| Synthesis, NMR characterization and in vitro antitumor evaluation of new aminophosphonic acid diesters. | |
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MedLine Citation:
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PMID: 19361895 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The synthesis of three novel alpha-aminophosphonic acid diesters N,N-dimethyl-[N'-methyl(diethoxyphosphonyl)-(2-furyl)]-1,3-diaminopropane, p-[N-methyl(diethoxyphosphonyl)-(2-furyl)]toluidine and p-[N-methyl(diethoxyphosphonyl)-(4-dimethylaminophenyl)]toluidine through an addition of diethyl phosphite to N,N-dimethyl-N'-furfurylidene-1,3-diaminopropane, N-furfurylidene-p-toluidine and N-(4-dimethylaminobenzylidene)-p-toluidine, respectively, is reported. The alpha-aminophosphonates have been characterized by elemental analysis, IR and NMR ((1)H, (13)C and (31)P) spectra. The compounds were tested for antiproliferative effects against 4 human leukemic cell lines, namely LAMA-84, K-562 (chronic myeloid leukemias), HL-60 (acute promyelocyte leukemia) and HL-60/Dox (multi-drug-resistant sub-line, characterized by overexpression of MRP-1 (ABC-C1)) and were found to exert concentration-dependent cytotoxic effects. A representative aminophosphonate compound was shown to induce oligonucleosomal DNA fragmentation which implies that the induction of cell death through apoptosis plays an important role for its cytotoxicity mode of action. |
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Authors:
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I Kraicheva; A Bogomilova; I Tsacheva; G Momekov; K Troev |
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Publication Detail:
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Type: Journal Article Date: 2009-03-24 |
Journal Detail:
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Title: European journal of medicinal chemistry Volume: 44 ISSN: 1768-3254 ISO Abbreviation: Eur J Med Chem Publication Date: 2009 Aug |
Date Detail:
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Created Date: 2009-05-18 Completed Date: 2009-07-13 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0420510 Medline TA: Eur J Med Chem Country: France |
Other Details:
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Languages: eng Pagination: 3363-7 Citation Subset: IM |
Affiliation:
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Institute of Polymers, Bulgarian Academy of Sciences, Sofia, Bulgaria. kraicheva@yahoo.com |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Animals Antineoplastic Agents / chemical synthesis, chemistry*, pharmacology* Cell Line, Tumor Cell Survival / drug effects Drug Design* Drug Resistance, Multiple Drug Resistance, Neoplasm Gene Expression Regulation, Neoplastic / drug effects Humans Inhibitory Concentration 50 Magnetic Resonance Spectroscopy Multidrug Resistance-Associated Proteins / metabolism Phosphonic Acids / chemical synthesis, chemistry*, pharmacology* |
| Chemical | |
Reg. No./Substance:
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0/Antineoplastic Agents; 0/Multidrug Resistance-Associated Proteins; 0/Phosphonic Acids; 0/multidrug resistance-associated protein 1 |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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