Discovery of novel human acrosin inhibitors by virtual screening

Journal of Computer-Aided Molecular Design

Volumn 25, Issue 10, 2011, Pages 977-985

  Liu, Xuefei ^a   Dong, Guoqiang ^a   Zhang, Jue ^a   Qi, Jingjing ^a   Zheng, Canhui ^a   Zhou, Youjun ^a   Zhu, Ju ^a   Sheng, Chunquan ^a   Lü, Jiaguo ^a  

^a SECOND MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

Human acrosin; Lead structure; Male contraceptives; Virtual screening

Indexed keywords

BINDING ENERGY; HYDROGEN BONDS; STRUCTURAL OPTIMIZATION; VIRTUAL REALITY;

BINDING MODES; DYNAMICS SIMULATION; HUMAN ACROSIN; HYDROPHOBICS; LEAD STRUCTURE; MALE CONTRACEPTIVE; PHARMACOPHORES; STRUCTURE BASED DRUG DESIGNS; VIRTUAL SCREENING; VIRTUAL SCREENING STRATEGIES;

MOLECULAR DYNAMICS;

ACROSIN; SERINE PROTEINASE INHIBITOR;

ARTICLE; CONTROLLED STUDY; DRUG BINDING; DRUG DESIGN; DRUG SCREENING; DRUG STRUCTURE; ENZYME INHIBITION; HUMAN; HYDROGEN BOND; IC 50; MALE; MOLECULAR DOCKING; MOLECULAR DYNAMICS; PHARMACOPHORE; PRIORITY JOURNAL; VIRTUAL REALITY;

EID: 84855202919     PISSN: 0920654X     EISSN: 15734951     Source Type: Journal    
DOI: 10.1007/s10822-011-9476-3     Document Type: Article

References (35)

1. U Klemm W Muller-Esterl W Engel 1991 Acrosin, the peculiar sperm-specific serine protease Hum Genet 87 635 641 10.1007/BF00201716 1:CAS:528:DyaK38XisFOj
2. L Howes R Jones 2002 Interactions between zona pellucida glycoproteins and sperm proacrosin/acrosin during fertilization J Reprod Immunol 53 181 192 10.1016/S0165-0378(01)00101-2 1:CAS:528:DC%2BD3MXos1Kjtrg%3D (Pubitemid 34569216)
3. IP Baskova LL Zavalova 2001 Proteinase inhibitors from the medicinal leech Hirudo medicinalis Biochemistry (Mosc) 66 703 714 10.1023/A:1010223325313 1:CAS:528:DC%2BD3MXmvV2gtLs%3D (Pubitemid 32915620)
4. R Pakzad 1989 The effect of the trypsin inhibitor aprotinin (Trasylol) and TLCK on the gelatinolytic activity of acrosin and the motility of rabbit sperm in vitro Z Mikrosk Anat Forsch 103 8 13 1:CAS:528:DyaL1MXltFaktLk%3D (Pubitemid 19119629)
5. R Jones R Parry L Lo Leggio P Nickel 1996 Inhibition of sperm-zona binding by suramin, a potential 'lead' compound for design of new anti-fertility agents Mol Hum Reprod 2 597 605 10.1093/molehr/2.8.597 1:CAS:528: DyaK28XmsFWjsbw%3D (Pubitemid 126720780)
6. LR Fraser 1982 p-Aminobenzamidine, an acrosin inhibitor, inhibits mouse sperm penetration of the zona pellucida but not the acrosome reaction J Reprod Fertil 65 185 194 10.1530/jrf.0.0650185 1:CAS:528:DyaL38XitFGiurY%3D (Pubitemid 12093339)
7. G Gupta RK Jain JP Maikhuri PK Shukla M Kumar AK Roy A Patra V Singh S Batra 2005 Discovery of substituted isoxazolecarbaldehydes as potent spermicides, acrosin inhibitors and mild anti-fungal agents Hum Reprod 20 2301 2308 10.1093/humrep/dei041 1:CAS:528:DC%2BD2MXmt1Gnu7s%3D (Pubitemid 41418522)
8. AS Bourinbaiar S Lee-Huang 1995 Acrosin inhibitor, 4′- acetamidophenyl 4-guanidinobenzoate, an experimental vaginal contraceptive with anti-HIV activity Contraception 51 319 322 10.1016/0010-7824(95)00094-Q 1:CAS:528:DyaK2MXmt1Omsbs%3D
9. R Tranter JA Read R Jones RL Brady 2000 Effector sites in the three-dimensional structure of mammalian sperm beta-acrosin Structure 8 1179 1188 10.1016/S0969-2126(00)00523-2 1:CAS:528:DC%2BD3cXotVOhsrc%3D (Pubitemid 32667483)
10. JG Lu CQ Sheng M Zhang HT Ji WN Zhang YJ Zhou J Zhu JH Jiang 2006 Homology modeling of human acrosin and its molecular docking study with KF950 Acta Chimica Sinica 64 1073 1078 1:CAS:528:DC%2BD28XlsVOgu70%3D (Pubitemid 44663004)
11. J Zhang C Zheng C Sheng Y Zhou J Zhu J Lv 2009 Characterization of human acrosin active site and binding modes with its inhibitors Chem J Chinese U 30 2409 2414 1:CAS:528:DC%2BC3cXht1ymsbs%3D
12. P Kolb DM Rosenbaum JJ Irwin JJ Fung BK Kobilka BK Shoichet 2009 Structure-based discovery of beta2-adrenergic receptor ligands Proc Natl Acad Sci U S A 106 6843 6848 10.1073/pnas.0812657106 1:CAS:528:DC%2BD1MXlsV2qsro%3D
13. H Li J Huang L Chen X Liu T Chen J Zhu W Lu X Shen J Li R Hilgenfeld H Jiang 2009 Identification of novel falcipain-2 inhibitors as potential antimalarial agents through structure-based virtual screening J Med Chem 52 4936 4940 10.1021/jm801622x 1:CAS:528:DC%2BD1MXot1GntLs%3D
14. BK Shoichet 2004 Virtual screening of chemical libraries Nature 432 862 865 10.1038/nature03197 1:CAS:528:DC%2BD2cXhtVOht7jK (Pubitemid 40037142)
15. AR Leach VJ Gillet RA Lewis R Taylor 2010 Three-dimensional pharmacophore methods in drug discovery J Med Chem 53 539 558 10.1021/jm900817u 1:CAS:528:DC%2BD1MXht1OktbjP
16. T Steindl T Langer 2004 Influenza virus neuraminidase inhibitors: generation and comparison of structure-based and common feature pharmacophore hypotheses and their application in virtual screening J Chem Inf Comput Sci 44 1849 1856 10.1021/ci049844i 1:CAS:528:DC%2BD2cXmslaqt7w%3D
17. Disocovery studio 2.5 software package AI, San Diego, CA (USA): http://www.accelrys.com
18. C La Motta S Sartini T Tuccinardi E Nerini F Da Settimo A Martinelli 2009 Computational studies of epidermal growth factor receptor: docking reliability, three-dimensional quantitative structure-activity relationship analysis, and virtual screening studies J Med Chem 52 964 975 10.1021/jm800829v 1:CAS:528:DC%2BD1MXht1Ogtb0%3D
19. SN Rao MS Head A Kulkarni JM LaLonde 2007 Validation studies of the site-directed docking program LibDock J Chem Inf Model 47 2159 2171 10.1021/ci6004299 1:CAS:528:DC%2BD2sXht1KitrvE (Pubitemid 350275082)
20. G Jones P Willett RC Glen AR Leach R Taylor 1997 Development and validation of a genetic algorithm for flexible docking J Mol Biol 267 727 748 10.1006/jmbi.1996.0897 1:CAS:528:DyaK2sXis1KntLo%3D (Pubitemid 27170693)
21. GM Morris DS Goodsell RS Halliday R Huey WE Hart RK Belew AJ Olson 1998 Automated docking using a lamarckian genetic algorithm and 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 1:CAS:528: DyaK1cXntFemur4%3D (Pubitemid 128590223)
22. H Lineweaver D Burk 1934 The determination of enzyme dissociation constants J Am Chem Soc 56 658 666 10.1021/ja01318a036 1:CAS:528: DyaA2cXisF2ltg%3D%3D
23. D Burk 1984 Enzyme kinetic constants: the double reciprocal plot Trends Biochem Sci 9 202 204 10.1016/0968-0004(84)90140-3
24. PA Greenidge B Carlsson LG Bladh M Gillner 1998 Pharmacophores incorporating numerous excluded volumes defined by X-ray crystallographic structure in three-dimensional database searching: application to the thyroid hormone receptor J Med Chem 41 2503 2512 10.1021/jm9708691 1:CAS:528: DyaK1cXkt12jt7c%3D (Pubitemid 28321900)
25. U Norinder 2000 Refinement of catalyst hypotheses using simplex optimisation J Comput Aided Mol Des 14 545 557 10.1023/A:1008191129541 1:CAS:528:DC%2BD3cXlsVGqsrY%3D (Pubitemid 30445058)
26. A Palomer F Cabre J Pascual J Campos MA Trujillo A Entrena MA Gallo L Garcia D Mauleon A Espinosa 2002 Identification of novel cyclooxygenase-2 selective inhibitors using pharmacophore models J Med Chem 45 1402 1411 10.1021/jm010458r 1:CAS:528:DC%2BD38XhsVGjsbY%3D (Pubitemid 34246103)
27. DE Shaw 2005 A fast, scalable method for the parallel evaluation of distance-limited pairwise particle interactions J Comput Chem 26 1318 1328 10.1002/jcc.20267 1:CAS:528:DC%2BD2MXpsFKhtL4%3D (Pubitemid 41454622)
28. Bowers KJ, Chow E, Xu H, Dror RO, Eastwood MP, Gregersen BA, Klepeis JL, Kolossváry I, Moraes MA, Sacerdoti JK, Shan Y, Shaw DE (2006) Scalable algorithms for molecular dynamics simulations on commodity clusters. In: Proceedings of the ACM/IEEE conference on supercomputing (SC06), Tampa, Florida, November 11-17
29. KJ Bowers RO Dror DE Shaw 2006 The midpoint method for parallelization of particle simulations J Chem Phys 124 184109 10.1063/1.2191489 (Pubitemid 43736791)
30. KJ Bowers RO Dror DE Shaw 2007 Zonal methods for the parallel execution of range-limited N-body simulations J Comput Phys 221 303 329 10.1016/j.jcp.2006.06.014
31. G Chillemi I D'Annessa P Fiorani C Losasso P Benedetti A Desideri 2008 Thr729 in human topoisomerase I modulates anti-cancer drug resistance by altering protein domain communications as suggested by molecular dynamics simulations Nucleic Acids Res 36 5645 5651 10.1093/nar/gkn558 1:CAS:528:DC%2BD1MXisFOltA%3D%3D
32. E Marco W Laine C Tardy A Lansiaux M Iwao F Ishibashi C Bailly F Gago 2005 Molecular determinants of topoisomerase I poisoning by lamellarins: comparison with camptothecin and structure-activity relationships J Med Chem 48 3796 3807 10.1021/jm049060w 1:CAS:528:DC%2BD2MXjvVeit7g%3D (Pubitemid 40776854)
33. WP Kennedy JM Kaminski HH Van der Ven RS Jeyendran DS Reid J Blackwell P Bielfeld LJ Zaneveld 1989 A simple, clinical assay to evaluate the acrosin activity of human spermatozoa J Androl 10 221 231 1:CAS:528:DyaL1MXksFaru78%3D (Pubitemid 19163595)
34. GL Hortin I Warshawsky M Laude-Sharp 2001 Macromolecular chromogenic substrates for measuring proteinase activity Clin Chem 47 215 222 1:CAS:528:DC%2BD3MXhtF2ru7c%3D (Pubitemid 32142919)
35. TC Yang YR Liu 1994 Kinetics of inhibitory effects of Phaseolus calcaratus inhibitor on acrosin of human body J Fujian Normal University (Natural Science) 10 8 12