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Structure of human monoamine oxidase A at 2.2-A resolution: the control of opening the entry for substrates/inhibitors.

Son SY, Ma J, Kondou Y, Yoshimura M, Yamashita E, Tsukihara T
Proc Natl Acad Sci U S A 105 5739-44 (2008)
Cited: 302 times
EuropePMC logo PMID: 18391214

Abstract

The mitochondrial outer membrane-anchored monoamine oxidase (MAO) is a biochemically important flavoenzyme that catalyzes the deamination of biogenic and xenobiotic amines. Its two subtypes, MAOA and MAOB, are linked to several psychiatric disorders and therefore are interesting targets for drug design. To understand the relationship between structure and function of this enzyme, we extended our previous low-resolution rat MAOA structure to the high-resolution wild-type and G110A mutant human MAOA structures at 2.2 and 2.17 A, respectively. The high-resolution MAOA structures are similar to those of rat MAOA and human MAOB, but different from the known structure of human MAOA [De Colibus L, et al. (2005) Proc Natl Acad Sci USA 102:12684-12689], specifically regarding residues 108-118 and 210-216, which surround the substrate/inhibitor cavity. The results confirm that the inhibitor selectivity of MAOA and MAOB is caused by the structural differences arising from Ile-335 in MAOA vs. Tyr-326 in MAOB. The structures exhibit a C-terminal transmembrane helix with clear electron density, as is also seen in rat MAOA. Mutations on one residue of loop 108-118, G110, which is far from the active center but close to the membrane surface, cause the solubilized enzyme to undergo a dramatic drop in activity, but have less effect when the enzyme is anchored in the membrane. These results suggest that the flexibility of loop 108-118, facilitated by anchoring the enzyme into the membrane, is essential for controlling substrate access to the active site. We report on the observation of the structure-function relationship between a transmembrane helical anchor and an extra-membrane domain.

Reviews - 2z5x mentioned but not cited (13)

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  7. Early Life Stress Induced DNA Methylation of Monoamine Oxidases Leads to Depressive-Like Behavior. Xu Q, Jiang M, Gu S, Wang F, Yuan B. Front Cell Dev Biol 8 582247 (2020)
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  10. Exploration of the Detailed Structure-Activity Relationships of Isatin and Their Isomers As Monoamine Oxidase Inhibitors. Kumar S, Nair AS, Abdelgawad MA, Mathew B. ACS Omega 7 16244-16259 (2022)
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Articles - 2z5x mentioned but not cited (117)

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  10. Crystallographic snapshots of the complete reaction cycle of nicotine degradation by an amine oxidase of the monoamine oxidase (MAO) family. Kachalova G, Decker K, Holt A, Bartunik HD. Proc Natl Acad Sci U S A 108 4800-4805 (2011)
  11. Monoamine Oxidase Inhibitory Activity of Novel Pyrazoline Analogues: Curcumin Based Design and Synthesis. Badavath VN, Baysal İ, Ucar G, Sinha BN, Jayaprakash V. ACS Med Chem Lett 7 56-61 (2016)
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  13. Probing Multi-Target Action of Phlorotannins as New Monoamine Oxidase Inhibitors and Dopaminergic Receptor Modulators with the Potential for Treatment of Neuronal Disorders. Seong SH, Paudel P, Choi JW, Ahn DH, Nam TJ, Jung HA, Choi JS. Mar Drugs 17 E377 (2019)
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  22. High-Throughput Screening and Molecular Dynamics Simulation of Natural Product-like Compounds against Alzheimer's Disease through Multitarget Approach. Iqbal D, Rehman MT, Bin Dukhyil A, Rizvi SMD, Al Ajmi MF, Alshehri BM, Banawas S, Khan MS, Alturaiki W, Alsaweed M. Pharmaceuticals (Basel) 14 937 (2021)
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  24. Synthesis of New Hydrazone Derivatives for MAO Enzymes Inhibitory Activity. Can NÖ, Osmaniye D, Levent S, Sağlık BN, İnci B, Ilgın S, Özkay Y, Kaplancıklı ZA. Molecules 22 E1381 (2017)
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  26. Selective Inhibition of Human Monoamine Oxidase B by Acacetin 7-Methyl Ether Isolated from Turnera diffusa (Damiana). Chaurasiya ND, Zhao J, Pandey P, Doerksen RJ, Muhammad I, Tekwani BL. Molecules 24 E810 (2019)
  27. 4-(3-Nitrophenyl)thiazol-2-ylhydrazone derivatives as antioxidants and selective hMAO-B inhibitors: synthesis, biological activity and computational analysis. Secci D, Carradori S, Petzer A, Guglielmi P, D'Ascenzio M, Chimenti P, Bagetta D, Alcaro S, Zengin G, Petzer JP, Ortuso F. J Enzyme Inhib Med Chem 34 597-612 (2019)
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  29. Selective Inhibition of Human Monoamine Oxidase B by 5-hydroxy-2-methyl-chroman-4-one Isolated from an Endogenous Lichen Fungus Daldinia fissa. Jeong GS, Kang MG, Han SA, Noh JI, Park JE, Nam SJ, Park D, Yee ST, Kim H. J Fungi (Basel) 7 84 (2021)
  30. The Benzopyrone Biochanin-A as a reversible, competitive, and selective monoamine oxidase B inhibitor. Zarmouh NO, Eyunni SK, Soliman KF. BMC Complement Altern Med 17 34 (2017)
  31. Crystallography Coupled with Kinetic Analysis Provides Mechanistic Underpinnings of a Nicotine-Degrading Enzyme. Tararina MA, Xue S, Smith LC, Muellers SN, Miranda PO, Janda KD, Allen KN. Biochemistry 57 3741-3751 (2018)
  32. Halogenated Coumarin-Chalcones as Multifunctional Monoamine Oxidase-B and Butyrylcholinesterase Inhibitors. Rehuman NA, Oh JM, Nath LR, Khames A, Abdelgawad MA, Gambacorta N, Nicolotti O, Jat RK, Kim H, Mathew B. ACS Omega 6 28182-28193 (2021)
  33. Stereoselective Activity of 1-Propargyl-4-styrylpiperidine-like Analogues That Can Discriminate between Monoamine Oxidase Isoforms A and B. Knez D, Colettis N, Iacovino LG, Sova M, Pišlar A, Konc J, Lešnik S, Higgs J, Kamecki F, Mangialavori I, Dolšak A, Žakelj S, Trontelj J, Kos J, Binda C, Marder M, Gobec S. J Med Chem 63 1361-1387 (2020)
  34. Trimethoxylated Halogenated Chalcones as Dual Inhibitors of MAO-B and BACE-1 for the Treatment of Neurodegenerative Disorders. Vishal PK, Oh JM, Khames A, Abdelgawad MA, Nair AS, Nath LR, Gambacorta N, Ciriaco F, Nicolotti O, Kim H, Mathew B. Pharmaceutics 13 850 (2021)
  35. Evaluation of the Inhibitory Effects of Bavachinin and Bavachin on Human Monoamine Oxidases A and B. Zarmouh NO, Mazzio EA, Elshami FM, Messeha SS, Eyunni SV, Soliman KF. Evid Based Complement Alternat Med 2015 852194 (2015)
  36. In Vitro and in Silico Human Monoamine Oxidase Inhibitory Potential of Anthraquinones, Naphthopyrones, and Naphthalenic Lactones from Cassia obtusifolia Linn Seeds. Paudel P, Seong SH, Shrestha S, Jung HA, Choi JS. ACS Omega 4 16139-16152 (2019)
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  38. Dietary Phenolic Compounds Interfere with the Fate of Hydrogen Peroxide in Human Adipose Tissue but Do Not Directly Inhibit Primary Amine Oxidase Activity. Carpéné C, Hasnaoui M, Balogh B, Matyus P, Fernández-Quintela A, Rodríguez V, Mercader J, Portillo MP. Oxid Med Cell Longev 2016 2427618 (2016)
  39. Discovery of N-(1-(3-fluorobenzoyl)-1H-indol-5-yl)pyrazine-2-carboxamide: a novel, selective, and competitive indole-based lead inhibitor for human monoamine oxidase B. Elkamhawy A, Paik S, Kim HJ, Park JH, Londhe AM, Lee K, Pae AN, Park KD, Roh EJ. J Enzyme Inhib Med Chem 35 1568-1580 (2020)
  40. Morpholine-based chalcones as dual-acting monoamine oxidase-B and acetylcholinesterase inhibitors: synthesis and biochemical investigations. Sasidharan R, Eom BH, Heo JH, Park JE, Abdelgawad MA, Musa A, Gambacorta N, Nicolotti O, Manju SL, Mathew B, Kim H. J Enzyme Inhib Med Chem 36 188-197 (2021)
  41. Positional scanning of natural product hispidol's ring-B: discovery of highly selective human monoamine oxidase-B inhibitor analogues downregulating neuroinflammation for management of neurodegenerative diseases. Hassan AHE, Kim HJ, Gee MS, Park JH, Jeon HR, Lee CJ, Choi Y, Moon S, Lee D, Lee JK, Park KD, Lee YS. J Enzyme Inhib Med Chem 37 768-780 (2022)
  42. Highly Potent, Selective, and Competitive Indole-Based MAO-B Inhibitors Protect PC12 Cells against 6-Hydroxydopamine- and Rotenone-Induced Oxidative Stress. Elsherbeny MH, Kim J, Gouda NA, Gotina L, Cho J, Pae AN, Lee K, Park KD, Elkamhawy A, Roh EJ. Antioxidants (Basel) 10 1641 (2021)
  43. Insights into a dual function amide oxidase/macrocyclase from lankacidin biosynthesis. Dorival J, Risser F, Jacob C, Collin S, Dräger G, Paris C, Chagot B, Kirschning A, Gruez A, Weissman KJ. Nat Commun 9 3998 (2018)
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  45. Resveratrol Analogues as Dual Inhibitors of Monoamine Oxidase B and Carbonic Anhydrase VII: A New Multi-Target Combination for Neurodegenerative Diseases? Carradori S, Fantacuzzi M, Ammazzalorso A, Angeli A, De Filippis B, Galati S, Petzer A, Petzer JP, Poli G, Tuccinardi T, Agamennone M, Supuran CT. Molecules 27 7816 (2022)
  46. Curcumin-based pyrazoline analogues as selective inhibitors of human monoamine oxidase A. Nath C, Badavath VN, Thakur A, Ucar G, Acevedo O, Mohd Siddique MU, Jayaprakash V. Medchemcomm 9 1164-1171 (2018)
  47. Design, Synthesis, and Bioevaluation of Indole Core Containing 2-Arylidine Derivatives of Thiazolopyrimidine as Multitarget Inhibitors of Cholinesterases and Monoamine Oxidase A/B for the Treatment of Alzheimer Disease. Shahid Nadeem M, Azam Khan J, Kazmi I, Rashid U. ACS Omega 7 9369-9379 (2022)
  48. Design, synthesis, and evaluation of 1, 4-benzodioxan-substituted chalcones as selective and reversible inhibitors of human monoamine oxidase B. Kong Z, Sun D, Jiang Y, Hu Y. J Enzyme Inhib Med Chem 35 1513-1523 (2020)
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  50. How to Separate Kinase Inhibition from Undesired Monoamine Oxidase A Inhibition-The Development of the DYRK1A Inhibitor AnnH75 from the Alkaloid Harmine. Wurzlbauer A, Rüben K, Gürdal E, Chaikuad A, Knapp S, Sippl W, Becker W, Bracher F. Molecules 25 E5962 (2020)
  51. Interactions of endocannabinoid virodhamine and related analogs with human monoamine oxidase-A and -B. Pandey P, Chaurasiya ND, Tekwani BL, Doerksen RJ. Biochem Pharmacol 155 82-91 (2018)
  52. Metabonomics Combined with UPLC-MS Chemical Profile for Discovery of Antidepressant Ingredients of a Traditional Chinese Medicines Formula, Chaihu-Shu-Gan-San. Jia H, Su Z, Long W, Liu Y, Chang X, Zhang H, Ding G, Feng Y, Cai D, Zou Z. Evid Based Complement Alternat Med 2013 487158 (2013)
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  54. Reversible Small Molecule Inhibitors of MAO A and MAO B with Anilide Motifs. Hagenow J, Hagenow S, Grau K, Khanfar M, Hefke L, Proschak E, Stark H. Drug Des Devel Ther 14 371-393 (2020)
  55. Rubrofusarin as a Dual Protein Tyrosine Phosphate 1B and Human Monoamine Oxidase-A Inhibitor: An in Vitro and in Silico Study. Paudel P, Seong SH, Jung HA, Choi JS. ACS Omega 4 11621-11630 (2019)
  56. Development of a Novel Class of Pyridazinone Derivatives as Selective MAO-B Inhibitors. Alagöz MA, Oh JM, Zenni YN, Özdemir Z, Abdelgawad MA, Naguib IA, Ghoneim MM, Gambacorta N, Nicolotti O, Kim H, Mathew B. Molecules 27 3801 (2022)
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  58. Inhibition of Tryptophan Hydroxylases and Monoamine Oxidase-A by the Proton Pump Inhibitor, Omeprazole-In Vitro and In Vivo Investigations. Betari N, Sahlholm K, Morató X, Godoy-Marín H, Jáuregui O, Teigen K, Ciruela F, Haavik J. Front Pharmacol 11 593416 (2020)
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  61. Selective Interactions of O-Methylated Flavonoid Natural Products with Human Monoamine Oxidase-A and -B. Chaurasiya ND, Midiwo J, Pandey P, Bwire RN, Doerksen RJ, Muhammad I, Tekwani BL. Molecules 25 E5358 (2020)
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  75. Design, Synthesis and Biological Evaluation of Novel N-Pyridyl-Hydrazone Derivatives as Potential Monoamine Oxidase (MAO) Inhibitors. Turan-Zitouni G, Hussein W, Sağlık BN, Tabbi A, Korkut B. Molecules 23 E113 (2018)
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  77. Emodin Derivatives as Multi-Target-Directed Ligands Inhibiting Monoamine Oxidase and Antagonizing Vasopressin V1A Receptors. Paudel P, Shrestha S, Park SE, Seong SH, Fauzi FM, Jung HA, Choi JS. ACS Omega 5 26720-26731 (2020)
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