Relationship Between Anticancer Activity and Stereochemistry of Saldach Ligands and their Iron(III) Complexes

Abstract

(R,R)-, (S,S)- and (R,S)-N,N'-bis(salicylidene)-1,2-diaminocyclohexane (saldach) and their iron(III) complexes were screened for anticancer activity against MCF-7 and MDA-MB 231 breast cancer as well as HT-29 colon carcinoma cells. Antiproliferative effects depended on the presence of the central atom iron but were independent on the configuration at the saldach ligand. While the free ligands were inactive, the iron(III) derivatives displayed anticancer activity within a concentration range of 1 to 5 microM irrespective of the used cell line. At 5 microM they were even more active than cis-platin. A mode of action comparable to cis-platin can be excluded because it is very likely that the DNA is not the primary target of [Fe(III) (saldach)] complexes.

Synthesis and Biological Activities of 2‐Amino‐thiazole‐5‐carboxylic Acid Phenylamide Derivatives

“…All target compounds were first evaluated for growth inhibitory activity against MCF‐7 and MDA‐MB 231 breast cancer and HT‐29 colon cancer cell lines according to a previous method 19. In addition to the target compounds 6a–f , 7a–f , gefitinib, dasatinib as well as the established cytostatic agent 5‐fluorouracil (5‐FU) were used as additional references.…”

“…The experiments were performed according to established procedures with some modifications 19. In 96‐well plates 100 µL of a cell suspension in culture medium (7500 cells/mL (MCF‐7 and MDA‐MB 231) or 3000 cells/mL (HT‐29)) were plated into each well and were incubated for three days under culture conditions.…”

Diastereoselective synthesis of tetraalkyl (R,R)-1,2-cyclohexylene-diamino-di-phosphonates bearing thiophene, furan and pyrrole moieties. Computational and experimental study on their formation

“…7,9 Interestingly, applications of salen compounds are not confined to catalysis, since some were found to have particular cytotoxic properties. 10 Considering that the phosphonic moiety provides distinct complexing 11 and pharmacological 12,13 properties to a molecule, and that 5-membered heteroaromatic rings are of importance for pharmacological activity of compounds, our studies have been focused on the aza-Pudovik reaction of variously modified salen-like imines. Thus, the most interesting aspect of this work concerns the stereochemistry of the reaction.…”

Effects of Metal Salophene and Saldach Complexes on Lymphoma and Leukemia Cells

“…Its use in pharmaceutical research increased with the observation made by Kidani et al in the early 1980s, namely that platinum complexes bearing DACH exhibit excellent antitumor activity which ultimately led to the development of oxaliplatin and its benefits for therapy 13–15. However, detailed information on the antileukemic activity of non‐platinum 1,2‐diaminocyclohexane and 1,2‐diarylethylenediamine complexes is still limited 16–18.…”

“…In the next step, the 1,2‐diarylethane moiety was replaced with cyclohexane or benzene in order to modulate the oxygen attachment, thus resulting in [ N , N ′‐bis(salicylidene)‐1,2‐phenylenediamine]iron(II/III) and ‐manganese(II/III) as well as [ rac ‐trans‐ N , N ′‐bis(salicylidene)‐1,2‐cyclohexanediamine]iron(II/II) complexes that induce cytotoxic effects on mammary and colon carcinoma cells (see C in Scheme ) 18, 23.…”