title: 3D-QSAR, synthesis, and antimicrobial activity of 1-alkylpyridinium compounds as potential agents to improve food safety.
abstract: Cetylpyridinium chloride (CPC), an alkylpyridinium compound has been recently approved by the US Food and Drug Administration to reduce bacterial contamination in poultry. Although CPC is very effective and has a very good safety record, its relatively high lipophilicity may limit its use in high fat containing foods such as beef. In this study we present the CoMFA analysis (3D-QSAR) of the antimicrobial activity of 60 N-alkylpyridinium compounds against different bacteria. CoMFA contours showed that the activity is highly influenced by the steric factor. Based in these contours we designed new candidates, which were synthesized and characterized by spectroscopic data. MIC activity over Gram positive and Gram negative microorganisms validated the 3D-QSAR study.
authors.affiliation: Departamento de Farmacia, Facultad de Química UNAM, CU Mexico, DF 04510, Mexico.
authors.forename: Sergio
authors.initials: S
authors.lastname: Rodríguez-Morales
authors.forename: R Lilia
authors.initials: RL
authors.lastname: Compadre
authors.forename: Rafael
authors.initials: R
authors.lastname: Castillo
authors.forename: Philip J
authors.initials: PJ
authors.lastname: Breen
authors.forename: Cesar M
authors.initials: CM
authors.lastname: Compadre
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015195:Drug Design; D004926:Escherichia coli / Q000187:drug effects; D005516:Food Microbiology; D005520:Food Preservatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D011726:Pyridinium Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D021281:Quantitative Structure-Activity Relationship; D012486:Salmonella typhimurium / Q000187:drug effects; D012984:Software
chemical_list: D000900:Anti-Bacterial Agents; D005520:Food Preservatives; D011726:Pyridinium Compounds