Tuning the anticancer properties of Pt(ii) complexes via structurally flexible N-(2-picolyl)salicylimine ligands

Abstract

Three tridentate Schiff base ligands were synthesized from the reactions between 2-picolylamine and salicylaldehyde derivatives (3-ethoxy (OEt), 4-diethylamino (NEt2) and 4-hydroxy (OH)).

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“…Other complexes have different anions at nearly the same positions; the better cytotoxicity of some complexes compared to others could be due to one or more of the following factors: (1) the basic nature of the anion group, (2) the more lipophilic nature of the anion, and/or (3) the lower capability of the ligand H 3 TPBS hydrogen bonding (compared to the other ligand H 3 IPBS ). [ 64 ]…”

“…Other complexes have different anions at nearly the same positions; the better cytotoxicity of some complexes compared to others could be due to one or more of the following factors: (1) the basic nature of the anion group, (2) the more lipophilic nature of the anion, and/or (3) the lower capability of the ligand H 3 TPBS hydrogen bonding (compared to the other ligand H 3 IPBS). [64] A possible mechanism of action through which metal complexes manifest their antitumor activity is suggested depending on screening of previous similar studies. [63,64] These studies confirmed that the optimized structures of the B-DNA trimer adduct with the metal complexes showed hydrogen-bonding interactions between the ligands and nucleobases, affecting the inter-strand hydrogen bonding within the DNA, and highlighting the strong ability of the complexes to induce conformational changes in the DNA, leading to the activation of apoptotic cell death.…”

“…[64] A possible mechanism of action through which metal complexes manifest their antitumor activity is suggested depending on screening of previous similar studies. [63,64] These studies confirmed that the optimized structures of the B-DNA trimer adduct with the metal complexes showed hydrogen-bonding interactions between the ligands and nucleobases, affecting the inter-strand hydrogen bonding within the DNA, and highlighting the strong ability of the complexes to induce conformational changes in the DNA, leading to the activation of apoptotic cell death. For metal complexes with highly flexible multidentate ligands under study; the functional groups on the ligands are important in tuning their DNA binding/anticancer properties.…”

Tuning anticancer properties and DNA-binding of Pt(ii) complexes via alteration of nitrogen softness/basicity of tridentate ligands

“…We concluded that the intercalation mode of binding with DNA changes over time to covalent binding, with Pt-Py-NEt 2 exhibiting the largest apparent binding constant. 23 We explored the binding behavior of the other six complexes with ct-DNA by studying changes in (a) the fluorescence behavior of EB-DNA upon addition of platinum( ii ) complexes, and (b) the relative viscosity of ct-DNA upon addition of platinum( ii ) complexes. Ethidium bromide (EB) binds to DNA via intercalation, resulting in an intense fluorescent adduct with a wavelength maximum at 590 nm.…”

“…2 ), employing tridentate Schiff base ligands synthesized from 2-picolylamine and salicylaldehyde derivatives {3-ethoxy (OEt), 4-diethylamino (NEt 2 ) and 4-hydroxy (OH)}. 23 The DNA-binding studies of these platinum( ii ) complexes suggested fast intercalation followed by a slow shift towards covalent binding. Among the platinum( ii ) complexes, the ethoxy-containing complex exhibited the most promising IC 50 against both MCF-7 and HepG2 cell lines, and comparable to that observed for cisplatin.…”