Aminopyrrolic Synthetic Receptors for Monosaccharides: A Class of Carbohydrate-Binding Agents Endowed with Antibiotic Activity versus Pathogenic Yeasts

作者：Nativi Cristina; Francesconi Oscar; Gabrielli Gabriele; De Simone Irene; Turchetti Benedetta; Mello Tommaso; Mannelli Lorenzo Di Cesare; Ghelardini Carla; Buzzini Pietro; Roelens Stefano^*

来源：Chemistry - A European Journal, 2012, 18(16): 5064-5072.

DOI：10.1002/chem.201103318

• antibiotics
• carbohydrates
• microbiology
• molecular recognition
• synthetic receptors

The biological activity of a set of structurally related aminopyrrolic synthetic receptors for monosaccharides has been tested versus yeast and yeast-like microorganisms and compared to their binding affinity toward mannosides. Antibiotic activity comparable to that of well-known polyene (amphotericin B) or azole (ketoconazole) drugs has been found for some members of the family, along with a general correlation with binding abilities. A systematic structureactivityaffinity investigation shed light on the structural and functional requirements necessary for antibiotic activity and identified the tripodal compound 1 as the most potent compound of the set. Together with toxicity tests and inhibitor localization experiments performed through fluorescence microscopy, these studies led to the characterization of a new class of carbohydrate binding agents possessing antibiotic activity, in which pyrrolic groups precisely structured on a tripodal architecture appear to be responsible for permeability through the cell wall of pathogens, as well as for antibiotic activity inside the cytoplasm.

• 出版日期2012-4