Structure activity relationships of β-hydroxyphosphonate nucleoside analogues as cytosolic 5′-nucleotidase II potential inhibitors: Synthesis, in vitro evaluation and molecular modeling studies

被引：24

作者：

Meurillon, Maia ^{[1
]}

Marton, Zsuzsanna ^{[2
]}

Hospital, Audrey ^{[1
]}

Jordheim, Lars Petter ^{[3
]}

Bejaud, Jerome ^{[1
]}

Lionne, Corinne ^{[2
]}

Dumontet, Charles ^{[3
]}

Perigaud, Christian ^{[1
]}

Chaloin, Laurent ^{[2
]}

Peyrottes, Suzanne ^{[1
]}

机构：

[1] Univ Montpellier 2, UMR CNRS 5247 UM1 UM2, Inst Biomol Max Mousseron, F-34095 Montpellier 5, France

[2] Ctr Etud Agents Pathogenes & Biotechnol Sante CPB, UMR CNRS 5236 UM1 UM2, F-34293 Montpellier 5, France

[3] Univ Lyon 1, INSERM CNRS UMR U1052 5286, Ctr Rech Cancerol Lyon, Ctr Leon Berard, F-69000 Lyon, France

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2014年 / 77卷

关键词：

Nucleotides; Enzyme inhibitors; Phosphonate; Leukemia; CN-II; DYNAMICS; HEXOFURANOSE; DERIVATIVES; EXPRESSION; RESISTANCE; CONVERSION; MUTATIONS; SURVIVAL; NT5C2;

D O I：

10.1016/j.ejmech.2014.02.055

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The cytosolic 5'-nucleotidase II (cN-II) has been proposed as an attractive molecular target for the development of novel drugs circumventing resistance to cytotoxic nucleoside analogues currently used for treating leukemia and other malignant hemopathies. In the present work, synthesis of beta-hydroxyphosphonate nucleoside analogues incorporating modifications either on the sugar residue or the nucleobase, and their in vitro evaluation towards the purified enzyme were carried out in order to determine their potency towards the inhibition of cN-II. In addition to the biochemical investigations, molecular modeling studies revealed important structural features for binding affinities towards the target enzyme. (C) 2014 Elsevier Masson SAS. All rights reserved.

引用

页码：18 / 37

页数：20

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