PMID: 2498272Apr 1, 1989Paper

Structure activity relationships in PIPC-analogues against Pseudomonas aeruginosa

The Journal of Antibiotics
J MitsuyamaI Saikawa

Abstract

The relationship between the chemical structure and mode of action of piperacillin-analogues (PIPC-analogues) against Pseudomonas aeruginosa was investigated. The antibacterial activities of PIPC-analogues became stronger as the chain length of the alkyl group on the N-4 position in 2,3-dioxopiperazine when tested in constitutively beta-lactamase-producing strain, but not paralleled in wild and beta-lactamase-less strains. The outer membrane permeability was hardly affected by the chain length of the alkyl group at the N-4 position. The stability to beta-lactamase was stronger with the increase of the number of the carbon atoms of N-4 position. In the binding-affinities to the lethal penicillin-binding proteins (PBPs), compounds PIPC (C-2), C-3 and C-4 showed lower ID50 values than compounds C-1, C-6 and C-8. These results suggested that the stability to beta-lactamase was the governing part for the antibacterial activity in constitutively beta-lactamase-producing strain, and the binding affinity to lethal PBPs directly contributed to the antibacterial activity in wild and beta-lactamase-less strains.

Related Concepts

Related Feeds

Bacterial Cell Wall Structure

Bacterial cell walls are made of peptidoglycan (also called murein), which is made from polysaccharide chains cross-linked by unusual peptides containing D-amino acids. Here is the latest research on bacterial cell wall structures.

Bacterial Cell Wall Structure (ASM)

Bacterial cell walls are made of peptidoglycan (also called murein), which is made from polysaccharide chains cross-linked by unusual peptides containing D-amino acids. Here is the latest research on bacterial cell wall structures.