752
Views
83
CrossRef citations to date
0
Altmetric
Review

MAO inhibitors and their wider applications: a patent review

ORCID Icon, &
Pages 211-226 | Received 15 Dec 2017, Accepted 10 Jan 2018, Published online: 17 Jan 2018

References

  • Binda C , Newton-Vinson P , Hubálek F , et al. Structure of human monoamine oxidase B, a drug target for the treatment of neurological disorders. Nat Struct Biol. 2002;9:22–26.
  • Shih JC , Chen K , Ridd MJ. Monoamine oxidase: from genes to behavior. Annu Rev Neurosci. 1999;22:197–217.
  • Son SY , Ma J , Kondou Y , et al. Structure of human monoamine oxidase A at 2.2 A resolution: the control of opening the entry for substrates/inhibitors. Proc Natl Acad Sci U S A. 2008;105:5739–5744.
  • Youdim MB , Bakhle YS. Monoamine oxidase: isoforms and inhibitors in Parkinson’s disease and depressive illness. Br J Pharmacol. 2006;147(Suppl 1):S287–S296.
  • Chiba K , Trevor A , Castagnoli N Jr . Metabolism of the neurotoxic tertiary amine, MPTP, by brain monoamine oxidase. Biochem Biophys Res Commun. 1984;120:574–578.
  • Edmondson DE , Mattevi A , Binda C , et al. Structure and mechanism of monoamine oxidase. Curr Med Chem. 2004;11:1983–1993.
  • Youdim MB , Edmondson D , Tipton KF. The therapeutic potential of monoamine oxidase inhibitors. Nat Rev Neurosci. 2006;7:295–309.
  • Hubálek F , Binda C , Khalil A , et al. Demonstration of isoleucine 199 as a structural determinant for the selective inhibition of human monoamine oxidase B by specific reversible inhibitors. J Biol Chem. 2005;280:15761–15766.
  • Ramsay RR . Monoamine oxidases: the biochemistry of the proteins as targets in medicinal chemistry and drug discovery. Curr Top Med Chem. 2012;12:2189–2209.
  • Brown C , Taniguchi G , Yip K . The monoamine oxidase inhibitor-tyramine interaction. J Clin Pharmacol. 1989;29:529–532.
  • Lasbennes F , Sercombe R , Seylaz J . Monoamine oxidase activity in brain microvessels determined using natural and artificial substrates: relevance to the blood-brain barrier. J Cereb Blood Flow Metab. 1983;3:521–528.
  • Berry MD . Mammalian central nervous system trace amines. Pharmacologic amphetamines, physiologic neuromodulators. J Neurochem. 2004;90:257–271.
  • Zecca L , Youdim MB , Riederer P , et al. Iron, brain ageing and neurodegenerative disorders. Nat Rev Neurosci. 2004;5:863–873.
  • Ward RJ , Zucca FA , Duyn JH , et al. The role of iron in brain ageing and neurodegenerative disorders. Lancet Neurol. 2014;13:1045–1060.
  • Xuan M , Guan X , Gu Q , et al. Different iron deposition patterns in early- and middle-late-onset Parkinson’s disease. Parkinsonism Relat Disord. 2017;44:23–27.
  • Sian J , Dexter DT , Lees AJ , et al. Alterations in glutathione levels in Parkinson’s disease and other neurodegenerative disorders affecting basal ganglia. Ann Neurol. 1994;36:348–355.
  • Sofic E , Lange KW , Jellinger K , et al. Reduced and oxidized glutathione in the substantia nigra of patients with Parkinson’s disease. Neurosci Lett. 1992;142:128–130.
  • Fowler JS , Volkow ND , Wang GJ , et al. Age-related increases in brain monoamine oxidase B in living healthy human subjects. Neurobiol Aging. 1997;18:431–435.
  • Kaludercic N , Mialet-Perez J , Paolocci N , et al. Monoamine oxidases as sources of oxidants in the heart. J Mol Cell Cardiol. 2014;73:34–42.
  • Deshwal S , Di Sante M , Di Lisa F , et al. Emerging role of monoamine oxidase as a therapeutic target for cardiovascular disease. Curr Opin Pharmacol. 2017;33:64–69.
  • Grünblatt E , Riederer P . Aldehyde dehydrogenase (ALDH) in Alzheimer’s and Parkinson’s disease. J Neural Transm. 2016;123:83–90.
  • Burke WJ , Kumar VB , Pandey N , et al. Aggregation of alpha-synuclein by DOPAL, the monoamine oxidase metabolite of dopamine. Acta Neuropathol. 2008;115:193–203.
  • Schwartz TL . A neuroscientific update on monoamine oxidase and its inhibitors. CNS Spectr. 2013;18(Suppl 1):25–32.
  • Lum CT , Stahl SM . Opportunities for reversible inhibitors of monoamine oxidase-A (RIMAs) in the treatment of depression. CNS Spectr. 2012;17:107–120.
  • Ulrich S , Ricken R , Adli M . Tranylcypromine in mind (Part I): review of pharmacology. Eur Neuropsychopharmacol. 2017;27:697–713.
  • Riederer P , Müller T . Use of monoamine oxidase inhibitors in chronic neurodegeneration. Expert Opin Drug Metab Toxicol. 2017;13:233–240.
  • Fernandez HH , Chen JJ . Monoamine oxidase-B inhibition in the treatment of Parkinson’s disease. Pharmacotherapy. 2007;27(12 Pt 2):174S–185S.
  • Finberg JP , Wang J , Bankiewicz K , et al. Increased striatal dopamine production from L-DOPA following selective inhibition of monoamine oxidase B by R(+)-N-propargyl-1-aminoindan (rasagiline) in the monkey. J Neural Transm Suppl. 1998;52:279–285.
  • Pålhagen S , Heinonen EH , Hägglund J , et al. Selegiline delays the onset of disability in de novo parkinsonian patients. Swedish Parkinson Study Group Neurol. 1998;51:520–525.
  • Borroni E , Bohrmann B , Grueninger F , et al. Sembragiline: A novel, selective monoamine oxidase type B inhibitor for the treatment of Alzheimer’s disease. J Pharmacol Exp Ther. 2017;362:413–423.
  • Maurel A , Hernandez C , Kunduzova O , et al. Age-dependent increase in hydrogen peroxide production by cardiac monoamine oxidase A in rats. Am J Physiol Heart Circ Physiol. 2003;284:H1460–7.
  • Xu S , Adisetiyo H , Tamura S , et al. Dual inhibition of survivin and MAOA synergistically impairs growth of PTEN-negative prostate cancer. Br J Cancer. 2015;113:242–251.
  • Wu JB , Shao C , Li X , et al. Monoamine oxidase A mediates prostate tumorigenesis and cancer metastasis. J Clin Invest. 2014;124:2891–2908.
  • Berlin I , Aubin HJ , Pedarriosse AM , et al. Lazabemide in Smoking Cessation Study Investigators. Lazabemide, a selective, reversible monoamine oxidase B inhibitor, as an aid to smoking cessation. Addiction. 2002;97:1347–1354.
  • George TP , Weinberger AH . Monoamine oxidase inhibition for tobacco pharmacotherapy. Clin Pharmacol Ther. 2008;83:619–621.
  • Finberg JP . Update on the pharmacology of selective inhibitors of MAO-A and MAO-B: focus on modulation of CNS monoamine neurotransmitter release. Pharmacol Ther. 2014;143:133–152.
  • Binda C , Hubálek F , Li M , et al. Crystal structures of monoamine oxidase B in complex with four inhibitors of the N-propargylaminoindan class. J Med Chem. 2004;47:1767–1774.
  • Binda C , Hubálek F , Li M , et al. Binding of rasagiline-related inhibitors to human monoamine oxidases: a kinetic and crystallographic analysis. J Med Chem. 2005;48:8148–8154.
  • Milczek EM , Bonivento D , Binda C , et al. Structural and mechanistic studies of mofegiline inhibition of recombinant human monoamine oxidase B. J Med Chem. 2008;51:8019–8026.
  • Bonnet U . Moclobemide: therapeutic use and clinical studies. CNS Drug Rev. 2003;9:97–140.
  • Provost JC , Funck-Brentano C , Rovei V , et al. Pharmacokinetic and pharmacodynamic interaction between toloxatone, a new reversible monoamine oxidase-A inhibitor, and oral tyramine in healthy subjects. Clin Pharmacol Ther. 1992;52:384–393.
  • Pae CU , Patkar AA , Jang S , et al. Efficacy and safety of selegiline transdermal system (STS) for the atypical subtype of major depressive disorder: pooled analysis of 5 short-term, placebo-controlled trials. CNS Spectr. 2014;19:324–329.
  • Borgohain R , Szasz J , Stanzione P , et al. Study 018 Investigators. Two-year, randomized, controlled study of safinamide as add-on to levodopa in mid to late Parkinson’s disease. Mov Disord. 2014;29:1273–1280.
  • Dézsi L , Vécsei L . Safinamide for the treatment of Parkinson’s disease. Expert Opin Investig Drugs. 2014;23:729–742.
  • Ramsay RR . Inhibitor design for monoamine oxidases. Curr Pharm Des. 2013;19:2529–2539.
  • Carradori S , Petzer JP . Novel monoamine oxidase inhibitors: a patent review (2012-2014). Expert Opin Ther Pat. 2015;25:91–110.
  • Carradori S , Secci D , Bolasco A , et al. Patent-related survey on new monoamine oxidase inhibitors and their therapeutic potential. Expert Opin Ther Pat. 2012;22:759–801.
  • Bolasco A , Carradori S , Fioravanti R . Focusing on new monoamine oxidase inhibitors. Expert Opin Ther Pat. 2010;20:909–939.
  • Bolasco A , Fioravanti R , Carradori S . Recent development of monoamine oxidase inhibitors. Expert Opin Ther Pat. 2005;15:1763–1782.
  • Fonseca A , Reis J , Silva T , et al. Coumarin versus chromone monoamine oxidase B inhibitors: quo vadis?. J Med Chem. 2017;60:7206–7212.
  • Mathew B , Mathew GE , Petzer JP , et al. Structural exploration of synthetic chromones as selective MAO-B inhibitors: a mini review. Comb Chem High Throughput Screen. 2017;20:522–532.
  • Carradori S , Silvestri R . New frontiers in selective human MAO-B inhibitors. J Med Chem. 2015;58:6717–6732.
  • Chimenti F , Secci D , Bolasco A , et al. Synthesis, molecular modeling, and selective inhibitory activity against human monoamine oxidases of 3-carboxamido-7-substituted coumarins. J Med Chem. 2009;52:1935–1942.
  • Catto M , Nicolotti O , Leonetti F , et al. Structural insights into monoamine oxidase inhibitory potency and selectivity of 7-substituted coumarins from ligand- and target-based approaches. J Med Chem. 2006;49:4912–4925.
  • University Zhejiang Technology . Application of substituted aryl amides, or nitrogen-containing heterocyclic compounds in manufacture of monoamine oxidase inhibitor. CN105534964. 2016.
  • University Zhejiang Technology . 6-Chloro-N-(4-(6-chloro-nicotinamide)benzyl) nicotinamide, and preparation and application thereof. CN105601563. 2016.
  • Wenjian T . Tricyclo-pyrazole [1,5-d] [1,4] benzo oxazepine-one derivatives and preparation method and application thereof. CN105153195. 2015.
  • University China Pharma . 4-Hydroxycoumarin-3-Schiff base derivate and use thereof for curing Alzheimer’s disease. CN105017195. 2015.
  • University Hefei Technology . Stilbene coumarin derivative as well as preparation method and application thereof. CN104892556. 2015.
  • Secci D , Carradori S , Bolasco A , et al. Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives. Eur J Med Chem. 2011;46:4846–4852.
  • Detsi A , Kontogiorgis C , Hadjipavlou-Litina D . Coumarin derivatives: an updated patent review (2015-2016). Expert Opin Ther Pat. 2017;27:1201–1226.
  • Joubert J , Foka GB , Repsold BP , et al. Synthesis and evaluation of 7-substituted coumarin derivatives as multimodal monoamine oxidase-B and cholinesterase inhibitors for the treatment of Alzheimer’s disease. Eur J Med Chem. 2017;125:853–864.
  • Chimenti F , Secci D , Bolasco A , et al. Synthesis, molecular modeling studies, and selective inhibitory activity against monoamine oxidase of N,N’-bis[2-oxo-2H-benzopyran]-3-carboxamides. Bioorg Med Chem Lett. 2006;16:4135–4140.
  • University of Shanghai Traditional Chinese Medicine . Dihydrocoumarin derivatives as well as preparation method and application thereof. CN106588847. 2017.
  • Xie SS , Wang X , Jiang N , et al. Multi-target tacrine-coumarin hybrids: cholinesterase and monoamine oxidase B inhibition properties against Alzheimer’s disease. Eur J Med Chem. 2015;95:153–165.
  • University Guangdong Technology . Tacrine-coumarin derivative containing triazole and application of derivative. CN105503840. 2016.
  • Carradori S , D’Ascenzio M , Chimenti P , et al. Selective MAO-B inhibitors: a lesson from natural products. Mol Div. 2014;18:219–243.
  • Dhiman P , Malik N , Khatkar A . 3D-QSAR and in-silico studies of natural products and related derivatives as monoamine oxidase inhibitors. Curr Neuropharmacol. 2017. DOI:10.2174/1570159X15666171128143650
  • Nanjing Huakuan Information Consulting CT . Monoamine oxidase (MAO) inhibitor and application thereof. CN105106230. 2015.
  • Zibo Qidingli Patent Information Consultation Co Ltd . Use of Daphnilongeranin A in preparation of monoamine oxidase (MAO) inhibitor. CN105287548. 2016.
  • Zibo Qidingli Patent Information Consultation Co Ltd . Application of ieodoglucomides B to prepare monoamine oxidase (MAO) inhibitor CN105287609. 2016.
  • Zibo Qidingli Patent Information Consultation Co Ltd . Application of Sorgomol in preparing monoamine oxidase (MAO) inhibitor. CN105326829. 2016.
  • Zibo Qidingli Patent Information Consultation Co Ltd . Application of Norsampsone B in preparing MAO (monoamine oxidase) inhibitor. CN105412053. 2016.
  • Zibo Qidingli Patent Information Consultation Co Ltd . Application of Heyneanones A in preparing MAO (monoamine oxidase) inhibitor. CN105412054. 2016.
  • Zibo Qidingli Patent Information Consultation Co Ltd . Application of Herqueidiketal in preparation of MAO (monoamine oxidase) inhibitor. CN105412093. 2016.
  • Zibo Qidingli Patent Information Consultation Co Ltd . Application of Friedolanostanes in preparation of monoamine oxidase (MAO) inhibitor. CN106265687. 2017.
  • Zibo Qidingli Patent Information Consultation Co Ltd . Applications of Ternatusine A in preparing monoamine oxidase MAO inhibitor. CN106491599. 2017.
  • Weins A-F A chocolate composition comprising a monoamine oxidase inhibitor. GB25327444. 2015.
  • Carradori S , Gidaro MC , Petzer A , et al. Inhibition of human monoamine oxidase: biological and molecular modeling studies on selected natural flavonoids. J Agric Food Chem. 2016;64:9004–9011.
  • Gidaro MC , Astorino C , Petzer A , et al. Kaempferol as selective human MAO-A inhibitor: analytical detection in calabrian red wines, biological and molecular modelling studies. J Agric Food Chem. 2016;64:1394–1400.
  • Jäger AK , Saaby L . Flavonoids and the CNS. Molecules. 2011;16:1471–1485.
  • Yu Y , Wang R , Chen C , et al. Antidepressant-like effect of trans-resveratrol in chronic stress model: behavioral and neurochemical evidences. J Psychiatr Res. 2013;47:315–322.
  • De Monte C , Carradori S , Chimenti P , et al. New insights into the biological properties of Crocus sativus L.: chemical modifications, human monoamine oxidases inhibition and molecular modeling studies. Eur J Med Chem. 2014;82:164–171.
  • Santos MA , Chand K , Chaves S . Recent progress in repositioning Alzheimer’s disease drugs based on a multitarget strategy. Future Med Chem. 2016. DOI:10.4155/fmc-2016-0103
  • De Monte C , D’Ascenzio M , Guglielmi P , et al. Opening new scenarios for human MAO inhibitors. CNS Agents Med Chem. 2016;16:98–104.
  • Università degli Studi di Padova, Italy . Treatment of muscular distrophies and associated conditions by administration of monoamine oxidase inhibitors. US0290201. 2015.
  • Northwestern University, Illinois, USA . Treatment of dopaminergic disorders. US0182018. 2017.
  • Kinzer CE Methods and compositions for treating conditions associated with memory loss. US0038550. 2016.
  • The WWK TRUST & JD MED Services . Combinations for the treatment of dementia, and the enhancement of cognitive function. WO085437. 2017.
  • Validus Pharmaceuticals LLC. Methods for treating or preventing migraines. US0067187. 2016.
  • Filic V , Vladic A , Stefulj J , et al. Monoamine oxidases A and B gene polymorphisms in migraine patients. J Neurol Sci. 2005;228:149–153.
  • Concert Pharmaceuticals, Inc . Combination of morphinan compounds and antidepressant for the treatment of pseudobulbar affect, neurological diseases, intractable and chronic pain and brain injury. US0143902. 2016.
  • Shih JC , Hoffman FM , Chen TC MAO inhibitors and their conjugates as therapeutics for the treatment of brain cancer. US0029371. 2017.
  • Axovant Sciences Ltd . Combinations comprising 3-phenyl-sulfonyl-8-piperazin-1-yl-quinoline. US0320742. 2015.
  • Bautista-Aguilera ÓM , Hagenow S , Palomino-Antolin A , et al. Multitarget-directed ligands combining cholinesterase and monoamine oxidase inhibition with histamine H3R antagonism for neurodegenerative diseases. Angew Chem Int Ed. 2017;56:12765–12769.

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.