Fluorescent lactose-derived catanionic aggregates: synthesis, characterisation and potential use as antibacterial agents

Abstract

The spread of infections from multi-resistant bacteria in hospitals around the world is raising at an alarming\ud rate. With the increasing capacity of bacteria to develop resistance to traditional antibiotics that target\ud a particular metabolic pathway inside the cell, the use of nanoparticles as therapeutic agents is gaining\ud importance because of their ability to attack bacterial membranes without evoking resistance. We have\ud synthesized the catanionic surfactants Coum12–Coum18, based on fluorescent lactose-derivative\ud organic salts using low-cost starting materials. In water, they self-assemble spontaneously to form stable\ud aggregates at a physiological pH. The antibacterial properties of Coum12–Coum18 were investigated\ud towards multi-drug-resistant Gram-positive bacteria (Staphylococcus aureus and Enterococcus faecalis)\ud and Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa). Compound Coum18 was\ud found to have both a bacteriostatic and a bactericidal activity towards Gram-positive bacteria, although\ud the values of both the MIC and MBC (32 mg mL-1) suggest only a topical use of the molecule. The\ud valuable results that were found provide a challenging task for further investigation aimed at the\ud development of this class of antibacterial drugs. In vitro fluorescence microscopy gave insight into the\ud interaction between the aggregates and the cellular membranes on HeLa and CHO cell

Self-Assembly of Amphiphilic Compounds as a Versatile Tool for Construction of Nanoscale Drug Carriers

“…The presence of a lactose moiety in the molecule provides both industrial and biotechnological significance to these compositions. These compounds could be used as efficient micellar catalysts of Ullmann C-S coupling reactions in water (the yield of product could reach 90% by selecting an appropriate alkyl tail length) [ 59 ]; highly-effective antibacterial agents against a wide spectrum of microorganisms [ 60 ]; coatings interrupting undesired adsorption processes [ 61 ]; compounds for condensation with DNA, that could be accurately tuned by selection of the counterion [ 62 ]; a basis of a vehicle for ketoprofen delivery [ 63 ]. Maltose and sucrose amphiphilic derivatives were recommended as components of microemulsions—potential alternative fuel [ 64 ], regulators of wettability of various solid surfaces like quartz and polyethylene [ 65 ] and modifiers of adsorption parameters at the air/liquid interface of systems [ 66 ].…”