Synthesis, characterization and biological activity of copper(II) complexes with ligands derived from β-amino acids

被引：12

作者：

Bukonjic, Andriana M. ^{[1
]}

Tomovic, Duan Lj. ^{[1
]}

Stankovic, Ana S. ^{[1
]}

Jevtic, Verica V. ^{[2
]}

Ratkovic, Zoran R. ^{[2
]}

Bogojeski, Jovana V. ^{[2
]}

Milovanovic, Jelena Z. ^{[3
]}

Dordevic, Dragana B. ^{[3
]}

Arsenijevic, Aleksandar N. ^{[3
]}

Milovanovic, Marija Z. ^{[3
]}

Potocnak, Ivan ^{[4
]}

Trifunovic, Srecko R. ^{[2
]}

Radic, Gordana P. ^{[1
]}

机构：

[1] Univ Kragujevac, Fac Med Sci, Dept Pharm, Svetozara Markovica 69, Kragujevac 34000, Serbia

[2] Univ Kragujevac, Fac Sci, Dept Chem, Radoja Domanovica 12, Kragujevac 34000, Serbia

[3] Univ Kragujevac, Fac Med Sci, Ctr Mol Med & Stem Cell Res, Dept Microbiol & Immunol, Svetozara Markovica 69, Kragujevac 34000, Serbia

[4] Safarik Univ, Inst Chem, Moyzesova 11, Kosice 04154, Slovakia

来源：

TRANSITION METAL CHEMISTRY | 2019年 / 44卷 / 01期

关键词：

DNA-BINDING; SPECTROSCOPIC CHARACTERIZATION; CYTOTOXIC ACTIVITY; ZN(II) COMPLEXES; DNA/PROTEIN; MECHANISM; CLEAVAGE; AFFINITY; DOCKING; DESIGN;

D O I：

10.1007/s11243-018-0270-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Two copper(II) complexes with ligands derived from beta-amino acids, 2-(1-aminocyclohexyl)acetic acid L1 and 2-(1-amino-4-(tert-butyl)cyclohexyl)acetic acid L2, were synthesized and characterized by microanalysis, infrared, UV-Vis and EPR spectra. The spectroscopically predicted structure of the square-planar copper(II) complex with 2-(1-aminocyclohexyl)-acetic acid C1 was confirmed by single-crystal X-ray analysis. The biological activities (antitumor activities and interaction with DNA) of the compounds were also investigated. The interactions of both complexes with calf thymus (CT) and herring testes (HT) DNA were examined by stopped-flow spectroscopy, by absorption (UV-Vis) and by emission spectral studies (ethidium bromide displacement studies). Both complexes were found to react a bit faster with HT-DNA than with CT-DNA. The obtained binding constants suggested a moderate intercalative binding mode between the complexes and DNA. In addition, fluorescence spectrometry of bovine serum albumin with the complexes showed a good fluorescence quenching of the complexes. The obtained copper(II) complexes have a relatively low cytotoxic effect on murine mammary carcinoma cell line, 4T1, a moderate effect on murine colon carcinoma cell line, CT26, and a relatively high cytotoxicity toward murine lung cancer cells, LLC1.

引用

页码：65 / 76

页数：12

共 50 条

[11] The Cambridge Structural Database [J].

Groom, Colin R. ;

Bruno, Ian J. ;

Lightfoot, Matthew P. ;

Ward, Suzanna C. .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2016, 72 :171-179

[12] BINDING OF PLATINUM AND PALLADIUM METALLOINTERCALATION REAGENTS AND ANTITUMOR DRUGS TO CLOSED AND OPEN DNAS [J].

HOWEGRANT, M ;

WU, KC ;

BAUER, WR ;

LIPPARD, SJ .

BIOCHEMISTRY, 1976, 15 (19) :4339-4346

[13]

Iakovidis Isidoros, 2011, Mol Biol Int, V2011, P594529, DOI 10.4061/2011/594529

[14] Lead(II) Complex Formation with L-Cysteine in Aqueous Solution [J].

Jalilehvand, Farideh ;

Sisombath, Natalie S. ;

Schell, Adam C. ;

Facey, Glenn A. .

INORGANIC CHEMISTRY, 2015, 54 (05) :2160-2170

[15] Synthesis, crystal structure, cytotoxic activities and DNA-binding properties of new binuclear copper(II) complexes bridged by N,N′-bis(N-hydroxyethylaminoethyl)oxamide [J].

Jiang, Man ;

Li, Yan-Tuan ;

Wu, Zhi-Yong ;

Liu, Zhi-Qiang ;

Yan, Cui-Wei .

JOURNAL OF INORGANIC BIOCHEMISTRY, 2009, 103 (05) :833-844

[16]

Kamwaya ME, 1984, MALAYSIA, V5, P1

[17]

Karsten Rippe BIF, 1997, FUTURA, V12, P20

[18] First Palladium(II) and Platinum(II) Complexes from Employment of 2,6-Diacetylpyridine Dioxime: Synthesis, Structural and Spectroscopic Characterization, and Biological Evaluation [J].

Koumousi, Evangelia S. ;

Zampakou, Marianthi ;

Raptopoulou, Catherine P. ;

Psycharis, Vassilis ;

Beavers, Christine M. ;

Teat, Simon J. ;

Psomas, George ;

Stamatatos, Theocharis C. .

INORGANIC CHEMISTRY, 2012, 51 (14) :7699-7710

[19] Competitive formation of β-amino acids, propenoic, and ylidenemalonic acids by the rodionov reaction from malonic acid, aldehydes, and ammonium acetate in alcoholic medium [J].

Lebedev, AV ;

Lebedeva, AB ;

Sheludyakov, VD ;

Kovaleva, EA ;

Ustinova, OL ;

Kozhevnikov, IB .

RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2005, 75 (07) :1113-1124

[20] Association of structural modifications with bioactivity in three new copper(II) complexes of Schiff base ligands derived from 5-chlorosalicylaldehyde and amino acids [J].

Li, Ang ;

Liu, Ya-Hong ;

Yuan, Ling-Zhi ;

Ma, Zhong-Ying ;

Zhao, Chun-Lai ;

Xie, Cheng-Zhi ;

Bao, Wei-Guo ;

Xu, Jing-Yuan .

JOURNAL OF INORGANIC BIOCHEMISTRY, 2015, 146 :52-60

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