Document Detail

Comparison of the antiviral activity of hydrophobic amino acid phosphoramidate monoesters of 2'3'-dideoxyadenosine (DDA) and 3'-azido-3'-deoxythymidine (AZT).
MedLine Citation:
PMID:  11554546     Owner:  NLM     Status:  MEDLINE    
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.
S L Chang; G Griesgraber; C R Wagner
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Nucleosides, nucleotides & nucleic acids     Volume:  20     ISSN:  1525-7770     ISO Abbreviation:  Nucleosides Nucleotides Nucleic Acids     Publication Date:  2001 Aug 
Date Detail:
Created Date:  2001-09-13     Completed Date:  2002-02-19     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  100892832     Medline TA:  Nucleosides Nucleotides Nucleic Acids     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1571-82     Citation Subset:  IM    
Department of Medicinal Chemistry, University of Minnesota, Minneapolis 55455, USA.
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MeSH Terms
Amides / 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*
Magnetic Resonance Spectroscopy
Phosphoric Acids / chemistry*
Spectrometry, Mass, Fast Atom Bombardment
Zidovudine / analogs & derivatives*,  chemistry,  pharmacology*
Reg. No./Substance:
0/Amides; 0/Amino Acids; 0/Antiviral Agents; 0/Phosphoric Acids; 2817-45-0/phosphoramidic acid; 30516-87-1/Zidovudine; 4097-22-7/Dideoxyadenosine

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