Synthesis and antimicrobial activity of the symmetric dimeric form of temporin A based on 3-N,N-di(3-aminopropyl)amino propanoic acid as the branching unit
| Autor: | Reino Laatikainen, Hilkka Lankinen, Pentti Kuusela, Ale Närvänen, Jari Ratilainen, Timo Korjamo, Harri Santa, Helena Hujakka |
|---|---|
| Rok vydání: | 2001 |
| Předmět: |
Staphylococcus aureus
Stereochemistry medicine.drug_class Clinical Biochemistry Pharmaceutical Science Carboxamide Peptide Microbial Sensitivity Tests Biochemistry Chemical synthesis 03 medical and health sciences chemistry.chemical_compound Amide Drug Discovery Escherichia coli medicine Peptide synthesis Molecular Biology 030304 developmental biology Antibacterial agent chemistry.chemical_classification 0303 health sciences 030306 microbiology Organic Chemistry Proteins Temporin Anti-Bacterial Agents Propanoic acid chemistry Molecular Medicine Antimicrobial Cationic Peptides |
| Zdroj: | Bioorganic & Medicinal Chemistry. 9:1601-1607 |
| ISSN: | 0968-0896 |
| Popis: | Dimeric derivative of antimicrobial peptide amide Temporin A (TA) was synthesized by using a new branching unit 3-N,N-di(3-aminopropyl)amino propanoic acid (DAPPA), which allows building of the parallelly symmetric alpha-helical structures. Antimicrobial effect of the original peptide amide, its monomeric carboxy (TAc) and novel dimeric (TAd) analogues were tested against Staphylococcus aureus (Gram-positive) and Escherichia coli (Gram-negative). Both TA and TAd completely inhibited the growth of S. aureus at the concentrations of 5 and 10 microM, respectively, whereas TAc did not show any inhibitory activity. The activities of TAc, TA and TAd correlate directly with the net charges of the molecules, +1, +2 and +4, respectively. Interestingly, TAd displayed antibacterial effect against E. coli at a concentration of 10 microM, where as monomeric TA did not show any activity at concentration as high as 20 microM. The results indicate that the novel structural modification improves the antibacterial properties of Temporin A especially towards Gram-negative bacteria. |
| Databáze: | OpenAIRE |
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