Transition metal complexes of 6-mercaptopurine: Characterization, Theoretical calculation, DNA-Binding, molecular docking, and anticancer activity
Type
ArticleKAUST Department
Biological and Environmental Sciences and Engineering (BESE) DivisionBioscience Program
NMR
Date
2020-11-03Online Publication Date
2020-11-03Print Publication Date
2021-01Submitted Date
2020-05-29Permanent link to this record
http://hdl.handle.net/10754/665800
Metadata
Show full item recordAbstract
6-mercaptopurine (6-MP) is used for treating various cancers and autoimmune disorders. A few examples of transition metal complexes of 6-MP have been shown to enhance its anticancer activity, but many remain untested. We isolated five highly stable and colored metal complexes of 6-MP and confirmed their structures by elemental analysis, spectral, and thermal techniques. Infrared (IR) spectra revealed that 6-MP is a bidentate ligand that interacts through sulfur and pyrimidine nitrogen in a 1:2 (M:L) molar ratio. The magnetic susceptibility and electron paramagnetic resonance (EPR) spectra for the Cu(II) complex revealed an octahedral arrangement around the metal ion with strong covalent bonding. The fully optimized geometries of the metal structures obtained using density function theory (DFT)/B3LYP calculations were used to verify the structural and biological features. DNA titration revealed that the octahedral Cu(II) complex has a critical binding constant value of Kb = 8 × 105. Docking studies using three different cancer protein receptors were used to predict the biological applications of the synthesized drug-metal complexes. Finally, cytotoxicity assays against a myeloma cancer cell line (MM) and a colon cancer cell line (Caco-2) revealed favorable anticancer activity for the copper complex, exceeding that of the gold-standard chemotherapeutic cisplatin.Citation
Sharfalddin, A. A., Emwas, A., Jaremko, M., & Hussien, M. A. (2020). Transition metal complexes of 6-mercaptopurine: Characterization, Theoretical calculation, DNA-Binding, molecular docking, and anticancer activity. Applied Organometallic Chemistry. doi:10.1002/aoc.6041Publisher
WileyJournal
Applied Organometallic ChemistryDOI
10.1002/aoc.6041Additional Links
https://onlinelibrary.wiley.com/doi/10.1002/aoc.6041ae974a485f413a2113503eed53cd6c53
10.1002/aoc.6041
Scopus Count
Except where otherwise noted, this item's license is described as This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.