PMID- 10028372
OWN - NLM
STAT- MEDLINE
DCOM- 19990322
LR  - 20141120
IS  - 0004-4172 (Print)
IS  - 0004-4172 (Linking)
VI  - 49
IP  - 1
DP  - 1999 Jan
TI  - Opioid deltorphin C analogues containing cis- or trans-2- or 3- or 
      4-aminocyclohexanecarboxylic acid residues.
PG  - 6-12
AB  - The solid phase synthesis, based on the Fmoc chemical protocol, was used to 
      prepare ten deltorphin C (Del-C; H-Tyr-D-Ala-Phe-Asp-Val-Val-Gly-NH2) analogues 
      containing cis- and trans- 2 or 3- or 4- aminocyclohexanecarboxylic acid (ACCA) 
      residues at position 2. ACCA-peptides showed high resistance to degradation by 
      plasma or brain enzymes, negligible affinity for the kappa-binding site and 
      modest delta- and/or mu-receptor affinities. Both [cis-3-ACCA2]Del-C analogues 
      and one trans isomer are the only deltorphin analogues of this series exhibiting 
      an appreciable delta-affinity and selectivity. These data suggest that the 
      presence of a conformationally constrained ACCA residue in position 2 of the 
      "message" sequence of deltorphin C is slightly tolerated.
FAU - Marastoni, M
AU  - Marastoni M
AD  - Department of Pharmaceutical Sciences and Biotechnology Center, University of 
      Ferrara, Italy.
FAU - Guerrini, R
AU  - Guerrini R
FAU - Balboni, G
AU  - Balboni G
FAU - Salvadori, S
AU  - Salvadori S
FAU - Fantin, G
AU  - Fantin G
FAU - Fogagnolo, M
AU  - Fogagnolo M
FAU - Lazarus, L H
AU  - Lazarus LH
FAU - Tomatis, R
AU  - Tomatis R
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - Germany
TA  - Arzneimittelforschung
JT  - Arzneimittel-Forschung
JID - 0372660
RN  - 0 (Amino Acids)
RN  - 0 (Amino Acids, Cyclic)
RN  - 0 (Analgesics, Opioid)
RN  - 0 (Cyclohexanecarboxylic Acids)
RN  - 0 (Cyclohexylamines)
RN  - 0 (Oligopeptides)
RN  - 0 (Receptors, Opioid)
RN  - 0 (Receptors, Opioid, delta)
RN  - 0 (Receptors, Opioid, kappa)
RN  - 0 (Receptors, Opioid, mu)
RN  - 122752-15-2 (deltorphin I, Ala(2)-)
RN  - 38541-66-1 (3-aminocyclohexanecarboxylic acid)
RN  - 5691-19-0 (2-aminocyclohexanecarboxylic acid)
RN  - 57043-03-5 (4-aminocyclohexanecarboxylic acid)
SB  - IM
MH  - Amino Acids/*chemistry
MH  - *Amino Acids, Cyclic
MH  - Analgesics, Opioid/*chemical synthesis/chemistry/pharmacology
MH  - Animals
MH  - Brain/enzymology/metabolism
MH  - Cyclohexanecarboxylic Acids/*chemistry
MH  - Cyclohexylamines/*chemistry
MH  - Guinea Pigs
MH  - Ileum/drug effects
MH  - In Vitro Techniques
MH  - Male
MH  - Mice
MH  - Molecular Conformation
MH  - Oligopeptides/*chemical synthesis/chemistry/pharmacology
MH  - Rats
MH  - Rats, Sprague-Dawley
MH  - Receptors, Opioid/*drug effects
MH  - Receptors, Opioid, delta/drug effects
MH  - Receptors, Opioid, kappa/drug effects
MH  - Receptors, Opioid, mu/drug effects
MH  - Spectrophotometry, Ultraviolet
MH  - Stereoisomerism
MH  - Vas Deferens/drug effects
EDAT- 1999/02/24 00:00
MHDA- 1999/02/24 00:01
CRDT- 1999/02/24 00:00
PHST- 1999/02/24 00:00 [pubmed]
PHST- 1999/02/24 00:01 [medline]
PHST- 1999/02/24 00:00 [entrez]
AID - 10.1055/s-0031-1300350 [doi]
PST - ppublish
SO  - Arzneimittelforschung. 1999 Jan;49(1):6-12. doi: 10.1055/s-0031-1300350.