Document Detail

Synthesis and evaluation of fatty acyl ester derivatives of cytarabine as anti-leukemia agents.
MedLine Citation:
PMID:  20692740     Owner:  NLM     Status:  MEDLINE    
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.
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.
Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, 41 Lower College Road, Kingston, RI 02881, USA.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Antimetabolites, Antineoplastic / chemistry*,  pharmacology*
Cell Proliferation / drug effects
Cytarabine / analogs & derivatives*,  pharmacology*
Esters / chemistry,  pharmacology
Fatty Acids / chemistry,  pharmacology
Leukemia / drug therapy*
Prodrugs / chemistry*,  pharmacology*
Tumor Cells, Cultured
Reg. No./Substance:
0/Antimetabolites, Antineoplastic; 0/Esters; 0/Fatty Acids; 0/Prodrugs; 147-94-4/Cytarabine

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

Previous Document:  Synthesis, characterization, interaction with DNA and cytotoxicity in vitro of novel pyridine comple...
Next Document:  Synthesis and anticancer activity of 5-(3-indolyl)-1,3,4-thiadiazoles.