Aminoguanidine-based bioactive proligand as AIEE probe for anticancer and anticovid studies

Area of Science:

• Supramolecular Chemistry
• Materials Science
• Medicinal Chemistry

Background:

• Novel bioactive compounds are crucial for developing new therapeutic agents.
• Aggregation-Induced Emission (AIE) phenomena offer unique optical properties for molecular design.
• Understanding intermolecular interactions is key to solid-state properties and biological activity.

Purpose of the Study:

• To synthesize and characterize a novel nitrogen and iodine-rich proligand.
• To investigate its aggregation-induced emission enhancement (AIEE) characteristics.
• To evaluate its potential as an anticancer agent and antiviral candidate against SARS-CoV-2.

Main Methods:

• Physicochemical characterization, including Single Crystal X-ray Diffraction (SCXRD) and Hirshfeld surface analysis.
• Experimental and theoretical estimation of the band gap and solid-state fluorescence quantum yield.
• In vitro anticancer assays on MCF-7 and L929 cell lines, DNA binding studies, and in silico docking against SARS-CoV-2 targets (3CLpro and spike glycoprotein).

Main Results:

• The compound exhibits significant AIEE with a solid-state fluorescence quantum yield of Φ = 0.36.
• Crystal structure reveals extensive hydrogen bonding and triangular iodine bonding, influencing molecular packing.
• Demonstrated potent in vitro cytotoxicity against MCF-7 cells (IC50 = 181.05 μg mL⁻¹) with lower toxicity to normal cells (IC50 = 356.54 μg mL⁻¹).
• Showed exceptional binding affinity to SARS-CoV-2 3CLpro and spike glycoprotein in computational studies.

Conclusions:

• The novel proligand possesses impressive AIEE properties driven by restricted intramolecular motions.
• Its strong DNA interaction and selective cytotoxicity highlight potential anticancer applications.
• High binding affinity to SARS-CoV-2 proteins suggests promise as an antiviral therapeutic lead.
• The compound's multifaceted properties make it a valuable candidate for further biomedical research.