Triterpenoid-PEG Ribbons Targeting Selectivity in Pharmacological Effects.

(1) Background: To compare the effect of selected triterpenoids with their structurally resembling derivatives, designing of the molecular ribbons was targeted to develop compounds with selectivity in their pharmacological effects. (2) Methods: In the synthetic procedures, Huisgen 1,3-dipolar cycloaddition was applied as a key synthetic step for introducing a 1,2,3-triazole ring as a part of a junction unit in the molecular ribbons. (3) Results: The antimicrobial activity, antiviral activity, and cytotoxicity of the prepared compounds were studied. Most of the molecular ribbons showed antimicrobial activity, especially on , and , with a 50-90% inhibition effect ( = 25 µg·mL). No target compound was effective against HSV-1, but displayed activity against HIV-1 (EC = 50.6 ± 7.8 µM). Cytotoxicity was tested on several cancer cell lines, and showed cytotoxicity in the malignant melanoma cancer cell line (G-361; IC = 20.0 ± 0.6 µM). Physicochemical characteristics of the prepared compounds were investigated, namely a formation of supramolecular gels and a self-assembly potential in general, with positive results achieved with several target compounds. (4) Conclusions: Several compounds of a series of triterpenoid molecular ribbons showed better pharmacological profiles than the parent compounds and displayed certain selectivity in their effects.