6sdt › Citations

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.

Figure 1
Figure 2
Scheme 1
Nocentini A, Alterio V, Bua S, Micheli L, Esposito D, Buonanno M, Bartolucci G, Osman SM, ALOthman ZA, Cirilli R, Pierini M, Monti SM, Di Cesare Mannelli L, Gratteri P, Ghelardini C, De Simone G, Supuran CT
OpenAccess logo J Med Chem 63 5185-5200 (2020)
Cited: 11 times
EuropePMC logo PMID: 32364386

Abstract

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

Articles - 6sdt mentioned but not cited (1)

  1. 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. Nocentini A, Alterio V, Bua S, Micheli L, Esposito D, Buonanno M, Bartolucci G, Osman SM, ALOthman ZA, Cirilli R, Pierini M, Monti SM, Di Cesare Mannelli L, Gratteri P, Ghelardini C, De Simone G, Supuran CT. J Med Chem 63 5185-5200 (2020)


Reviews citing this publication (1)

  1. Organocatalytic asymmetric synthesis of P-stereogenic molecules. Liu J, Chen H, Wang M, He W, Yan JL. Front Chem 11 1132025 (2023)

Articles citing this publication (9)

  1. Activation of carbonic anhydrases from human brain by amino alcohol oxime ethers: towards human carbonic anhydrase VII selective activators. Nocentini A, Cuffaro D, Ciccone L, Orlandini E, Nencetti S, Nuti E, Rossello A, Supuran CT. J Enzyme Inhib Med Chem 36 48-57 (2021)
  2. Enantioselective hydrogen-bond-donor catalysis to access diverse stereogenic-at-P(V) compounds. Forbes KC, Jacobsen EN. Science 376 1230-1236 (2022)
  3. 2-Aminobenzoxazole-appended coumarins as potent and selective inhibitors of tumour-associated carbonic anhydrases. Fuentes-Aguilar A, Merino-Montiel P, Montiel-Smith S, Meza-Reyes S, Vega-Báez JL, Puerta A, Fernandes MX, Padrón JM, Petreni A, Nocentini A, Supuran CT, López Ó, Fernández-Bolaños JG. J Enzyme Inhib Med Chem 37 168-177 (2022)
  4. Carbonic Anhydrase IV Selective Inhibitors Counteract the Development of Colitis-Associated Visceral Pain in Rats. Lucarini E, Nocentini A, Bonardi A, Chiaramonte N, Parisio C, Micheli L, Toti A, Ferrara V, Carrino D, Pacini A, Romanelli MN, Supuran CT, Ghelardini C, Di Cesare Mannelli L. Cells 10 2540 (2021)
  5. Inhibitors of Mitochondrial Human Carbonic Anhydrases VA and VB as a Therapeutic Strategy against Paclitaxel-Induced Neuropathic Pain in Mice. Micheli L, Testai L, Angeli A, Carrino D, Pacini A, Margiotta F, Flori L, Supuran CT, Calderone V, Ghelardini C, Di Cesare Mannelli L. Int J Mol Sci 23 6229 (2022)
  6. 3H-1,2-Benzoxaphosphepine 2-oxides as selective inhibitors of carbonic anhydrase IX and XII. Pustenko A, Balašova A, Nocentini A, Supuran CT, Žalubovskis R. J Enzyme Inhib Med Chem 38 216-224 (2023)
  7. Alkylboronic acids as alkylating agents: photoredox-catalyzed alkylation reactions assisted by K3PO4. Yue F, Ma H, Song H, Liu Y, Dong J, Wang Q. Chem Sci 13 13466-13474 (2022)
  8. Computational Prediction of the Binding Pose of Metal-Binding Pharmacophores. Karges J, Stokes RW, Cohen SM. ACS Med Chem Lett 13 428-435 (2022)
  9. Aryl derivatives of 3H-1,2-benzoxaphosphepine 2-oxides as inhibitors of cancer-related carbonic anhydrase isoforms IX and XII. Balašova A, Pustenko A, Nocentini A, Vullo D, Supuran CT, Žalubovskis R. J Enzyme Inhib Med Chem 38 2249267 (2023)


Quick links