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Updated: Jul 1, 2026

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
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Nucleoside Triphosphates - From Synthesis to Biochemical Characterization

Published on: April 3, 2014

Nucleoside diphosphate prodrugs.

C Meier1, H J Jessen, J Balzarini

  • 1Organic Chemistry, Department of Chemistry, Faculty of Science, University of Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany. chris.meier@chemie.uni-hamburg.de

Nucleic Acids Symposium Series (2004)
|September 9, 2008
PubMed
Summary
This summary is machine-generated.

Researchers developed novel prodrugs for antiviral therapies, bypassing the need for kinase activation. These bis-(acyloxybenzyl)-masked nucleoside diphosphates (BAB-NDPs) offer controlled release of active drugs like AZT and d4T.

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Quantitative Structure-Activity Relationship, Activity Prediction, and Molecular Dynamics of Non-nucleotide Reverse Transcriptase Inhibitors

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Area of Science:

  • Medicinal Chemistry
  • Pharmacology
  • Biochemistry

Background:

  • Nucleoside analogs are crucial in antiviral and antitumor treatments.
  • Activation requires intracellular phosphorylation by kinases, a rate-limiting step.
  • Existing prodrug strategies primarily target nucleoside monophosphates.

Purpose of the Study:

  • To adapt the bis-(acyloxybenzyl) (BAB) masking strategy for nucleoside diphosphates (NDPs).
  • To synthesize and characterize BAB-masked NDPs of anti-HIV drugs AZT and d4T.
  • To evaluate the hydrolytic properties and drug release mechanisms of these novel NDP prodrugs.

Main Methods:

  • Chemical synthesis of bis-(acyloxybenzyl)-masked nucleoside diphosphates (BAB-NDPs).
  • Hydrolytic stability studies at physiological pH and in cellular extracts.
  • Assessment of selective cleavage and drug delivery kinetics.

Main Results:

  • Successful synthesis and isolation of BAB-NDPs derived from AZT and d4T.
  • Demonstrated tunable hydrolytic stability: stable at pH 7.4, labile in cellular environments.
  • Observed selective cleavage, releasing nucleoside diphosphates within 15 minutes without pyrophosphate degradation.

Conclusions:

  • The BAB-concept is effectively extended to nucleoside diphosphates.
  • These BAB-NDPs exhibit desirable stability and release profiles for prodrug applications.
  • This represents a significant advancement in developing efficient nucleoside diphosphate prodrugs.