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 (230 views)
J Med Chem (ISSN: 0022-2623linking, 0022-2623print, 1520-4804), 2020 May 28; 63(10): 5185-5200.
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Paper type: Research Journal Article, Research Support, Non-U. S. Gov'T,
Impact factor: 6.205, 5-year impact factor: 5.18
Url: Not available.
Keywords: Animals , Antineoplastic Agents Toxicity , Carbonic Anhydrase Ii Antagonists, Inhibitors Metabolism , Carbonic Anhydrase Inhibitors Chemistry Pharmacology Therapeutic Use , Carbonic Anhydrases Metabolism , Cold Temperature Adverse Effects , Crystallography, X-Ray Methods , Disease Models, Humans , Hyperalgesia Chemically Induced Drug Therapy Enzymology , Neuralgia Chemically Induced Drug Therapy Enzymology , Oxaliplatin Toxicity , Sulfonamides Chemistry Pharmacology Therapeutic Use,
Affiliations:
*** IBB - CNR ***
Department of NEUROFARBA, Pharmaceutical and Nutraceutical Section, University of Florence, Via Ugo Schiff 6, 50019 Sesto Fiorentino, Italy.
Istituto di Biostrutture e Bioimmagini, CNR, Via Mezzocannone 16, 80134 Napoli, Italy.
Chemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
Centro nazionale per il controllo e la valutazione dei farmaci, Istituto Superiore di Sanità, Viale Regina Elena 299, 00161 Rome, Italy.
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza University of Rome, P.le A. Moro 5, 00185 Rome, Italy.
References:
Not available.
J Med Chem (ISSN: 0022-2623linking, 0022-2623print, 1520-4804), 2020 May 28; 63(10): 5185-5200.
Export to BibTeX Export to EndNote
Paper type: Research Journal Article, Research Support, Non-U. S. Gov'T,
Impact factor: 6.205, 5-year impact factor: 5.18
Url: Not available.
Keywords: Animals , Antineoplastic Agents Toxicity , Carbonic Anhydrase Ii Antagonists, Inhibitors Metabolism , Carbonic Anhydrase Inhibitors Chemistry Pharmacology Therapeutic Use , Carbonic Anhydrases Metabolism , Cold Temperature Adverse Effects , Crystallography, X-Ray Methods , Disease Models, Humans , Hyperalgesia Chemically Induced Drug Therapy Enzymology , Neuralgia Chemically Induced Drug Therapy Enzymology , Oxaliplatin Toxicity , Sulfonamides Chemistry Pharmacology Therapeutic Use,
Affiliations:
*** IBB - CNR ***
Department of NEUROFARBA, Pharmaceutical and Nutraceutical Section, University of Florence, Via Ugo Schiff 6, 50019 Sesto Fiorentino, Italy.
Istituto di Biostrutture e Bioimmagini, CNR, Via Mezzocannone 16, 80134 Napoli, Italy.
Chemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
Centro nazionale per il controllo e la valutazione dei farmaci, Istituto Superiore di Sanità, Viale Regina Elena 299, 00161 Rome, Italy.
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza University of Rome, P.le A. Moro 5, 00185 Rome, Italy.
References:
Not available.
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
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 3-22. X-ray crystallography depicted the binding mode of phosphonic acid 3 to both CAs II and VII. The most promising derivatives, after evaluation of their stability in acidic media, were tested in a mouse model of oxaliplatin-induced neuropathy. The most potent compound racemic mixture was subjected to HPLC enantioseparation, and the identification of the eutomer, the (S)-enantiomer, allowed to halve the dose totally relieving allodynia in mice.
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 3-22. X-ray crystallography depicted the binding mode of phosphonic acid 3 to both CAs II and VII. The most promising derivatives, after evaluation of their stability in acidic media, were tested in a mouse model of oxaliplatin-induced neuropathy. The most potent compound racemic mixture was subjected to HPLC enantioseparation, and the identification of the eutomer, the (S)-enantiomer, allowed to halve the dose totally relieving allodynia in mice.
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
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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
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22 Records (22 excluding Abstracts).
Total impact factor: 90.777 (90.777 excluding Abstracts).
Total 5 year impact factor: 83.795 (83.795 excluding Abstracts).
Total impact factor: 90.777 (90.777 excluding Abstracts).
Total 5 year impact factor: 83.795 (83.795 excluding Abstracts).
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