Synthesis, spectroscopic characterization, electrochemical behavior and computational analysis of mixed diamine ligand gold(III) complexes: Antiproliferative and in vitro cytotoxic evaluations against human cancer cell lines

Said S. Al-Jaroudi, M. Monim-ul-Mehboob, Muhammad Altaf, Abdulaziz A. Al-Saadi, Mohammed I.M. Wazeer, Saleh Altuwaijri, Anvarhusein A. Isab*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

The gold(III) complexes of the type [(DACH)Au(en)]Cl3, 1,2-Diaminocyclohexane ethylenediamine gold(III) chloride [where 1,2-DACH = cis-, trans-1,2- and S,S-1,2diaminocyclohexane and en = ethylenediamine] have been synthesized and characterized using various analytical and spectroscopic techniques including elemental analysis, UV-Vis and FTIR spectra; and solution as well as solid-state NMR measurements. The solid-state 13C NMR shows that 1,2-diaminocyclohexane (1,2-DACH) and ethylenediamine (en) are strongly bound to the gold(III) center via N donor atoms. The stability of the mixed diamine ligand gold(III) was determined by 1H and 13C NMR spectra. Their electrochemical behavior was studied by cyclic voltammetry. The structural details and relative stabilities of the four possible isomers of the complexes were also reported at the B3LYP/LANL2DZ level of theory. The coordination sphere of these complexes around gold(III) center adopts distorted square planar geometry. The computational study also demonstrates that trans-conformations is slightly more stable than the cis-conformations. The antiproliferative effects and cytotoxic properties of the mixed diamine ligand gold(III) complexes were evaluated in vitro on human gastric SGC7901 and prostate PC3 cancer cells using MTT assay. The antiproliferative study of the gold(III) complexes on PC3 and SGC7901 cells indicate that complex 1 is the most effective antiproliferative agent among mixed ligand based gold(III) complexes 1-3. The IC50 data reveal that the in vitro cytotoxicity of complexes 1 and 3 against SGC7901 cancer cells are fairly better than that of cisplatin.

Original languageEnglish
Pages (from-to)1115-1136
Number of pages22
JournalBioMetals
Volume27
Issue number6
DOIs
StatePublished - Dec 2014

Bibliographical note

Publisher Copyright:
© Springer Science+Business Media 2014.

Keywords

  • 1,2-Diaminocyclohexane (1,2-DACH)
  • Antiproliferative effect
  • Ethylenediamine (en)
  • Gastric cancer (SGC7901)
  • Gold(III) complex
  • In vitro cytototoxicity
  • Prostate cancer (PC3)

ASJC Scopus subject areas

  • Biomaterials
  • General Biochemistry, Genetics and Molecular Biology
  • General Agricultural and Biological Sciences
  • Metals and Alloys

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