The new metal-based compound from anticancer drug cytarabine: Spectral, electrochemical, DNA-binding, antiproliferative effect and in silico studies

Özge Güngör, Mustafa Çeşme, M. Emin Çınar, Ayşegül Gölcü*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Within the scope of this study, new dimeric zinc(II)-based analog of Cytarabine (Cyt) (an anticancer drug) was synthesized by considering different analytical conditions and characterized using analytical and spectroscopic methods. The proposed structure of this dimeric metal-based compound was characterized as Zn2(Cyt)2Cl4. Geometry optimizations of the compound were performed in a vacuum without any symmetry constraints at density functional theory (DFT) level using the Gaussian 09 package program. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) have been given a DFT calculation section. Thermal behavior of the compound was investigated by thermal gravimetric analysis (TGA) and differential thermal analysis (DTA) techniques. This compound was transformed into metal oxides after thermal degradation. The electrochemical properties of both ligand and Zn2(Cyt)2Cl4 were analyzed by Cyclic Voltammetry (CV) using glassy carbon electrode at different pH values. Also, the interactions of Cyt and Zn2(Cyt)2Cl4 compound with fish sperm double strain deoxyribonucleic acid (FSdsDNA) were investigated by measuring their binding constant (Kb) to FSdsDNA. The results showed that Cyt and Zn2(Cyt)2Cl4 metal-based compound could bind to FSdsDNA through groove-binding mode into the DNA helix. The antiproliferative activities of Cyt and the obtained new metal-based compound were investigated using three different concentrations on the HeLa cell line and the obtained values were compared with the commercially available metal-based drugs cisplatin, oxaliplatin, and carboplatin.

Original languageEnglish
Pages (from-to)532-543
Number of pages12
JournalJournal of Molecular Structure
Volume1193
DOIs
Publication statusPublished - 5 Oct 2019

Bibliographical note

Publisher Copyright:
© 2019

Funding

The authors wish to thank TUBITAK (Project No: 112T721 , COST/CM1105 ), Kahramanmaraş Sütçü İmam University (Project No: 2015/1-68YLS ) for the financial support and Prof. Dr. İbrahim Demirtaş (Karatekin University, Chemistry Department) for cell culture studies. We are indebted to the High-Performance-Computing (HPC) Linux Cluster HorUS of University of Siegen for the computer time provided. The authors wish to thank TUBITAK (Project No: 112T721, COST/CM1105), Kahramanmaraş Sütçü İmam University (Project No: 2015/1-68YLS) for the financial support and Prof. Dr. İbrahim Demirtaş (Karatekin University, Chemistry Department) for cell culture studies. We are indebted to the High-Performance-Computing (HPC) Linux Cluster HorUS of University of Siegen for the computer time provided.

FundersFunder number
TUBITAK112T721, COST/CM1105
Kansas State University2015/1-68YLS
Kahramanmaraş Sütçü Imam Üniversitesi

    Keywords

    • Antiproliferative effect
    • Cytarabine
    • DFT
    • DNA binding
    • Metal-based compound
    • xCELLigence

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