Supramolecular Amphiphiles Based on Pillar[5]arene and Meroterpenoids: Synthesis, Self-Association and Interaction with Floxuridine

Abstract

In recent years, meroterpenoids have found wide biomedical application due to their synthetic availability, low toxicity, and biocompatibility. However, these compounds are not used in targeted drug delivery systems due to their high affinity for cell membranes, both healthy and in cancer cells. Using the approach of creating supramolecular amphiphiles, we have developed self-assembling systems based on water-soluble pillar[5]arene and synthetic meroterpenoids containing geraniol, myrtenol, farnesol, and phytol fragments. The resulting systems can be used as universal drug delivery systems. It was shown by turbidimetry that the obtained pillar[5]arene/synthetic meroterpenoid systems do not interact with the model cell membrane at pH = 7.4, but the associates are destroyed at pH = 4.1. In this case, the synthetic meroterpenoid is incorporated into the lipid bilayer of the model membrane. The characteristics of supramolecular self-assembly, association constants and stoichiometry of the most stable pillar[5]arene/synthetic meroterpenoid complexes were established by UV-vis spectroscopy and dynamic light scattering (DLS). It was shown that supramolecular amphiphiles based on pillar[5]arene/synthetic meroterpenoid systems form monodisperse associates in a wide range of concentrations. The inclusion of the antitumor drug 5-fluoro-2′-deoxyuridine (floxuridine) into the structure of the supramolecular associate was demonstrated by DLS, 19F, 2D DOSY NMR spectroscopy.

Towards potential antifungal agents: synthesis, supramolecular self-assembly and in vitro activity of azole mono-, sesqui- and diterpenoids

“…and Aspergillus spp. 22 Thus, terpenes and their derivatives 23 have both fungicidal/ fungistatic and skin penetration enhancer properties, making them ideal candidates for the drug design in antifungal therapy of skin diseases. As is known, 7 that azole (imidazole) antifungal drugs are one of the synthetic types of fungistatic drugs.…”

Syntheses and polymerization of monoterpene-based (meth)acrylates: IBO(M)A as a relevant monomer for industrial applications

“…For the integration of that chemical motif, Akhmedov et al converted several terpenes, such as geraniol (15) and myrtenol (11), with stochiometric amounts of acryloyl chloride and Hünig-base in chloroform to the corresponding acrylates in small-scale reactions. 41 The reaction time was 10 h at room temperature, and purification by column chromatography was required. The yield of myrtenyl acrylate (A11) was 72%.…”

On the way to potential antifungal compounds: synthesis and in vitro activity of 2-benzofuranylacetic acid amides

“…13 C NMR (100 MHz, DMSO-d 6 ): 166.7, 159.1 (d, J = 240.4 Hz), 154.4, 153.5, 149.7 (d, J = 11.1 Hz), 128.6, 123.9, 123.7 (d, J = 9.9 Hz), 122.9, 122.8 (d, J = 2.9 Hz), 120.9, 111.0, 105.2 (d, J = 21.9 Hz), 104.9, 102.7 (d, J = 24.9 Hz), 36.3. 19 Methyl 2-(benzofuran-2-yl)acetate (11). 2-Benzofuranyl acetic acid 3a (4.54 mmol, 0.800 g) in methanol (5 mL) was added, then H 2 SO 4 (0.91 mmol, 253 mL) was added; the mixture was reuxed for 12 h using a CaCl 2 trap.…”

“…The crude mixture was puried using ash chromatography to afford the pure product. Methyl 2-(benzofuran-2-yl)acetate (11). 2-Benzofuranyl acetic acid 3a (4.54 mmol, 0.800 g) in methanol (5 mL) was added, then H 2 SO 4 (0.91 mmol, 253 mL) was added; the mixture was reuxed for 12 h using a CaCl 2 trap.…”

“…In this context, remarkable progress is being made in the development of new bioactive compounds against phytopathogens such as FOX on a weekly basis. [10][11][12][13][14][15][16][17][18] However, many of these advancements come with a signicant drawback. Most active compounds are derived from natural sources, resulting in limited quantities that make it challenging to conduct thorough testing and eld evaluations.…”