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Synthesis, mechanistic studies, and anti-proliferative activity of glutathione/glutathione S-transferase-activated nitric oxide prodrugs.谷胱甘肽/谷胱甘肽S-转移酶激活的一氧化氮前药的合成、机理研究及抗增殖活性
Bioorg Med Chem. 2008 Nov 15;16(22):9764-71. doi: 10.1016/j.bmc.2008.09.063. Epub 2008 Sep 30.
2
JS-K, a glutathione/glutathione S-transferase-activated nitric oxide donor of the diazeniumdiolate class with potent antineoplastic activity.JS-K，一种二氮烯二醇盐类的谷胱甘肽/谷胱甘肽S-转移酶激活的一氧化氮供体，具有强大的抗肿瘤活性。
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3
Nitric oxide-releasing prodrug triggers cancer cell death through deregulation of cellular redox balance.释放一氧化氮的前药通过破坏细胞氧化还原平衡引发癌细胞死亡。
Redox Biol. 2013 Feb 1;1(1):115-24. doi: 10.1016/j.redox.2012.12.002. eCollection 2013.
4
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.
5
Synthesis and in vitro anti-leukemic activity of structural analogues of JS-K, an anti-cancer lead compound.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
Bioorg Med Chem Lett. 2008 Feb 1;18(3):950-3. doi: 10.1016/j.bmcl.2007.12.044. Epub 2008 Jan 4.
6
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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7
Activation of the c-Jun N-terminal kinase/activating transcription factor 3 (ATF3) pathway characterizes effective arylated diazeniumdiolate-based nitric oxide-releasing anticancer prodrugs.c-Jun N-末端激酶/激活转录因子 3（ATF3）通路的激活是有效的芳基化重氮二氧戊环类一氧化氮供体抗癌前药的特征。
J Med Chem. 2011 Nov 24;54(22):7751-8. doi: 10.1021/jm2004128. Epub 2011 Oct 28.
8
Role of human glutathione transferases in biotransformation of the nitric oxide prodrug JS-K.人谷胱甘肽转移酶在一氧化氮前体药物 JS-K 的生物转化中的作用。
Sci Rep. 2021 Oct 21;11(1):20765. doi: 10.1038/s41598-021-00327-1.
9
Hybrid molecule from O2-(2,4-dinitrophenyl)diazeniumdiolate and oleanolic acid: a glutathione S-transferase π-activated nitric oxide prodrug with selective anti-human hepatocellular carcinoma activity and improved stability.O2-(2,4-二硝基苯基)重氮氨基醇和齐墩果酸的杂交分子：一种谷胱甘肽 S-转移酶 π 激活的一氧化氮前药，具有选择性的抗人肝癌活性和提高的稳定性。
J Med Chem. 2013 Jun 13;56(11):4641-55. doi: 10.1021/jm400393u. Epub 2013 May 16.
10
Cellular distribution studies of the nitric oxide-generating antineoplastic prodrug O(2) -(2,4-dinitrophenyl)1-((4-ethoxycarbonyl)piperazin-1-yl)diazen-1-ium-1,2-diolate formulated in Pluronic P123 micelles.O(2)-(2,4-二硝基苯基）1-((4-乙氧羰基)哌嗪-1-基）二氮烯-1,2-二醇ate 在 Pluronic P123 胶束中制成的抗肿瘤前药的细胞分布研究。
J Pharm Pharmacol. 2013 Sep;65(9):1329-36. doi: 10.1111/jphp.12100. Epub 2013 Jul 10.

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JS-K induces ferroptosis in renal carcinoma cells by regulating the c-Myc-GSTP1 Axis.JS-K通过调节c-Myc-GSTP1轴诱导肾癌细胞发生铁死亡。
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Opportunities for Nitric Oxide in Potentiating Cancer Immunotherapy.一氧化氮在增强癌症免疫疗法中的作用机会。
Pharmacol Rev. 2022 Oct;74(4):1146-1175. doi: 10.1124/pharmrev.121.000500.
3
Role of human glutathione transferases in biotransformation of the nitric oxide prodrug JS-K.人谷胱甘肽转移酶在一氧化氮前体药物 JS-K 的生物转化中的作用。
Sci Rep. 2021 Oct 21;11(1):20765. doi: 10.1038/s41598-021-00327-1.
4
Exogenous NO induces apoptosis of hepatocellular carcinoma cells via positive p38/JNK signaling pathway and negative ERK signaling pathways.外源性一氧化氮通过正性 p38/JNK 信号通路和负性 ERK 信号通路诱导肝癌细胞凋亡。
Mol Cell Biochem. 2021 Apr;476(4):1651-1661. doi: 10.1007/s11010-020-04032-x. Epub 2021 Jan 9.
5
JS-K, a nitric oxide donor, induces autophagy as a complementary mechanism inhibiting ovarian cancer.JS-K，一种一氧化氮供体，通过诱导自噬作为一种补充机制来抑制卵巢癌。
BMC Cancer. 2019 Jul 1;19(1):645. doi: 10.1186/s12885-019-5619-z.
6
JS-K induces reactive oxygen species-dependent anti-cancer effects by targeting mitochondria respiratory chain complexes in gastric cancer.JS-K 通过靶向胃癌中线粒体呼吸链复合物诱导活性氧依赖的抗癌作用。
J Cell Mol Med. 2019 Apr;23(4):2489-2504. doi: 10.1111/jcmm.14122. Epub 2019 Jan 22.
7
Glutathione -transferase π: a potential role in antitumor therapy.谷胱甘肽-S-转移酶π：在抗肿瘤治疗中的潜在作用
Drug Des Devel Ther. 2018 Oct 23;12:3535-3547. doi: 10.2147/DDDT.S169833. eCollection 2018.
8
Glutathione transferases: substrates, inihibitors and pro-drugs in cancer and neurodegenerative diseases.谷胱甘肽转移酶：癌症和神经退行性疾病中的底物、抑制剂及前药
Oncogenesis. 2018 Jan 24;7(1):8. doi: 10.1038/s41389-017-0025-3.
9
Synthesis and characterization of a multi-arm poly(acrylic acid) star polymer for application in sustained delivery of cisplatin and a nitric oxide prodrug.一种用于顺铂和一氧化氮前药持续递送的多臂聚（丙烯酸）星形聚合物的合成与表征
J Polym Sci A Polym Chem. 2012 Jul 1;50(13):2715-2724. doi: 10.1002/pola.26059. Epub 2012 Apr 16.
10
Mechanism of action for the cytotoxic effects of the nitric oxide prodrug JS-K in murine erythroleukemia cells.一氧化氮前体药物 JS-K 在小鼠红白血病细胞中细胞毒性作用的作用机制。
Leuk Res. 2014 Mar;38(3):377-82. doi: 10.1016/j.leukres.2013.12.002. Epub 2013 Dec 12.

本文引用的文献

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Nitric Oxide: A Unique Endogenous Signaling Molecule in Vascular Biology (Nobel Lecture).一氧化氮：血管生物学中独特的内源性信号分子（诺贝尔演讲）
Angew Chem Int Ed Engl. 1999 Jul 12;38(13-14):1882-1892. doi: 10.1002/(SICI)1521-3773(19990712)38:13/14<1882::AID-ANIE1882>3.0.CO;2-V.
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Discovery of Some of the Biological Effects of Nitric Oxide and Its Role in Cell Signaling (Nobel Lecture).一氧化氮的一些生物学效应的发现及其在细胞信号传导中的作用（诺贝尔演讲）
Angew Chem Int Ed Engl. 1999 Jul 12;38(13-14):1856-1868. doi: 10.1002/(SICI)1521-3773(19990712)38:13/14<1856::AID-ANIE1856>3.0.CO;2-D.
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Endothelium-Derived Relaxing Factor: Discovery, Early Studies, and Identifcation as Nitric Oxide (Nobel Lecture).内皮衍生舒张因子：发现、早期研究及一氧化氮的鉴定（诺贝尔演讲）
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Experimental chemotherapy of filariasis; the preparation of derivatives of piperazine.
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Synthesis and in vitro anti-leukemic activity of structural analogues of JS-K, an anti-cancer lead compound.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
Bioorg Med Chem Lett. 2008 Feb 1;18(3):950-3. doi: 10.1016/j.bmcl.2007.12.044. Epub 2008 Jan 4.
6
Synthesis, nitric oxide release, and anti-leukemic activity of glutathione-activated nitric oxide prodrugs: Structural analogues of PABA/NO, an anti-cancer lead compound.谷胱甘肽激活的一氧化氮前药的合成、一氧化氮释放及抗白血病活性：抗癌先导化合物PABA/NO的结构类似物
Bioorg Med Chem. 2008 Mar 1;16(5):2657-64. doi: 10.1016/j.bmc.2007.11.035. Epub 2007 Nov 17.
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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。
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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.
9
Therapeutic potential of nitric oxide in cancer.一氧化氮在癌症治疗中的潜力。
Drug Resist Updat. 2006 Jun;9(3):157-73. doi: 10.1016/j.drup.2006.05.003. Epub 2006 Jul 5.
10
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
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谷胱甘肽/谷胱甘肽S-转移酶激活的一氧化氮前药的合成、机理研究及抗增殖活性

Synthesis, mechanistic studies, and anti-proliferative activity of glutathione/glutathione S-transferase-activated nitric oxide prodrugs.

作者信息

Chakrapani Harinath, Kalathur Ravi C, Maciag Anna E, Citro Michael L, Ji Xinhua, Keefer Larry K, Saavedra Joseph E

机构信息

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

出版信息

Bioorg Med Chem. 2008 Nov 15;16(22):9764-71. doi: 10.1016/j.bmc.2008.09.063. Epub 2008 Sep 30.

DOI:10.1016/j.bmc.2008.09.063
PMID:18930407
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2631660/
Abstract

Nitric oxide (NO) prodrugs such as O(2)-(2,4-dinitrophenyl) 1-[(4-ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate (JS-K) are a growing class of promising NO-based therapeutics. Nitric oxide release from the anti-cancer lead compound, JS-K, is proposed to occur through a nucleophilic aromatic substitution by glutathione (GSH) catalyzed by glutathione S-transferase (GST) to form a diazeniumdiolate anion that spontaneously releases NO. In this study, a number of structural analogues of JS-K were synthesized and their chemical and biological properties were compared with those of JS-K. The homopiperazine analogue of JS-K showed anti-cancer activity that is comparable with that of JS-K but with a diminished reactivity towards both GSH and GSH/GST; both the aforementioned compounds displayed no cytotoxic activity towards normal renal epithelial cell line at concentrations where they significantly diminished the proliferation of a panel of renal cancer cell lines. These properties may prove advantageous in the further development of this class of nitric oxide prodrugs as cancer therapeutic agents.

摘要

一氧化氮（NO）前药，如O(2)-(2,4-二硝基苯基) 1-[(4-乙氧基羰基)哌嗪-1-基]重氮-1,2-二醇盐（JS-K），是一类不断发展的、有前景的基于NO的治疗药物。抗癌先导化合物JS-K释放一氧化氮的过程，被认为是通过谷胱甘肽S-转移酶（GST）催化的谷胱甘肽（GSH）进行亲核芳香取代反应，形成重氮二醇盐阴离子，该阴离子会自发释放NO。在本研究中，合成了多种JS-K的结构类似物，并将它们的化学和生物学性质与JS-K进行了比较。JS-K的高哌嗪类似物显示出与JS-K相当的抗癌活性，但对GSH和GSH/GST的反应性降低；在显著降低一组肾癌细胞系增殖的浓度下，上述两种化合物对正常肾上皮细胞系均无细胞毒性活性。这些特性可能在将这类一氧化氮前药进一步开发为癌症治疗药物方面具有优势。