Amino acids and peptides. XXIII. Leu-enkephalin analogs containing a fluorinated amino acid at position 2, 4 or 5.
Fluorinated analogs of Leu-enkephalin were synthesized by the solution method and the solid-phase method. The synthetic peptides were examined for opioid activities on mouse vas deferens and guinea pig ileum. Among the synthetic peptides,[D-Ala2,Leu(F3)(2R,4S)5]enkephalin and [D-Ala2,Leu(F3)(2S,4R)5]enkephalin exhibited potent opioid activity, and [Leu(F3)(2S,4R)5]enkephalin exhibited high delta-receptor selectivity.
Maeda
M
M
Faculty of Pharmaceutical Sciences, Kobe-Gakuin University, Japan.
Kawasaki
K
K
Taguchi
T
T
Kobayashi
Y
Y
Yamamoto
Y
Y
Shimokawa
K
K
Takahashi
M
M
Nakao
K
K
Kaneto
H
H
D000595:Amino Acid Sequence; D000596:Amino Acids / Q000032:analysis; D000818:Animals; D004743:Enkephalin, Leucine / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D005461:Fluorine / Q000737:chemistry; D006168:Guinea Pigs; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D008969:Molecular Sequence Data; D009130:Muscle, Smooth / Q000187:drug effects*; D009197:Myenteric Plexus / Q000187:drug effects; D013329:Structure-Activity Relationship; D014649:Vas Deferens / Q000187:drug effects
D000596:Amino Acids; D005461:Fluorine; D004743:Enkephalin, Leucine