Copper(II) complexes with derivatives of pyrazole as potential antioxidant enzyme mimics

被引:40
|
作者
Kupcewicz, Bogumila [1 ]
Sobiesiak, Krzysztof [1 ]
Malinowska, Katarzyna [2 ]
Koprowska, Kamila [3 ]
Czyz, Malgorzata [3 ]
Keppler, Bernhard [4 ]
Budzisz, Elzbieta [1 ,5 ]
机构
[1] Nicolaus Copernicus Univ Torun, Coll Med Bydgoszcz, Fac Pharm, Dept Inorgan & Analyt Chem, PL-85094 Bydgoszcz, Poland
[2] Med Univ Lodz, Dept Chem & Clin Biochem, PL-90647 Lodz, Poland
[3] Med Univ Lodz, Dept Mol Biol Canc, PL-92215 Lodz, Poland
[4] Univ Vienna, Inst Inorgan Chem, A-1090 Vienna, Austria
[5] Med Univ Lodz, Fac Pharm, Dept Cosmet Raw Mat Chem, PL-90151 Lodz, Poland
关键词
Enzyme mimic; Copper(II) complexes; Pyrazoles; Reactive oxygen species; Cyclic voltammetry; SUPEROXIDE-DISMUTASE; CYTOTOXIC ACTIVITY; ANTITUMOR-ACTIVITY; CRYSTAL-STRUCTURE; IN-VITRO; PALLADIUM(II); PLATINUM(II); LIGANDS; PEROXIDASE; MEPIRIZOLE;
D O I
10.1007/s00044-012-0233-5
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of six mononuclear Cu(II) complexes with pyrazole-based ligands: 5-(2-hydroxybenzoyl)-3-methyl-1-(2-pyridinyl)-1H-pyrazol-4-phosphonic acid dimethyl ester (1a), 5-(2-hydroxyphenyl)-3-methyl-1-(2-pyridylo)-1H-pyrazole-4-carboxylic acid methyl ester (1b) and 1-benzothiazol-2-yl-5-(2-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carboxylic acid methyl ester (1c) were characterized regarding to electrochemical and antioxidant properties. All complexes exhibit suitable Cu(II)/Cu(I) redox potential (E (1/2)) to act as antioxidant enzymes mimic. The five of these complexes were found to be trifunctional enzyme mimics possessing SOD, CAT and GPx-like catalytic activities. Moreover, Cu(II) complexes were capable to decrease ROS level in melanoma cells and observed effects were not merely a reflection of cytotoxicity.
引用
收藏
页码:2395 / 2402
页数:8
相关论文
共 50 条
  • [31] Electrochemical behavior and antioxidant activity of tetradentate Schiff bases and their copper(II) complexes
    Aburas, Najat
    Lolic, Aleksandar
    Stevanovic, Nikola
    Tripkovic, Tatjana
    Nikolic-Mandic, Snezana
    Baosic, Rada
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2012, 9 (06) : 859 - 864
  • [32] Development of copper(II)-diimine-iminodiacetate mixed ligand complexes as potential antitumor agents
    Alvarez, Natalia
    Mendes, Luis F. S.
    Gabriela Kramer, M.
    Torre, Maria H.
    Costa-Filho, Antonio J.
    Ellena, Javier
    Facchin, Gianella
    INORGANICA CHIMICA ACTA, 2018, 483 : 61 - 70
  • [33] Synthesis, characterization and antifungal activity of copper (II) complexes of sterically hindered o-diphenol derivatives
    Loginova, N. V.
    Koval'chuk, T. V.
    Zheldakova, R. A.
    Chernyavskaya, A. A.
    Osipovich, N. P.
    Glushonok, G. K.
    Polozov, G. I.
    Povalishev, V. N.
    Sorokin, V. L.
    Shadyro, O. I.
    POLYHEDRON, 2006, 25 (18) : 3603 - 3610
  • [34] Novel conformationally constrained pyrazole derivatives as potential anti-cancer agents
    Kasiotis, Konstantinos M.
    Tzanetou, Evangelia N.
    Stagos, Dimitrios
    Fokialakis, Nikolas
    Koutsotheodorou, Eleni
    Kouretas, Dimitrios
    Haroutounian, Serkos A.
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2015, 70 (09): : 677 - 690
  • [35] Synthesis of Two Novel Copper (II) Complexes as Potential Inhibitors of HIV-1 Protease Enzyme: Experimental and Theoretical Investigations
    Hamlaoui, Meriem
    Hamlaoui, Ikram
    Damous, Maamar
    Belhocine, Youghourta
    Sbei, Najoua
    Ali, Fatima Adam Mohamed
    Alghamdi, Mashael A.
    Talab, Sarra
    Rahali, Seyfeddine
    Merazig, Hocine
    CRYSTALS, 2022, 12 (08)
  • [36] Experimental and theoretical investigation into the design of nickel(II) copper(II), and zinc(II) complexes substituted with pyrazole ligand
    Alenzi, Malak Khalaf
    Azam, Mohammad
    Al-Resayes, Saud I.
    Kansiz, Sevgi
    Camas, Anil Sazak
    Agurokpon, Danial Clement
    Louis, Hitler
    Kumar, Vikas
    Dege, Necmi
    Alam, Mahboob
    POLYHEDRON, 2024, 259
  • [37] Synthesis, characterization, and structural determination of copper(II) complexes with alkyl derivatives of hydroxybenzophenones
    Goncalves, Cristiane Batista
    Marinho, Maria Vanda
    Dias, Danielle Ferreira
    Dos Santos, Marcelo Henrique
    Martins, Felipe Terra
    Doriguetto, Antonio Carlos
    JOURNAL OF COORDINATION CHEMISTRY, 2017, 70 (05) : 898 - 913
  • [38] Synthesis, structures and magnetic properties of two copper(II) complexes with pyrazole and pivalate ligands
    Zhou, JH
    Liu, Z
    Li, YZ
    Song, Y
    Chen, XT
    You, XZ
    JOURNAL OF COORDINATION CHEMISTRY, 2006, 59 (02) : 147 - 156
  • [39] Characterization of Copper(II) and Zinc(II) Complexes of Peptides Mimicking the CuZnSOD Enzyme
    Szekely, Eniko
    Molnar, Mariann
    Lihi, Norbert
    Varnagy, Katalin
    MOLECULES, 2024, 29 (04):
  • [40] Copper(II) Complexes of 5-Fluoro-Salicylaldehyde: Synthesis, Characterization, Antioxidant Properties, Interaction with DNA and Serum Albumins
    Papadopoulos, Zisis
    Doulopoulou, Efstratia
    Zianna, Ariadni
    Hatzidimitriou, Antonios G.
    Psomas, George
    MOLECULES, 2022, 27 (24):