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Iron(III) and nickel(II) complexes of tetradentate thiosemicarbazones: Synthesis, structure, cytotoxicity, and lipophilicity
Author(s) -
Süleymanoğlu Mediha,
Kaya Büşra,
ErdemKuruca Serap,
Ülküseven Bahri
Publication year - 2019
Publication title -
journal of biochemical and molecular toxicology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.526
H-Index - 58
eISSN - 1099-0461
pISSN - 1095-6670
DOI - 10.1002/jbt.22383
Subject(s) - lipophilicity , chemistry , substituent , nickel , cytotoxicity , k562 cells , bromide , stereochemistry , context (archaeology) , cell culture , umbilical vein , in vitro , biochemistry , organic chemistry , biology , paleontology , genetics
Eighteen of the iron(III) and nickel(II) complexes with tetradentate thiosemicarbazidato ligands were synthesized and described, by analytical and spectroscopic methods. Two complexes as an example to the iron and nickel centered ones were crystallographically analyzed to confirm the molecular structures. Cytotoxic effects of the complexes on K562 chronic myeloid leukemia cells were determined by 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide assay. For comparison, human umbilical vein endothelial cells (HUVECs) was used as a noncancerous cell line. While four of the iron(III) complexes exhibited the antileukemic effect with 50% inhibition of cell growth (IC 50 ) values in the 3.4 to 6.9 μg/mL range on K562 cell line, the nickel(II) complexes showed no significant effect on both cell lines. The complexes Fe4, Fe5, and Fe6, bearing 4‐methoxy substituent exhibited relatively high antiproliferative activity on both cell lines. Complex Fe3 with 3‐methoxy and S ‐allyl groups exhibited a selectivity between K562 and HUVEC cells by IC 50 values of 6.9 and >10 μg/mL, respectively. Lipophilicity, a key parameter for bioavailability and oral administration, was found in the range of −0.3 and +1.3 that desired for drug active ingredients. The results were discussed in the context of a structure‐activity relationship.