Antimicrobial Agents - Cell Wall Inhibitors
Antimicrobial Agents - Cell wall inhibitors
Based on mode of action • divided into families based on chemical structure
Modes of action Interference with:
cell wall synthesis
protein synthesis
nucleic acid synthesis
plasma membrane integrity
metabolic pathway
Inhibitors of Bacterial Cell Wall (peptidoglycan) Synthesis
The Beta-lactam Family
The Glycopeptides
Peptidoglycan is composed of N-acetylglucosamine (NAG) and N-acetylmuramic acid (NAM) repeat units, and amino acids. Each NAM is linked to peptide chain and the peptide chains are cross-linked.
β-lactams
Includes penicillin derivatives (penams), cephalosporins (cephems), monobactams, and carbapenems.
class of broad-spectrum antibiotics containing a β-lactam ring
Bacterial transpeptidase enzymes are responsible for catalysing cross-linking of the peptide chains
β-lactam ring bind to these transpeptidases – this inhibits cross-linking between peptide chains and prevents synthesis of stable PG
Cell wall synthesis ceases and the bacterial cells eventually die due to osmotic instability or autolysis.
Glycopeptides
Polypeptide agents - basic structural elements amino acids
Vancomycin:
complexes with peptide portion of peptidoglycan’s precursor units
vancomycin is a large hydrophilic molecule able to form hydrogen bonds with the terminal D-alanyl-D-alanine moieties of the NAM/NAG-peptides
preventing PG transglycosylation reaction – PG precursor subunits (NAG-NAM+peptide) cannot be inserted into peptidoglycan matrix;
Vancomycin also alters bacterial-cell-membrane permeability and RNA synthesis
Uses: serious Gram positive infections e.g. MRSA wound infection
Adverse effects:
damage to auditory nerve
hearing loss (ototoxicity)
“Red man/neck” syndrome - rash on face, neck, upper torso
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