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: |
chemistry.chemical_classification
Chemistry Esters Microbial Sensitivity Tests Gram-Positive Bacteria Antimicrobial Chemical synthesis Capacity factor Anti-Bacterial Agents Quaternary Ammonium Compounds Partition coefficient Structure-Activity Relationship Anti-Infective Agents Carnitine Yeasts Gram-Negative Bacteria Drug Discovery Lipophilicity Molecular Medicine Molecule Organic chemistry Chromatography High Pressure Liquid Alkyl Antibacterial agent |
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 |
Externí odkaz: |