芳基化诺维霉素类似物的合成与生物评价作为 HSP90 抑制剂。
Synthesis and biological evaluation of arylated novobiocin analogs as Hsp90 inhibitors.
机构信息
Department of Medicinal Chemistry, The University of Kansas, Lawrence, KS 66045-7563, USA.
出版信息
Bioorg Med Chem Lett. 2011 Dec 1;21(23):7170-4. doi: 10.1016/j.bmcl.2011.09.073. Epub 2011 Oct 1.
Abstract
Novobiocin analogs lacking labile glycosidic ether have been designed, synthesized and evaluated for Hsp90 inhibitory activity. Replacement of the synthetically complex noviose sugar with simple aromatic side chains produced analogs that maintain moderate cytotoxic activity against MCF7 and SkBR3 breast cancer cell-lines. Rationale for the preparation of des-noviose novobiocin analogs in addition to their synthesis and biological evaluation are presented herein.
摘要
已设计、合成并评估了缺乏不稳定糖苷醚的新生霉素类似物的热休克蛋白 90（Hsp90）抑制活性。用简单的芳族侧链替代合成复杂的新戊糖，得到了对 MCF7 和 SkBR3 乳腺癌细胞系具有中等细胞毒性的类似物。本文介绍了除合成和生物评价外，还制备去新戊糖新生霉素类似物的理由。
相似文献
1
Synthesis and biological evaluation of arylated novobiocin analogs as Hsp90 inhibitors.芳基化诺维霉素类似物的合成与生物评价作为 HSP90 抑制剂。
Bioorg Med Chem Lett. 2011 Dec 1;21(23):7170-4. doi: 10.1016/j.bmcl.2011.09.073. Epub 2011 Oct 1.
2
Click chemistry to probe Hsp90: Synthesis and evaluation of a series of triazole-containing novobiocin analogues.点击化学法探测 Hsp90：一系列含三唑的诺氟沙星类似物的合成与评价。
Bioorg Med Chem Lett. 2010 Jul 1;20(13):3957-60. doi: 10.1016/j.bmcl.2010.04.140. Epub 2010 May 6.
3
Synthesis and Biological Evaluation of Novobiocin Core Analogues as Hsp90 Inhibitors.作为热休克蛋白90抑制剂的新生霉素核心类似物的合成与生物学评价
Chemistry. 2016 May 10;22(20):6921-31. doi: 10.1002/chem.201504955. Epub 2016 Apr 1.
4
Synthesis and biological evaluation of coumarin replacements of novobiocin as Hsp90 inhibitors.作为热休克蛋白90（Hsp90）抑制剂的新生霉素香豆素替代物的合成及生物学评价
Bioorg Med Chem. 2014 Feb 15;22(4):1441-9. doi: 10.1016/j.bmc.2013.12.056. Epub 2014 Jan 3.
5
Synthesis and antiproliferative activity of novobiocin analogues as potential hsp90 inhibitors.新型诺氟沙星类似物的合成及其作为潜在的 HSP90 抑制剂的抗增殖活性。
Eur J Med Chem. 2014 Aug 18;83:498-507. doi: 10.1016/j.ejmech.2014.06.067. Epub 2014 Jun 28.
6
The synthesis and evaluation of flavone and isoflavone chimeras of novobiocin and derrubone.新型诺氟沙星和去甲二氢愈创木酸黄酮和异黄酮嵌合体的合成与评价。
Bioorg Med Chem. 2010 Jan 1;18(1):249-66. doi: 10.1016/j.bmc.2009.10.061. Epub 2009 Oct 31.
7
Synthesis and biological activity of simplified denoviose-coumarins related to novobiocin as potent inhibitors of heat-shock protein 90 (hsp90).作为热休克蛋白90（hsp90）强效抑制剂的与新生霉素相关的简化去氧戊糖香豆素的合成及生物活性
Bioorg Med Chem Lett. 2008 Apr 1;18(7):2495-8. doi: 10.1016/j.bmcl.2008.01.128. Epub 2008 Feb 14.
8
New novobiocin analogues as antiproliferative agents in breast cancer cells and potential inhibitors of heat shock protein 90.新型新生霉素类似物作为乳腺癌细胞中的抗增殖剂及热休克蛋白90的潜在抑制剂
J Med Chem. 2007 Nov 29;50(24):6189-200. doi: 10.1021/jm0707774. Epub 2007 Nov 3.
9
Novobiocin Analogs as Potential Anticancer Agents.新霉素类似物作为潜在的抗癌剂。
Mini Rev Med Chem. 2017;17(9):728-733. doi: 10.2174/1389557516666161223155525.
10
Novobiocin-ferrocene conjugates possessing anticancer and antiplasmodial activity independent of HSP90 inhibition.具有独立于 HSP90 抑制的抗癌和抗疟原虫活性的新生霉素-二茂铁轭合物。
J Biol Inorg Chem. 2019 Mar;24(2):139-149. doi: 10.1007/s00775-018-1634-9. Epub 2018 Dec 12.
引用本文的文献
1
Development of Hsp90 C-terminal inhibitors with noviomimetics that manifest anti-proliferative activities.具有表现出抗增殖活性的新诺米模拟物的Hsp90 C末端抑制剂的开发。
RSC Med Chem. 2024 Jan 18;15(3):888-894. doi: 10.1039/d3md00529a. eCollection 2024 Mar 20.
2
A silicon-containing aryl/penta-1,4-dien-3-one/amine hybrid exhibits antiproliferative effects on breast cancer cells by targeting the HSP90 C-terminus without inducing heat-shock response.一种含硅芳基/戊-1,4-二烯-3-酮/胺杂化物通过靶向热休克蛋白90（HSP90）的C末端对乳腺癌细胞发挥抗增殖作用，且不会诱导热休克反应。
RSC Med Chem. 2023 Oct 23;14(12):2625-2639. doi: 10.1039/d3md00431g. eCollection 2023 Dec 13.
3
Novobiocin Analogues That Inhibit the MAPK Pathway.抑制丝裂原活化蛋白激酶（MAPK）信号通路的新生霉素类似物
J Med Chem. 2016 Feb 11;59(3):925-33. doi: 10.1021/acs.jmedchem.5b01354. Epub 2016 Jan 27.
4
Alternative approaches to Hsp90 modulation for the treatment of cancer.用于癌症治疗的Hsp90调节的替代方法。
Future Med Chem. 2014 Sep;6(14):1587-605. doi: 10.4155/fmc.14.89.
5
Synthesis and biological evaluation of coumarin replacements of novobiocin as Hsp90 inhibitors.作为热休克蛋白90（Hsp90）抑制剂的新生霉素香豆素替代物的合成及生物学评价
Bioorg Med Chem. 2014 Feb 15;22(4):1441-9. doi: 10.1016/j.bmc.2013.12.056. Epub 2014 Jan 3.
6
Development of a high-throughput screening cancer cell-based luciferase refolding assay for identifying Hsp90 inhibitors.开发一种基于高通量筛选癌细胞的荧光素酶重折叠检测方法以鉴定热休克蛋白90（Hsp90）抑制剂。
Assay Drug Dev Technol. 2013 Oct;11(8):478-88. doi: 10.1089/adt.2012.498. Epub 2013 Oct 15.
7
A novel function of novobiocin: disrupting the interaction of HIF 1α and p300/CBP through direct binding to the HIF1α C-terminal activation domain.新生霉素的新功能：通过直接结合到 HIF1α C 端激活结构域，破坏 HIF 1α 与 p300/CBP 的相互作用。
PLoS One. 2013 May 6;8(5):e62014. doi: 10.1371/journal.pone.0062014. Print 2013.
8
KU-32, a novel drug for diabetic neuropathy, is safe for human islets and improves in vitro insulin secretion and viability.KU-32是一种用于治疗糖尿病神经病变的新型药物，对人胰岛安全，并能改善体外胰岛素分泌和活力。
Exp Diabetes Res. 2012;2012:671673. doi: 10.1155/2012/671673. Epub 2012 Nov 1.
本文引用的文献
1
Synthesis and Evaluation of Noviose Replacements on Novobiocin that Manifest Anti-proliferative Activity.新生霉素替代物的合成及其对具有抗增殖活性的新生霉素的评估。
ACS Med Chem Lett. 2010 Jul 13;1(7):311-315. doi: 10.1021/ml100070r.
2
Targeting the heat shock protein 90 dimer with dimeric inhibitors.靶向热休克蛋白 90 二聚体的二聚抑制剂。
J Med Chem. 2011 Sep 22;54(18):6234-53. doi: 10.1021/jm200553w. Epub 2011 Aug 23.
3
Aminations of Aryl Bromides in Water at Room Temperature.室温下水中芳基溴的胺化反应
Adv Synth Catal. 2009 Aug;351(11-12):1717-1721. doi: 10.1002/adsc.200900323.
4
Heat-shock protein 90 inhibitors as antitumor agents: a survey of the literature from 2005 to 2010.热休克蛋白 90 抑制剂作为抗肿瘤药物：2005 年至 2010 年文献综述。
Expert Opin Ther Pat. 2011 Oct;21(10):1501-42. doi: 10.1517/13543776.2011.594041. Epub 2011 Jun 21.
5
Engineering an antibiotic to fight cancer: optimization of the novobiocin scaffold to produce anti-proliferative agents.工程抗生素抗癌：优化新生霉素骨架产生抗增殖剂。
J Med Chem. 2011 Jun 9;54(11):3839-53. doi: 10.1021/jm200148p. Epub 2011 May 9.
6
Elucidation of the Hsp90 C-terminal inhibitor binding site.阐明热休克蛋白 90C 端抑制剂结合位点。
ACS Chem Biol. 2011 Aug 19;6(8):800-7. doi: 10.1021/cb200052x. Epub 2011 May 17.
7
Rational design of an aryl-C-glycoside catalyst from a natural product O-glycosyltransferase.基于天然产物O-糖基转移酶的芳基-C-糖苷催化剂的合理设计。
Chem Biol. 2011 Apr 22;18(4):520-30. doi: 10.1016/j.chembiol.2011.02.013.
8
A systematic protocol for the characterization of Hsp90 modulators.一种 HSP90 调节剂特征分析的系统方案
Bioorg Med Chem. 2011 Jan 1;19(1):684-92. doi: 10.1016/j.bmc.2010.10.029. Epub 2010 Oct 19.
9
DNA-dependent protein kinase (DNA-PK) inhibitors. Synthesis and biological activity of quinolin-4-one and pyridopyrimidin-4-one surrogates for the chromen-4-one chemotype.DNA 依赖性蛋白激酶（DNA-PK）抑制剂。色烯-4-酮化学型的喹啉-4-酮和吡啶并嘧啶-4-酮替代物的合成和生物活性。
J Med Chem. 2010 Dec 23;53(24):8498-507. doi: 10.1021/jm100608j. Epub 2010 Nov 16.
10
Synthesis and biological evaluations of P4-benzoxaborole-substituted macrocyclic inhibitors of HCV NS3 protease.P4-苯并硼唑取代的 HCV NS3 蛋白酶大环抑制剂的合成与生物评价。
Bioorg Med Chem Lett. 2010 Dec 15;20(24):7317-22. doi: 10.1016/j.bmcl.2010.10.071. Epub 2010 Oct 21.
Zotero 插件