A Benzimidazolium-Based Organic Cage with Antimicrobial Activity

Considering the wide interest in (benz)imidazolium-based drugs, we here report our study on a benzimidazolium-based organic cage as potential antimicrobial and antifungal agent. Cytotoxicity studies on a human derived cell line, SH-SY5Y, showed that the cage is not cytotoxic at all at the investigated concentrations. Anion binding studies demonstrated that the cage can bind anions (chloride and nitrate, in particular) both in organic solvent and 20%v D2O/CD3CN mixture. The cage was also tested as anionophore, showing a weak but measurable transport of chloride and nitrate across LUVs vesicles. Nonetheless, the compounds have antimicrobial activity towards Staphylococcus aureus (Gram-positive bacteria). This is probably the first organic cage studied as anionophore and antimicrobial agent.

[1]  D. Mondal,et al.  Anion Recognition through Multivalent C-H Hydrogen Bonds: Anion-Induced Foldamer Formation and Transport across Phospholipid Membranes. , 2021, The Journal of organic chemistry.

[2]  P. Pallavicini,et al.  Gold Nanostars Embedded in PDMS Films: A Photothermal Material for Antibacterial Applications , 2021, Nanomaterials.

[3]  P. Perugini,et al.  A New In Vitro Model to Evaluate Anti-Adhesive Effect against Fungal Nail Infections , 2021, Applied Sciences.

[4]  Philip A. Gale,et al.  Advances in fluorescent and colorimetric sensors for anionic species , 2021, Coordination Chemistry Reviews.

[5]  G. Parati,et al.  Use of dual-flow bioreactor to develop a simplified model of nervous-cardiovascular systems crosstalk: A preliminary assessment , 2020, PloS one.

[6]  M. Boiocchi,et al.  Sensing and Liquid–Liquid Extraction of Dicarboxylates Using Dicopper Cryptates , 2020, ACS omega.

[7]  R. Quesada,et al.  pH-dependent chloride transport by pseudopeptidic cages for the selective killing of cancer cells in acidic microenvironments. , 2019, Angewandte Chemie.

[8]  T. Gunnlaugsson,et al.  Halide-Controlled Extending-Shrinking Motion of a Covalent Cage. , 2019, The Journal of organic chemistry.

[9]  Joan M Racicot,et al.  Supramolecular Luminescent Sensors. , 2018, Chemical reviews.

[10]  Philip A. Gale,et al.  Supramolecular Transmembrane Anion Transport: New Assays and Insights. , 2018, Accounts of chemical research.

[11]  Toru Tanaka,et al.  Synthesis and Antimicrobial Activity of 2-Trifluoroacetonylbenzoxazole Ligands and Their Metal Complexes. , 2018, Chemical & pharmaceutical bulletin.

[12]  A. Pascale,et al.  Tailored coating of gold nanostars: rational approach to prototype of theranostic device based on SERS and photothermal effects at ultralow irradiance , 2018, Nanotechnology.

[13]  G. Bergamaschi,et al.  Azacryptands as molecular cages for anions and metal ions , 2018 .

[14]  J. Pastor,et al.  Comparison between direct contact and extract exposure methods for PFO cytotoxicity evaluation , 2018, Scientific Reports.

[15]  T. Gunnlaugsson,et al.  Luminescent/colorimetric probes and (chemo-) sensors for detecting anions based on transition and lanthanide ion receptor/binding complexes , 2018 .

[16]  K. Raghavachari,et al.  Anion Binding in Solution: Beyond the Electrostatic Regime , 2017 .

[17]  M. Patrini,et al.  Bulk Surfaces Coated with Triangular Silver Nanoplates: Antibacterial Action Based on Silver Release and Photo-Thermal Effect , 2017, Nanomaterials.

[18]  S. Hussain,et al.  Efficient, non-toxic anion transport by synthetic carriers in cells and epithelia , 2015, Nature Chemistry.

[19]  A. Schmitzer,et al.  Strong antibacterial properties of anion transporters: a result of depolarization and weakening of the bacterial membrane. , 2015, Journal of medicinal chemistry.

[20]  S. Hussain,et al.  Preorganized bis-thioureas as powerful anion carriers: chloride transport by single molecules in large unilamellar vesicles. , 2014, Journal of the American Chemical Society.

[21]  Hongjun Zhou,et al.  Highly selective fluorescent recognition of sulfate in water by two rigid tetrakisimidazolium macrocycles with peripheral chains. , 2013, Journal of the American Chemical Society.

[22]  Philip A. Gale,et al.  Anion transporters and biological systems. , 2013, Accounts of chemical research.

[23]  G. Bergamaschi,et al.  Cavity Effect on Perrhenate Recognition by Polyammonium Cages , 2012 .

[24]  M. Boiocchi,et al.  Putting the Anion into the Cage – Fluoride Inclusion in the Smallest Trisimidazolium Macrotricycle , 2011 .

[25]  C. Milanese,et al.  Synthesis, characterization and antibacterial activity against Gram positive and Gram negative bacteria of biomimetically coated silver nanoparticles. , 2011, Langmuir : the ACS journal of surfaces and colloids.

[26]  P. Grisoli,et al.  Antimicrobial properties of stem bark extracts from Phyllanthus muellerianus (Kuntze) Excell. , 2011, Journal of ethnopharmacology.

[27]  M. Boiocchi,et al.  A metal-based trisimidazolium cage that provides six C-H hydrogen-bond-donor fragments and includes anions. , 2006, Angewandte Chemie.

[28]  Juyoung Yoon,et al.  Imidazolium receptors for the recognition of anions. , 2006, Chemical Society reviews.

[29]  Kwang S. Kim,et al.  Tripodal nitro-imidazolium receptor for anion binding driven by (C-H)+- - -X- hydrogen bonds. , 2002, Organic letters.

[30]  P. Gans,et al.  Investigation of equilibria in solution. Determination of equilibrium constants with the HYPERQUAD suite of programs. , 1996, Talanta.

[31]  J. Waitz.  Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically , 1990 .

[32]  E. Bruck,et al.  National Committee for Clinical Laboratory Standards. , 1980, Pediatrics.