369
Views
116
CrossRef citations to date
0
Altmetric
Review

Carbonic anhydrase inhibition and the management of neuropathic pain

Pages 961-968 | Received 11 Apr 2016, Accepted 19 May 2016, Published online: 02 Jun 2016

References

  • Bouhassira D, Attal N, Translational neuropathic pain research: a clinical perspective. Neuroscience. in press 2016. doi:10.1016/j.neuroscience.2016.03.029.
  • Watson JC, Sandroni P. Central neuropathic pain syndromes. Mayo Clin Proc. 2016;91:372–385.
  • Torrance N, Smith BH, Bennett MI, et al. The epidemiology of chronic pain of predominantly neuropathic origin. Results from a general population survey. J Pain. 2006;7:281–289.
  • Bouhassira D, Lantéri-Minet M, Attal N, et al. Prevalence of chronic pain with neuropathic characteristics in the general population. Pain. 2008;136:380–387.
  • Dworkin RH, O’Connor AB, Audette J, et al. Recommendations for the pharmacological management of neuropathic pain: an overview and literature update. Mayo Clinic Proc. 2010;85(3 Suppl):S3–S14.
  • Wieseler-Frank J, Maier SF, Watkins LR. Central proinflammatory cytokines and pain enhancement. Neuro-Signals. 2005;14:166–174.
  • Finnerup NB, Attal N, Haroutounian S, et al. Pharmacotherapy for neuropathic pain in adults: a systematic review and meta-analysis. Lancet Neurol. 2015;14:162–173.
  • Freeman R. Newer agents for the treatment of painful diabetic peripheral neuropathy. Curr Diab Rep. 2005;5:409–416.
  • Thiry A, Dognè JM, Masereel B, et al. Carbonic anhydrase inhibitors as anticonvulsant agents. Curr Top Med Chem. 2007;7:855–864.
  • Supuran CT. Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity. Expert Opin Emerg Drugs. 2012;17:11–15.
  • Snedecor SJ, Sudharshan L, Cappelleri JC, et al. Systematic review and meta-analysis of pharmacological therapies for painful diabetic peripheral neuropathy. Pain Pract. 2014;14:167–184.
  • McDonald AA, Portenoy RK. How to use antidepressants and anticonvulsants as adjuvant analgesics in the treatment of neuropathic cancer pain. J Support Oncol. 2006;4:43–52.
  • Di Cesare Mannelli L, Micheli L, Ghelardini C. Nociceptin/orphanin FQ receptor and pain: feasibility of the fourth opioid family member. Eur J Pharmacol. 2015;766:151–154.
  • Sanna MD, Stark H, Lucarini L, et al. Histamine H4 receptor activation alleviates neuropathic pain through differential regulation of ERK, JNK, and P38 MAPK phosphorylation. Pain. 2015;156:2492–2504.
  • Di Cesare Mannelli L, Pacini A, Corti F, et al. Antineuropathic profile of N-palmitoylethanolamine in a rat model of oxaliplatin-induced neurotoxicity. PLoS One. 2015;10:e0128080.
  • Carta F, Di Cesare Mannelli L, Pinard M, et al. A class of sulfonamide carbonic anhydrase inhibitors with neuropathic pain modulating effects. Bioorg Med Chem. 2015;23:1828–1840.
  • Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nature Rev Drug Discov. 2008;7:168–181.
  • Aggarwal M, McKenna R. Update on carbonic anhydrase inhibitors: a patent review (2008-2011). Expert Opin Ther Pat. 2012;22:903–915.
  • Alterio V, Di Fiore A, D’Ambrosio K, et al. Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms? Chem Rev. 2012;112:4421–4468.
  • Supuran CT. Structure-based drug discovery of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem. 2012;27:759–772.
  • Supuran CT. How many carbonic anhydrase inhibition mechanisms exist? J Enzyme Inhib Med Chem. 2016;31:345–360.
  • Supuran CT. Carbonic anhydrases: from biomedical applications of the inhibitors and activators to biotechnologic use for CO2 capture. J Enzyme Inhib Med Chem. 2013;28:229–230.
  • Supuran CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett. 2010;20:3467–3474.
  • Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nature Rev Drug Discov. 2011;10:767–777.
  • Halmi P, Parkkila S, Honkaniemi J. Expression of carbonic anhydrases II, IV, VII, VIII and XII in rat brain after kainic acid induced status epilepticus. Neurochem Int. 2006;48:24–30.
  • Supuran CT. Acetazolamide for the treatment of idiopathic intracranial hypertension. Expert Rev Neurother. 2015;15:851–856.
  • Scozzafava A, Supuran CT, Carta F. Antiobesity carbonic anhydrase inhibitors: a literature and patent review. Expert Opin Ther Pat. 2013;23:725–735.
  • Milhorat TH, Hammocck MK. Cerebrospinal fluid as a reflection of internal milieu of brain. In: Wood JH, Editor. Neurobiology of cerebrospinal fluid. New York (NY): Plenum Press; 1983. p. 1–23.
  • Brown PD, Davies SL, Speake T, et al. Molecular mechanisms of cerebrospinal fluid production. Neuroscience. 2004;129:957–970.
  • Masuzawa T, Sato F. The enzyme histochemistry of the choroid plexus. Brain. 1983;106(Pt 1):55–99.
  • Szabolcs MJ, Kopp M, Schaden GE. Carbonic anhydrase activity in the peripheral nervous system of rat: the enzyme as a marker for muscle afferents. Brain Res. 1989;492:129–138.
  • Ogawa T, Noguchi K, Saito M, et al. Carbonyl sulfidehydrolase from Thiobacillusthioparus strain THI115 is one of the β-carbonic anhydrase family enzymes. J Am Chem Soc. 2013;135:3818–3825.
  • Smeulders MJ, Barends TR, Pol A, et al. Evolution of a new enzyme for carbon disulphide conversion by an acidothermophilic archaeon. Nature. 2011;478:412–416.
  • Briganti F, Mangani S, Scozzafava A, et al. Carbonic anhydrase catalyzescyanamide hydration to urea: is it mimicking the physiological reaction? J Biol Inorg Chem. 1999;4:528–536.
  • Guerri A, Briganti F, Scozzafava A, et al. Mechanism of cyanamide hydration catalyzed by carbonic anhydrase II suggested by cryogenic X-ray diffraction. Biochemistry. 2000;39:12391–12397.
  • Pocker Y, Meany JE. The catalytic versatility of carbonic anhydrase from erythrocytes. The enzymatic catalyzed hydration of acetaldehyde. J Am Chem Soc. 1965;87:1809–1811.
  • Pocker Y, Stone JT. The catalytic versatility of erythrocyte carbonic anhydrase. The enzyme-catalyzed hydrolysis of para-nitrophenyl acetate. J Am Chem Soc. 1965;87:5497–5498.
  • Innocenti A, Supuran CT. Paraoxon, 4-nitrophenyl phosphate and acetate are substrates of α- but not of β-, γ- and ζ-carbonic anhydrases. Bioorg Med Chem Let. 2010;20:6208–6212.
  • Innocenti A, Scozzafava A, Parkkila S, et al. Investigations of the esterase, phosphatase, and sulfatase activities of the cytosolic mammalian carbonic anhydrase isoforms I, II, and XIII with 4-nitrophenyl esters as substrates. Bioorg Med Chem Lett. 2008;18:2267–2271.
  • Kazancioğlu EA, Güney M, Şentürk M, et al. Simple methanesulfonates are hydrolyzed by the sulfatase carbonic anhydrase activity. J Enzyme Inhib Med Chem. 2012;27:880–885.
  • Cavdar H, Ekinci D, Talaz O, et al. α-Carbonic anhydrases are sulfatases with cyclic diol monosulfate esters. J Enzyme Inhib Med Chem. 2012;27:148–154.
  • Carta F, Maresca A, Scozzafava A, et al. 5- and 6-membered (thio)lactones are prodrug type carbonic anhydrase inhibitors. Bioorg Med Chem Lett. 2012;22:267–270.
  • Tanc M, Carta F, Scozzafava A, et al. α-Carbonic anhydrases possess thioesterase activity. ACS Med Chem Lett. 2015;6:292–295.
  • Supuran CT, Conroy CW, Maren TH. Is cyanate a carbonic anhydrase substrate? Proteins. 1997;27:272–278.
  • Asiedu M, Ossipov MH, Kaila K, et al. Acetazolamide and midazolam act synergistically to inhibit neuropathic pain. Pain. 2010;148:302–308.
  • Asiedu MN, Mejia GL, Hübner CA, et al. Inhibition of carbonic anhydrase augments GABAA receptor-mediated analgesia via a spinal mechanism of action. J Pain. 2014;15:395–406.
  • Carta F, Scozzafava A, Supuran CT. Sulfonamides (RSO2NH2): a patent review 2008-2012. Expert Opin Ther Pat. 2012;22:747–758.
  • Scozzafava A, Carta F, Supuran CT. Secondary and tertiary sulfonamides: a patent review (2008-2012). Expert Opin Ther Pat. 2013;23:203–213.
  • Carta F, Supuran CT. Diuretics with carbonic anhydrase inhibitory action: a patent and literature review (2005-2013). Expert Opin Ther Pat. 2013;23:681–691.
  • Carta F, Supuran CT, Scozzafava A. Novel therapies for glaucoma: a patent review 2007-2011. Expert Opin Ther Pat. 2012;22:79–88.
  • Fabrizi F, Mincione F, Somma T, et al. A new approach to antiglaucoma drugs: carbonic anhydrase inhibitors with or without NO donating moieties. Mechanism of action and preliminary pharmacology. J Enzyme Inhib Med Chem. 2012;27:138–147.
  • Masini E, Carta F, Scozzafava A, et al. Antiglaucoma carbonic anhydrase inhibitors: a patent review. Expert Opin Ther Pat. 2013;23:705–716.
  • Monti SM, Supuran CT, De Simone G. Anticancer carbonic anhydrase inhibitors: a patent review (2008-2013). Expert Opin Ther Pat. 2013;23:737–749.
  • Lock FE, McDonald PC, Lou Y, et al. Targeting carbonic anhydrase IX depletes breast cancer stem cell within the hypoxic niche. Oncogene. 2013;32:5210–5219.
  • Supuran CT, Casini A, Mastrolorenzo A, et al. COX-2 selective inhibitors, carbonic anhydrase inhibition and anticancer properties of sulfonamides belonging to this class of pharmacological agents. Mini Rev Med Chem. 2004;4:625–632.
  • Sachdeo RC. Topiramate. Clinical profile in epilepsy. Clin Pharmacokinet. 1998;34:335–346.
  • Casini A, Antel J, Abbate F, et al. Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II and IV. Bioorg Med Chem Lett. 2003;13:841–845.
  • Leppik IE. Zonisamide: chemistry, mechanism of action, and pharmacokinetics. Seizure. 2004;13(Suppl 1):S5–S9.
  • De Simone G, Di Fiore A, Menchise V, et al. Carbonic anhydrase inhibitors. Zonisamide is an effective inhibitor of the cytosolic isozyme II and mitochondrial isozyme V: solution and X-ray crystallographic studies. Bioorg Med Chem Lett. 2005;15:2315–2320.
  • Weber A, Casini A, Heine A, et al. Unexpected nanomolar inhibition of carbonic anhydrase by COX-2 selective celecoxib: new pharmacological opportunities due to related binding site recognition. J Med Chem. 2004;47:550–557.
  • Supuran CT. Drug interaction considerations in the therapeutic use of carbonic anhydrase inhibitors. Expert Opin Drug Metab Toxicol. 2016;12:423–431.
  • Sun Y-J, Chen Y, Pang C, et al. Acetazolamide attenuates chemical-stimulated but not thermal-stimulated acute pain in mice. Acta Pharmacol Sin. 2014;35:41–47.
  • Rezende RM, Dos Reis WG, Duarte ID, et al. The analgesic actions of centrally administered celecoxib are mediated by endogenous opioids. Pain. 2009;142:94–100.
  • Gassani BC, Rezende RM, Paiva-Lima P, et al. Is the sulphonamide radical in the celecoxib molecule essential for its analgesic activity? Pharmacol Res. 2010;62:439–443.
  • Supuran CT. Diuretics: from classical carbonic anhydrase inhibitors to novel applications of the sulfonamides. Curr Pharm Des. 2008;14:641–648.
  • Temperini C, Cecchi A, Scozzafava A, et al. Carbonic anhydrase inhibitors. Comparison of chlorthalidone, indapamide, trichloromethiazide, and furosemide X-ray crystal structures in adducts with isozyme II, when several water molecules make the difference. Bioorg Med Chem. 2009;17:1214–1221.
  • Temperini C, Cecchi A, Scozzafava A, et al. Carbonic anhydrase inhibitors. Sulfonamide diuretics revisited–old leads for new applications? Org Biomol Chem. 2008;6:2499–2506.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.