the need for phosphorylation by endogenous enzymes, and if the analogue is orally administered, by low bioavailability due to the presence of an pan class="Disease">ionizable diacid groupn>. To circumvent these limitations, a number of prodrug appropan class="Gene">aches have been proposed. The ideal prodrug achieves delivery of a parent drug by attachment of a non-toxic moiety that is stable during transport and delivery, but is readily cleaved to release the parent drug once at the target. Here, a brief overview of several promising prodrug strategies currently under development is given.

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Year:  2009        PMID: 19382883      PMCID: PMC5117106          DOI: 10.1517/17425240902824808

Source DB:  PubMed          Journal:  Expert Opin Drug Deliv        ISSN: 1742-5247            Impact factor:   6.648


  83 in total

1.  Synthesis and evaluation of novel amidate prodrugs of PMEA and PMPA.

Authors:  C Ballatore; C McGuigan; E De Clercq; J Balzarini
Journal:  Bioorg Med Chem Lett       Date:  2001-04-23       Impact factor: 2.823

Review 2.  Targeted prodrug design to optimize drug delivery.

Authors:  H K Han; G L Amidon
Journal:  AAPS PharmSci       Date:  2000

Review 3.  Prodrugs of biologically active phosphate esters.

Authors:  Carsten Schultz
Journal:  Bioorg Med Chem       Date:  2003-03-20       Impact factor: 3.641

4.  cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.

Authors:  C Meier; T Knispel; E De Clercq; J Balzarini
Journal:  J Med Chem       Date:  1999-05-06       Impact factor: 7.446

5.  Phosphoramidate derivatives of d4T as inhibitors of HIV: the effect of amino acid variation.

Authors:  C McGuigan; H W Tsang; D Cahard; K Turner; S Velazquez; A Salgado; L Bidois; L Naesens; E De Clercq; J Balzarini
Journal:  Antiviral Res       Date:  1997-08       Impact factor: 5.970

6.  Novel cyclosal nucleotides with reduced inhibitory potency toward human butyrylcholinesterase.

Authors:  C Ducho; S Jessel; N Gisch; J Balzarini; C Meier
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2005       Impact factor: 1.381

7.  Synthesis and biological activity of aromatic amino acid phosphoramidates of 5-fluoro-2'-deoxyuridine and 1-beta-arabinofuranosylcytosine: evidence of phosphoramidase activity.

Authors:  T W Abraham; T I Kalman; E J McIntee; C R Wagner
Journal:  J Med Chem       Date:  1996-11-08       Impact factor: 7.446

8.  Application of phosphoramidate ProTide technology significantly improves antiviral potency of carbocyclic adenosine derivatives.

Authors:  Christopher McGuigan; Alshaimaa Hassan-Abdallah; Sheila Srinivasan; Yikang Wang; Adam Siddiqui; Susan M Daluge; Kristjan S Gudmundsson; Huiqiang Zhou; Ed W McLean; Jennifer P Peckham; Thimysta C Burnette; Harry Marr; Richard Hazen; Lynn D Condreay; Lance Johnson; Jan Balzarini
Journal:  J Med Chem       Date:  2006-11-30       Impact factor: 7.446

9.  Intracellular trapping of cycloSal-pronucleotides: modification of prodrugs with amino acid esters.

Authors:  Henning J Jessen; Jan Balzarini; Chris Meier
Journal:  J Med Chem       Date:  2008-10-01       Impact factor: 7.446

10.  Design, synthesis, and anti-HIV activity of 2',3'-didehydro-2',3'-dideoxyuridine (d4U), 2',3'-dideoxyuridine (ddU) phosphoramidate 'ProTide' derivatives.

Authors:  Youcef Mehellou; Christopher McGuigan; Andrea Brancale; Jan Balzarini
Journal:  Bioorg Med Chem Lett       Date:  2007-04-22       Impact factor: 2.823

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  19 in total

1.  Serine side chain-linked peptidomimetic conjugates of cyclic HPMPC and HPMPA: synthesis and interaction with hPEPT1.

Authors:  Larryn W Peterson; Monica Sala-Rabanal; Ivan S Krylov; Michaela Serpi; Boris A Kashemirov; Charles E McKenna
Journal:  Mol Pharm       Date:  2010-10-07       Impact factor: 4.939

2.  Chemoenzymatic syntheses and anti-HIV-1 activity of glucose-nucleoside conjugates as prodrugs.

Authors:  Tatiana Rodríguez-Pérez; Susana Fernández; Yogesh S Sanghvi; Mervi Detorio; Raymond F Schinazi; Vicente Gotor; Miguel Ferrero
Journal:  Bioconjug Chem       Date:  2010-11-15       Impact factor: 4.774

3.  Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: synthesis, stability, antiviral activity, and in vivo transport studies.

Authors:  Valeria M Zakharova; Michaela Serpi; Ivan S Krylov; Larryn W Peterson; Julie M Breitenbach; Katherine Z Borysko; John C Drach; Mindy Collins; John M Hilfinger; Boris A Kashemirov; Charles E McKenna
Journal:  J Med Chem       Date:  2011-08-03       Impact factor: 7.446

4.  Approaches to tyrosine-linked peptidomimetic prodrugs of (S)-HPMP-based acyclic nucleoside phosphonates.

Authors:  Valeria M Zakharova; Ivan S Krylov; Michaela Serpi; Boris A Kashemirov; Charles E McKenna
Journal:  Phosphorus Sulfur Silicon Relat Elem       Date:  2011

5.  Synthesis, transport and antiviral activity of Ala-Ser and Val-Ser prodrugs of cidofovir.

Authors:  Larryn W Peterson; Jae-Seung Kim; Paul Kijek; Stefanie Mitchell; John Hilfinger; Julie Breitenbach; Kathy Borysko; John C Drach; Boris A Kashemirov; Charles E McKenna
Journal:  Bioorg Med Chem Lett       Date:  2011-05-03       Impact factor: 2.823

6.  Structure of cyclic nucleoside phosphonate ester prodrugs: an inquiry.

Authors:  Ivan S Krylov; Valeria M Zakharova; Michaela Serpi; Ralf Haiges; Boris A Kashemirov; Charles E McKenna
Journal:  J Org Chem       Date:  2011-11-30       Impact factor: 4.354

7.  Synthesis of peptidomimetic conjugates of cyclic nucleoside phosphonates.

Authors:  Michaela Serpi; Ivan S Krylov; Valeria M Zakharova; Charles E McKenna
Journal:  Curr Protoc Nucleic Acid Chem       Date:  2010-12

8.  Evolution of an amino acid based prodrug approach: stay tuned.

Authors:  Ivan S Krylov; Boris A Kashemirov; John M Hilfinger; Charles E McKenna
Journal:  Mol Pharm       Date:  2013-01-22       Impact factor: 4.939

9.  Photoactivatable prodrug for simultaneous release of mertansine and CO along with a BODIPY derivative as a luminescent marker in mitochondria: a proof of concept for NIR image-guided cancer therapy.

Authors:  Rajeshwari Tiwari; Prashant S Shinde; Sreejesh Sreedharan; Anik Kumar Dey; Katherine A Vallis; Santosh B Mhaske; Sumit Kumar Pramanik; Amitava Das
Journal:  Chem Sci       Date:  2020-12-23       Impact factor: 9.825

10.  Sublingual nucleotides prolong run time to exhaustion in young physically active men.

Authors:  Sergej M Ostojic; Kemal Idrizovic; Marko D Stojanovic
Journal:  Nutrients       Date:  2013-11-21       Impact factor: 5.717

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