pH-Prism

New stimuli-responsive pharmacological chaperones based on prismarenes

2022F5C2FA, CUP D53D23010330006

The Scientific Contribution of SupraChem@Unisa Group

Pubblications

Thermodynamically Templated Macrocyclizations: Enhancing the Synthesis of Prism [5] arenes with Tailor-Made Guests

The macrocyclization of 2,6-dialkoxynaphthalene monomers to prism[5]arenes is thermodynamically templated by DABCO cations. In this study, we demonstrate that a greater template affinity for prism[5]arene improves the macrocyclization yield. By using novel templating cations, the yield of alkoxy-prism[5]arenes increases significantly compared with those of previously reported procedures, while the purification process becomes easier and faster.

Org. Lett. 2024, 26, 39, 8228–8232

Under the Influence of Water: Molecular Recognition of Organic Hydrophilic Molecules in Water with a Prismarene Host Driven by Hydration Effects

A water-soluble prism[5]arene host can form endo-cavity complexes with hydrophilic organic substances in water by displacing frustrated water molecules from its deep cavity. Water molecules structured at both rims of the prismarene host can mediate hydrogen bonding interactions with the guest. Water-mediated hydrogen bonding interactions were invoked here to elucidate the elevated binding affinities and selectivity of the prismarene host toward hydrophilic organic guests. We show that water at the interface of a host-guest complex can act as an extension of the host structure, facilitating the accommodation of neutral guests within the binding site. This study highlights the crucial role of water in facilitating supramolecular interactions between a deep-cavity prismarene host and organic hydrophilic guests in aqueous medium.

Chem. Eur. J. 2024, 30(44), e202401734

Conference contributions

  • Flash Presentation on Supramolecular Chemistry Days for Young Researchers 2025, Salerno, Italy – June 11th – 13th, 2025 – Title: Synthesis of coprism[4+1]arene macrocycles via selective comacrocyclization of 2,6-dialkoxynaphthalene monomers – Authors: A. Palmieri, P. Della Sala, I. Vollono, D. Coscia, R. Citro, V. Iuliano, M.M. Ignoto, C. Talotta, M. De Rosa, C. Gaeta

  • Poster Presentation on on XLII Convegno Nazionale della Divisione di Chimica Organica CDCO 2025, Cagliari, Italy, September 21th-25th, 2025 – Title: Multivalent Prism[5]arene Glycoconjugates: A New Class of Pharmacological Chaperones Based on Iminosugar Multimerization. – Authors: A. Palmieri, P. Della Sala, R. Del Regno, M. De Rosa, F. Buonsenso, F. Clemente, F. Cardona, A. Goti, C. Matassini, C. Gaeta