title: Antibacterial and antifungal activities of 2,3-pyrrolidinedione derivatives against oral pathogens.
abstract: Among the novel approaches applied to antimicrobial drug development, natural product-inspired synthesis plays a major role, by providing biologically validated starting points. Tetramic acids, a class of natural products containing a 2,4-pyrrolidinedione ring system, have attracted considerable attention for their antibacterial, antiviral, antifungal and anticancer activities. On the contrary, compounds with a 2,3-pyrrolidinedione skeleton have been considerably less investigated. In this work, we established chemical routes to the substituted 2,3-pyrrolidinedione core, which enabled the introduction of a wide range of diversity. In the perspective of a potential application for oral healthcare, a number of analogues with various substituents on the 2,3-pyrrolidinedione core were investigated for their antimicrobial and antifungal activities. The most promising compound showed a significant antimicrobial activity on Streptococcus mutans and Candida albicans, comparable to that of chlorhexidine, the gold standard in oral healthcare.
authors: Department of Food, Environmental and Nutritional Sciences, Division of Chemistry and Molecular Biology, University of Milan, via Celoria 2, 20133 Milan, Italy.
authors: Atul A
authors: AA
authors: Dhavan
authors: Department of Biomedical, Surgical and Dental Sciences, IRCCS Galeazzi Hospital, University of Milan, Milan, Italy.
authors: Andrei C
authors: AC
authors: Ionescu
authors: Department of Food, Environmental and Nutritional Sciences, Division of Chemistry and Molecular Biology, University of Milan, via Celoria 2, 20133 Milan, Italy.
authors: Rahul D
authors: RD
authors: Kaduskar
authors: Department of Biomedical, Surgical and Dental Sciences, IRCCS Galeazzi Hospital, University of Milan, Milan, Italy.
authors: Eugenio
authors: E
authors: Brambilla
authors: Department of Food, Environmental and Nutritional Sciences, Division of Chemistry and Molecular Biology, University of Milan, via Celoria 2, 20133 Milan, Italy. Electronic address: sabrina.dallavalle@unimi.it.
authors: Sabrina
authors: S
authors: Dallavalle
authors: Department of Biomedical, Surgical and Dental Sciences, University of Milan, Milan, Italy.
authors: Elena Maria
authors: EM
authors: Varoni
authors: Department of Agricultural and Environmental Sciences, University of Milan, Milan, Italy.
authors: Marcello
authors: M
authors: Iriti
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009055:Mouth / Q000382:microbiology*; D011760:Pyrrolidinones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013295:Streptococcus mutans / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D011760:Pyrrolidinones
keywords: 2,3-Pyrrolidinedione; Antibiofilm activity; Candida albicans; Chlorhexidine; Natural product-inspired synthesis; Oral health; Streptococcus mutans