Synthesis and anti-HIV activity of nonatyrosine N- and O1-9-decasulfate.
To develop a potent and effective anti-HIV compound with a definite polyanionic structure, synthesis of oligotyrosine sulfates by oligomerization with simultaneous sulfation of tyrosine was tried. One component was successfully isolated from the mixture containing many products as its sodium salt (Y-ART-4) and was identified as the salt of nonatyrosine N- and O1-9-decasulfate, NaO3S-[Tyr(SO3Na)]9-ONa. Anti-HIV activity of Y-ART-4, determined from the protection it provided against HIV-induced cytopathic effects, was almost the same with that of dextran sulfate and curdlan sulfate.
Ueki
M
M
Department of Applied Chemistry, Science University of Tokyo, Japan. maueki@ch.kagu.sut.ac.jp
Watanabe
S
S
Ishii
Y
Y
Okunaka
O
O
Uchino
K
K
Saitoh
T
T
Higashi
K
K
Nakashima
H
H
Yamamoto
N
N
Ogawara
H
H
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002461:Cell Line, Transformed / Q000187:drug effects / Q000382:microbiology; D002851:Chromatography, High Pressure Liquid; D003588:Cytopathogenic Effect, Viral; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D009842:Oligopeptides; D010770:Phosphotransferases / Q000037:antagonists & inhibitors; D012194:RNA-Directed DNA Polymerase / Q000378:metabolism; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D014443:Tyrosine / Q000031:analogs & derivatives
D019380:Anti-HIV Agents; D004791:Enzyme Inhibitors; D009842:Oligopeptides; D018894:Reverse Transcriptase Inhibitors; C005662:tyrosine O-sulfate; D014443:Tyrosine; D010770:Phosphotransferases; D012194:RNA-Directed DNA Polymerase