The effect of hydrophobicity of β‐lactam antibiotics on their phospholipid bilayer permeability

FEBS Letters

Yamaguchi, Akihito¹  Sawai, Tetsuo¹  Hiruma, Ryoichi¹ 

[1] Division of Microbial Chemistry, Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Chiba 260, Japan

关键词: β-Lactam;    Lipid-bilayer permeability;    Hydrophobicity;    Liposome;    Outer membrane;    β-Lactamase;   

DOI  :  10.1016/0014-5793(83)80323-8

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

Phospholipid bilayer permeability of β-lactam antibiotics was determined using liposomes enclosing β-lactamase. There was good correlation between the permeability and hydrophobicity within the analogous β-lactams. However, the effect of hydrophobic character on the permeability parameter was very different between the groups. Moderately hydrophilic penicillins such as benzylpenicillin and ampicillin showed very high permeability compared with cephalosporins. Penicillins having hindered side chains such as oxacillin and methicillin showed moderate permeability taking into account their hydrophobicity. These observations are suggestive of outer membrane permeation of these β-lactams via routes other than the porin pore, especially in porin-deficient mutants of gram-negative bacteria.

【 授权许可】

Unknown