Synthesis of Bioinspired Carbohydrate Amphiphiles that Promote and Inhibit Biofilms.

Citation data:

Chemical science, ISSN: 2041-6520, Vol: 5, Issue: 2, Page: 551-557

Publication Year:
2014
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Repository URL:
https://digitalcommons.dartmouth.edu/facoa/702
PMID:
24376911
DOI:
10.1039/c3sc52777h
PMCID:
PMC3873002
Author(s):
Dane, Eric L; Ballok, Alicia E; O'Toole, George A; Grinstaff, Mark W
Publisher(s):
Royal Society of Chemistry (RSC); The Royal Society of Chemistry
Tags:
Chemistry; Biochemistry; Life Sciences; Microbiology
article description
The synthesis and characterization of a new class of bioinspired carbohydrate amphiphiles that modulate biofilm formation are reported. The carbohydrate head is an enantiopure poly-amido-saccharide (PAS) prepared by a controlled anionic polymerization of β-lactam monomers derived from either glucose or galactose. The supramolecular assemblies formed by PAS amphiphiles are investigated in solution using fluorescence assays and dynamic light scattering. Dried samples are investigated using X-ray, infrared spectroscopy, and transmission electron microscopy. Additionally, the amphiphiles are evaluated for their ability to modulate biofilm formation by the Gram-negative bacterium . Remarkably, from a library of eight amphiphiles, we identify a structure that promotes biofilm formation and two structures that inhibit biofilm formation. Using biological assays and electron microscopy, we relate the chemical structure of the amphiphiles to the observed activity. Materials that modulate the formation of biofilms by bacteria are important both as research tools for microbiologists to study the process of biofilm formation and for their potential to provide new drug candidates for treating biofilm-associated infections.