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Synthesis and biological activity of (D)Ala 2 , Leu 5 ‐enkephalins containing hydrophilic or hydrophobic moieties
Author(s) -
Filippi Bruno,
Biondi Laura,
Filira Fernando,
Rocchi Raniero,
Bellini Cecilia,
Sarto Giampietro
Publication year - 1983
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.360220170
Subject(s) - chemistry , enkephalin , in vitro , in vivo , enzyme , stereochemistry , organic chemistry , biochemistry , receptor , microbiology and biotechnology , opioid , biology
The synthesis in solution of some modified (D)Ala 2 ,Leu 5 ‐enkephalins has been carried out. The lipophilic properties of the parent compound have been modified by amidation of the carboxyl function with alkylamines of increasing hydrophilicity to increase permeability of the blood‐brain barrier. Attempts to reduce enzymatic degradation have been carried out either by reductive glucosamination or by amidation of the carboxyl function with 2‐amino‐2‐deoxy‐β‐D‐glucopyranose. Esterification of the carboxyl function of (D)Ala 2 ,Leu 5 ‐enkephalin with polyethylenglycole 1000 has also been carried out. The effects induced by these modifications have been evaluated by in vitro and in vivo tests.