Top

Published in:

01-06-2013 | Translational Neurosciences - Short communication

Insights into the binding mode of new N-substituted pyrazoline derivatives to MAO-A: docking and quantum chemical calculations

Authors: Safiye Sağ Erdem, Seyhan Türkkan, Kemal Yelekçi, Nesrin Gökhan-Kelekçi

Published in: Journal of Neural Transmission | Issue 6/2013

Abstract

The binding modes of four N-substituted pyrazoline derivatives as novel MAO-A inhibitory agents were investigated using docking and quantum chemical molecular modelling tools.

Akyüz M, Erdem SS, Edmondson DE (2007) Aromatic cage in the active site of monoamine oxidase B: effect on the structural and electronic properties of bound benzylamine and p-nitrobenzylamine. J Neural Transm 114:693–698PubMedCrossRef

Binda C, Huba’lek F, Li M, DE Edmondson, Mattevi A (2004) Crystal structure of human monoamine oxidase B, a drug target enzyme monotopically inserted into the mitochondrial outer membrane. FEBS Lett 564:225–228PubMedCrossRef

Discovery Studio Modeling Environment (2011) Release 3.1. Accelrys Software Inc., San Diego

Edmondson DE, Mattevi A, Binda C, Li M, Huba’lek F (2004) Structure and mechanism of monoamine oxidase. Curr Med Chem 11:1983–1993PubMedCrossRef

Erdem SS, Büyükmenekşe B (2011) Computational investigation on the structure-activity relationship of the biradical mechanism for monoamine oxidase. J Neural Transm 118:1021–1029PubMedCrossRef

Erdem SS, Yelekçi K (2001) Computer modeling of oxygen containing heptylamines as monoamine oxidase inactivators. J Mol Struct Theochem 572:97–106CrossRef

Erdem SS, Karahan Ö, Yıldız İ, Yelekçi K (2006) A computational study on the amine-oxidation mechanism of monoamine oxidase: insight into the polar nucleophilic mechanism. Org Biomol Chem 4:646–658PubMedCrossRef

Frisch MJ et al (2009) Gaussian 09, Revision A1. Gaussian, Inc., Wallingford CT

Gasteiger J, Marsili M (1980) Iterative partial equalization of orbital electronegativity—a rapid access to atomic charges. Tetrahedron 36:3219–3228CrossRef

Gökhan-Kelekçi N, Küpeli E, Salgın U, Özgen Ö, Uçar G, Yeşilada E, Kendi E, Yeşilada A, Bilgin AA (2007) A new therapeutic approach in Alzheimer disease: some novel pyrazole derivatives as dual MAO-B inhibitors and antiinflammatory analgesics. Bioorg Med Chem 15:5775–5786PubMedCrossRef

Huey R, Morris GM, Olson AJ, Goodsell DS (2007) A semi-empirical free energy force field with charge-based desolvation. J Comput Chem 28:1145–1152PubMedCrossRef

Jayaprakash V, Sinha BN, Uçar G, Ercan A (2008) Pyrazoline-based mycobactin analogues as MAO-inhibitors. Bioorg Med Chem Lett 18:6362–6368PubMedCrossRef

Li M, Binda C, Mattevi A, Edmondson DE (2006) Functional role of the “aromatic cage” in human monoamine oxidase b: structures and catalytic properties of Tyr435 mutant proteins. Biochemistry 45:4775–4784PubMedCrossRef

Michel F, Saner P (1999) Python: a programming language for software integration and development. J Mol Graph Model 17:57–61

Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, Olsan AJ (1998) Automated docking using a Lamarckian genetic algorithm and empirical binding free energy function. J Comp Chem 19:1639–1662CrossRef

Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, Goodsell DS, Olson AJ (2009) Autodock4 and AutoDockTools4: automated docking with selective receptor flexibility. J Comput Chem 16:2785–2791CrossRef

Phillips JC, Braun R, Wang W, Gumbart J, Tajkhorshid E, Villa E, Chipot C, Skeel RD, Kale L, Schulten K (2005) Scalable molecular dynamics with NAMD. J Comput Chem 26:1781–1802PubMedCrossRef

Rezac J, Fanfrlik J, Salahub D, Hobza P (2009) Semiempirical quantum chemical PM6 method augmented by dispersion and h-bonding correction terms reliably describes various types of noncovalent complexes. J Chem Theory Comput 5:1749–1760CrossRef

Riederer P, Lachenmayer L, Laux G (2004) Clinical applications of MAO inhibitors. Curr Med Chem 11:2033–2043PubMedCrossRef

Shih JC (2004) Cloning, after cloning, knock-out mice and physiological functions of MAO A and B. Neurotoxicology 25:21–30PubMedCrossRef

Son Y, Ma J, Kondou Y, Yoshimura M, Yamashita E, Tsukihara T (2008) Structure of human monoamine oxidase A at 2.2-A resolution: the control of opening the entry for substrates/inhibitors. Proc Natl Acad Sci USA 105:5739–5744PubMedCrossRef

Stewart JJP (2007) Optimization of parameters for semiempirical methods V: modification of NDDO approximations and application to 70 elements. J Mol Mod 13:1173–1213CrossRef

Toprakçi M, Yelekçi K (2005) Docking studies on monoamine oxidase-B inhibitors: estimation of inhibition constants (Ki) of a series of experimentally tested compounds. Bioorg Med Chem Lett 15:4438–4446PubMedCrossRef

Yelekçi K, Karahan Ö, Toprakçı M (2007) Docking of novel reversible monoamine oxidase-B inhibitors: efficient prediction of ligand binding sites and estimation of inhibitors thermodynamic properties. J Neural Transm 114:725–732PubMedCrossRef

Title: Insights into the binding mode of new N-substituted pyrazoline derivatives to MAO-A: docking and quantum chemical calculations
Authors: Safiye Sağ Erdem
Seyhan Türkkan
Kemal Yelekçi
Nesrin Gökhan-Kelekçi
Publication date: 01-06-2013
Publisher: Springer Vienna
Published in: Journal of Neural Transmission / Issue 6/2013
Print ISSN: 0300-9564
Electronic ISSN: 1435-1463
DOI: https://doi.org/10.1007/s00702-012-0950-4

Keynote webinar | Spotlight on medication adherence

Springer Medicine

Insights into the binding mode of new N-substituted pyrazoline derivatives to MAO-A: docking and quantum chemical calculations

Abstract

Keynote webinar | Spotlight on medication adherence

Springer Medicine

Abstract

Please log in to get access to this content

Other articles of this Issue 6/2013

A comparison between radiometric and fluorimetric methods for measuring SSAO activity

Characterization of diamine oxidase from human seminal plasma

Study on SSAO enzyme activity and anti-inflammatory effect of SSAO inhibitors in animal model of inflammation

Special Issue: 15th amine oxidase conference: re-examine the amines

Cellular localization and trafficking of vascular adhesion protein-1 as revealed by an N-terminal GFP fusion protein

Do MAO A and MAO B utilize the same mechanism for the C–H bond cleavage step in catalysis? Evidence suggesting differing mechanisms