Lipophilicity of teicoplanin antibiotics as assessed by reversed phase high-performance liquid chromatography: quantitative structure-property and structure-activity relationships
Altomare, C.; Carotti, A.; Cellamare, S.; Carrieri, A.; Ciabatti, R.; Malabarba, A.
Journal of Pharmacy and Pharmacology 46(12): 994-999
1994
ISSN/ISBN: 0022-3573 PMID: 7714724 Document Number: 428420
Structure-lipophilicity relationships of a large series of 63-COX teicoplanin antibiotic derivatives were examined, by correlating their capacity factors (log k-w), measured through reversed-phase high-performance liquid chromatography on Deltabond C-8 stationary phase, with some computed molecular properties such as fragmental log P constants (pi-X), molecular volumes (V-x) and factors imparting hydrophilicity (e.g. amino groups in the X chain, nN). A number of equations were derived which demonstrate that variations of log k-w are mainly related to changes in bulk (modelled by V-x) and polarity (primarily modelled by nN) of X chains of teicoplanin derivatives. QSAR analysis revealed that in-vitro activity against E. coli increases as lipophilicity decreases and isoelectric point increases.