阿糖腺苷一些新型磷酸盐和次膦酸盐衍生物的合成与评价。磷酸三酯作用机制的研究。
Synthesis and evaluation of some novel phosphate and phosphinate derivatives of araA. Studies on the mechanism of action of phosphate triesters.
作者信息
McGuigan C, Shackleton J M, Tollerfield S M, Riley P A
机构信息
Department of Chemistry, University College London, UK.
出版信息
Nucleic Acids Res. 1989 Dec 25;17(24):10171-7. doi: 10.1093/nar/17.24.10171.
Abstract
A number of novel phosphinate and phosphate triester derivatives of the anti-viral nucleoside analogue araA have been prepared. Spectroscopic and analytical data have been collected on both the reagents and the nucleotides. An in vitro assay indicated inhibition of DNA synthesis by mammalian cells, by each of the nucleotide derivatives, in the range 3-30 microM. Inhibition was reduced, but not abolished, for the phosphinates relative to the phosphates. These results are consistent with a mode of action involving release of the free nucleoside araA and the nucleotide araAMP.
摘要
已经制备了抗病毒核苷类似物阿糖腺苷（araA）的多种新型次膦酸酯和磷酸三酯衍生物。已收集了试剂和核苷酸的光谱及分析数据。体外试验表明，每种核苷酸衍生物在3 - 30微摩尔范围内均可抑制哺乳动物细胞的DNA合成。相对于磷酸盐，次膦酸酯的抑制作用有所降低，但并未消除。这些结果与涉及游离核苷阿糖腺苷和核苷酸阿糖腺苷一磷酸（araAMP）释放的作用模式一致。
相似文献
1
Synthesis and evaluation of some novel phosphate and phosphinate derivatives of araA. Studies on the mechanism of action of phosphate triesters.阿糖腺苷一些新型磷酸盐和次膦酸盐衍生物的合成与评价。磷酸三酯作用机制的研究。
Nucleic Acids Res. 1989 Dec 25;17(24):10171-7. doi: 10.1093/nar/17.24.10171.
2
Synthesis and biological evaluation of some phosphate triester derivatives of the anti-viral drug AraA.抗病毒药物阿糖腺苷（AraA）的一些磷酸三酯衍生物的合成及生物学评价
Nucleic Acids Res. 1989 Aug 11;17(15):6065-75. doi: 10.1093/nar/17.15.6065.
3
Synthesis and biological evaluation of some phosphate triester derivatives of the anti-cancer drug araC.抗癌药物阿糖胞苷的一些磷酸三酯衍生物的合成与生物学评价
Nucleic Acids Res. 1989 Sep 25;17(18):7195-201. doi: 10.1093/nar/17.18.7195.
4
Synthesis and biological evaluation of phosphate triester alkyl lysophospholipids (ALPs) as novel potential anti-neoplastic agents.
Anticancer Drug Des. 1994 Dec;9(6):539-48.
5
Synthesis and Preliminary Evaluation of an ASGPr-Targeted Polycationic -Cyclodextrin Carrier for Nucleosides and Nucleotides.一种用于核苷和核苷酸的ASGPr靶向聚阳离子-β-环糊精载体的合成与初步评价
Pharmaceutics. 2024 Feb 26;16(3):323. doi: 10.3390/pharmaceutics16030323.
6
The utilization of nucleotides by animal cells.动物细胞对核苷酸的利用。
Ann N Y Acad Sci. 1975 Aug 8;255:269-86. doi: 10.1111/j.1749-6632.1975.tb29235.x.
7
Synthesis and biological evaluation of substituted phosphate triester alkyl lyso phospholipids (ALPs) as novel potential anti-neoplastic agents.
FEBS Lett. 1995 Sep 25;372(2-3):259-63. doi: 10.1016/0014-5793(95)00959-d.
8
Disposition of 9-beta-D-arabinofuranosyl-2-fluoroadenine 5'-phosphate in mice and dogs.9-β-D-阿拉伯呋喃糖基-2-氟腺嘌呤5'-磷酸在小鼠和犬体内的处置情况。
Cancer Treat Rep. 1983 May;67(5):445-56.
9
Fluoride ion promoted deprotection and transesterification in nucleotide triesters.氟离子促进核苷酸三酯的脱保护和酯交换反应。
Nucleic Acids Res. 1979 Oct 10;7(3):805-23. doi: 10.1093/nar/7.3.805.
10
Phosphinic acid pseudopeptides analogous to glutamyl-gamma-glutamate: synthesis and coupling to pteroyl azides leads to potent inhibitors of folylpoly-gamma-glutamate synthetase.
J Org Chem. 2001 Jul 27;66(15):5146-54. doi: 10.1021/jo010283t.
引用本文的文献
1
Genome-scale CRISPR/Cas9 screen determines factors modulating sensitivity to ProTide NUC-1031.基于全基因组 CRISPR/Cas9 筛选确定影响 ProTide NUC-1031 敏感性的因素
Sci Rep. 2019 May 21;9(1):7643. doi: 10.1038/s41598-019-44089-3.
2
Anti-tumour activity of a first-in-class agent NUC-1031 in patients with advanced cancer: results of a phase I study.在晚期癌症患者中，首创类药物 NUC-1031 的抗肿瘤活性：I 期研究结果。
Br J Cancer. 2018 Oct;119(7):815-822. doi: 10.1038/s41416-018-0244-1. Epub 2018 Sep 12.
3
The ProTide Prodrug Technology: From the Concept to the Clinic.前药 ProTide 技术：从概念到临床。
J Med Chem. 2018 Mar 22;61(6):2211-2226. doi: 10.1021/acs.jmedchem.7b00734. Epub 2017 Aug 24.
4
Improving nucleoside analogs via lipid conjugation: Is fatter any better?通过脂质偶联改善核苷类似物：更“胖”就更好吗？
Crit Rev Oncol Hematol. 2016 Apr;100:46-56. doi: 10.1016/j.critrevonc.2016.01.015. Epub 2016 Jan 21.
5
Thiophene-expanded guanosine analogues of Gemcitabine.吉西他滨的噻吩扩展鸟苷类似物。
Bioorg Med Chem Lett. 2015 Oct 1;25(19):4274-6. doi: 10.1016/j.bmcl.2015.07.086. Epub 2015 Jul 30.
6
Antiviral lead compounds from marine sponges.海洋海绵中的抗病毒先导化合物。
Mar Drugs. 2010 Oct 11;8(10):2619-38. doi: 10.3390/md8102619.
本文引用的文献
1
2
The metabolism of exogenously supplied nucleotides by Escherichia coli.大肠杆菌对外源供应核苷酸的代谢。
J Biol Chem. 1960 Feb;235:457-65.
3
Fluorinated pyrimidines. XII. Effects of simple nucleotides on transplanted tumors.氟化嘧啶。十二。单核苷酸对移植肿瘤的影响。
Proc Soc Exp Biol Med. 1960 May;104:127-9. doi: 10.3181/00379727-104-25752.
4
The metabolism of P32-labeled ribonucleotides in tissue slices and cell suspensions.P32标记的核糖核苷酸在组织切片和细胞悬液中的代谢
J Biol Chem. 1955 Oct;216(2):823-30.
5
Synthesis and biological properties of some cyclic phosphotriesters derived from 2'-deoxy-5-fluorouridine.
J Med Chem. 1984 Apr;27(4):440-4. doi: 10.1021/jm00370a005.
6
Bis(m-nitrophenyl) and bis(p-nitrophenyl) esters and the phosphorodiamidate of thymidine 5'-phosphate as potential sources of intracellular thymidine 5'-phosphate in mouse cells in culture.
J Med Chem. 1984 Dec;27(12):1733-6. doi: 10.1021/jm00378a036.
7
Synthesis and biological evaluation of neutral derivatives of 5-fluoro-2'-deoxyuridine 5'-phosphate.
J Med Chem. 1983 Aug;26(8):1153-8. doi: 10.1021/jm00362a013.
8
Human leukemic cells resistant to 5-fluoro-2'-deoxyuridine contain a thymidylate synthetase with lower affinity for nucleotides.
J Biol Chem. 1983 Apr 10;258(7):4130-6.
9
The antiviral activity of 9-beta-D-arabinofuranosyladenine (ARA-A).9-β-D-阿拉伯呋喃糖基腺嘌呤（阿糖腺苷，ARA-A）的抗病毒活性。
Chemotherapia (Basel). 1968;13(6):321-38. doi: 10.1159/000220567.
10
Potential mechanisms of action of antiviral agents.抗病毒药物的潜在作用机制。
Fed Proc. 1973 Jun;32(6):1679-87.
Zotero 插件