Document Detail

New nucleoside-5'-alkylphosphonophosphates and related compounds containing 2'-deoxycytidine, thymidine and adenosine as nucleoside component. Syntheses and their effects on tumor cell growth in vitro.
MedLine Citation:
PMID:  9219347     Owner:  NLM     Status:  MEDLINE    
Recent studies have shown that phosphono analogs of cytidine-5'-diphosphate diacylglycerol (CDP-DAG) possessing a structurally modified lipid moiety exhibit antiproliferative activity in vitro. As an extension of our previous work we tried to elucidate whether the presence of the cytidine component is necessary for cytostatic activity. In this context we have synthesized similarly structured nucleoside-phospholipid conjugates containing nucleoside components other than cytidine, which also do not exhibit cytostatic properties as such. The compounds include 5'-alkyldiphosphates and 5'-alkylphosphonophosphates of 2'-deoxycytidine, thymidine and adenosine with different alkyl chain length as well as selected 3-hexadecyl-2-chloro-2-deoxyglycero-(1)-diphosphates and -phosphonophosphates of these nucleosides. The chemical structures of the newly synthesized nucleoside-phospholipid conjugates were confirmed by fast atom bombardment (FAB) and electrospray ionization (ESI) mass spectrometry. It was found that these compounds also inhibit the cell growth of different human cell lines, i.e. the presence of the cytidine component is not a necessary prerequisite for the antiproliferative activity of these nucleoside-phospholipid conjugates.
H Brachwitz; Y Thomas; J Bergmann; P Langen; W E Berdel
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Chemistry and physics of lipids     Volume:  87     ISSN:  0009-3084     ISO Abbreviation:  Chem. Phys. Lipids     Publication Date:  1997 May 
Date Detail:
Created Date:  1997-08-06     Completed Date:  1997-08-06     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0067206     Medline TA:  Chem Phys Lipids     Country:  IRELAND    
Other Details:
Languages:  eng     Pagination:  31-9     Citation Subset:  IM    
Max-Delbrück-Centrum für Molekulare Medizin, Berlin, Germany.
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MeSH Terms
Adenosine / analysis
Antineoplastic Agents / chemical synthesis,  chemistry,  pharmacology*
Breast Neoplasms
Cell Division / drug effects*
Chromatography, Thin Layer
Deoxycytidine / analysis
Mass Spectrometry
Molecular Structure
Nucleotides / chemical synthesis,  chemistry,  pharmacology*
Organophosphorus Compounds / chemical synthesis,  chemistry,  pharmacology*
Phospholipids / chemical synthesis,  pharmacology*
Thymidine / analysis
Tumor Cells, Cultured
Reg. No./Substance:
0/Antineoplastic Agents; 0/Nucleotides; 0/Organophosphorus Compounds; 0/Phospholipids; 50-89-5/Thymidine; 58-61-7/Adenosine; 951-77-9/Deoxycytidine

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