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DNA-Binding and Anticancer Activity of Binuclear Gold(I) Alkynyl Complexes with a Phenanthrenyl Bridging Ligand.
- Source :
-
Molecules (Basel, Switzerland) [Molecules] 2020 Feb 25; Vol. 25 (5). Date of Electronic Publication: 2020 Feb 25. - Publication Year :
- 2020
-
Abstract
- 3,6-Diethynyl-9,10-diethoxyphenanthrene ( 4 ) was synthesized from phenanthrene and employed in the synthesis of the binuclear gold(I) alkynyl complexes (R <subscript>3</subscript> P)Au(C≡C-3-[C <subscript>14</subscript> H <subscript>6</subscript> -9,10-diethoxy]-6-C≡C)Au(PR <subscript>3</subscript> ) (R = Ph ( 5a ), Cy ( 5b )). The diyne 4 and complexes 5a and 5b were characterized by NMR spectroscopy, mass spectrometry, and elemental analysis. UV-Vis spectroscopy studies of the metal complexes and precursor diyne show strong p à p* transitions in the near UV region that red shift by ca. 50 nm upon coordination at the gold centers. The emission spectrum of 4 shows an intense fluorescence band centered at 420 nm which red shifts, slightly upon coordination of 4 to gold. Binding studies of 4 , 5a, and 5b against calf thymus DNA were carried out, revealing that 4, 5a, and 5b have >40% stronger binding affinities than the commonly used intercalating agent ethidium bromide. The molecular docking scores of 4 , 5a, and 5b with B-DNA suggest a similar trend in behavior to that observed in the DNA-binding study. Unlike the ligand 4 , promising anticancer properties for 5a and 5b were observed against several cell lines; the DNA binding capability of the precursor alkyne was maintained, and its anticancer efficacy enhanced by the gold centers. Such phenanthrenyl complexes could be promising candidates in certain biological applications because the two components (phenanthrenyl bridge and metal centers) can be altered independently to improve the targeting of the complex, as well as the biological and physicochemical properties.
- Subjects :
- Alkynes chemical synthesis
Alkynes chemistry
Alkynes pharmacology
Antineoplastic Agents chemical synthesis
Antineoplastic Agents pharmacology
Cell Line, Tumor
Cell Proliferation drug effects
Coordination Complexes chemical synthesis
Coordination Complexes chemistry
DNA antagonists & inhibitors
Drug Screening Assays, Antitumor
Ethidium chemistry
Gold chemistry
Humans
Ligands
Magnetic Resonance Spectroscopy
Molecular Docking Simulation
Neoplasms chemistry
Antineoplastic Agents chemistry
Coordination Complexes pharmacology
DNA chemistry
Neoplasms drug therapy
Subjects
Details
- Language :
- English
- ISSN :
- 1420-3049
- Volume :
- 25
- Issue :
- 5
- Database :
- MEDLINE
- Journal :
- Molecules (Basel, Switzerland)
- Publication Type :
- Academic Journal
- Accession number :
- 32106590
- Full Text :
- https://doi.org/10.3390/molecules25051033