Copper(II/I) complexes of 5-pyridin-2-yl-[1,3]dioxolo[4,5-g] isoquinoline: Synthesis, crystal structure, antitumor activity and DNA interaction

被引:32
作者
Huang, Ke-Bin [1 ,2 ]
Chen, Zhen-Feng [1 ]
Liu, Yan-Cheng [1 ]
Wang, Meng [1 ]
Wei, Jian-Hua [1 ]
Xie, Xiao-Li [1 ]
Zhang, Jian-Lian [1 ]
Hu, Kun [1 ]
Liang, Hong [1 ,2 ]
机构
[1] Guangxi Normal Univ, Sch Pharm & Chem, Guangxi Key Lab Chem & Mol Engn Med Resources, Guilin 541004, Peoples R China
[2] Nankai Univ, Sch Chem, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
Isoquinoline; Copper(II) complexes; Synthesis; Crystal structure; Cytotoxicity; PLATINUM COMPOUNDS; IN-VITRO; BINDING; CYTOTOXICITY; ENHANCEMENT; INHIBITOR; RUTHENIUM; CLEAVAGE; BASE;
D O I
10.1016/j.ejmech.2013.10.031
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Three new copper(II) complexes of 5-pyridin-2-yl-[1,3]dioxolo[4,5-g]isoquinoline (PYP), i.e. [Cu-2(PYP)(2)Cl-4] (1), [Cu-4(PYP)(4)(ClO4)(2)(H2O)(2)](ClO4)(2)center dot 2H(2)O (2), and [Cu-2(PYP)(2)Cl-4](n) (3), were synthesized and fully characterized. In comparison to free PYP, complexes 1-3 exhibited enhanced cytotoxicity against tested human tumor cell lines BEL-7404, SK-OV-3, A549, A375, MGC-803 and NCI-H460, with IC50 values ranging from 0.31 to 30.76 mu M. Complexes 1-3 exhibited lower cytotoxicity to HL-7702 than them to cancer cells. Complex 1 induced apoptotic death of BEL-7404, which involved mitochondria in the process. Caspase-3 activation assay indicated that 1 could be an efficient activator of caspase-3. DNA binding studies by UV-vis, DNA-melting, competitive binding, CD, viscosity measurement and agarose gel electrophoresis, revealed that intercalation might be the most likely binding mode of 1 with DNA. (C) 2013 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:640 / 648
页数:9
相关论文
共 50 条
[31]   Synthesis, crystal structure, antiproliferative activity, DNA binding and density functional theory calculations of 3-(pyridin-2-yl)-8-tert-butylcoumarin and its copper(II) complex [J].
Lu, Wen ;
Shi, Jiuzhou ;
Nie, YingFang ;
Yang, Lu ;
Chen, Jichao ;
Zhao, Fengyi ;
Yang, Shilong ;
Xu, Li ;
Chi, Xingwei .
APPLIED ORGANOMETALLIC CHEMISTRY, 2020, 34 (10)
[32]   7-Methyl-5-[(4-methylbenzene)sulfonyl]-2H,5H-[1,3]dioxolo[4,5-f]indole: crystal structure and Hirshfeld analysis [J].
Ali, Akbar ;
Zukerman-Schpector, Julio ;
Paixao, Marcio Weber ;
Jotani, Mukesh M. ;
Tiekink, Edward R. T. .
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2018, 74 :184-+
[33]   Copper(II) and Zinc(II) Coordination Compounds with 4-(Pyridin-2-yl)methyleneamino-1,2,4-triazole: Synthesis, Crystal Structure, Thermal Stability, and Antimicrobial Activity [J].
Bovkunova, Anna A. ;
Bazhina, Evgeniya S. ;
Shmelev, Maxim A. ;
Gogoleva, Natalia V. ;
Andros, Natalia O. ;
Zubenko, Alexander A. ;
Ismatullin, Danir D. ;
Lyamin, Artem V. ;
Kiskin, Mikhail A. ;
Eremenko, Igor L. .
CHEMISTRYSELECT, 2025, 10 (16)
[34]   Synthesis, crystal structure and superoxide dismutase activity of two new bis(μ-acetato/μ-nitrato) bridged copper(II) complexes with N′-[phenyl(pyridin-2-yl)methylidene]benzohydrazone [J].
Patel, R. N. ;
Patel, Dinesh K. ;
Sondhiya, Vishnu P. ;
Shukla, K. K. ;
Singh, Y. ;
Kumar, A. .
INORGANICA CHIMICA ACTA, 2013, 405 :209-217
[35]   Synthesis and Crystal Structure of Cu(II)/Zn(II)/Mn(II) Complexes Containing 3-((5-(Pyridin-3-yl)-1,3,4-oxadiazol-2-yl)thio)pentane-2,4-dione Ligand [J].
Zhang Qi-Long ;
Sun Le-Tao ;
Yang Xian-Jiong ;
Xu Hong ;
Li Li-Lang ;
Yang Xiao-Sheng .
CHINESE JOURNAL OF INORGANIC CHEMISTRY, 2021, 37 (06) :989-994
[36]   Synthesis, Crystal Structure and DNA Interaction Study of 3-(2-(3,5-Diphenyl-4,5-dihydropyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one [J].
MURTAZA Madni ;
SHAHID Hameed ;
MUHAMMAD Naeem Ahmed ;
KHAWAJA Ansar Yasin ;
MUHAMMAD Nawaz Tahir .
结构化学, 2015, 34 (07) :1013-1018
[37]   Synthesis, Crystal Structure and DNA Interaction of a Chiral Platinum(II) Complex with 2-(2,3-Dimethoxyphenyl)-1H-imidazo[4,5-f][1,10] phenanthroline [J].
Luo Xu-Jian ;
Wang Shu-Long ;
Yang Yan ;
Luo Zhi-Hui ;
Liu Rong-Jun ;
Liang Wei-Jiang .
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2017, 36 (09) :1486-1492
[38]   Synthesis, Crystal Structure and Fluorescent Properties of a Cadmium(II) Complex with 3-(Pyridin-4-yl)-5-(pyrazin-2-yl)-1H-1,2,4-triazole [J].
Wang Yu-Fang ;
Sun Xiao-Yuan ;
Geng Jun -Lei .
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2016, 35 (03) :397-403
[39]   Synthesis, Crystal Structure and Neuroprotective Activity of(E)-1-(4-(4-Chlorobenzyl)piperazin-1-yl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one [J].
徐兆颖 ;
仲琰 ;
刘亚麟 ;
许逸 ;
李萍 ;
吴斌 .
结构化学, 2016, 35 (09) :1348-1354
[40]   Synthesis, Crystal Structure and Neuroprotective Activity of (E)-1-(4-(4-Chlorobenzyl)piperazin-1-yl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one [J].
Xu Zhao-Ying ;
Zhong Yan ;
Liu Ya-Lin ;
Xu Yi ;
Li Ping ;
Wu Bin .
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2016, 35 (09) :1348-1354