Syntheses and structure-membrane active antimicrobial activity relationship of alkylamino-modified glucose, maltooligosaccharide, and amylose

Chem Biol Drug Des. 2017 Nov;90(5):1012-1018. doi: 10.1111/cbdd.12989. Epub 2017 May 6.

Abstract

Antimicrobial alkylamine-modified sugars were prepared. Microwave-assisted click reaction efficiently achieved poly-functionalization of oligo- and polysaccharides. The sugars exhibited a unique relationship of their bacterial membrane permeabilization and antimicrobial activity with the number of functional groups and the structure of the molecular scaffold. It shows that the assembly of the functional groups is necessary for being antimicrobial. The amylose derivatives also exhibited synergy to minimize the necessary dose of conventional antibiotics and increase their antimicrobial potency.

Keywords: amylose; antimicrobial activity; maltooligosaccharide; microwave-assisted click reaction; synergistic activity.

Publication types

  • Letter

MeSH terms

  • Amylose / analogs & derivatives*
  • Amylose / chemical synthesis
  • Amylose / pharmacology*
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology*
  • Bacteria / drug effects*
  • Bacterial Infections / drug therapy
  • Click Chemistry
  • Glucose / analogs & derivatives
  • Glucose / chemical synthesis
  • Glucose / pharmacology
  • Humans
  • Microwaves
  • Oligosaccharides / chemical synthesis
  • Oligosaccharides / chemistry*
  • Oligosaccharides / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Oligosaccharides
  • maltooligosaccharides
  • Amylose
  • Glucose