Branched aminoglycosides: biochemical studies and antibacterial activity of neomycin B derivatives.
The C5''-OH group in neomycin B was glycosylated with a variety of mono- and di-saccharides to probe the effect of introduction of additional binding elements on antibacterial activity and interaction with the aminoglycosides modifying enzyme APH(3')-IIIa. The designed structures show antibacterial activity superior to that of neomycin B against pathogenic and resistant strains, while in parallel they demonstrate poor substrate activity with APH(3')-IIIa.
Department of Chemistry and Institute of Catalysis Science and Technology, Technion--Israel Institute of Technology, Haifa 32000, Israel.
Mariana
M
Hainrichson
Varvara
V
Pokrovskaya
Dalia
D
Shallom-Shezifi
Micha
M
Fridman
Valery
V
Belakhov
Dina
D
Shachar
Sima
S
Yaron
Timor
T
Baasov
D000617:Aminoglycosides / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D002236:Carbohydrate Conformation; D005601:Framycetin / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D021241:Spectrometry, Mass, Electrospray Ionization
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D005601:Framycetin