Synthesis and bioactivity studies of 1-adamantanamine derivatives of peptides.
Small enkephalin-related peptides containing a 1-adamantanamine moiety coupled through an amide linkage at the C-terminus were synthesized. Several of the compounds showed high mu opioid activity and mu receptor selectivity. The new adamantanamine derivatives were also examined for antiviral activity against HIV-1 in a cell culture system. Some of them inhibited syncytia formation even when the antigen assay gave evidence for viral replication.
Horvat
S
S
Department of Organic Chemistry and Biochemistry, Ruder Bosković Institute, Zagreb, Croatia.
Varga-Defterdarović
L
L
Horvat
J
J
Jukić
R
R
Kantoci
D
D
Chung
N N
NN
Schiller
P W
PW
Biesert
L
L
Pfützner
A
A
Suhartono
H
H
D000218:Adamantane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000595:Amino Acid Sequence; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004745:Enkephalins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006168:Guinea Pigs; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D007082:Ileum / Q000187:drug effects; D066298:In Vitro Techniques; D008297:Male; D051379:Mice; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017465:Receptors, Opioid, delta / Q000187:drug effects; D017450:Receptors, Opioid, mu / Q000187:drug effects; D014649:Vas Deferens / Q000187:drug effects
D000998:Antiviral Agents; D004745:Enkephalins; D009842:Oligopeptides; D017465:Receptors, Opioid, delta; D017450:Receptors, Opioid, mu; D000218:Adamantane