Document Detail

Synthesis and evaluation of anti-tumor activities of N4 fatty acyl amino acid derivatives of 1-beta-arabinofuranosylcytosine.
MedLine Citation:
PMID:  19321234     Owner:  NLM     Status:  MEDLINE    
1-Beta-D-arabinofuranosylcytosine (Ara-C, Cytarabine) is one of the drugs used for acute nonlymphocytic leukemia (ANLL). However, the bioavailability of Ara-C is relatively low due to its low lipophilicity. In order to improve the lipophilicity and bioavailability of Ara-C, a series of N(4) derivatives of Ara-C, i.e., (fatty acid)-(amino acid)-Ara-C analogues, were prepared. The 15 derivatives synthesized were characterized by their melting points, optical rotations and partition coefficients. It was found that the Ara-C derivatives synthesized in this study were more lipophilic than Ara-C as determined by their partition coefficients. Their in vitro cytotoxicity and in vivo anti-tumor activity were determined and compared with that of Ara-C. It was found that the derivatives were more active than Ara-C in Hela cells, but not in HL-60 cells. The in vivo results showed that some of the derivatives were more effective than Ara-C in mice bearing S(180) tumor while others showed a decreased activity in comparison with Ara-C.
Boyang Liu; Chunying Cui; Wei Duan; Ming Zhao; Shiqi Peng; Lili Wang; Hu Liu; Guohui Cui
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2009-03-06
Journal Detail:
Title:  European journal of medicinal chemistry     Volume:  44     ISSN:  1768-3254     ISO Abbreviation:  Eur J Med Chem     Publication Date:  2009 Sep 
Date Detail:
Created Date:  2009-07-20     Completed Date:  2009-10-14     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0420510     Medline TA:  Eur J Med Chem     Country:  France    
Other Details:
Languages:  eng     Pagination:  3596-600     Citation Subset:  IM    
School of Chemical Biology and Pharmaceutical Sciences, Capital Medical University, Beijing 100069, China.
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MeSH Terms
Antimetabolites, Antineoplastic / chemical synthesis,  chemistry*,  therapeutic use*,  toxicity
Cytarabine / analogs & derivatives*,  chemical synthesis,  therapeutic use*,  toxicity
Drug Screening Assays, Antitumor
HL-60 Cells
Hela Cells
Lipids / chemistry
Sarcoma 180 / drug therapy
Reg. No./Substance:
0/Antimetabolites, Antineoplastic; 0/Lipids; 147-94-4/Cytarabine

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