Synthesis and characterization of quinoxaline-based rhenium(I) organometallic compounds: Biological and computational applications

• Published in: Journal of molecular structure Vol. 1302; p. 137477
• Main Authors: Padariya, Aelvish D., Savaliya, Nirbhay K., Dhaduk, Milan P., Dabhi, Ravi A., Bhatt, Bhupesh S., Bhatt, Vaibhav D., Patel, Mohan N.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15-04-2024
• Subjects: ADME study; DFT; DNA/BSA binding; Docking; MCF-7 cancer cell line; Re(I) organometallic compounds; MCF-7 cancer cell line; DNA/BSA binding; Docking; DFT; ADME study; Re(I) organometallic compounds
• ISSN: 0022-2860
• DOI: 10.1016/j.molstruc.2023.137477

•Substituted quinoxaline Schiff base-based Re(I) complexes were synthesized and characterized by various spectrometric and analytical techniques.•The heterocyclic compounds and their Re(I) complexes were screened for biomolecular interactions and various medicinal activities.•The compounds are more cytotoxic compared to standard anticancer drugs.•The compounds can be used as prototypes for the development of novel chemotherapeutic agents.
Rhenium(I) organometallic compounds (C1-C6) with substituted quinoxaline Schiff base-based ligands (L1-L6) were synthesized and characterized using spectroscopic techniques such as 1HNMR , LC-MS, FT-IR spectroscopy, conductivity measurement, and elemental analysis. CT-DNA was tested under the impact of complexes using absorbance titration and viscosity measuring techniques to evaluate the binding capacities and manner. The compounds bind to the DNA by partial intercalation. The Kb values for all synthesized compounds are in the range of 0.44 to 1.72×105 M−1 in the absorption titration experiment. The evaluation of compounds binding to BSA was carried out using a fluorescence quenching study and the Ksv values were observed in the range of 0.93 to 1.67×104 M−1. The Ksv values for the fluorescence quenching-based DNA binding investigation were observed in the range of 0.75 to 1.87×104 M−1. The findings of the molecular docking investigations support the previously described point to an intercalation type of binding. The protein binding studies of all the synthesized compounds were examined using an absorption titration experiment, and the Kb values for all of the compounds range from 0.64 to 1.35×104 M−1. The structures of Re(I) complexes were optimized using DFT investigations. The antibacterial activity of organometallic compounds was tested against two Gram-positive and three Gram-negative pathogens, and the results showed that organometallic compounds outperform all ligands in this regard. The pharmacokinetic profile of each synthesized molecule was assessed as part of the ADME investigation using the online tools SwissADME and admetSAR. The MCF-7 cancer cell line was used to examine the anticancer effects of the compounds.