Triterpenoid-PEG Ribbons Targeting Selectivity in Pharmacological Effects

Area of Science:

• Medicinal Chemistry
• Organic Synthesis
• Pharmacology

Background:

• Investigated triterpenoid derivatives designed as molecular ribbons to achieve selective pharmacological effects.
• Compared selected triterpenoids with structurally similar derivatives.

Purpose of the Study:

• To synthesize and evaluate novel triterpenoid molecular ribbons for pharmacological activity.
• To assess antimicrobial, antiviral, and cytotoxic effects of the designed compounds.
• To investigate physicochemical properties, including self-assembly and gel formation.

Main Methods:

• Employed Huisgen 1,3-dipolar cycloaddition for synthesizing molecular ribbons incorporating a 1,2,3-triazole unit.
• Evaluated antimicrobial activity against Staphylococcus aureus, Pseudomonas aeruginosa, and Enterococcus faecalis.
• Assessed antiviral activity against HSV-1 and HIV-1, and cytotoxicity against cancer cell lines.

Main Results:

• Most compounds exhibited significant antimicrobial activity (50-90% inhibition).
• Compound 8a showed activity against HIV-1 (EC50 = 50.6 ± 7.8 µM), while no activity was observed against HSV-1.
• Compound 6d demonstrated cytotoxicity against malignant melanoma cells (IC50 = 20.0 ± 0.6 µM); several compounds formed supramolecular gels.

Conclusions:

• Triterpenoid molecular ribbons displayed improved pharmacological profiles compared to parent compounds.
• The synthesized compounds exhibited selective biological activities.
• Potential for developing new therapeutic agents based on these molecular ribbons.