A Chemoenzymatic Approach To Produce a Cyclic Analogue of the Analgesic Drug MVIIA (Ziconotide).
Chemoenzymatic Synthesis
Cyclization
Disulfide Bonds
Enzymes
Peptides
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
17 07 2023
17 07 2023
Historique:
received:
23
02
2023
medline:
12
7
2023
pubmed:
6
5
2023
entrez:
6
5
2023
Statut:
ppublish
Résumé
Ziconotide (ω-conotoxin MVIIA) is an approved analgesic for the treatment of chronic pain. However, the need for intrathecal administration and adverse effects have limited its widespread application. Backbone cyclization is one way to improve the pharmaceutical properties of conopeptides, but so far chemical synthesis alone has been unable to produce correctly folded and backbone cyclic analogues of MVIIA. In this study, an asparaginyl endopeptidase (AEP)-mediated cyclization was used to generate backbone cyclic analogues of MVIIA for the first time. Cyclization using six- to nine-residue linkers did not perturb the overall structure of MVIIA, and the cyclic analogues of MVIIA showed inhibition of voltage-gated calcium channels (Ca
Identifiants
pubmed: 37148162
doi: 10.1002/anie.202302812
doi:
Substances chimiques
ziconotide
7I64C51O16
omega-Conotoxins
0
Analgesics
0
Conotoxins
0
Calcium Channels
0
Calcium Channel Blockers
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202302812Informations de copyright
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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