English   español  
Por favor, use este identificador para citar o enlazar a este item: http://hdl.handle.net/10261/12544
Compartir / Impacto:
Estadísticas
Add this article to your Mendeley library MendeleyBASE
Citado 3 veces en Web of Knowledge®  |  Pub MebCentral Ver citas en PubMed Central  |  Ver citas en Google académico
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Título

Chemoenzymatic Synthesis and Antimicrobial and Haemolytic Activities of Amphiphilic Bis(phenylacetylarginine) Derivatives

AutorCastillo Expósito, José A.; Infante, María Rosa; Manresa, Ángeles; Vinardell, M. Pilar; Mitjans, Montserrat; Clapés Saborit, Pere
Palabras claveAmino acids
Amphiphiles
Antibacterial agents
Antifungal agents
Biotransformations
Fecha de publicación14-sep-2006
EditorJohn Wiley & Sons
CitaciónChemMedChem 1(10): 1091-10998 (2006)
ResumenNovel bis(Nα-phenylacetyl-L-arginine)-α,w-alkanediamide dihydrochloride (bis(PhAcArg)) derivatives with antimicrobial activity were designed and synthesised by a chemoenzymatic strategy. The new structures consist of two Nα-phenylacetyl-L-arginine moieties connected by an alkanediamine spacer chain of 6, 8, 10, 12, and 14 methylene units through amide bonds. The key step in the chemoenzymatic strategy is the double aminolysis of the Nα-phenylacetyl-L-arginine methyl ester by the corresponding α,w-alkanediamine catalyzed by papain in ethanolic media. The compounds synthesised were tested as antimicrobials against 15 bacterial and 8 fungal species. The antimicrobial activity and selectivity depend strongly on the spacer chain length. The bis(PhAcArg) derivative with the spacer chain of 12 methylene groups gave the lowest MIC values against Gram-positive bacteria, whereas that with 14 methylene units was the best against Gram-negative bacteria.
Interestingly, these novel compounds showed enhanced antibacterial activity relative to the lead compound, bis(Nα-caproyl-L-arginine)-1,3-propanediamide dihydrochloride (C3(CA)2), and moderate antifungal activity. Moreover, tests of haemolytic activity toward human erythrocytes revealed that haemolysis increases with spacer chain length. Importantly, the compounds were classified as not irritating to eyes, with the exception of the compound with the spacer chain of 14 methylene groups, which was a slight eye irritant.
Descripción8 pages, 3 figures, 6 tables.-- PMID: 16972292 [PubMed].
Versión del editorhttp://dx.doi.org/10.1002/cmdc.200600148
URIhttp://hdl.handle.net/10261/12544
DOI10.1002/cmdc.200600148
ISSN1860-7179 (Print)
1860-7187 (Online)
Aparece en las colecciones: (IQAC) Artículos
Ficheros en este ítem:
No hay ficheros asociados a este ítem.
Mostrar el registro completo
 



NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.