New copper (II) complexes bearing tryptophan-based Schiff bases and 2,2′-bipyridine: Crystal structures, DNA/BSA interactions and antiproliferative activities

被引:4
作者
Ozbagci, Duygu Inci [1 ]
Gultekin, Busra [1 ]
Aydin, Ipek [2 ]
Aydin, Rahmiye [1 ]
Ari, Ferda [2 ]
Zorlu, Yunus [3 ]
机构
[1] Bursa Uludag Univ, Fac Arts & Sci, Dept Chem, TR-16059 Bursa, Turkiye
[2] Bursa Uludag Univ, Fac Arts & Sci, Dept Biol, Bursa, Turkiye
[3] Gebze Tech Univ, Fac Sci, Dept Chem, Kocaeli, Turkiye
关键词
Antiproliferative activity; cu (II) complexes; DNA/BSA interactions; radical scavenging activity; Schiff base; tryptophan; HUMAN SERUM-ALBUMIN; DNA-BINDING; ANTICANCER ACTIVITY; OXIDATIVE STRESS; FREE-RADICALS; ACID; FLUORESCENCE; CLEAVAGE; LIGAND; ANTIOXIDANT;
D O I
10.1002/aoc.7369
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
[Cu(5-ClSal-Trp)(bpy)]center dot CH3OH (1) and [Cu(3,5-ClSal-Trp)(bpy)]center dot H2O (2) (5-ClSal-Trp: Schiff base derived from 5-chlorosalicylaldehyde and tryptophan, 3,5-ClSal-Trp: Schiff base derived from 3,5-dichlorosalicylaldehyde and tryptophan, bpy: 2,2 '-bipyridine) have been synthesized and analyzed by CHN analysis, FTIR, electronic absorption spectroscopy, ESI-MS and XRD techniques. Interaction of the complexes with biomolecules {calf thymus DNA (CT-DNA) and bovine serum albumin (BSA)} has been researched by fluorescence and electronic absorption spectroscopy. The results show that the complexes can bind via a moderate intercalation binding mode. According to the results obtained with both methods, the logKb and logKSV values of the complexes were found to be very close to each other. BSA quenching mechanism was found to be static. The results showed that the interaction between the complexes and BSA is driven by the hydrogen bond and van der Waals interaction. Additionally, the r values of the complexes (the complex 1 = 0.59 nm and the complex 2 = 0.53 nm) calculated from FRET theory suggested that the distance between the complexes (acceptor) and BSA (donor) is quite close. The complexes exhibited free radical scavenging activity compared to the standard antioxidant beta-carotene and catechin. Antiproliferative efficiency of the complexes on both breast cancer cells (MCF-7 and MDA-MB-231) were also researched using the Sulforhodamine B (SRB) viability assay. It was found that the complex 1 (IC50 = 10.99 mu M) exhibited higher cytotoxicity than cisplatin (IC50 = 15.6 mu M) against MDA-MB-231 cell line. Additionally, intracellular reactive oxygen species (ROS) formation was determined by dihydroethidium (DHE) fluorescent staining. N-acetylcysteine (NAC) was used as an efficient reactive oxygen species (ROS) scavenger. It was observed that newly synthesized Cu (II) complexes exhibited anti-growth potential in human breast cancer cells. Additionally, it was determined that the complexes induced reactive oxygen species (ROS) formation in cells in a dose-dependent manner. A potent drug candidature of two new copper (II) complexes have been synthesized and characterized by CHN analysis, FTIR, ESI-MS and XRD techniques. The complexes have been analyzed biomolecular interactions by spectroscopic methods. Furthermore, radical scavenging and antiproliferative activities of the complexes were also investigated. image
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页数:16
相关论文
共 73 条
[21]   Synthesis, structure, and anticancer studies of Cu (II) and Ni (II) complexes based on (5-chlorosalicylaldehyde)-4-aminoantipyrine Schiff base [J].
Hu, Jing ;
Luo, Yun ;
Hou, Min ;
Qi, Jia Jia ;
Liang, Li Li ;
Li, Wen Ge .
APPLIED ORGANOMETALLIC CHEMISTRY, 2022, 36 (10)
[22]   Cu(ii) complex with auxin (3-indoleacetic acid) and an aromatic planar ligand: synthesis, crystal structure, biomolecular interactions and radical scavenging activity [J].
Inci, Duygu ;
Aydin, Rahmiye ;
Zorlu, Yunus .
EUROPEAN BIOPHYSICS JOURNAL WITH BIOPHYSICS LETTERS, 2021, 50 (05) :771-785
[23]   Investigation on water soluble copper(II) mono-anionic glutamate complexes with planar aromatic ligands: synthesis, crystal structures, biomacromolecular interactions and radical scavenging activities [J].
Inci, Duygu ;
Aydin, Rahmiye ;
Zorlu, Yunus .
JOURNAL OF MOLECULAR STRUCTURE, 2021, 1225
[24]   NOO-type tridentate Schiff base ligand and its one-dimensional Cu(II) coordination polymer: Synthesis, crystal structure, biomacromolecular interactions and radical scavenging activities [J].
Inci, Duygu ;
Aydin, Rahmiye ;
Zorlu, Yunus .
INORGANICA CHIMICA ACTA, 2021, 514
[25]   A new ternary Cu (II) complex with 4,7-dimethyl-1,10-phenanthroline and NOO-type tridentate Schiff base ligand: Synthesis, crystal structure,biomacromolecular interactions, and radical scavenging activities [J].
Inci, Duygu .
APPLIED ORGANOMETALLIC CHEMISTRY, 2020, 34 (12)
[26]   Interactions of human serum albumin with chlorogenic acid and ferulic acid [J].
Kang, J ;
Liu, Y ;
Xie, MX ;
Li, S ;
Jiang, M ;
Wang, YD .
BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 2004, 1674 (02) :205-214
[27]   MODELS FOR METHEMOCYANIN DERIVATIVES - STRUCTURAL AND SPECTROSCOPIC COMPARISONS OF RELATED AZIDO-COORDINATED (N3-) MONONUCLEAR AND DINUCLEAR COPPER(II) COMPLEXES [J].
KARLIN, KD ;
COHEN, BI ;
HAYES, JC ;
FAROOQ, A ;
ZUBIETA, J .
INORGANIC CHEMISTRY, 1987, 26 (01) :147-153
[28]   Cu(II) complex of S-b enzyl- ?-N-(2-methoxyb enzylmethylene)dithiocarbazate: Synthesis, DFT calculations, cell cytotoxicity assay and DNA binding studies [J].
Khirudin, Nurul Natasya Muhamad ;
Yusof, Enis Nadia Md ;
Arshad, Suhana ;
Sirat, Siti Syaida .
JOURNAL OF MOLECULAR STRUCTURE, 2023, 1283
[29]   Fluorescence studies on PAMAM dendrimers interactions with bovine serum albumin [J].
Klajnert, B ;
Bryszewska, M .
BIOELECTROCHEMISTRY, 2002, 55 (1-2) :33-35
[30]  
Lakowicz J.R., 1999, PRINCIPLES FLUORESCE, V2nd