Sign Inversion in Photopharmacology: Incorporation of Cyclic Azobenzenes in Photoswitchable Potassium Channel Blockers and Openers.
GIRK channels
diazocines
photopharmacology
photoswitchable molecules
potassium channels
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:
21 10 2019
21 10 2019
Historique:
received:
09
05
2019
revised:
30
07
2019
pubmed:
24
8
2019
medline:
25
9
2020
entrez:
24
8
2019
Statut:
ppublish
Résumé
Photopharmacology relies on ligands that change their pharmacodynamics upon photoisomerization. Many of these ligands are azobenzenes that are thermodynamically more stable in their elongated trans-configuration. Often, they are biologically active in this form and lose activity upon irradiation and photoisomerization to their cis-isomer. Recently, cyclic azobenzenes, so-called diazocines, have emerged, which are thermodynamically more stable in their bent cis-form. Incorporation of these switches into a variety of photopharmaceuticals could convert dark-active ligands into dark-inactive ligands, which is preferred in most biological applications. This "pharmacological sign-inversion" is demonstrated for a photochromic blocker of voltage-gated potassium channels, termed CAL, and a photochromic opener of G protein-coupled inwardly rectifying potassium (GIRK) channels, termed CLOGO.
Identifiants
pubmed: 31441199
doi: 10.1002/anie.201905790
doi:
Substances chimiques
Azo Compounds
0
G Protein-Coupled Inwardly-Rectifying Potassium Channels
0
Potassium Channel Blockers
0
Lidocaine
98PI200987
azobenzene
F0U1H6UG5C
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
15421-15428Subventions
Organisme : NIH HHS
ID : S10 OD021734
Pays : United States
Organisme : Deutsche Forschungsgemeinschaft
ID : SFB1116, TPA01
Pays : International
Organisme : European Research Council
ID : 268795
Pays : International
Organisme : European Commission
ID : PIEF-GA-2013-627990
Pays : International
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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