Stability Studies of New Caged bis-deoxy-coelenterazine Derivatives and Their Potential Use as Cellular pH Probes.
Journal
Photochemistry and photobiology
ISSN: 1751-1097
Titre abrégé: Photochem Photobiol
Pays: United States
ID NLM: 0376425
Informations de publication
Date de publication:
03 2021
03 2021
Historique:
received:
29
07
2020
accepted:
16
10
2020
pubmed:
24
10
2020
medline:
7
10
2021
entrez:
23
10
2020
Statut:
ppublish
Résumé
The synthesis of new bis-deoxy-coelenterazine (1) derivatives bearing ester protective groups (acetate, propionate and butyrate esters) was accomplished. Moreover, their hydrolytic stability at room temperature was evaluated in dimethylsulfoxide (DMSO) as solvent, using the nuclear magnetic resonance (NMR) spectra of the key products at different time intervals. The results showed an increasing hydrolysis rate according to longest aliphatic chain, with a half-life of 24 days of the more stable acetate derivative (4a). Furthermore, the analysis of the experimental data revealed the greater stability of the enol tautomer in this aprotic polar solvent. This result was confirmed by theoretical calculations using the density functional theory (DFT) approach, which gave us the opportunity to propose a detailed decomposition mechanism. Additionally, the derivatives obtained were tested by bioluminescence luciferase assays to evaluate their potential use as extracellular pH-sensitive reporter substrates of luciferase. The biological data support the idea that further structural modifications of these molecules may open promising perspectives in this field of research.
Substances chimiques
Imidazoles
0
Molecular Probes
0
Pyrazines
0
coelenterazine
3O1CB88RRD
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
343-352Informations de copyright
© 2020 American Society for Photobiology.
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