l-Carnitine Esters as 'Soft', Broad-Spectrum Antimicrobial Amphiphiles

Autor: Nazareno Scafetta, Giancarlo Gramiccioli, Fabrizio Giorgi, Francesco De Angelis, Menotti Calvani, and Maria Ornella Tinti, Grazia Gallo, Mose Santaniello, Luciana Critelli
Rok vydání: 1998
Předmět:
Zdroj: Journal of Medicinal Chemistry. 41:2227-2233
ISSN: 1520-4804
0022-2623
DOI: 10.1021/jm970305x
Popis: A new class of antimicrobial, "soft", quaternary ammonium l-carnitine esters, of the type (CH3)3N+-CH2-CHOCO(R1)-CH2-COO(R2) Cl-, has been designed, with R1 and R2 being in general long-chain alkyl substituents. The series shows good activity against a wide range of bacteria, yeasts, and fungi. Lipophilicity has been measured by RP-HPLC method to give the logarithm of the experimental capacity factor (log k'), and a quantitative relationship has been determined between log k' and the theoretical partition coefficient (CLOGP); also, bond-dipole descriptors have been introduced into calculations by accounting for polar moieties present within the apolar cores of the molecules, giving a more refined calculated capacity factor (log k'calcd). Finally the latter has been related to the antimicrobial activity (MIC values). The proposed models are predictive for the best broad-spectrum antimicrobial compound within the series.
Databáze: OpenAIRE