A bactericidal calix[4]arene-based nanoconstruct with amplified NO photorelease

Abstract

A hydrophobic N-dodecyl-3-(trifluoromethyl)-4-nitrobenzenamine has been synthesized as a suitable NO photodonor and encapsulated in a nanocontainer based on a polycationic calix[4]arene derivative, leading to a supramolecular micellar-like nanoassembly ca. 45 nm in diameter. Visible light excitation of this nanoconstruct triggers NO generation with an efficiency remarkably higher than that observed for the free NO photoreleaser. This amplified NO release results in considerable antibacterial activity against Staphylococcus aureus (ATCC 6538) and Pseudomonas aeruginosa (ATCC 9027) as representative Gram positive and Gram negative bacteria, respectively.

A light-induced nitric oxide controllable release nano-platform based on diketopyrrolopyrrole derivatives for pH-responsive photodynamic/photothermal synergistic cancer therapy

“…Under light irradiation, an optical rearrangement of the nitro–nitrite occurred and generated phenoxy and NO radicals. 44 , 45 The light-induced absorption spectrum changes of DPP-NF NPs are shown in Fig. 3b and c .…”

Design, synthesis and antibacterial evaluation of a polycationic calix[4]arene derivative alone and in combination with antibiotics

“…5 The covalent conjugation of nalidixic acid to the calix[4]arene skeleton provided a prodrug with antibacterial activity, 6 and the clustering of multiple guanidinium units onto a calix[4]arene platform provided polycationic oligomers with higher antibacterial activity and lower cytotoxicity than the monomeric analogues versus eukaryotic cells. 7,8 We ourselves observed that the arrangement of multiple units of fucose onto a calix[4]arene platform gave a Pseudomonas aeruginosa biofilm inhibitor 9 and demonstrated that the entrapment of a nitric oxide radical photodonor 10 or photosensitizers 11 into a polycationic micellar calix[4]arene resulted in light-controlled bactericidal formulations. In the search for new antibacterial compounds, the ability of the hydrophobic cavity of calix[n]arene derivatives to form inclusion complexes with metals such as Ag ions 12 or antibiotics such as isoniazid 13 and fluoroquinolones 14 also appeared very promising.…”

Nanoscale lipid vesicles functionalized with a nitro-aniline derivative for photoinduced nitric oxide (NO) delivery

“…Recently, 4-nitro-3-(triuoromethyl)aniline (NTA) based NO donors chemically incorporated into calixarene, Pt-nanoparticle and cellulose modied NO donors have been reported [17][18][19] However, NO-releasing nano-scaffolds containing NTA with good biocompatibility and stability in physiological media are rarely reported. 20,21 This prompted us to investigate the NO releasing behaviour of NTA in a nanoscale vesicle surface.…”