The antibacterial activities of the para-guanidinoethylphenol and of its cyclic tetramer, the tetra-para-guanidinoethyl-calix[4]arene, have been evaluated on reference gram-positive and gram-negative bacteria. Antibiotic disk diffusion assays completed by micromethod technique were employed to determine if a synergistic effect could be expected from the spatial organisation of the monomer into its cyclic tetrameric analogue. Disk diffusion assays and microdilution experiments revealed better properties for the calixarene species, with a real and important gain of activity with regards to the monomer.