A calix[4]arene-based supramolecular nanoassembly targeting cancer cells and triggering the release of nitric oxide with green light

Cristina Parisi; Loredana Ferreri; Tassia J Martins; Francesca Laneri; Samantha Sollima; Antonina Azzolina; Antonella Cusimano; Nicola D'Antona; Grazia Maria Letizia Consoli; Salvatore Sortino

doi:10.3762/bxiv.2025.13.v1

A calix[4]arene-based supramolecular nanoassembly targeting cancer cells and triggering the release of nitric oxide with green light

Cristina Parisi ,
Loredana Ferreri ,
Tassia J Martins ,
Francesca Laneri ,
Samantha Sollima ,
Antonina Azzolina ,
Antonella Cusimano ,
Nicola D'Antona ,
Grazia Maria Letizia Consoli and
Salvatore Sortino

Submitting author affiliation:

University of Catania, Catania, Italy

Beilstein Arch. 2025, 202513. https://doi.org/10.3762/bxiv.2025.13.v1

Published 03 Mar 2025

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SUBJECT AREAS

Show All Preprints Nanotechnology Organic chemistry Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry Materials chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry

Abstract

We have designed and synthesized a novel calix[4]arene derivative bearing four choline appendages, as recognition targeting ligands, and one amino-nitrobenzofurazan, as a fluorescent labeling unit, at the opposite sides of the calixarene molecular scaffold. Due to its amphiphilic character, this compound is well soluble in water, forming supramolecular assemblies that are ca. 170 nm in diameter. The nanoassembly selectively targets cancer cells that overexpress the choline receptors, and it can be visualized thanks to the fluorescent tag. The fluorogenic unit also acts as a green light harvesting center, making the nanoassembly a photo-nanoreactor able to encapsulate a hydrophobic nitric oxide (NO) photodonor, otherwise activatable with blue light, and encouraging the NO release with the more biocompatible green light probably by an intra-cage photoinduced electron transfer.

Keywords: Calixarenes; Light; Fluorescence; Cell Targeting; Nitric Oxide.

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Parisi, C.; Ferreri, L.; Martins, T. J.; Laneri, F.; Sollima, S.; Azzolina, A.; Cusimano, A.; D'Antona, N.; Consoli, G. M. L.; Sortino, S. Beilstein Arch. 2025, 202513. doi:10.3762/bxiv.2025.13.v1

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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)