The introduction of fluorine atoms or trifluoromethyl groups in short cationic peptides enhances their antimicrobial activity

Diana Giménez; Cecilia Andreu; Marcel lí del Olmo; Teresa Varea; Dolores Diaz; Gregorio Asensio

doi:10.1016/j.bmc.2006.06.027

The introduction of fluorine atoms or trifluoromethyl groups in short cationic peptides enhances their antimicrobial activity

Bioorg Med Chem. 2006 Oct 15;14(20):6971-8. doi: 10.1016/j.bmc.2006.06.027. Epub 2006 Jun 30.

Authors

Diana Giménez¹, Cecilia Andreu, Marcel lí del Olmo, Teresa Varea, Dolores Diaz, Gregorio Asensio

Affiliation

¹ Departament de Química Orgànica, Facultat de Farmàcia, Universitat de València, 46100 Burjassot, València, Spain.

PMID: 16809042
DOI: 10.1016/j.bmc.2006.06.027

Abstract

The effect of introducing fluorine atoms or trifluoromethyl groups in either the peptidic chain or the C-terminal end of cationic pentapeptides is reported. Three series of amide and ester peptides were synthesised and their antimicrobial properties evaluated. An enhanced activity was found in those derivatives whose structure contained fluorine, suggesting an increase in their hydrophobicity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology*
Benzyl Compounds / chemistry*
Cations / chemistry
Drug Design
Eukaryotic Cells / drug effects
Fluorine / chemistry*
Humans
Hydrophobic and Hydrophilic Interactions
Microbial Sensitivity Tests
Molecular Structure
Oligopeptides / chemistry
Oligopeptides / pharmacology*
Stereoisomerism
Structure-Activity Relationship

Substances

Anti-Bacterial Agents
Benzyl Compounds
Cations
Oligopeptides
Fluorine