title: Synthesis, characterization and theoretical calculations of (1,2-diaminocyclohexane)(1,3-diaminopropane)gold(III) chloride complexes: in vitro cytotoxic evaluations against human cancer cell lines.
abstract: The gold(III) complexes of the type (1,2-diaminocyclohexane)(1,3-diaminopropane)gold(III) chloride, [(DACH)Au(pn)]Cl3, [where DACH = cis-, trans-1,2- and S,S-1,2-diaminocyclohexane and pn = 1,3-diaminopropane] have been synthesized and characterized using various spectroscopic and analytical techniques including elemental analysis, UV-Vis and FTIR spectroscopy; solution as well as solid-state NMR measurements. The solid-state (13)C NMR shows that 1,2-diaminocyclohexane (1,2-DACH) and 1,3-diaminopropane (pn) are strongly bound to the gold(III) center via N donor atoms. The stability of the mixed diamine ligand gold(III) was checked by UV-Vis spectroscopy and NMR measurements. The molecular structure of compound 1 (containing cis-1,2-DACH) was determined by X-ray diffraction analysis. The structure of 1 consists of [(cis-DACH)Au(pn)](3+) complex ion and chloride counter ions. Each gold atom in the complex ion adopts a distorted square-planar geometry. The structural details and relative stabilities of the four possible isomers of the complexes were also estimated at the B3LYP/LANL2DZ level of theoretical calculations. The computational study demonstrates that trans- conformations are slightly more stable than the cis- conformations. The antiproliferative effects and cytotoxic properties of the mixed 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 3 (containing 1S,2S-(+)-1,2-(DACH)) is the most effective antiproliferative agent. The IC50 data reveal that the in vitro cytotoxicity of complex 3 against SGC7901 cancer cells manifested similar and very pronounced cytotoxic effects with respect to cisplatin. Moreover, the electrochemical behavior, and the interaction of complex 3 with two well-known model proteins, namely, hen egg white lysozyme and bovine serum albumin is also reported.
authors.affiliation: Department of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran, 31261, Saudi Arabia.
authors.forename: Said S
authors.initials: SS
authors.lastname: Al-Jaroudi
authors.affiliation: Center of Research Excellence in Nanotechnology (CENT), King Fahd University of Petroleum and Minerals, Dhahran, 31261, Saudi Arabia.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Altaf
authors.affiliation: Department of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran, 31261, Saudi Arabia.
authors.forename: Abdulaziz A
authors.initials: AA
authors.lastname: Al-Saadi
authors.affiliation: Department of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran, 31261, Saudi Arabia.
authors.forename: Abdel-Nasser
authors.initials: AN
authors.lastname: Kawde
authors.affiliation: Clinical Research Laboratory, SAAD Research Development Center, SAAD Specialist Hospital, Al-Khobar, 31952, Saudi Arabia.
authors.forename: Saleh
authors.initials: S
authors.lastname: Altuwaijri
authors.affiliation: Department of Chemistry, University of Engineering and Technology, Lahore, 54890, Pakistan.
authors.forename: Saeed
authors.initials: S
authors.lastname: Ahmad
authors.affiliation: Department of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran, 31261, Saudi Arabia. aisab@kfupm.edu.sa.
authors.forename: Anvarhusein A
authors.initials: AA
authors.lastname: Isab
mesh_terms: D000818:Animals; D002417:Cattle; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002645:Chickens; D002712:Chlorides / Q000138:chemical synthesis / Q000737:chemistry; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D003514:Cyclohexylamines / Q000138:chemical synthesis / Q000737:chemistry*; D003959:Diamines / Q000138:chemical synthesis / Q000737:chemistry*; D006046:Gold / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D009113:Muramidase / Q000737:chemistry; D012710:Serum Albumin, Bovine / Q000737:chemistry; D014466:Ultraviolet Rays; D014961:X-Ray Diffraction
chemical_list: D002712:Chlorides; D056831:Coordination Complexes; D003514:Cyclohexylamines; D003959:Diamines; D012710:Serum Albumin, Bovine; D006046:Gold; C030435:1,2-cyclohexanediamine; C009475:trimethylenediamine; D009113:Muramidase
keywords: 1,2-Diaminocyclohexane; 1,3-Diaminopropane; Anticancer; Gastric carcinogenesis (SGC-7901); Gold(III) complex; Prostate cancer (PC-3)