1, 2, 3-Triazole-based inhibitors of Porphyromonas gingivalis adherence to oral streptococci and biofilm formation. Issue 21 (1st November 2016)

• Record Type: Journal Article
• Authors: Patil, Pravin C.; Tan, Jinlian; Demuth, Donald R.; Luzzio, Frederick A.
• Is Part Of: Bioorganic & medicinal chemistry. Volume 24:Issue 21(2016)
• Page Start: 5410
• Page End: 5417
• Publication Date: 2016-11-01
• Subjects: Azides -- Biofilms -- Click chemistry -- Oxazoles -- Peptidomimetics; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2016.08.059
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Abstract: The development and use of small-molecule inhibitors of the adherence of Porphyromonas gingivalis to oral streptococci represents a potential therapy for the treatment of periodontal disease as these organisms work in tandem to colonize the oral cavity. Earlier work from these laboratories demonstrated that a small synthetic peptide was an effective inhibitor of the interaction between P. gingivalis and Streptococcus gordonii and that a small-molecule peptidomimetic would provide a more stable, less expensive and more effective inhibitor. An array of 2-(azidomethyl)- and 2-(azidophenyl)-4, 5-diaryloxazoles having a full range of hydrophobic groups were prepared and reacted with substituted arylacetylenes to afford the corresponding 'click' products. The title compounds were evaluated for their ability to inhibit P. gingivalis ' adherence to oral streptococci and several were found to be inhibitory in the range of (IC50 ) 5.3–67 μM.