Synthesis and biological evaluation of two glycerolipidic prodrugs of didanosine for direct lymphatic delivery against HIV

被引：30
|
作者：
Lalanne, Muriel
Paci, Angelo
Andrieux, Karine
Dereuddre-Bosquet, Nathalie
Clayette, Pascal
Deroussent, Alain
Re, Micheline
Vassal, Gilles
Couvreur, Patrick
Desmaele, Didier [1 ]
机构：
[1] Univ Paris Sud, CNRS, UMR 8076, IFR 141, F-92296 Chatenay Malabry, France
[2] Univ Paris Sud, UMR 8612, CNRS, IFR 141, F-92296 Chatenay Malabry, France
[3] Univ Paris Sud, UPRES, EA 3535, IGR, F-94805 Villejuif, France
[4] CEA, SPI, BIO, Lab Neurovirol,DSV,DRM, F-92265 Fontenay Aux Roses, France
[5] IGR, IFR54, Serv Commun Spectrometrie Masse, F-94805 Villejuif, France
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2007年 / 17卷 / 08期
关键词：
anti-HIV nucleoside; enzyme inhibitors; prodrugs; lipid-nucleoside conjugate; bioavailability;
D O I：
10.1016/j.bmcl.2007.01.062
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Novel glycerolipidic prodrugs of didanosine and didanosine monophosphate designed to by-pass the hepatic first pass metabolism were synthesized and tested for their cytotoxicity and anti-HIV-1 activity. Formulation as liposomes of dipalmitoylphosphatidylcholine was elaborated. A simple quantitative HPLC-UV method was developed and validated, and ESI-MS was used for qualitative purpose. These two prodrugs exhibited promising biological activities against HIV-1 in in vitro infected cell culture. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2237 / 2240
页数：4
相关论文
共 50 条
  • [1] Liposomal formulation of a glycerolipidic prodrug for lymphatic delivery of didanosine via oral route
    Lalanne, M.
    Andrieux, K.
    Paci, A.
    Besnard, M.
    Re, M.
    Bourgaux, C.
    Ollivon, M.
    Desmaele, D.
    Couvreur, P.
    [J]. INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2007, 344 (1-2) : 62 - 70
  • [2] Synthesis and in vitro anti-HIV activities of didanosine prodrugs
    Sriram, Dhrmarajan
    Yogeeswari, Perumal
    Babu, Nagell Raveendra
    Kurre, Purna Nagashree
    [J]. JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2007, 22 (01) : 51 - 55
  • [3] Synthesis and evaluation of 5' alkyl ester prodrugs of zidovudine for directed lymphatic delivery
    Bibby, DC
    Charman, WN
    Charman, SA
    Iskander, MN
    Porter, CJH
    [J]. INTERNATIONAL JOURNAL OF PHARMACEUTICS, 1996, 144 (01) : 61 - 70
  • [4] SYNTHESIS AND BIOLOGICAL EVALUATION OF PRODRUGS OF ZIDOVUDINE
    AGGARWAL, SK
    GOGU, SR
    RANGAN, SRS
    AGRAWAL, KC
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (05) : 1505 - 1510
  • [5] Synthesis and evaluation of esmolol prodrugs for transdermal delivery
    Bijaya, Ghosh
    Kaushal, Dave
    Sonal, Dubey
    Pallavi, K.
    [J]. DRUG DELIVERY, 2010, 17 (07) : 532 - 540
  • [6] SYNTHESIS AND BIOLOGICAL EVALUATION OF A SERIES OF PRODRUGS OF ZIDOVUDINE
    AGGARWAL, SK
    GOGU, SR
    RANGAN, SRS
    AGRAWAL, KC
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 199 : 18 - MEDI
  • [7] Synthesis and biological evaluation of pyrimidine nucleoside monophosphate prodrugs targeted against influenza virus
    Meneghesso, Silvia
    Vanderlinden, Evelien
    Stevaert, Annelies
    McGuigan, Christopher
    Balzarini, Jan
    Naesens, Lieve
    [J]. ANTIVIRAL RESEARCH, 2012, 94 (01) : 35 - 43
  • [8] Synthesis and evaluation of ketorolac ester prodrugs for transdermal delivery
    Doh, HJ
    Cho, WJ
    Yong, CS
    Choi, HG
    Kim, JS
    Lee, CH
    Kim, DD
    [J]. JOURNAL OF PHARMACEUTICAL SCIENCES, 2003, 92 (05) : 1008 - 1017
  • [9] Synthesis, Characterization, and Biological Evaluation of Novel Diclofenac Prodrugs
    Bandgar, Babasaheb P.
    Sarangdhar, Rajendra Janardan
    Ahamed, Fakrudeen Ali
    Viswakarma, Santosh
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (05) : 1202 - 1210
  • [10] Synthesis and Biological Evaluation of Orally Active Prodrugs of Indomethacin
    Bandgar, Babasaheb P.
    Sarangdhar, Rajendra Janardan
    Viswakarma, Santosh
    Ahamed, Fakrudeen Ali
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (05) : 1191 - 1201
12345