Influence of satellite groups on telechelic antimicrobial functions of polyoxazolines.
The antimicrobial activity of poly(alkyloxazoline) telechelics with one quaternary N,N-dimethyldodecylammonium (DDA) end group was found to be greatly controlled by the non-bioactive distal end group, the so-called satellite group. In systematic investigations, the nature of the latter groups was varied to explore the mechanism of the satellite effect. To this end, poly(2-alkyl-1,3-oxazoline)s (alkyl = ethyl, methyl) with a DDA-group at the terminating end and varying alkyl, aminoalkyl, and polyphenyloxazoline block satellite groups, have been synthesized. Poly(oxazoline) derivatives with polydispersity indices of 1.06-1.20 and molecular weights from 2,200 to 12,800 g . mol(-1) could be obtained. The macromolecular structures have been confirmed by NMR spectroscopy and ESI-MS measurements. The polymers were investigated with regard to their antibacterial efficiency towards the Gram-positive bacterium Staphylococcus aureus and the Gram-negative bacterium Escherichia coli. It was found that the introduction of alkyl chain satellites of 4-10 carbon atoms in length afforded antimicrobial activity of the polymers against both microbes that was about 2-3 times higher than that of the well-known structurally comparable low molecular weight biocide, dodecyltrimethylammonium chloride (DTAC). Based on the antimicrobial effects of the investigated polymers, a mechanism for the satellite effect was proposed.
Waschinski
Christian J
CJ
Freiburg Materials Research Center and Institute for Macromolecular Chemistry, University of Freiburg, Germany.
Herdes
Vera
V
Schueler
Fabian
F
Tiller
Joerg C
JC
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D002462:Cell Membrane / Q000378:metabolism; D004926:Escherichia coli / Q000187:drug effects*; D010080:Oxazoles / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D011108:Polymers / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization; D013211:Staphylococcus aureus / Q000187:drug effects*; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D010080:Oxazoles; D011108:Polymers