Phosphate-Based Self-Immolative Linkers for the Delivery of Amine-Containing Drugs.
31P-NMR spectroscopy
amine-containing drugs
phosphate-based linkers
prodrugs
self-immolative linkers
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
25 Aug 2021
25 Aug 2021
Historique:
received:
23
07
2021
revised:
12
08
2021
accepted:
20
08
2021
entrez:
10
9
2021
pubmed:
11
9
2021
medline:
29
9
2021
Statut:
epublish
Résumé
Amine-containing drugs often show poor pharmacological properties, but these disadvantages can be overcome by using a prodrug approach involving self-immolative linkers. Accordingly, we designed l-lactate linkers as ideal candidates for amine delivery. Furthermore, we designed linkers bearing two different cargos (aniline and phenol) for preferential amine cargo release within 15 min. Since the linkers carrying secondary amine cargo showed high stability at physiological pH, we used our strategy to prepare phosphate-based prodrugs of the antibiotic Ciprofloxacin. Therefore, our study will facilitate the rational design of new and more effective drug delivery systems for amine-containing drugs.
Identifiants
pubmed: 34500595
pii: molecules26175160
doi: 10.3390/molecules26175160
pmc: PMC8434617
pii:
doi:
Substances chimiques
Amines
0
Anti-Bacterial Agents
0
Pharmaceutical Preparations
0
Phosphates
0
Prodrugs
0
Lactic Acid
33X04XA5AT
Ciprofloxacin
5E8K9I0O4U
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : Grantová Agentura České Republiky
ID : 20-25137Y
Organisme : Grantová Agentura České Republiky
ID : 21-23014S
Organisme : Nadace Experientia
ID : SG-2018-1
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