Journal
ACS APPLIED BIO MATERIALS
Volume 1, Issue 4, Pages 1066-1073Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsabm.8b00304
Keywords
nitric oxide; hyperbranched polyaminoglycosides; antibacterial; dental pathogens
Funding
- NIH [DE025207]
- U.S. Department of Energy [DE-SC0001011]
- U.S. Department of Energy (DOE) [DE-SC0001011] Funding Source: U.S. Department of Energy (DOE)
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Hyperbranched polyaminoglycosides were prepared by the polymerization of kanamycin, gentamicin, and neomycin, and N,N'-methylenebis(acrylamide) via a one-pot reaction. The secondary amines at the linear units of the hyperbranched polymers were subsequently reacted with nitric oxide (NO) gas at high pressure under alkaline conditions to form N-diazeniumdiolate NO donors. The resulting NO-releasing hyperbranched polyaminoglycosides exhibited a wide range of NO payloads (similar to 0.4-1.3 mu mol mg(-1)) and release kinetics (half-lives similar to 70-180 min). The therapeutic utility of these materials was evaluated by examining their bactericidal activity against common dental pathogens and toxicity to human gingival fibroblast cells. The antibacterial efficacy of NO-releasing hyperbranched polyaminoglycosides was dependent on specific physiochemical properties, with greater degrees of branching and aminoglycoside terminal groups correlating to enhanced action. Nitric oxide-releasing hyperbranched polykanamycin and polyneomycin elicited the least cytotoxicity at bactericidal concentrations, indicating the greatest therapeutic index for future biomedical applications.
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