Spectroscopic and single‐crystal X‐ray diffraction studies of enantiomeric copper(II) Schiff base one‐dimensional coordination polymers with 4‐(2‐aminoethyl)benzenesulfonamide appendage: Comprehensive biological evaluation (DNA binding, cleavage, superoxide dismutase mimetic activity, topoisomerase I inhibition and cytotoxicity)

Abstract

New chiral Cu(II)‐based one‐dimensional coordination polymers [l‐C25H27CuN3O6S] (1a) and [d‐C25H27CuN3O6S] (1b) were designed and synthesized by in situ reaction of Schiff base (o‐vanillin and l‐/d‐phenylalanine) and appended ligand 4‐(2‐aminoethyl)benzenesulfonamide incorporated with Cu(II) ion. The enantiomeric complexes 1a and 1b were fully characterized using various spectroscopic techniques and single‐crystal X‐ray diffraction studies. The enantiomeric analogues 1a and 1b crystallized in chiral monoclinic P21 space group with z = 2 exhibiting a distorted square pyramidal environment around Cu(II) metal centre coordinated to N2O3 donor atoms with apical position occupied by adjacent bridging carboxylate oxygen, resulting in one‐dimensional polymeric chain structures. Comprehensive biological studies of 1a and 1b (DNA binding, superoxide dismutase (SOD), topoisomerase I and cytotoxic activity) were performed which revealed that 1a showed better prospects as a therapeutic drug candidate as compared to 1b as quantified by their comparative DNA binding (Kb, K and Ksv values), SOD mimetic activity (IC50 values of 0.160 and 0.198, respectively) and anticancer properties.

Synthesis, DNA-binding abilities, and in vitro antitumor activity of water-soluble copper porphyrin and its Schiff-base complexes

“…These spectral characteristics suggested that CuP-2–3 could interact with ct-DNA through insertion. 19,20 To quantify the binding affinities of the interactions between ct-DNA and CuP-1–3 , the intrinsic binding constant ( K b ) values of all porphyrin complexes with ct-DNA were determined based on the Stern–Volmer equation: 21 [DNA]/( ε a − ε f ) = [DNA]/( ε b − ε f ) + 1/[ K b ( ε b − ε f )], where [DNA] is the concentration of ct-DNA in base pairs, ε a is the apparent absorption coefficient A obsd /[Por] (where [Por] is the concentration of porphyrin), ε f is the extinction coefficient of free porphyrin, and ε b is the extinction coefficient of the porphyrin complex in fully-bound form. As shown in Table 1, the intrinsic binding constant ( K b ) values were calculated to be 2.794 × 10 4 M −1 , 2.378 × 10 4 M −1 , and 2.299 × 10 4 M −1 for the test complexes CuP-1–3 , respectively.…”

Transition Metal Complexes with Tridentate Schiff Bases (O N O and O N N) Derived from Salicylaldehyde: An Analysis of Their Potential Anticancer Activity

“…The best result of Cu‐19 was also in the cell line MCF‐7 (GI 50 value=45.79 μg mL −1 and TGI value=87.04 μg mL −1 ), while in the other four lines the result was very weak. Neither compound was able to exceed the activity achieved by the reference drug in all cell lines (GI 50 <10 μg mL −1 and TGI<10 μg mL −1 ) [65] …”

“…Neither compound was able to exceed the activity achieved by the reference drug in all cell lines (GI 50 < 10 μg mL À 1 and TGI < 10 μg mL À 1 ). [65] VB 6 is known to be necessary for the survival and proliferation of cancer cells since they require increased uptake to diffuse it through membrane carriers. On the other hand, BODIPY has a selective ability to locate mitochondria, as well as a strong emissive property and photosensitising ability that is increased by the inclusion of heavy atoms such as iodine.…”

“…Neither compound was able to exceed the activity achieved by the reference drug in all cell lines (GI 50 <10 μg mL −1 and TGI<10 μg mL −1 ). [65] …”

Synthesis, spectroscopic characterization and in vitro antibacterial and antiviral activities of novel silver(I) complexes with mafenide and ethyl-mafenide

“…Zafsan et al reported the synthesis of a pair of enantiomeric copper(II) complex with eMaf and a Schiff base. Biological studies showed that both complexes presented antitumor activity, whereas the l form showed to be more efficient toward Topoisomerase I (Topo I) and superoxide dismutase (SOD) enzymes [29].…”