Probiotics: antistaphylococcal activity of 4-aminocyclohexanecarboxylic acid, aminobenzoic acid, and their derivatives and structure-activity relationships

Derivatives of 4-aminocyclohexanecarboxylic acid and aminobenzoic acid were prepared and tested against experimentally induced Staphylococcus aureus infections in mice, cis- and irons-Gua-nidinocyclohexanecarboxylic acid, trans-4-aminomethylcyclohexane- carboxylic acid, trans -4-guanidinomethylcyclohexanecarboxylic acid, 4-aminomethylbenzoic acid, 4-guanidinomethylbenzoic acid, 4-(2-ami-noethyl)benzoie acid, 4-(2-guanidinoethyl)benzoic acid, and most of the ω-aminoacyl-4-aminobenzoic acids possessed antistaphylococcal activity. The R m values of these compounds were determined by a reversed-phase TLC system. Experimental R m values of several additional series of probiotics (ω-amino acids, ω-aminoacyl-L-histidines, ω-guanidino acids, ω-guanidinoacyl-L-histidines, and ω-aminoalkanesulfonic acids) were also obtained. A regular relationship was observed between the constitution of the mobile phases and the R m values; the optimal mobile phase was 70% acetone in water on silica gel G TLC plates. In all series, relationships were obtained between the biological response (antistaphylococcal activity per millimole) and the R m values, with an increased R m value paralleling an increased antistaphylococcal activity.