Enkephalin analogues with 2',6'-dimethylphenylalanine replacing phenylalanine in position 4

Y Sasaki; M Hirabuki; A Ambo; H Ouchi; Y Yamamoto

doi:10.1016/s0960-894x(00)00665-x

Enkephalin analogues with 2',6'-dimethylphenylalanine replacing phenylalanine in position 4

Bioorg Med Chem Lett. 2001 Feb 12;11(3):327-9. doi: 10.1016/s0960-894x(00)00665-x.

Authors

Y Sasaki¹, M Hirabuki, A Ambo, H Ouchi, Y Yamamoto

Affiliation

¹ Tohoku Pharmaceutical University, Sendai, Japan. ysasaki@tohoku-pharm.ac.jp

PMID: 11212102
DOI: 10.1016/s0960-894x(00)00665-x

Abstract

Four Leu-enkephalin (Enk) analogues containing 2',6'-dimethyphenylalanine (Dmp) in position 4 were prepared and tested for their receptor binding and biological activities. Among the analogues prepared, [2', 6'-dimethyltyrosine, D-Dmp4]Enk was found to be an antagonist toward mu and delta opioid receptors with pA2 values of 6.90 and 5.57, respectively.

MeSH terms

Animals
Binding, Competitive
Brain
Enkephalin, Leucine / chemical synthesis*
Enkephalin, Leucine / metabolism
Enkephalin, Leucine / pharmacology
Ileum / drug effects
Inhibitory Concentration 50
Male
Muscle Contraction / drug effects
Phenylalanine / analogs & derivatives*
Phenylalanine / chemical synthesis
Phenylalanine / pharmacology*
Protein Binding
Rats
Receptors, Opioid, delta / antagonists & inhibitors*
Receptors, Opioid, delta / metabolism
Receptors, Opioid, mu / antagonists & inhibitors
Receptors, Opioid, mu / metabolism
Structure-Activity Relationship
Synaptosomes / chemistry
Vas Deferens / drug effects

Substances

2',6'-dimethylphenylalanine
Receptors, Opioid, delta
Receptors, Opioid, mu
Phenylalanine
Enkephalin, Leucine