Docking and quantitative structure-activity relationship studies for sulfonyl hydrazides as inhibitors of cytosolic human branched-chain amino acid aminotransferase

Molecular Diversity

Volumn 13, Issue 4, 2009, Pages 493-500

  Caballero, Julio ^a   Vergara Jaque, Ariela ^a   Fernández, Michael ^b,c   Coll, Deysma ^d  

^a UNIVERSIDAD DE TALCA   (Chile)

^b UNIVERSITY OF MATANZAS   (Cuba)

^c KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

^d UNIVERSITY OF HAVANA   (Cuba)

Author keywords

Branched chain amino acid aminotransferase inhibitors; Molecular docking; Quantitative structure activity relationships; Three dimensional descriptors

Indexed keywords

BRANCHED CHAIN AMINO ACID AMINOTRANSFERASE; ENZYME INHIBITOR; HYDRAZIDE DERIVATIVE; SULFONYL HYDRAZIDE; UNCLASSIFIED DRUG;

ARTICLE; COMPUTER PROGRAM; CORRELATION COEFFICIENT; CRYSTAL STRUCTURE; CYTOSOL; ELECTRON DIFFRACTION; HUMAN; HYDROGEN BOND; HYDROPHOBICITY; IC 50; MOLECULAR DOCKING; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; VALIDATION PROCESS;

CATALYTIC DOMAIN; CYTOSOL; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; HYDRAZINES; LINEAR MODELS; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; TRANSAMINASES;

EID: 70349907660     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-009-9140-1     Document Type: Article

References (32)

1. Ichihara A (1985) Aminotransferases of branched-chain amino acids. In: Christen P, Metzler DE (eds) Transaminases. Wiley, New York, pp 430-439
2. MG Bixel SM Hutson B Hamprecht 1997 Cellular distribution of branched-chain amino acid aminotransferase isoenzymes among rat brain glial cells in culture J Histochem Cytochem 45 685 694 9154155 1:CAS:528: DyaK2sXjtFKrsLg%3D
3. SM Hutson D Fenstermacher C Mahar 1988 Role of mitochondrial transamination in branched chain amino acid metabolism J Biol Chem 263 3618 3625 3346211 1:CAS:528:DyaL1cXhs1egurY%3D
4. SM Hutson R Wallin TR Hall 1992 Identification of mitochondrial branched chain aminotransferase and its isoforms in rat tissues J Biol Chem 267 15681 15686 1639805 1:CAS:528:DyaK38Xlt1ymurs%3D
5. TR Hall R Wallin GD Reinhart SM Hutson 1993 Branched chain aminotransferase isoenzymes J Biol Chem 268 3092 3098 8381418 1:CAS:528:DyaK3sXhsVags78%3D
6. E Lieth K LaNoue D Berkich B Xu M Ratz C Taylor SM Hutson 2001 Nitrogen shuttling between neurons and glial cells during glutamate synthesis J Neurochem 76 1712 1723 10.1046/j.1471-4159.2001.00156.x 11259489 10.1046/j.1471-4159. 2001.00156.x 1:CAS:528:DC%2BD3MXitlSktrs%3D (Pubitemid 32221111)
7. S Hutson 2001 Structure and function of branched chain aminotransferases Prog Nucleic Acid Res Mol Biol 70 175 206 10.1016/S0079-6603(01)70017-7 11642362 10.1016/S0079-6603(01)70017-7 1:CAS:528:DC%2BD3MXotFejsbk%3D
8. Hays SJ, Hu L-Y, Lei H, Scholten JD, Wustrow DJ (2002) US Patent 6632831
9. SM Hutson DA Berkich P Drown B Xu KF LaNoue 1998 Role of branched-chain aminotransferase isoenzymes and gabapentin in neurotransmitter metabolism J Neurochem 71 863 874 9681479 1:CAS:528:DyaK1cXkslKksLo%3D
10. L-Y Hu PA Boxer SR Kesten HJ Lei DJ Wustrow DW Moreland L Zhang K Ahn TR Ryder X Liu JR Rubin K Fahnoe R Carroll T Dutta S Fahnoe DC Probert AW Roof RL Rafferty MF Kostlan CR Scholten JD Hood M Ren X-D Schielke GP Su T-Z Taylor CP Mistry A Mc P Connell C Hasemann J Ohren 2006 The design and synthesis of human branched-chain amino acid aminotransferase inhibitors for treatment of neurodegenerative diseases Bioorg Med Chem Lett 16 2337 2340 10.1016/j.bmcl.2005.07.058 16143519 10.1016/j.bmcl.2005.07.058 1:CAS:528:DC%2BD28XislChur4%3D
11. PN Sekhar RN Amrutha S Sangam DPS Verma PBK Kishor 2007 Biochemical characterization, homology modeling and docking studies of ornithine δ-aminotransferase-an important enzyme in proline biosynthesis of plants J Mol Graph Model 26 709 719 10.1016/j.jmgm.2007.04.006 17604199 10.1016/j.jmgm.2007.04.006 1:CAS:528:DC%2BD2sXht1ams7jK (Pubitemid 47615555)
12. J-H Seo H-Y Park J Kim B-S Lee B-G Kim 2008 Exploring sequence space: profile analysis and protein-ligand docking to screen ω-aminotransferases with expanded substrate specificity Biotechnol J 3 676 686 10.1002/biot. 200700264 18398873 10.1002/biot.200700264 1:CAS:528:DC%2BD1cXntVejt7o%3D (Pubitemid 351803378)
13. L Pârvu 2003 QSAR-a piece of drug design J Cell Mol Med 7 333 335 10.1111/j.1582-4934.2003.tb00235.x 14594559 10.1111/j.1582-4934.2003.tb00235.x
14. MJS Dewar W Thiel 1977 Ground states of molecules. 38. The MNDO method. Approximations and parameters J Am Chem Soc 99 4899 4907 10.1021/ja00457a004 10.1021/ja00457a004 1:CAS:528:DyaE2sXkslelt7g%3D
15. Biosym Technologies (1993) Insight II Version 2.3, Discover Version 2.9.5 Biosym Technologies, San Diego, USA
16. GM Morris DS Goodsell RS Halliday R Huey WE Hart RK Belew AJ Olson 1998 Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function J Comput Chem 19 1639 1662 10.1002/(SICI)1096- 987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B 10.1002/(SICI)1096- 987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B 1:CAS:528: DyaK1cXntFemur4%3D
17. Tripos Inc. (2006) SYBYL version 7.3, Tripos Inc., 1699 South Hanley Road, St. Louis, MO 63144, USA
18. Todeschini R, Consonni V, Pavan M (2002) Dragon Software version 2.1
19. MC Hemmer V Steinhauer J Gasteiger 1999 Deriving the 3D structure of organic molecules from their infrared spectra Vib Spectrosc 19 151 164 10.1016/S0924-2031(99)00014-4 10.1016/S0924-2031(99)00014-4 1:CAS:528: DyaK1MXitlKhsb0%3D
20. MC Hemmer J Gasteiger 2000 Prediction of three-dimensional molecular structures using information from infrared spectra Anal Chim Acta 420 145 154 10.1016/S0003-2670(00)00876-X 10.1016/S0003-2670(00)00876-X 1:CAS:528: DC%2BD3cXmtVanu7s%3D (Pubitemid 30706362)
21. J Schuur P Selzer J Gasteiger 1996 The coding of the three-dimensional structure of molecules by molecular transforms and its application to structure-spectra correlations and studies of biological activity J Chem Inf Comput Sci 36 334 344 10.1021/ci950164c 1:CAS:528:DyaK28Xhtlygtb4%3D
22. R Todeschini M Lansagni E Marengo 1994 New molecular descriptors for 2D and 3D structures theory J Chemometr 8 263 272 10.1002/cem.1180080405 10.1002/cem.1180080405 1:CAS:528:DyaK2cXmtFentLo%3D
23. V Consonni R Todeschini M Pavan 2002 Structure/response correlations and similarity/diversity analysis by GETAWAY descriptors: 1. Theory of the novel 3D molecular descriptors J Chem Inf Comput Sci 42 682 692 10.1021/ci015504a 12086530 1:CAS:528:DC%2BD38XivFCgtrY%3D (Pubitemid 35355277)
24. The Mathworks Inc. (2004) MATLAB version 7.0. The Mathworks Inc., Natick, MA, http://www.mathworks.com
25. MTD Cronin TW Schultz 2003 Pitfalls in QSAR J Mol Struct THEOCHEM 622 39 51 10.1016/S0166-1280(02)00616-4 10.1016/S0166-1280(02)00616-4 1:CAS:528:DC%2BD3sXhsVSrurg%3D
26. M Fernández A Tundidor-Camba J Caballero 2005 Modeling of cyclin-dependent kinase inhibition by 1H-pyrazolo [3,4-d] pyrimidine derivatives using artificial neural network ensembles J Chem Inf Model 45 1884 1895 10.1021/ci050263i 16309296 10.1021/ci050263i
27. J Caballero M Fernández 2006 Linear and nonlinear modeling of antifungal activity of some heterocyclic ring derivatives using multiple linear regression and Bayesian-regularized neural networks J Mol Model 12 168 181 10.1007/s00894-005-0014-x 16205958 10.1007/s00894-005-0014-x 1:CAS:528:DC%2BD28XhsF2qs7c%3D (Pubitemid 43090583)
28. M Fernández J Caballero 2006 Ensembles of Bayesian-regularized genetic neural networks for modeling of acetylcholinesterase inhibition by huprines Chem Biol Drug Des 68 201 212 10.1111/j.1747-0285.2006.00435.x 17105484 10.1111/j.1747-0285.2006.00435.x (Pubitemid 44760245)
29. M Fernández MC Carreiras JL Marco J Caballero 2006 Modeling of acetylcholinesterase inhibition by tacrine analogues using Bayesian-regularized Genetic Neural Networks and ensemble averaging J Enzyme Inhib Med Chem 21 647 661 10.1080/14756360600862366 17252937 10.1080/14756360600862366 (Pubitemid 44970953)
30. PR Duchowicz M Fernández J Caballero EA Castro FM Fernández 2006 QSAR for non-nucleoside inhibitors of HIV-1 reverse transcriptase Bioorg Med Chem 14 5876 5889 10.1016/j.bmc.2006.05.027 16766190 10.1016/j.bmc.2006.05. 027 1:CAS:528:DC%2BD28Xntl2gtLs%3D (Pubitemid 44096998)
31. ® in medicinal chemistry. Bayesian-regularized genetic neural networks (BRGNN): Application to the prediction of the antagonistic activity against human platelet thrombin receptor (PAR-1) Curr Top Med Chem 8 1580 1605 10.2174/156802608786786570 19075769 10.2174/156802608786786570 1:CAS:528:DC%2BD1MXhtlCgsbo%3D
32. L Saíz-Urra MP González M Teijeira 2006 QSAR studies about cytotoxicity of benzophenazines with dual inhibition toward both topoisomerases I and II: 3D-MoRSE descriptors and statistical considerations about variable selection Bioorg Med Chem 14 7347 7358 10.1016/j.bmc.2006.05.081 16962784 10.1016/j.bmc.2006.05.081 (Pubitemid 44425416)