| Synthesis and evaluation of fatty acyl ester derivatives of cytarabine as anti-leukemia agents. | |
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MedLine Citation:
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PMID: 20692740 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Cytarabine is a chemotherapeutic agent predominately used for the treatment of acute myeloid leukemia and lymphoblastic leukemia. Cytarabine is a polar nucleoside, has a short plasma half-life, and its use is associated with severe side effects. Fatty acyl derivatives of cytarabine were synthesized with the expectation to improve cellular uptake and generate derivatives with a longer duration of action. Multi-step protection and deprotection reactions of hydroxyl and amino groups and conjugation with a fatty acid (i.e., myristic acid and 12-thioethyldodecanoic acid) afforded 5'-O-substituted, 2'-O-substituted, and 2',5'-disubstituted fatty acyl derivatives of cytarabine. 2',5'-Dimyristoyl derivative of cytarabine was found to inhibit the growth of CCRF-CEM cells by approximately 76% at concentration of 1 microM after 96 h incubation. |
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Authors:
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Bhupender S Chhikara; Deendayal Mandal; Keykavous Parang |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2010-07-21 |
Journal Detail:
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Title: European journal of medicinal chemistry Volume: 45 ISSN: 1768-3254 ISO Abbreviation: Eur J Med Chem Publication Date: 2010 Oct |
Date Detail:
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Created Date: 2010-08-30 Completed Date: 2010-12-28 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: 4601-8 Citation Subset: IM |
Copyright Information:
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Copyright (c) 2010 Elsevier Masson SAS. All rights reserved. |
Affiliation:
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Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, 41 Lower College Road, Kingston, RI 02881, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Antimetabolites, Antineoplastic
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chemistry*,
pharmacology* Cell Proliferation / drug effects Cytarabine / analogs & derivatives*, pharmacology* Esters / chemistry, pharmacology Fatty Acids / chemistry, pharmacology Humans Leukemia / drug therapy* Prodrugs / chemistry*, pharmacology* Tumor Cells, Cultured |
| Chemical | |
Reg. No./Substance:
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0/Antimetabolites, Antineoplastic; 0/Esters; 0/Fatty Acids; 0/Prodrugs; 147-94-4/Cytarabine |
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