title: 1,2,3-Triazole-based inhibitors of Porphyromonas gingivalis adherence to oral streptococci and biofilm formation.
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) 5.3-67μM.
authors.affiliation: Department of Chemistry, University of Louisville, 2320 South Brook Street, Louisville, KY 40292, USA.
authors.forename: Pravin C
authors.initials: PC
authors.lastname: Patil
authors.affiliation: Department of Oral Immunology and Infectious Diseases, University of Louisville School of Dentistry, 501 S. Preston St., Louisville, KY 40292, USA.
authors.forename: Jinlian
authors.initials: J
authors.lastname: Tan
authors.affiliation: Department of Oral Immunology and Infectious Diseases, University of Louisville School of Dentistry, 501 S. Preston St., Louisville, KY 40292, USA.
authors.forename: Donald R
authors.initials: DR
authors.lastname: Demuth
authors.affiliation: Department of Chemistry, University of Louisville, 2320 South Brook Street, Louisville, KY 40292, USA.
authors.forename: Frederick A
authors.initials: FA
authors.lastname: Luzzio
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D018441:Biofilms / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D016966:Porphyromonas gingivalis / Q000187:drug effects*; D054852:Small Molecule Libraries / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D054773:Streptococcus gordonii / Q000187:drug effects*; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D054852:Small Molecule Libraries; D014230:Triazoles
keywords: Azides; Biofilms; Click chemistry; Oxazoles; Peptidomimetics