Synthesis and binding properties of deltorphin I analogues containing (R) and (S)-alpha-hydroxymethylnaphtylalanine.
New analogues of deltorphin I (DT I), in which the phenylalanine residue in position 3 is substituted with amphiphilic alpha,alpha-disubstituted amino acid enantiomers, (R) and (S)-alpha-hydroxymethylnaphtylalanine, were synthesized and tested for mu and delta opioid receptor affinity and selectivity. Although both analogues have lower affinity to delta receptors than DT I, they both expressed specificity to delta receptors.
Olma
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Institute of Organic Chemistry, Technical University, Lódź, Poland. olmaola@ck-sg.p.lodz.pl
Gniadzik
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Lipkowski
A W
AW
Lachwa
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D000409:Alanine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry; D000701:Analgesics, Opioid / Q000737:chemistry* / Q000378:metabolism; D008956:Models, Chemical; D009281:Naphthalenes / Q000138:chemical synthesis / Q000737:chemistry*; D009842:Oligopeptides / Q000737:chemistry* / Q000378:metabolism*; D010452:Peptide Biosynthesis; D010455:Peptides / Q000737:chemistry; D011485:Protein Binding; D017465:Receptors, Opioid, delta / Q000378:metabolism; D017450:Receptors, Opioid, mu / Q000378:metabolism
D000596:Amino Acids; D000701:Analgesics, Opioid; D009281:Naphthalenes; D009842:Oligopeptides; D010455:Peptides; D017465:Receptors, Opioid, delta; D017450:Receptors, Opioid, mu; C457539:hydroxymethylnaphthylalanine; C060208:deltorphin I, Ala(2)-; D000409:Alanine