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Crystal structures of monoamine oxidase B in complex with four inhibitors of the N-propargylaminoindan class.

Binda C, Hubálek F, Li M, Herzig Y, Sterling J, Edmondson DE, Mattevi A
J Med Chem 47 1767-74 (2004)
Related entries: 1s2y, 1s3b, 1s3e

Cited: 83 times
EuropePMC logo PMID: 15027868

Abstract

Monoamine oxidase B (MAO B) is an outer mitochondrial membrane enzyme that catalyzes the oxidation of arylalkylamine neurotransmitters. The crystal structures of MAO B in complex with four of the N-propargylaminoindan class of MAO covalent inhibitors (rasagiline, N-propargyl-1(S)-aminoindan, 6-hydroxy-N-propargyl-1(R)-aminoindan, and N-methyl-N-propargyl-1(R)-aminoindan) have been determined at a resolution of better than 2.1 A. Rasagiline, 6-hydroxy-N-propargyl-1(R)-aminoindan, and N-methyl-N-propargyl-1(R)-aminoindan adopt essentially the same conformation with the extended propargyl chain covalently bound to the flavin and the indan ring located in the rear of the substrate cavity. N-Propargyl-1(S)-aminoindan binds with the indan ring in a flipped conformation with respect to the other inhibitors, which causes a slight movement of the Tyr326 side chain. Four ordered water molecules are an integral part of the active site and establish H-bond interactions to the inhibitor atoms. These structural studies may guide future drug design to improve selectivity and efficacy by introducing appropriate substituents on the rasagiline molecular scaffold.

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Reviews citing this publication (20)

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Articles citing this publication (53)

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  16. 8-Substituted 3-arylcoumarins as potent and selective MAO-B inhibitors: synthesis, pharmacological evaluation, and docking studies. Viña D, Matos MJ, Ferino G, Cadoni E, Laguna R, Borges F, Uriarte E, Santana L. ChemMedChem 7 464-470 (2012)
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  24. Synthesis and molecular modeling of some novel hexahydroindazole derivatives as potent monoamine oxidase inhibitors. Gökhan-Kelekçi N, Simşek OO, Ercan A, Yelekçi K, Sahin ZS, Işik S, Uçar G, Bilgin AA. Bioorg. Med. Chem. 17 6761-6772 (2009)
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  29. Design, synthesis, in vitro MAO-B inhibitory evaluation, and computational studies of some 6-nitrobenzothiazole-derived semicarbazones. Tripathi RK, Goshain O, Ayyannan SR. ChemMedChem 8 462-474 (2013)
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  34. Insight into the functional and structural properties of 3-arylcoumarin as an interesting scaffold in monoamine oxidase B inhibition. Matos MJ, Vilar S, García-Morales V, Tatonetti NP, Uriarte E, Santana L, Viña D. ChemMedChem 9 1488-1500 (2014)
  35. Reversible and irreversible small molecule inhibitors of monoamine oxidase B (MAO-B) investigated by biophysical techniques. Rojas RJ, Edmondson DE, Almos T, Scott R, Massari ME. Bioorg. Med. Chem. 23 770-778 (2015)
  36. Irreversible inactivation of snake venom l-amino acid oxidase by covalent modification during catalysis of l-propargylglycine. Mitra J, Bhattacharyya D. FEBS Open Bio 3 135-143 (2013)
  37. Is It Reliable to Take the Molecular Docking Top Scoring Position as the Best Solution without Considering Available Structural Data? Ramírez D, Caballero J. Molecules 23 (2018)
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  39. Adjunctive therapy in Parkinson's disease: the role of rasagiline. Gaines KD, Hinson VK. Neuropsychiatr Dis Treat 8 285-294 (2012)
  40. Design of novel nicotinamides as potent and selective monoamine oxidase a inhibitors. Shi L, Yang Y, Li ZL, Zhu ZW, Liu CH, Zhu HL. Bioorg. Med. Chem. 18 1659-1664 (2010)
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  43. Binding mechanism of naringenin with monoamine oxidase - B enzyme: QM/MM and molecular dynamics perspective. Govindasamy H, Magudeeswaran S, Kandasamy S, Poomani K. Heliyon 7 e06684 (2021)
  44. Evidence for a Cyanine Link Between Propargylamine Drugs and Monoamine Oxidase Clarifies the Inactivation Mechanism. Albreht A, Vovk I, Mavri J, Marco-Contelles J, Ramsay RR. Front Chem 6 169 (2018)
  45. Insight into Ginkgo biloba L. Extract on the Improved Spatial Learning and Memory by Chemogenomics Knowledgebase, Molecular Docking, Molecular Dynamics Simulation, and Bioassay Validations. Chen Y, Feng Z, Shen M, Lin W, Wang Y, Wang S, Li C, Wang S, Chen M, Shan W, Xie XQ. ACS Omega 5 2428-2439 (2020)
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  49. ZnCl2 loaded TiO2 nanomaterial: an efficient green catalyst to one-pot solvent-free synthesis of propargylamines. Bankar DB, Hawaldar RR, Arbuj SS, Moulavi MH, Shinde ST, Takle SP, Shinde MD, Amalnerkar DP, Kanade KG. RSC Adv 9 32735-32743 (2019)
  50. Fluorescent Mechanism-Based Probe for Aerobic Flavin-Dependent Enzyme Activity. McCulloch IP, La Clair JJ, Jaremko MJ, Burkart MD. Chembiochem 17 1598-1601 (2016)
  51. Monoamine Oxidases (MAOs) as Privileged Molecular Targets in Neuroscience: Research Literature Analysis. Yeung AWK, Georgieva MG, Atanasov AG, Tzvetkov NT. Front Mol Neurosci 12 143 (2019)
  52. Riluzole-Rasagiline Hybrids: Toward the Development of Multi-Target-Directed Ligands for Amyotrophic Lateral Sclerosis. Albertini C, Salerno A, Atzeni S, Uliassi E, Massenzio F, Maruca A, Rocca R, Mecava M, Silva FSG, Mena D, Valente P, Duarte AI, Chavarria D, Bissaro M, Moro S, Federico S, Spalluto G, Soukup O, Borges F, Alcaro S, Monti B, Oliveira PJ, Menéndez JC, Bolognesi ML. ACS Chem Neurosci 13 2252-2260 (2022)
  53. Study on the Neuroprotective, Radical-Scavenging and MAO-B Inhibiting Properties of New Benzimidazole Arylhydrazones as Potential Multi-Target Drugs for the Treatment of Parkinson's Disease. Anastassova N, Aluani D, Hristova-Avakumova N, Tzankova V, Kondeva-Burdina M, Rangelov M, Todorova N, Yancheva D. Antioxidants (Basel) 11 884 (2022)


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