Document Detail


Synthesis and evaluation of fatty acyl ester derivatives of cytarabine as anti-leukemia agents.
MedLine Citation:
PMID:  20692740     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Bhupender S Chhikara; Deendayal Mandal; Keykavous Parang
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2010-07-21
Journal Detail:
Title:  European journal of medicinal chemistry     Volume:  45     ISSN:  1768-3254     ISO Abbreviation:  Eur J Med Chem     Publication Date:  2010 Oct 
Date Detail:
Created Date:  2010-08-30     Completed Date:  2010-12-28     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0420510     Medline TA:  Eur J Med Chem     Country:  France    
Other Details:
Languages:  eng     Pagination:  4601-8     Citation Subset:  IM    
Copyright Information:
Copyright (c) 2010 Elsevier Masson SAS. All rights reserved.
Affiliation:
Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, 41 Lower College Road, Kingston, RI 02881, USA.
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MeSH Terms
Descriptor/Qualifier:
Antimetabolites, Antineoplastic / 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:
0/Antimetabolites, Antineoplastic; 0/Esters; 0/Fatty Acids; 0/Prodrugs; 147-94-4/Cytarabine

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