Design, synthesis, structural inspection, and DFT calculation of some novel imine ciprofloxacin metal chelates: A novel approach for pharmaceutical applications and DNA interaction

Author:

Abu‐Dief Ahmed M.12ORCID,Al‐hawamy Yasser2ORCID,Abdou Aly2ORCID,Alsehli Amal H.1ORCID,Altayeb Bader M.1ORCID,Alqurashi Abdulmajeed3ORCID,Mohamed Gehad G.45ORCID

Affiliation:

1. Chemistry Department College of Science, Taibah University P.O. Box 344 Madinah 42353 Saudi Arabia

2. Department of Chemistry, Faculty of Science Sohag University Sohag 82524 Egypt

3. Department of Biological Sciences, Faculty of Science Taibah University Al‐Madinah Al‐Munawwarah 41321 Saudi Arabia

4. Chemistry Department, Faculty of Science Cairo University Giza 12613 Egypt

5. Nanoscience Department Basic and Applied Sciences Institute, Egypt‐Japan University of Science and Technology New Borg El Arab, Alexandria 21934 Egypt

Abstract

Novel compounds with pharmacological activity were synthesized from Pd (II), Fe (III), Cr (III), Ni (II), and Cu (II) ions with 4‐{2‐(3‐carboxy‐1‐cyclopropyl‐6‐fluoro‐7‐piperazin‐1‐yl‐2,3‐dihydro‐1H‐quinolin‐4‐ylideneamino)‐phenylimino}‐1‐cyclopropyl‐6‐fluoro‐7‐piperazin‐1‐yl‐1,4‐dihydro‐quinoline‐3‐carboxylic acid (CFPD). The newly synthesized compounds have been investigated by 1H‐ and 13C‐NMR spectra, Fourier transform infrared spectra, CHN analyses, ultraviolet‐visible spectra, mass spectra, molar conductivity, and magnetic moment measurements. In addition, the pH profile of the CFPD complexes showed remarkable stability, and their stability constant was identified in solution. To find out essential characteristics for CFPD and its complexes and to investigate the molecular geometry, computational analysis occurred. Through its nitrogen and OH of carboxylate groups, the ligand interacted with the metal ions to form CFPDPd complex with a square planar geometry and CFPDCu, CFPDCr, CFPDNi, and CFPDFe complexes with octahedral geometry. The M:L ratio of 1:1 was demonstrated by the molar ratio and sequence variation techniques’ outcomes. The effect of the investigated CFPD imine ligand on bacterial community and its metal chelate was examined within vitro using a range of fungal and viral pathogens The findings showed that the effectiveness of antimicrobial went with the directive: CFPDPd complex when compared to the highly suppressor complex, fluconazol and ofloxacin as model medication. The novel ligand’s and its complexes’ in vitro cytotoxic potential against the Hep‐G2, MCF‐7, and HCT‐116 cell lines was also studied. The findings once more indicated that, when compared to vinblastine medication, the CFPDPd chelate is the most active agent. In addition, the complexes showed high reactivity in catching free radicals when their antioxidant activity was examined. By the application of viscosity, spectrum analysis, and gel electrophoreses, the interaction among metal chelates and DNA was determined. Studies on viscosity and spectrophotometric titration showed that every substance in test is a strong DNA binder. Increased hydrophobic and electrostatic interactions between aromatic rings could be the cause of this. In conclusion, these complexes have the potential to be effective bioactive agents.

Publisher

Wiley

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