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Hyaluronan/Tannic Acid Nanoparticles Via Catechol/Boronate Complexation as a Smart Antibacterial System
Author(s) -
Montanari Elita,
Gennari Arianna,
Pelliccia Maria,
Gourmel Charlotte,
Lallana Enrique,
Matricardi Pietro,
McBain Andrew J.,
Tirelli Nicola
Publication year - 2016
Publication title -
macromolecular bioscience
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.924
H-Index - 105
eISSN - 1616-5195
pISSN - 1616-5187
DOI - 10.1002/mabi.201600311
Subject(s) - tannic acid , chemistry , nanoparticle , hyaluronic acid , ascorbic acid , antimicrobial , hydrolysis , catechol , nuclear chemistry , combinatorial chemistry , organic chemistry , nanotechnology , materials science , food science , biology , genetics
Nanoparticles based on hyaluronic acid (HA) are designed to deliver tannic acid (TA) as an antimicrobial agent. The presence of HA makes these particles potentially useful to target bacteria that colonize cells presenting HA membrane receptors (e.g. CD44), such as macrophages. HA bearing 3‐aminophenyl boronic acid groups (HA‐APBA) is reacted with TA, yielding nanoparticles with a size that decreases with decreasing HA molecular weight (e.g. 200 nm for 44 kDa, 400 nm for 737 kDa). The boronate esters make the nanoparticles stable at physiological pH, but their hydrolysis in an acidic environment (pH = 5) leads to swelling/solubilization, therefore potentially allowing TA release in endosomal compartments. We have assessed the nanoparticle toxicity profile (on RAW 264.7 macrophages) and their antimicrobial activity (on E. coli and on both methicillin‐sensitive and ‐resistant S. aureus ). The antibacterial effect of HA‐APBA/TA nanoparticles was significantly higher than that of TA alone, and has very similar activity to TA coformulated with a reducing agent (ascorbic acid), which indicates both the nanoparticles to protect TA catechols from oxidation, and the effective release of TA after nanoparticle internalization. Therefore, there is potential for these nanoparticles to be used in stable, effective, and potentially targetable nanoparticle‐based antimicrobial formulations.