TY - JOUR
T1 - Some new morpholine-based Schiff-base complexes; Synthesis, characterization, anticancer activities and theoretical studies
AU - Rezaeivala, Majid
AU - Ahmadi, Musa
AU - Captain, Burjor
AU - Bayat, Mehdi
AU - Saeidirad, Mahdi
AU - Şahin-Bölükbaşı, Serap
AU - Yıldız, Batuhan
AU - Gable, Robert William
N1 - Funding Information:
We thank the Iran National Science Foundation ( INSF ) (grant no. 97005780 ), Hamedan University of Technology , and the University of Miami for financial support. Anticancer activity studies were done at Sivas Cumhuriyet University Advanced Technology Application and Research Center (SCUTAM).
PY - 2020/12/1
Y1 - 2020/12/1
N2 - A new morpholine-based ligand (2) has been prepared from condensation of a branched amine containing morpholine, N1-(3-morpholinopropyl)-N1-((pyridine-2-yl)methyl)ethane-1,2-diamine (1), and salicylaldehyde. Metal complexes were synthesized by reaction of the ligand and metal salts in ethanol and the resulting products were characterized by elemental analyses, ESI-MS, 1H and 13C NMR spectra, infrared, and UV–Vis spectroscopy. The structure of two complexes including [ZnL](ClO4) (3) and [NiHL](ClO4)·H2O (6a) have been determined by single crystal X-ray structural analysis, showing that the metal atoms are in a distorted trigonal bipyramidal (Zn) and a square planar (Ni) environment, respectively. Compounds were assayed for their anticancer activities against a panel of human tumor cell lines, including breast cancer cells (MCF-7, MDA-MB-231), prostate cancer cells (PC-3) and human normal lung fibroblast cells (WI-38). Compounds 1, 2, 7, 9 and 10 demonstrated lower activity against MCF-7, MDA-MB-231 and PC-3 cell lines (IC50s > 100 µM) compared to other compounds. It has been shown that complexes 3, 4, 5, 6, and 8 possess different anticancer potentials against MCF-7, MDA-MB-231 and PC-3. More importantly, it was observed that compounds 3, 5 and 6 demonstrate a lower activity against WI-38 normal cell line than they do against cancer cell lines. Our results indicated that compound 8 has the highest anticancer activity on cancer cell lines, and the reason for that can be attributed to the presence of a silver atom in the complex. These results clearly showed that the anticancer activities of these compounds depend on the type of metal in the complex as well as the tested cancer cell line. Furthermore, the geometries of the [ML]n+ (M = Zn2+, Cd2+, Mn2+, Cu2+, Ni2+, Ag+, Fe3+ and Co2+, n = 0, 1, 2) complexes have been optimized at the BP86/def2-SVP level of theory. The nature of M → L bonds in [ML]n+ complexes have been studied with the help of NBO analysis.
AB - A new morpholine-based ligand (2) has been prepared from condensation of a branched amine containing morpholine, N1-(3-morpholinopropyl)-N1-((pyridine-2-yl)methyl)ethane-1,2-diamine (1), and salicylaldehyde. Metal complexes were synthesized by reaction of the ligand and metal salts in ethanol and the resulting products were characterized by elemental analyses, ESI-MS, 1H and 13C NMR spectra, infrared, and UV–Vis spectroscopy. The structure of two complexes including [ZnL](ClO4) (3) and [NiHL](ClO4)·H2O (6a) have been determined by single crystal X-ray structural analysis, showing that the metal atoms are in a distorted trigonal bipyramidal (Zn) and a square planar (Ni) environment, respectively. Compounds were assayed for their anticancer activities against a panel of human tumor cell lines, including breast cancer cells (MCF-7, MDA-MB-231), prostate cancer cells (PC-3) and human normal lung fibroblast cells (WI-38). Compounds 1, 2, 7, 9 and 10 demonstrated lower activity against MCF-7, MDA-MB-231 and PC-3 cell lines (IC50s > 100 µM) compared to other compounds. It has been shown that complexes 3, 4, 5, 6, and 8 possess different anticancer potentials against MCF-7, MDA-MB-231 and PC-3. More importantly, it was observed that compounds 3, 5 and 6 demonstrate a lower activity against WI-38 normal cell line than they do against cancer cell lines. Our results indicated that compound 8 has the highest anticancer activity on cancer cell lines, and the reason for that can be attributed to the presence of a silver atom in the complex. These results clearly showed that the anticancer activities of these compounds depend on the type of metal in the complex as well as the tested cancer cell line. Furthermore, the geometries of the [ML]n+ (M = Zn2+, Cd2+, Mn2+, Cu2+, Ni2+, Ag+, Fe3+ and Co2+, n = 0, 1, 2) complexes have been optimized at the BP86/def2-SVP level of theory. The nature of M → L bonds in [ML]n+ complexes have been studied with the help of NBO analysis.
KW - Anticancer activity
KW - Morpholine-based complex
KW - Schiff-base
KW - Theoretical studies
KW - Tripodal amine
KW - X-ray
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U2 - 10.1016/j.ica.2020.119935
DO - 10.1016/j.ica.2020.119935
M3 - Article
AN - SCOPUS:85089215578
VL - 513
JO - Inorganica Chimica Acta
JF - Inorganica Chimica Acta
SN - 0020-1693
M1 - 119935
ER -