[Molecular design of anti-MRSA drugs]

Nihon Rinsho. 1997 May;55(5):1281-6.
[Article in Japanese]

Abstract

The true nature of resistance of methicillin-resistant Staphylococcus aureus (MRSA) is penicillin-binding protein 2' (PBP2'). Affinities of almost all beta-lactam antibiotics to PBP2' were very low. Therefore, MRSA which produces PBP2' shows resistance to all beta-lactam antibiotics. However, PBP2' has a different affinity to each beta-lactam antibiotic. For this reason, we thought that some derivatives of beta-lactam compounds could have high affinity to PBP2'. Accordingly, we developed cephem compounds which are more stabile and safe than previous penicillin and carbapenem compounds. Firstly, we investigated the side chain at C-7 position on 2-thioisocephem skeletal. Hydroxyimino-aminothiazol at C-7 position on 2-thioisocephem skeletal had the strongest activity against MRSA. Secondly, we investigated the linkage styles at C-3 position on 2-thioisocephem skeletal which were methylene, vinyl, and propylene. The compound of vinyl linkage style at C-3 position on 2-thioisocephem skeletal showed high activity against MRSA. Finally, we investigated 1-thiocephem, 2-thioisocephem, and 2-oxaisocephem as cephem-skeletals. Simultaneously, we studied C-3 linkage styles which were methylene, vinyl, and propylene. From these results, we found out that the compound of hydroxyiminoaminothiazol at C-7 position and vinyl linkage style at C-3 position on 1-thiocephem skeletal has superb activity against MRSA.

Publication types

  • English Abstract
  • Review

MeSH terms

  • Bacterial Proteins*
  • Carrier Proteins*
  • Cephalosporins / chemistry*
  • Cephalosporins / metabolism
  • Cephalosporins / pharmacology
  • Drug Design*
  • Hexosyltransferases / metabolism
  • Methicillin Resistance*
  • Multienzyme Complexes / metabolism
  • Muramoylpentapeptide Carboxypeptidase*
  • Penicillin-Binding Proteins
  • Peptidyl Transferases / metabolism
  • Protein Binding
  • Staphylococcus aureus / drug effects*
  • Structure-Activity Relationship

Substances

  • Bacterial Proteins
  • Carrier Proteins
  • Cephalosporins
  • Multienzyme Complexes
  • Penicillin-Binding Proteins
  • Peptidyl Transferases
  • Hexosyltransferases
  • Muramoylpentapeptide Carboxypeptidase