Synthesis, characterization and nociceptive screening of new VV-hemorphin-5 analogues
Autor: | Stela Georgieva, Petar Todorov, Petia Peneva, Daniela Pechlivanova, Elena Dzhambazova |
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Rok vydání: | 2018 |
Předmět: |
0301 basic medicine
Intracerebral injection Stereochemistry Clinical Biochemistry Drug Evaluation Preclinical Pain Pharmaceutical Science Peptide Biochemistry Redox Hemoglobins Mice Structure-Activity Relationship 03 medical and health sciences 0302 clinical medicine Drug Discovery Animals Amino Acids Molecular Biology Pain Measurement chemistry.chemical_classification Analgesics Behavior Animal Dose-Response Relationship Drug Molecular Structure Organic Chemistry Tryptophan VV-hemorphin-5 Peptide Fragments Amino acid Infusions Intraventricular 030104 developmental biology Nociception chemistry Molecular Medicine Hemorphin 030217 neurology & neurosurgery |
Zdroj: | Bioorganic & Medicinal Chemistry Letters. 28:3073-3079 |
ISSN: | 0960-894X |
DOI: | 10.1016/j.bmcl.2018.07.040 |
Popis: | In the present study, some new analogues of VV-hemorphin-5, modified at position 1 and 7 by the non-proteinogenic and/or natural amino acids followed the structures Xxx-Val-Val-Tyr-Pro-Trp-Thr-Gln-NH2 and Val-Val-Tyr-Pro-Trp-Thr-Yyy-NH2, where Xxx is Ile or Aib and Yyy is Lys/Orn/Dap/Dab were synthesized to investigate their potential antinociceptive activities. We report also the redox potentials and the acid/base properties as pKa values of these peptide analogues which were compared toward electrochemical behaviour of tryptophan containing peptides. All analogues showed a short lasting initial antinociceptive effect, however H2 hemorphin analogue is characterized with prolong and strong antinociceptive effect, while the other peptide analogues exerted more variable effects on the visceral nociception depending on the dose or time after the intracerebral injection. |
Databáze: | OpenAIRE |
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