Synthesis, CT-DNA Binding, and Cytotoxic Activity of Copper(Ⅱ) Complex {[Cu(OMBA)2]2·(DMF)2}

Abstract

Abstract: In this paper, a copper(Ⅱ) complex {[Cu(OMBA)₂]₂·(DMF)₂} (OMBA=o-methylbenzoic acid, DMF = N,N-dimethylformamide) was synthesized. The structure of the complex was characterized using elemental analysis, infrared (IR) and X-ray single crystal diffraction. The complex belongs to triclinic, P1 space group, with a=1.037 0(5) nm, b=1.053 6(4) nm, c=1.105 9(5) nm, α=62.737(6)°, β=73.355(7)°, γ=63.231(7)°, Z=1, D_c=1.416 g·cm^-3, F(000)=422 unit cell parameters. The final R₁=0.051 5, wR₂=0.140 4. The interaction between CT-DNA (calf thymus DNA) and the complex was evaluated by UV-Vis, fluorescence spectroscopy, and viscometry. When the complex bound to CT-DNA, the binding constant K_b=939.61 L·mol^-1, K_sv=3.00×10³ L·mol^-1, and K_q=3.00×10¹¹ L·mol^-1·s^-1. The complex quenched the intrinsic fluorescence of CT-DNA via static quenching, K_a=5.38×10³ L·mol^-1, n=1. The complex has anti-proliferation effects on A549, Hela and HepG2.

Key words: copper(Ⅱ), complex, synthesis, DNA binding, cytotoxic, antitumor activity, DNA replication

CLC Number:

O614.1

ZENG Zhenfang, CAI Jiehui, HUANG Qiuping, WEI Youhuan, CHEN Limiao, HUANG Qiuchan. Synthesis, CT-DNA Binding, and Cytotoxic Activity of Copper(Ⅱ) Complex {[Cu(OMBA)₂]₂·(DMF)₂}[J]. JOURNAL OF SYNTHETIC CRYSTALS, 2021, 50(12): 2300-2306.

References

[1] 徐中轩,李立凤,徐仕菲,等.2个具有四重穿插框架和dia网络的5-羟甲基间苯二甲酸类Zn(Ⅱ)配位聚合物的合成、结构和荧光性质[J].无机化学学报,2020,36(11):2087-2092.
XU Z X, LI L F, XU S F, et al. Two zinc(Ⅱ) coordination polymers with 4-fold interpenetration frameworks and dia nets based on 5-(hydroxymethyl) isophthalic acid: syntheses, crystal structures and fluorescence properties[J]. Chinese Journal of Inorganic Chemistry, 2020, 36(11): 2087-2092(in Chinese).
[2] TIAN J X, CHEN Y, VAYER M, et al. Exploring the limits of π-acid catalysis using strongly electrophilic main group metal complexes: the case of zinc and aluminium[J]. Chemistry - A European Journal, 2020, 26(56): 12831-12838.
[3] SANDOVAL-PAUKER C, MOLINA-AGUIRRE G, PINTER B. Status report on copper (I) complexes in photoredox catalysis; photophysical and electrochemical properties and future prospects[J]. Polyhedron, 2021, 199: 115105.
[4] 王子璇,王亚旭,刘晓莉,等.氰根桥连手性Fe^Ⅲ-Cu^Ⅱ-Ln^Ⅲ异三金属配合物的合成、结构和磁性研究[J].南开大学学报(自然科学版),2021,54(3):98-107.
WANG Z X, WANG Y X, LIU X L, et al. Cyanide-bridged chiral Fe^Ⅲ-Cu^Ⅱ-Ln^Ⅲ heterotrimetallic complexes: synthesis, structures and magnetic properties[J]. Acta Scientiarum Naturalium Universitatis Nankaiensis, 2021, 54(3): 98-107(in Chinese).
[5] WANG X, WANG L Y, WU S Y, et al. Ligand effect of two Dy(Ⅲ) complexes on single-molecule magnetism[J]. Polyhedron, 2020, 184: 114553.
[6] IIMORI T, SUGAWA H, UCHIDA N. Bright solvent-free luminescent liquid with magnetism composed of a thiocyanate complex of Ce(Ⅲ)[J]. The Journal of Physical Chemistry B, 2020, 124(38): 8317-8322.
[7] 宋发辉,祝心德,黎红梅,等.硫代磷酰肼席夫碱及其金属配合物的合成与生物活性[J].华中师范大学学报(自然科学版),2003,37(1):51-54.
SONG F H, ZHU X D, LI H M, et al. Synthesis, characterization and biological activities of the Schiff base of phosphorohydrazonothionate with 5-Br-salicylaldehyde and its metal complexes[J]. Journal of Central China Normal University (Natural Sciences), 2003, 37(1): 51-54(in Chinese).
[8] SULA A, MOLNAR E, WALLACE B A. The insecticide fenvalerate binds to NavMs sodium channels, making them a suitable template for modelling structures of housefly-insecticide complexes[J]. Biophysical Journal, 2019, 116(3): 389a-390a.
[9] SANTOS-V C D Jr, MARTÍNEZ L C, PLATA-RUEDA A, et al. Exposure to spinosad induces histopathological and cytotoxic effects on the salivary complex of the non-target predator Podisus nigrispinus[J]. Chemosphere, 2019, 225: 688-695.
[10] KAHYA N, GÖLCÜ A, ERIM F B. Barium ion cross-linked alginate-carboxymethyl cellulose composites for controlled release of anticancer drug methotrexate[J]. Journal of Drug Delivery Science and Technology, 2019, 54: 101324.
[11] TIWARI P, RANJAN R, DAS K, et al. Exfoliation and gelation in laponite-carboxymethyl cellulose complexes and its application in sustained drug release[J]. Polymer Bulletin, 2020, 77(10): 5389-5406.
[12] BATTISTIN F, BALDUCCI G, WEI J H, et al. Photolabile Ru model complexes with chelating diimine ligands for light-triggered drug release[J]. European Journal of Inorganic Chemistry, 2018, 2018(13): 1469-1480.
[13] PHAM C T, PHAM T T, NGUYEN H H, et al. Syntheses, structures, and bioactivities evaluation of some transition metal complexes with 4, 4'-diacetylcurcumin[J]. Zeitschrift Für Anorganische Und Allgemeine Chemie, 2020, 646(11/12): 495-499.
[14] 刘启雁,蔡戴宏,戚永育,等.司帕沙星及均三嗪衍生物铜(Ⅱ)配合物与DNA作用及其抗肿瘤活性[J].化学学报,2020,78(3):263-270.
LIU Q Y, CAI D H, QI Y Y, et al. DNA interaction and antitumor activity of A copper(Ⅱ) complex containing sparfloxacin and triazine derivatives[J]. Acta Chimica Sinica, 2020, 78(3): 263-270(in Chinese).
[15] CAI L X, YU C T, BA L K, et al. Anticancer platinum-based complexes with non-classical structures[J]. Applied Organometallic Chemistry, 2018, 32(4): e4228.
[16] CARRASCO A C, RODRÍGUEZ-FANJUL V, HABTEMARIAM A, et al. Structurally strained half-sandwich iridium(Ⅲ) complexes as highly potent anticancer agents[J]. Journal of Medicinal Chemistry, 2020, 63(8): 4005-4021.
[17] JABEEN E, JANJUA N K, AHMED S, et al. DNA binding interaction studies of flavonoid complexes of Cu(Ⅱ) and Fe(Ⅱ) and determination of their chemotherapeutic potential[J]. Inorganica Chimica Acta, 2019, 496: 119048.
[18] 黄俊腾,张阳,王湘利,等.磺酸咔咯及其镓(Ⅲ)配合物与DNA的相互作用和光核酸酶活性[J].无机化学学报,2013,29(8):1649-1656.
HUANG J T, ZHANG Y, WANG X L, et al. DNA binding and photonuclease activity of sulfonated corrole and its gallium(Ⅲ) complex[J]. Chinese Journal of Inorganic Chemistry, 2013, 29(8): 1649-1656(in Chinese).
[19] 史蕾,杨文聪,曾淑莹,等.咔咯钴(Ⅲ)配合物与DNA的相互作用及抗肿瘤活性[J].高等学校化学学报,2016,37(6):1059-1068.
SHI L, YANG W C, ZENG S Y, et al. DNA-binding and anti-tumor activities of cobalt corrole complexes[J]. Chemical Journal of Chinese Universities, 2016, 37(6): 1059-1068(in Chinese).
[20] 郁慧,程宁宁,许东芳,等.稀土-吡唑啉酮-2,6-吡啶二羧酸配合物的合成、表征及其性质研究[J].中国稀土学报,2014,32(3):328-337.
YU H, CHENG N N, XU D F, et al. Synthesis, characterization and properties of some rare earth complexes with pyrazolone and 2, 6-pyridinecarboxylic acid[J]. Journal of the Chinese Society of Rare Earths, 2014, 32(3): 328-337(in Chinese).
[21] 吉燕华,杨清泉,郭奇峰,等.酪氨酸-钴配合物的合成及性能[J].合成化学,2020,28(9):806-809.
JI Y H, YANG Q Q, GUO Q F, et al. Synthesis and properties of tyrosine-cobalt complex[J]. Chinese Journal of Synthetic Chemistry, 2020, 28(9): 806-809(in Chinese).

Synthesis, CT-DNA Binding, and Cytotoxic Activity of Copper(Ⅱ) Complex {[Cu(OMBA)₂]₂·(DMF)₂}

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