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Oxazoline‐Based Antimicrobial Oligomers: Synthesis by CROP Using Supercritical CO 2
Author(s) -
Correia Vanessa G.,
Bonifácio Vasco D.B.,
Raje Vivek P.,
Casimiro Teresa,
Moutinho Guilhermina,
da Silva Cláudia Lobato,
Pinho Mariana G.,
AguiarRicardo Ana
Publication year - 2011
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.201100126
Subject(s) - oxazoline , chemistry , antimicrobial , carbamic acid , supercritical fluid , hydrochloride , ammonium , amide , organic chemistry , combinatorial chemistry , catalysis
A method using supercritical CO 2 to obtain biocompatible 2‐oxazoline‐based oligomers quaternized with different amines is described. The synthesized oligo(2‐oxazoline)s display partial carbamic‐acid insertion at one end. The syntheses of quaternary oligo(2‐bisoxazoline)s and linear oligoethylenimine hydrochlorides are reported. Oligo(2‐methyl‐2‐oxazoline) and oligo(2‐bisoxazoline) quaternized with N,N‐ dimethyldodecylamine are the most efficient biocidal agents showing fast killing rates against Staphylococcus aureus and Escherichia coli . Linear oligoethylenimine hydrochloride shows the lowest MIC values but higher killing times against both bacteria. Based on the antimicrobial activity studies, a cooperative action of carbamic acid with the ammonium end group is proposed.