• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

含抗菌喹诺酮的钌η-对异丙基苯配合物的物理化学研究及抗癌活性

Physicochemical Studies and Anticancer Potency of Ruthenium η-p-Cymene Complexes Containing Antibacterial Quinolones.

作者信息

Kljun Jakob, Bytzek Anna K, Kandioller Wolfgang, Bartel Caroline, Jakupec Michael A, Hartinger Christian G, Keppler Bernhard K, Turel Iztok

出版信息

Organometallics. 2011 May 9;30(9):2506-2512. doi: 10.1021/om101180c. Epub 2011 Apr 6.

DOI:10.1021/om101180c
PMID:21552495
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3086571/
Abstract

With the aim of exploring the anticancer properties of organometallic compounds with bioactive ligands, Ru(arene) compounds of the antibacterial quinolones nalidixic acid (2) and cinoxacin (3) were synthesized, and their physicochemical properties were compared to those of chlorido(η(6)-p-cymene)(ofloxacinato-κ(2)O,O)ruthenium(II) (1). All compounds undergo a rapid ligand exchange reaction from chlorido to aqua species. 2 and 3 are significantly more stable than 1 and undergo minor conversion to an unreactive (cym)Ru(μ-OH)(3)Ru(cym) species (cym = η(6)-p-cymene). In the presence of human serum albumin 1-3 form adducts with this transport protein within 20 min of incubation. With guanosine 5'-monophosphate (5'-GMP; as a simple model for reactions with DNA) very rapid reactions yielding adducts via its N7 atom were observed, illustrating that DNA is a possible target for this compound class. A moderate capacity of inhibiting tumor cell proliferation in vitro was observed for 1 in CH1 ovarian cancer cells, whereas 2 and 3 turned out to be inactive.

摘要

为了探索具有生物活性配体的有机金属化合物的抗癌特性，合成了抗菌喹诺酮类药物萘啶酸（2）和西诺沙星（3）的钌（芳烃）化合物，并将它们的物理化学性质与氯代（η(6)-对异丙基苯）（氧氟沙星-κ(2)O，O）钌（II）（1）进行了比较。所有化合物都经历了从氯代物种到水合物种的快速配体交换反应。2和3比1稳定得多，并且会少量转化为无反应性的[(对异丙基苯)钌(μ-羟基)3钌(对异丙基苯)]+(对异丙基苯 = η(6)-对异丙基苯)物种。在人血清白蛋白存在的情况下，1 - 3在孵育20分钟内与这种转运蛋白形成加合物。对于鸟苷5'-单磷酸（5'-GMP；作为与DNA反应的简单模型），观察到通过其N7原子产生加合物的非常快速的反应，这表明DNA是这类化合物的一个可能靶点。在CH1卵巢癌细胞中，观察到1具有中等程度的体外抑制肿瘤细胞增殖的能力，而2和3则没有活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1d5/3086571/30b60a2513fd/om-2010-01180c_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1d5/3086571/8d6fed1c0363/om-2010-01180c_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1d5/3086571/e497fb0de96d/om-2010-01180c_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1d5/3086571/1655effb8510/om-2010-01180c_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1d5/3086571/9cd5c20c3ea3/om-2010-01180c_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1d5/3086571/67e6869bdc74/om-2010-01180c_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1d5/3086571/d383401e5e7d/om-2010-01180c_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1d5/3086571/30b60a2513fd/om-2010-01180c_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1d5/3086571/8d6fed1c0363/om-2010-01180c_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1d5/3086571/e497fb0de96d/om-2010-01180c_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1d5/3086571/1655effb8510/om-2010-01180c_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1d5/3086571/9cd5c20c3ea3/om-2010-01180c_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1d5/3086571/67e6869bdc74/om-2010-01180c_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1d5/3086571/d383401e5e7d/om-2010-01180c_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1d5/3086571/30b60a2513fd/om-2010-01180c_0001.jpg

相似文献

1
Physicochemical Studies and Anticancer Potency of Ruthenium η-p-Cymene Complexes Containing Antibacterial Quinolones.含抗菌喹诺酮的钌η-对异丙基苯配合物的物理化学研究及抗癌活性
Organometallics. 2011 May 9;30(9):2506-2512. doi: 10.1021/om101180c. Epub 2011 Apr 6.
2
Highly selective binding of organometallic ruthenium ethylenediamine complexes to nucleic acids: novel recognition mechanisms.有机金属钌乙二胺配合物与核酸的高选择性结合：新型识别机制
J Am Chem Soc. 2003 Jan 8;125(1):173-86. doi: 10.1021/ja027719m.
3
Chlorido-, aqua-, 9-ethylguanine- and 9-ethyladenine-adducts of cytotoxic ruthenium arene complexes containing O,O-chelating ligands.含有O,O-螯合配体的细胞毒性钌芳烃配合物的氯代、水合、9-乙基鸟嘌呤和9-乙基腺嘌呤加合物。
J Inorg Biochem. 2007 Nov;101(11-12):1903-12. doi: 10.1016/j.jinorgbio.2007.04.018. Epub 2007 May 10.
4
Bipyrimidine ruthenium(II) arene complexes: structure, reactivity and cytotoxicity.双嘧啶钌(II)芳环配合物：结构、反应性和细胞毒性。
J Biol Inorg Chem. 2012 Oct;17(7):1033-51. doi: 10.1007/s00775-012-0917-9. Epub 2012 Jul 12.
5
Organometallic ruthenium(II) diamine anticancer complexes: arene-nucleobase stacking and stereospecific hydrogen-bonding in guanine adducts.有机金属钌（II）二胺抗癌配合物：鸟嘌呤加合物中的芳烃-核碱基堆积和立体特异性氢键作用
J Am Chem Soc. 2002 Mar 27;124(12):3064-82. doi: 10.1021/ja017482e.
6
Ruthenium(II) arene anticancer complexes with redox-active diamine ligands.钌(II)芳环抗癌配合物与氧化还原活性二胺配体。
Inorg Chem. 2009 Oct 5;48(19):9444-53. doi: 10.1021/ic9013366.
7
Tuning the reactivity of osmium(II) and ruthenium(II) arene complexes under physiological conditions.在生理条件下调节锇（II）和钌（II）芳烃配合物的反应活性。
J Am Chem Soc. 2006 Feb 8;128(5):1739-48. doi: 10.1021/ja055886r.
8
Hydrolytic behaviour and chloride ion binding capability of [Ru(η6-p-cym)(H2O)3]2+: a solution equilibrium study.[Ru(η6-p-cym)(H2O)3]2+的水解行为和氯离子结合能力：溶液平衡研究。
Dalton Trans. 2012 Jan 7;41(1):285-91. doi: 10.1039/c1dt11405k. Epub 2011 Nov 3.
9
Derivation of structure-activity relationships from the anticancer properties of ruthenium(II) arene complexes with 2-aryldiazole ligands.基于钌（II）芳烃配合物与2-芳基二唑配体的抗癌特性推导构效关系
Inorg Chem. 2014 Oct 20;53(20):11274-88. doi: 10.1021/ic501865h. Epub 2014 Oct 10.
10
Identification of the structural determinants for anticancer activity of a ruthenium arene peptide conjugate.鉴定钌芳基肽缀合物抗癌活性的结构决定因素。
Chemistry. 2013 Jul 8;19(28):9297-307. doi: 10.1002/chem.201300889. Epub 2013 May 27.

引用本文的文献

1
Synthesis, Characterization and Biological Profile of Cationic Cobalt Complexes with First-Generation Quinolones.第一代喹诺酮类阳离子钴配合物的合成、表征及生物学特性
Molecules. 2025 Jun 19;30(12):2646. doi: 10.3390/molecules30122646.
2
A Study on Repositioning Nalidixic Acid via Lanthanide Complexation: Synthesis, Characterization, Cytotoxicity and DNA/Protein Binding Studies.通过镧系元素络合重新定位萘啶酸的研究：合成、表征、细胞毒性及DNA/蛋白质结合研究
Pharmaceuticals (Basel). 2022 Aug 17;15(8):1010. doi: 10.3390/ph15081010.
3
Microwave-assisted synthesis of ruthenium(ii) complexes containing levofloxacin-induced G2/M phase arrest by triggering DNA damage.

本文引用的文献

1
First ruthenium organometallic complex of antibacterial agent ofloxacin. Crystal structure and interactions with DNA.第一个含抗菌药氧氟沙星的钌金属有机配合物。晶体结构与 DNA 的相互作用。
Inorg Chem. 2010 Dec 6;49(23):10750-2. doi: 10.1021/ic101355d. Epub 2010 Oct 26.
2
Structural basis of quinolone inhibition of type IIA topoisomerases and target-mediated resistance.喹诺酮类药物抑制 IIA 拓扑异构酶和靶介导耐药性的结构基础。
Nat Struct Mol Biol. 2010 Sep;17(9):1152-3. doi: 10.1038/nsmb.1892. Epub 2010 Aug 29.
3
Is the reactivity of M(II)-arene complexes of 3-hydroxy-2(1H)-pyridones to biomolecules the anticancer activity determining parameter?
微波辅助合成含左氧氟沙星的钌（II）配合物，通过引发DNA损伤诱导G2/M期阻滞。
RSC Adv. 2021 Jan 22;11(8):4444-4453. doi: 10.1039/d0ra09418h. eCollection 2021 Jan 21.
4
Biological Effects of Quinolones: A Family of Broad-Spectrum Antimicrobial Agents.喹诺酮类的生物学效应：一类广谱抗菌药物。
Molecules. 2021 Nov 25;26(23):7153. doi: 10.3390/molecules26237153.
5
Ruthenium Complexes with 2-Pyridin-2-yl-1-benzimidazole as Potential Antimicrobial Agents: Correlation between Chemical Properties and Anti-Biofilm Effects.含 2-吡啶-2-基-1-苯并咪唑的钌配合物作为潜在的抗菌剂：化学性质与抗生物膜效应的相关性。
Int J Mol Sci. 2021 Sep 18;22(18):10113. doi: 10.3390/ijms221810113.
6
Impact of the Metal Center and Leaving Group on the Anticancer Activity of Organometallic Complexes of Pyridine-2-carbothioamide.金属中心和离去基团对吡啶-2-硫代甲酰胺有机金属配合物抗癌活性的影响。
Molecules. 2021 Feb 5;26(4):833. doi: 10.3390/molecules26040833.
7
Organometallic rhenium tricarbonyl-enrofloxacin and -levofloxacin complexes: synthesis, albumin-binding, DNA-interaction and cell viability studies.金属铼三羰基-恩诺沙星和 - 左氧氟沙星配合物的合成、白蛋白结合、DNA 相互作用和细胞活力研究。
J Biol Inorg Chem. 2019 Aug;24(5):609-619. doi: 10.1007/s00775-019-01666-1. Epub 2019 May 20.
8
Exploration of selected electronic characteristics of half-sandwich organoruthenium(II) β-diketonate complexes.半夹心型二酮钌（II）配合物特定电子特性的探索
J Mol Model. 2018 Mar 20;24(4):98. doi: 10.1007/s00894-018-3598-7.
9
Synthesis and Structural Evaluation of Organo-Ruthenium Complexes with β-Diketonates.含β-二酮酸酯的有机钌配合物的合成与结构评估
Molecules. 2017 Feb 20;22(2):326. doi: 10.3390/molecules22020326.
10
Synthesis, Characterization, and Antifungal Studies of Cr(III) Complex of Norfloxacin and Bipiridyl Ligand.合成、表征及双吡啶配体与诺氟沙星铬(III)配合物的抗真菌研究。
Bioinorg Chem Appl. 2014;2014:457478. doi: 10.1155/2014/457478. Epub 2014 Sep 3.
3-羟基-2(1H)-吡啶酮的 M(II)-芳基配合物与生物分子的反应性是否是抗癌活性的决定因素？
Inorg Chem. 2010 Sep 6;49(17):7953-63. doi: 10.1021/ic1009785.
4
The influence of electroporation on cytotoxicity of anticancer ruthenium(III) complex KP1339 in vitro and in vivo.电穿孔对顺铂（III）配合物 KP1339 体外和体内细胞毒性的影响。
Anticancer Res. 2010 Jun;30(6):2055-63.
5
Synthesis and Characterization of Novel Ruthenium(III) Complexes with Histamine.新型组胺钌（III）配合物的合成与表征。
Bioinorg Chem Appl. 2010;2010:183097. doi: 10.1155/2010/183097. Epub 2010 Jun 2.
6
Nickel-quinolones interaction. Part 2--interaction of nickel(II) with the antibacterial drug oxolinic acid.镍喹诺酮相互作用。第 2 部分——镍（II）与抗菌药物氧氟沙星的相互作用。
J Inorg Biochem. 2010 Feb;104(2):161-70. doi: 10.1016/j.jinorgbio.2009.10.017. Epub 2009 Oct 23.
7
Maltol-derived ruthenium-cymene complexes with tumor inhibiting properties: the impact of ligand-metal bond stability on anticancer activity in vitro.具有肿瘤抑制特性的麦芽酚衍生钌-柠檬烯配合物：配体-金属键稳定性对体外抗癌活性的影响。
Chemistry. 2009 Nov 16;15(45):12283-91. doi: 10.1002/chem.200901939.
8
The serum protein binding of pharmacologically active gallium(III) compounds assessed by hyphenated CE-MS techniques.采用联用CE-MS技术评估具有药理活性的镓（III）化合物的血清蛋白结合情况。
Electrophoresis. 2009 Aug;30(15):2720-7. doi: 10.1002/elps.200800745.
9
Bioorganometallic chemistry--from teaching paradigms to medicinal applications.生物有机金属化学——从教学范式到医学应用
Chem Soc Rev. 2009 Feb;38(2):391-401. doi: 10.1039/b707077m. Epub 2008 Nov 25.
10
Modulation of the biological properties of aspirin by formation of a bioorganometallic derivative.通过形成生物有机金属衍生物对阿司匹林生物学性质的调控。
Angew Chem Int Ed Engl. 2009;48(6):1160-3. doi: 10.1002/anie.200803347.