Single-walled carbon nanotubes-ciprofloxacin nanoantibiotic: strategy to improve ciprofloxacin antibacterial activity

Abstract

As infectious diseases continue to be one of the greatest health challenges worldwide, the demand toward alternative agents is continuously increasing. Recent advancement in nanotechnology has expanded our ability to design and construct nanomaterials to treat bacterial infections. Carbon nanotubes are one among these nanomaterials. Herein, we describe the covalent functionalization of the single-walled carbon nanotubes (SWCNTs) with multiple molecules of ciprofloxacin. The prepared nanoantibiotics were characterized using different techniques, including transmission electron microscopy, Raman spectroscopy, and thermogravimetric analysis. The characterization of the nanoantibiotics confirmed the successful covalent functionalization of the SWCNTs with 55% of functionalization as has been observed by thermogravimetric analysis. The release profile revealed that 90% of the loaded ciprofloxacin was released within 2.5 h at pH 7.4 showing a first-order release profile with R 2 >0.99. Interestingly, the results of the antibacterial activity indicated that the functionalized SWCNTs have significant increase in the antibacterial activity against the three strains of bacteria – by 16-fold for Staphylococcus aureus and Pseudomonas aeruginosa and by 8-fold for Escherichia coli – in comparison to the ciprofloxacin free drug. Moreover, the synthesized nanoantibiotic showed high hemocompatibility and cytocompatibility over a wide concentration range.

The Advances in Biomedical Applications of Carbon Nanotubes

“…However, the resistance to ciprofloxacin has been growing rapidly around the world [115,116]. To overcome this problem, Assali et al proposed a novel type of functionalized single-walled CNTs with loaded ciprofloxacin [117]. The newly fabricated CNTs have been characterized by using transmission electron microscopy (TEM), Raman spectroscopy, thermos-gravimetric, and microbiological analysis.…”

Single wall and multiwall carbon nanotubes induce different toxicological responses in rat alveolar macrophages

“…For example, carbon nanotubes (CNTs) offer a huge potential in nano‐electronics as semiconductors (Lefebvre et al, ). Their high thermal conductivity (Monea et al, ), resistance and intrinsic mechanical properties (Dresselhaus, Dresselhaus, Charlier, & Hernández, ) such as high tensile strength and flexibility, make them ideal for numerous applications in the biomedical domain, for instance drug delivery (Assali, Zaid, Abdallah, Almasri, & Khayyat, ; Khan et al, ; Samadishadlou et al, ). CNTs have been widely explored in structural polymer nanocomposites, conductive adhesives, fire retardant plastics, Li‐ion battery electrodes and metal matrix composites (Madian et al, ; Messina et al, ).…”

“…instance drug delivery (Assali, Zaid, Abdallah, Almasri, & Khayyat, 2017;Khan et al, 2017;Samadishadlou et al, 2017). CNTs have been widely explored in structural polymer nanocomposites, conductive adhesives, fire retardant plastics, Li-ion battery electrodes and metal matrix composites (Madian et al, 2017;Messina et al, 2016).…”

Microbial esterases and ester prodrugs: An unlikely marriage for combating antibiotic resistance

“…Another subcategory of ester prodrugs designed to be selectively activated by intracellular esterases are prodrug conjugates, where the active compound is bound to a secondary molecule. In one example, ciprofloxacin was bound to a single‐walled carbon nanotube through an ethylene glycol linker to create a nanoantibiotic (Figure e; Assali et al, ). Here, the nanotubes would enter the bacteria through damage to the bacterial cell wall, whereupon the linker could be cleaved by esterase enzymes within the bacteria.…”

“…PEGlyated prodrugs are designed to disrupt crystallinity and enhance solubility (Assali et al, 2016). The ciprofloxacin-anhydride coating is engineered to be cleaved by extracellular esterases (Komnatnyy et al, 2014), and the nanoantibiotic is designed to be cleaved by internal esterases following disruption of the bacterial cell wall by the carbon nanotube (Assali, Zaid, Abdallah, Almasri, & Khayyat, 2017). (f ) Fosmidomycin, FR900098, and two FR900098 phosphonate esters.…”