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Synthesis and evaluation of piperazine and homopiperazine analogues of JS-K, an anti-cancer lead compound.抗癌先导化合物JS-K的哌嗪和高哌嗪类似物的合成与评价
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The nitric oxide prodrug JS-K and its structural analogues as cancer therapeutic agents.一氧化氮前药JS-K及其结构类似物作为癌症治疗药物
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JS-K, a nitric oxide-releasing prodrug, modulates ß-catenin/TCF signaling in leukemic Jurkat cells: evidence of an S-nitrosylated mechanism.JS-K，一种一氧化氮供体型前药，调节白血病 Jurkat 细胞中的 β-连环蛋白/TCF 信号转导：一种 S-亚硝化作用机制的证据。
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Mechanistic studies on the reaction between R2N-NONOates and aquacobalamin: evidence for direct transfer of a nitroxyl group from R2N-NONOates to cobalt(III) centers.R2N - 亚硝酰基酯与水合钴胺素反应的机理研究：硝酰基从R2N - 亚硝酰基酯直接转移至钴（III）中心的证据
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Synthesis and evaluation of piperazine and homopiperazine analogues of JS-K, an anti-cancer lead compound.抗癌先导化合物JS-K的哌嗪和高哌嗪类似物的合成与评价
Bioorg Med Chem Lett. 2009 May 15;19(10):2760-2. doi: 10.1016/j.bmcl.2009.03.115. Epub 2009 Mar 28.

本文引用的文献

1
Piperazine as a Linker for Incorporating the Nitric Oxide-Releasing Diazeniumdiolate Group into Other Biomedically Relevant Functional Molecules.哌嗪作为一种连接基，用于将释放一氧化氮的二氮烯二醇盐基团引入其他具有生物医学相关性的功能分子中。
J Org Chem. 1999 Jul 9;64(14):5124-5131. doi: 10.1021/jo9901539.
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Nitric oxide prodrugs: diazeniumdiolate anions of hindered secondary amines.一氧化氮前药：受阻仲胺的二氮烯二醇盐阴离子
Org Lett. 2007 Oct 25;9(22):4551-4. doi: 10.1021/ol7019636. Epub 2007 Oct 5.
3
V-PROLI/NO, a prodrug of the nitric oxide donor, PROLI/NO.V-PROLI/NO，一氧化氮供体PROLI/NO的前体药物。
Org Lett. 2007 Aug 16;9(17):3409-12. doi: 10.1021/ol701419a. Epub 2007 Jul 20.
4
O2-acetoxymethyl-protected diazeniumdiolate-based NSAIDs (NONO-NSAIDs): synthesis, nitric oxide release, and biological evaluation studies.基于O2-乙酰氧基甲基保护的重氮二醇酸盐的非甾体抗炎药（NONO-NSAIDs）：合成、一氧化氮释放及生物学评价研究。
Bioorg Med Chem. 2007 Jul 15;15(14):4767-74. doi: 10.1016/j.bmc.2007.05.009. Epub 2007 May 6.
5
JS-K, a GST-activated nitric oxide generator, induces DNA double-strand breaks, activates DNA damage response pathways, and induces apoptosis in vitro and in vivo in human multiple myeloma cells.JS-K，一种谷胱甘肽S-转移酶激活的一氧化氮生成剂，可诱导DNA双链断裂，激活DNA损伤反应通路，并在体外和体内诱导人多发性骨髓瘤细胞凋亡。
Blood. 2007 Jul 15;110(2):709-18. doi: 10.1182/blood-2006-10-052845. Epub 2007 Mar 23.
6
Antitumor activity of JS-K [O2-(2,4-dinitrophenyl) 1-[(4-ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate] and related O2-aryl diazeniumdiolates in vitro and in vivo.JS-K [O2-(2,4-二硝基苯基)-1-[(4-乙氧羰基)哌嗪-1-基]重氮-1,2-二醇盐]及相关的O2-芳基重氮二醇盐的体内外抗肿瘤活性
J Med Chem. 2006 Jul 13;49(14):4356-66. doi: 10.1021/jm060022h.
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Advance in antitumor agents targeting glutathione-S-transferase.靶向谷胱甘肽-S-转移酶的抗肿瘤药物研究进展
Curr Med Chem. 2006;13(12):1461-71. doi: 10.2174/092986706776872934.
8
JS-K, a nitric oxide prodrug, induces cytochrome c release and caspase activation in HL-60 myeloid leukemia cells.JS-K，一种一氧化氮前体药物，可诱导HL-60髓系白血病细胞中的细胞色素c释放和半胱天冬酶激活。
Leuk Res. 2006 Oct;30(10):1279-83. doi: 10.1016/j.leukres.2005.12.007. Epub 2006 Jan 24.
9
Injectable formulation of disodium 1-[2-(carboxylato)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate (PROLI/NO), an ultrafast nitric oxide donor prodrug.1-[2-(羧基)吡咯烷-1-基]重氮-1,2-二醇二钠（PROLI/NO）的注射剂配方，一种超快速一氧化氮供体前药。
J Pharm Sci. 2006 Jan;95(1):108-15. doi: 10.1002/jps.20486.
10
Nitric oxide (NO)- and nitroxyl (HNO)-generating diazeniumdiolates (NONOates): emerging commercial opportunities.生成一氧化氮（NO）和硝酰基（HNO）的连二亚硝酸酯（NONOates）：新兴的商业机遇。
Curr Top Med Chem. 2005;5(7):625-36. doi: 10.2174/1568026054679380.

抗癌先导化合物JS-K的结构类似物的合成及其体外抗白血病活性

Synthesis and in vitro anti-leukemic activity of structural analogues of JS-K, an anti-cancer lead compound.

作者信息

Chakrapani Harinath, Goodblatt Michael M, Udupi Vidya, Malaviya Swati, Shami Paul J, Keefer Larry K, Saavedra Joseph E

机构信息

Chemistry Section, Laboratory of Comparative Carcinogenesis, National Cancer Institute at Frederick, PO Box B, Frederick, MD 21702, USA.

出版信息

Bioorg Med Chem Lett. 2008 Feb 1;18(3):950-3. doi: 10.1016/j.bmcl.2007.12.044. Epub 2008 Jan 4.

DOI:10.1016/j.bmcl.2007.12.044
PMID:18178089
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2278236/
Abstract

Structural analogues of JS-K, an anti-cancer lead compound, were prepared and their in vitro anti-leukemic activity was determined. The rate of nitric oxide release from the corresponding diazeniumdiolate anions did not appear to affect the anti-leukemic activity of the prodrug forms. Two compounds with potent inhibitory activity and a potentially favorable toxicological profile were identified.

摘要

制备了抗癌先导化合物JS-K的结构类似物，并测定了它们的体外抗白血病活性。相应的二氮烯二醇盐阴离子释放一氧化氮的速率似乎不影响前药形式的抗白血病活性。鉴定出两种具有强效抑制活性和潜在良好毒理学特征的化合物。