Studies on the chemical modification of monensin. IV. Synthesis, sodium ion permeability, and biological activity of 7-O-acyl- and 7-O-alkylmonensins.
7-O-Acyl-(4a-e) and 7-O-alkylmonensins (5a-d) were prepared from monensin (1). Their lipophilicity, sodium ion permeability in human erythrocytes, antibacterial activity and effect on rat tail artery were examined. There was a correlation between lipophilicity and sodium ion permeability as well as between lipophilicity and antibacterial activity. We also found that the compound having larger sodium ion permeability, showed stronger contraction of rat tail artery. 7-O-Benzylmonensin (5c) exhibited higher lipophilicity and larger sodium ion permeability than monensin (1) among the tested monensin derivatives. In addition, antibacterial activity and contractile effect on rat tail artery of 5c were comparable to those of 1.
Nakamura
A
A
Faculty of Pharmaceutical Sciences, Nagoya City University, Japan.
Nagai
S
S
Takahashi
T
T
Malhan
R
R
Murakami
N
N
Ueda
T
T
Sakakibara
J
J
Asano
M
M
D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004912:Erythrocytes / Q000187:drug effects; D006801:Humans; D066298:In Vitro Techniques; D008826:Microbial Sensitivity Tests; D008985:Monensin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D009131:Muscle, Smooth, Vascular / Q000187:drug effects; D051381:Rats; D011921:Rats, Inbred WKY
D000890:Anti-Infective Agents; D008985:Monensin