| Comparison of the antiviral activity of hydrophobic amino acid phosphoramidate monoesters of 2'3'-dideoxyadenosine (DDA) and 3'-azido-3'-deoxythymidine (AZT). | |
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MedLine Citation:
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PMID: 11554546 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A series of hydrophobic, water soluble and non-toxic amino acid phosphoramidate monoesters of dideoxyadenosine (ddA) and 3'-azido-3'-deoxythymidine were shown to inhibit the replication of HIV-1 in human peripheral blood mononuclear cells (PBMC) from two donors. The tryptophan methyl ester phosphoramidates of AZT and ddA were equally potent (EC50S = 0.3-0.4 microM), while the phenyl methyl ester of ddA was 40- to 100- fold more potent than the AZT derivatives. The alaninyl methyl ester of AZT was found to be 70- fold more potent than the ddA derivative. The methyl amide derivatives were found to be 5-20 fold less active than the methyl esters for the ddA series, while for AZT the derivatives were found to be of similar potency or 60- to 166- fold more potent than the methylesters. |
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Authors:
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S L Chang; G Griesgraber; C R Wagner |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Nucleosides, nucleotides & nucleic acids Volume: 20 ISSN: 1525-7770 ISO Abbreviation: Nucleosides Nucleotides Nucleic Acids Publication Date: 2001 Aug |
Date Detail:
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Created Date: 2001-09-13 Completed Date: 2002-02-19 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 100892832 Medline TA: Nucleosides Nucleotides Nucleic Acids Country: United States |
Other Details:
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Languages: eng Pagination: 1571-82 Citation Subset: IM |
Affiliation:
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Department of Medicinal Chemistry, University of Minnesota, Minneapolis 55455, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Amides
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chemistry* Amino Acids / chemical synthesis, chemistry, pharmacology Antiviral Agents / chemical synthesis*, chemistry, pharmacology Cells, Cultured Chromatography, Thin Layer Dideoxyadenosine / analogs & derivatives*, chemistry, pharmacology* HIV-1 / drug effects* Humans Hydrophobicity Magnetic Resonance Spectroscopy Phosphoric Acids / chemistry* Spectrometry, Mass, Fast Atom Bombardment Zidovudine / analogs & derivatives*, chemistry, pharmacology* |
| Chemical | |
Reg. No./Substance:
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0/Amides; 0/Amino Acids; 0/Antiviral Agents; 0/Phosphoric Acids; 2817-45-0/phosphoramidic acid; 30516-87-1/Zidovudine; 4097-22-7/Dideoxyadenosine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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