期刊
BIOORGANIC & MEDICINAL CHEMISTRY
卷 19, 期 11, 页码 3462-3473出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2011.04.026
关键词
Biofilm formation; Biofilm prevention; Salmonella Typhimurium; Pseudomonas aeruginosa; 2-Aminoimidazoles; 2-Hydroxy-2-aryl-2,3-dihydro-imidazo[1,2-a]pyrimidinium salts
资金
- Industrial Research Fund of K. U. Leuven [KP/06/014]
- Research Council of K. U. Leuven [CoE EF/05/007 SymBioSys]
- F.W.O. (Fund for Scientific Research Flanders (Belgium)
- Institute for the Promotion of Innovation through Science and Technology in Flanders (IWT-Vlaanderen)
- IAP
- K. U. Leuven
- Erasmus Mundus External Cooperation Window Lot 15 India [EMECW15]
A library of 80 1-substituted 2-hydroxy-2-aryl-2,3-dihydro-imidazo[1,2-a]pyrimidinium salts and 54 2N-substituted 4(5)-aryl-2-amino-1H-imidazoles was synthesized and tested for the antagonistic effect against biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa. The nature of the substituent at the 1-position of the salts was found to have a major effect on their biofilm inhibitory activity. Salts with an intermediate length n-alkyl or cyclo-alkyl chain (C7-C10) substituted at the 1-position in general prevented the biofilm formation of both species at low micromolar concentrations, while salts with a shorter n-alkyl or cyclo-alkyl chain (C1-C5) or longer n-alkyl chain (C11-C14) were much less potent. Salts with a long cyclo-alkyl chain however were found to be strong biofilm inhibitors. Furthermore, we demonstrated the biofilm inhibitory potential of salts with certain aromatic substituents at the 1-position, such as piperonyl or 3-methoxyphenetyl. The activity of the 2-aminomidazoles was found to be dependent on the nature of the 2N-substituent. Compounds with a n-butyl, iso-butyl, n-pentyl, cyclopentyl or n-hexyl chain at the 2N-position have an improved activity as compared to their unsubstituted counterparts, whereas compounds with shorter 2N-alkyl chains do have a reduced activity and compounds with longer 2N-alkyl chains do have an effect that is dependent on the nature of the substitution pattern of the 4(5)-phenyl ring. Finally, we demonstrated that introduction of a 3-methoxyphenethyl or piperonyl group at the 2N-position of the imidazoles could also result in an enhanced biofilm inhibition. (C) 2011 Elsevier Ltd. All rights reserved.
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