The potential of carbocyclic nucleosides for the treatment of AIDS: synthesis of some diphosphorylphosphonates possessing potent activity against HIV-coded reverse transcriptase

Coe, Diane M.; Roberts, Stanley M.; Storer, Richard

doi:10.1039/p19920002695

Cited by 45 publications

(23 citation statements)

References 24 publications

(8 reference statements)

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“…In particular, it has been found that the D isomer Ib displays a 50-fold higher affinity to HIV RT than the L isomer III [7]. It has been also shown that the L isomer of 2'-deoxy-3'-thio-5-fluorocytosine 5'-triphosphate is a better The results obtained in this work are in agreement with our data on modified dNTPs with conformationally rigid flattened glycones [3,5,7] (for more references see [6]) and support the hypothesis that such compounds fit the structure of the RT active center modelling the transition state of dNTPs in the RT-dNTP complex [ 151. The results presented here, as well as our earlier data [3,5,7,15, indicate that the absence of the 3' hydroxyl does not inactivate the nucleotide substrate.…”

Section: Discussionsupporting

confidence: 83%

Selectivity of DNA polymerases toward α and β nucleotide substrates of d and l series

et al. 1994

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Abslraet The substrate properties of four carbocyclic D and L nucleoside 5'-triphosphate analogs toward HIV and AMV reverse transcriptases and terminal deoxynucleotidyl transferase were evaluated. The compounds of the D-B and L-B series were found to be terminating substrates for these enzymes, while the derivatives of the o-d and ~-a series were recognized only by terminal deoxynucleotidyl transferase, suggesting that for the template-independent enzyme the mutual orientation of the two fragments is of no significance. A hypothesis for binding of nucleotides to the DNA polymerase active center was proposed.

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Section: Discussionsupporting

confidence: 83%

Selectivity of DNA polymerases toward α and β nucleotide substrates of d and l series

et al. 1994

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“…17) were reported to be potent inhibitors of HIV reverse transcriptase with a comparable activity. 83 The following studies showed that the compound 54 (IC 50 = 0.52 μg/mL, Fig. 17.)…”

Section: Cnps With Fluorine Atom(s) At Phosphonate α-Carbonmentioning

confidence: 92%

Medicinal Chemistry of Fluorinated Cyclic and Acyclic Nucleoside Phosphonates

Baszczyňski

Janeba

2013

Medicinal Research Reviews

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The fluorine atom plays an important role in medicinal chemistry because fluorine substitution has a strong impact on the physical, chemical, and biological properties of bioactive compounds. Such fluorine modifications have also been extensively studied among the pharmaceutically important class of nucleoside phosphonates, nucleotide analogues in which the phosphate group is replaced by the enzymatically and chemically stable phosphonate moiety. The fluorinated nucleoside phosphonates abound with antiviral, antiparasitic, and anticancer properties because they are able to act as inhibitors of important enzymes of nucleoside/nucleotide metabolism. In this paper, we review the biological properties of cyclic and acyclic nucleoside phosphonates modified by the attachment of one or more fluorine atoms to various parts of the molecule, namely to nucleobases, alkylphosphonate groups, cyclic or acyclic linkers, or to prodrug moieties.

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“…1), using amino acids as chiral templates (Balayiannis et al, 2000;Balayiannis et al, personal data). These compounds, by sharing common structural features with the classical ddN (Phadtare and Zemlicka 1989;Coe et al, 1992) and the iso-ddN, are expected to show increased hydrolytic stability (Franchetti et al, 1994) and possibly exhibit anti-HIV activity.…”

Section: Introductionmentioning

confidence: 98%

Application of capillary electrophoresis in the analysis of novel synthetic dideoxynucleoside analogues with potential anti‐HIV activity

Balayiannis

Papaioannou

Karamanos

2001

Biomedical Chromatography

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The aim of this study was the development of a capillary electrophoretic method for the analysis of a series of novel synthetic dideoxynucleoside analogues with potential anti-HIV activity. These analogues consist of a tetrahydrofuranyl or a tetrahydropyranyl ring as the pseudosugar part and bear a hydroxyethyl side-chain and a nucleobase of the pyrimidine (eg thymine or uracil) or the purine (adenine) type with cis or trans configuration. Analysis of these derivatives was performed by capillary zone electrophoresis using 25 mM phosphate pH 3.00 and 4.00 as operating buffers for pyrimidine and purine analogues, respectively, and detection of separated species at 254 nm.

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The potential of carbocyclic nucleosides for the treatment of AIDS: synthesis of some diphosphorylphosphonates possessing potent activity against HIV-coded reverse transcriptase

Cited by 45 publications

References 24 publications

Selectivity of DNA polymerases toward α and β nucleotide substrates of d and l series

Selectivity of DNA polymerases toward α and β nucleotide substrates of d and l series

Medicinal Chemistry of Fluorinated Cyclic and Acyclic Nucleoside Phosphonates

Application of capillary electrophoresis in the analysis of novel synthetic dideoxynucleoside analogues with potential anti‐HIV activity

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