Novel anticancer and antibacterial organometallic polymer based on ferrocene as a building block and xanthone bioactive scaffolds: Synthesis, characterization, and biological study

Abstract

Poly(azine ferrocene‐triazole‐xanthone amide) (PAFTXA) was successfully synthesized from azine ferrocene bisacetylene (AFcB) and 2,7‐(N‐2‐azidoacetamide) xanthone (NAzX) by using click chemistry protocol. In this paper, innovative AFcB moiety incorporated in this procedure as a monomer. This monomer was prepared in three steps from ferrocene scaffold, and the synthetic processes were discussed in details. Characterization of the synthesized novel intermediate materials, monomer, and the resulting polymer was performed by nuclear magnetic resonance, Fourier transform infrared, thermal gravimetric analysis, differential scanning calorimetry, and ultraviolet‐visible spectrophotometer. In addition, the in vitro antibacterial activity of the polymer was appraised against Gram‐positive and Gram‐negative bacteria by using minimum inhibitory concentration method. Moreover; antitumoral effects of synthesized polymer were evaluated on Hela, MCF‐7, and Saos cancer cell lines and compared with normal fibroblast cell line by means of 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide assay. Promising antiproliferative effects were detected on both epitheloid and mesenchymal cancer cell lines depending on PAFTXA concentration and time. Survey on its characteristic features revealed the proficiencies of our prepared biomaterial such as its high thermal stability as well as valuable antitumoral and antibacterial capabilities that make it an appreciable candidate for further bioapplications.

Ferrocene-triazole conjugates: do we know why they are biologically active?

“…The 1,5-disubstitution of the 1H-1,2,3-triazole ring could be considered as a worthwhile option since certain conjugates Scheme 4 Click-assembled polymer 11 composed of ferrocene, azine and xanthone scaffolds as potential pharmacophores. 64 .…”

“…A different approach was adopted by Lakouraj et al who obtained a ferrocene-embedded polymer 11 containing azine and xanthone scaffolds as potential pharmacophores (Scheme 4). 64 A click-chemistry approach was used to assemble the target polymer 11 from monomers 9 and 10 . Polymer 11 showed antibacterial activity towards E. coli , P. aeruginosa , K. pneumoniae , B. subtilis , and S. aureus with a MIC concentration of 125 μg mL −1 and MBC concentrations ranging from 250 to 500 μg mL −1 .…”

Electrospun nanofibers fromferrocene‐containingmultiblock copolymers prepared viaRAFTpolymerization withF127modified precursor

“…Ferrocene and ferrocene derivatives have been focused on attributed to their unique applications such as electrochemistry, 10 biosensors, 10–11 molecular recognition, 11–12 catalysis, 13–14 fertilizers, 15 magnetism, 16 cancer treatment 17 and others 18–19 . Especially, ferrocene‐bearing polymers were of interest in the excellent combination of redox, mechanical, semi‐conductive, photo‐physical, and opto‐electronic properties 11,20–21 .…”

Ferrocene-based polyesters with azobenzene linker: Synthesis and biological evaluation

“…Ferrocene based materials have attracted active interest in recent years within the eld of medicinal and bio-organometallic chemistry [5]- [9]. The organometallic analogues of antimalarial drug chloroquine (derivatives of the ferroquine) and the breast cancer drug tamoxifen (ferrocifen) being the most widely known ferrocene based cures [10,11].…”

“…In addition to the aforementioned groups, the presence of aromatic and aliphatic moieties in chain could also affect the properties of material [18]- [21]. In addition incorporation of different aliphatic diols along with aromatic diols in parent macromolecules ensures their better solubility and hence could enhance their utility for biological systems [11], [22,23].…”