Phenyl(thio)phosphon(amid)ate Benzenesulfonamides as Potent and Selective Inhibitors of Human Carbonic Anhydrases II and VII Counteract Allodynia in a Mouse Model of Oxaliplatin-Induced Neuropathy.
Animals
Antineoplastic Agents
/ toxicity
Carbonic Anhydrase II
/ antagonists & inhibitors
Carbonic Anhydrase Inhibitors
/ chemistry
Carbonic Anhydrases
/ metabolism
Cold Temperature
/ adverse effects
Crystallography, X-Ray
/ methods
Disease Models, Animal
Humans
Hyperalgesia
/ chemically induced
Male
Mice
Neuralgia
/ chemically induced
Oxaliplatin
/ toxicity
Sulfonamides
/ chemistry
Benzenesulfonamides
Journal
Journal of medicinal chemistry
ISSN: 1520-4804
Titre abrégé: J Med Chem
Pays: United States
ID NLM: 9716531
Informations de publication
Date de publication:
28 05 2020
28 05 2020
Historique:
pubmed:
5
5
2020
medline:
24
10
2020
entrez:
5
5
2020
Statut:
ppublish
Résumé
Human carbonic anhydrase (CA; EC 4.2.1.1) isoforms II and VII are implicated in neuronal excitation, seizures, and neuropathic pain (NP). Their selective inhibition over off-target CAs is expected to produce an anti-NP action devoid of side effects due to promiscuous CA modulation. Here, a drug design strategy based on the observation of (dis)similarities between the target CA active sites was planned with benzenesulfonamide derivatives and, for the first time, a phosphorus-based linker. Potent and selective CA II/VII inhibitors were identified among the synthesized phenyl(thio)phosphon(amid)ates
Identifiants
pubmed: 32364386
doi: 10.1021/acs.jmedchem.9b02135
pmc: PMC8007106
doi:
Substances chimiques
Antineoplastic Agents
0
Carbonic Anhydrase Inhibitors
0
Sulfonamides
0
Oxaliplatin
04ZR38536J
Carbonic Anhydrase II
EC 4.2.1.-
Carbonic Anhydrases
EC 4.2.1.1
carbonic anhydrase 7, mouse
EC 4.2.1.1
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
5185-5200Références
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