QSAR and complex network study of the chiral HMGR inhibitor structural diversity

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 1, 2009, Pages 165-175

  García, Isela ^a   Munteanu, Cristian Robert ^b,c   Fall, Yagamare ^a   Gómez, Generosa ^a   Uriarte, Eugenio ^c   González Díaz, Humberto ^c  

^a UNIVERSITY OF VIGO   (Spain)

^b UNIVERSITY OF PORTO   (Portugal)

^c UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

3 Hydroxy 3 methyl glutaryl coenzyme A reductase; Anti parasite drug; Atherosclerotic disease; Chagas' disease; Chiral compound; Cholesterol level; Complex network; Lipid lowering agent; QSAR; Topological indices; Trypanosoma cruzi

Indexed keywords

3 HYDROXY 3 METHYLGLUTARYL COENZYME A; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; MEVALONIC ACID; MEVINIC ACID DERIVATIVE;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CHIRALITY; CHOLESTEROL SYNTHESIS; COMPUTER PREDICTION; CONTROLLED STUDY; DRUG STRUCTURE; MOLECULAR MODEL; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT;

HUMANS; HYDROXYMETHYLGLUTARYL COA REDUCTASES; HYDROXYMETHYLGLUTARYL-COA REDUCTASE INHIBITORS; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; STEREOISOMERISM;

TRYPANOSOMA CRUZI;

EID: 57749180853     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.11.007     Document Type: Article

References (97)

1. Shimokata K., Yamada Y., Kondo T., Ichihara S., Izawa H., Nagata K., Murohara T., Ohno M., and Yokota M. Atherosclerosis 172 (2004) 167
2. Smilde T.J., van Wissen S., Wollersheim H., Kastelein J.J., and Stalenhoef A.F. Neth. J. Med. 59 (2001) 184
3. Leitersdorf E., Eisenberg S., Eliav O., Friedlander Y., Berkman N., Dann E.J., Landsberger D., Sehayek E., Meiner V., Wurm M., et al. Circulation 87 (1993) III35
4. Salazar L.A., Hirata M.H., Quintao E.C., and Hirata R.D. J. Clin. Lab. Anal. 14 (2000) 125
5. Suzuki M., Iwasaki H., Fujikawa Y., Sakashita M., Kitahara M., and Sakoda R. Bioorg. Med. Chem. 9 (2001) 2727
6. Urbina J.A., Lazardi K., Marchan E., Visbal G., Aguirre T., Piras M.M., Piras R., Maldonado R.A., Payares G., and de Souza W. Antimicrob. Agents Chemother. 37 (1993) 580
7. Sit S.Y., Parker R.A., Motoc I., Han W., Balasubramanian N., Catt J.D., Brown P.J., Harte W.E., Thompson M.D., and Wright J.J. J. Med. Chem. 33 (1990) 2982
8. Choulier L., Andersson K., Hamalainen M.D., van Regenmortel M.H., Malmqvist M., and Altschuh D. Protein Eng. 15 (2002) 373
9. Du Q.S., Huang R.B., Wei Y.T., Du L.Q., and Chou K.C. J. Comput. Chem. 29 (2008) 211
10. Li Y., Wei D.Q., Gao W.N., Gao H., Liu B.N., Huang C.J., Xu W.R., Liu D.K., Chen H.F., and Chou K.C. Med. Chem. (Shariqah, United Arab Emirates) 3 (2007) 576
11. Sirois S., Tsoukas C.M., Chou K.C., Wei D., Boucher C., and Hatzakis G.E. Med. Chem. (Shariqah, United Arab Emirates) 1 (2005) 173
12. Thilagavathi R., Kumar R., Aparna V., Sobhia M.E., Gopalakrishnan B., and Chakraborti A.K. Bioorg. Med. Chem. Lett. 15 (2005) 1027
13. Prabhakar Y.S. Drug Des. Discov. 9 (1992) 145
14. Prabhakar Y.S., Saxena A.K., and Doss M.J. Drug Des. Deliv. 4 (1989) 97
15. González-Díaz H., Vilar S., Santana L., and Uriarte E. Curr. Top. Med. Chem. 7 (2007) 1015
16. Gozalbes R., Doucet J.P., and Derouin F. Curr. Drug Targets Infect. Disord. 2 (2002) 93
17. Estrada E., and Uriarte E. Curr. Med. Chem. 8 (2001) 1573
18. González-Díaz H., González-Díaz Y., Santana L., Ubeira F.M., and Uriarte E. Proteomics 8 (2008) 750
19. González-Díaz H., Prado-Prado F.J., Santana L., and Uriarte E. Bioorg. Med. Chem. 14 (2006) 5973
20. Helguera A.M., Rodriguez-Borges J.E., Garcia-Mera X., Fernandez F., and Cordeiro M.N. J. Med. Chem. 50 (2007) 1537
21. Marrero-Ponce Y., Castillo-Garit J.A., Olazabal E., Serrano H.S., Morales A., Castanedo N., Ibarra-Velarde F., Huesca-Guillen A., Sanchez A.M., Torrens F., and Castro E.A. Bioorg. Med. Chem. 13 (2005) 1005
22. González-Díaz H., Olazábal E., Santana L., Uriarte E., and Castañedo N. Bioorg. Med. Chem. 15 (2007) 962
23. Murcia-Soler M., Perez-Gimenez F., Garcia-March F.J., Salabert-Salvador M.T., Diaz-Villanueva W., and Medina-Casamayor P. J. Mol. Graph. Model. 21 (2003) 375
24. Prado-Prado F., González-Díaz H., Santana L., and Uriarte E. Bioorg. Med. Chem. 15 (2007) 897
25. Mathur K.C., Gupta S., and Khadikar P.V. Bioorg. Med. Chem. 11 (2003) 1915
26. Calabuig C., Anton-Fos G.M., Galvez J., and Garcia-Domenech R. Int. J. Pharm. 278 (2004) 111
27. González M.P., González-Díaz H., Molina Ruiz R., Cabrera M.A., and Ramos de Armas R. J. Chem. Inf. Comput. Sci. 43 (2003) 1192
28. Votano J.R., Parham M., Hall L.H., Kier L.B., Oloff S., Tropsha A., Xie Q., and Tong W. Mutagenesis 19 (2004) 365
29. Santana L., Uriarte E., González-Díaz H., Zagotto G., Soto-Otero R., and Mendez-Alvarez E. J. Med. Chem. 49 (2006) 1149
30. Marrero-Ponce Y. J. Chem. Inf. Comput. Sci. 44 (2004) 2010
31. Vilar S., Santana L., and Uriarte E. J. Med. Chem. 49 (2006) 1118
32. Marrero-Ponce Y., Khan M.T., Casanola-Martin G.M., Ather A., Sultankhodzhaev M.N., Torrens F., and Rotondo R. ChemMedChem 2 (2007) 449
33. Casanola-Martin G.M., Marrero-Ponce Y., Khan M.T., Ather A., Sultan S., Torrens F., and Rotondo R. Bioorg. Med. Chem. 15 (2007) 1483
34. Casanola-Martin G.M., Marrero-Ponce Y., Khan M.T., Ather A., Khan K.M., Torrens F., and Rotondo R. Eur. J. Med. Chem. 42 (2007) 1370
35. González-Díaz H., Sanchez I.H., Uriarte E., and Santana L. Comput. Biol. Chem. 27 (2003) 217
36. Marrero-Ponce Y., and Castillo-Garit J.A. J. Comput. Aided Mol. Des. 19 (2005) 369
37. Fabian W.M., Stampfer W., Mazur M., and Uray G. Chirality 15 (2003) 271
38. Golbraikh A., and Tropsha A. J. Chem. Inf. Comput. Sci. 43 (2003) 144
39. Golbraikh A., Bonchev D., and Tropsha A. J. Chem. Inf. Comput. Sci. 41 (2001) 147
40. Castillo-Garit J.A., Marrero-Ponce Y., and Torrens F. Bioorg. Med. Chem. 14 (2006) 2398
41. de Julián-Ortiz J.V., de Gregorio Alapont C., Ríos-Santamarina I., García-Doménech R., and Gálvez J. J. Mol. Graph. Model. 16 (1998) 14
42. Castillo-Garit J.A., Marrero-Ponce Y., Torrens F., and Rotondo R. J. Mol. Graph. Model. 26 (2007) 32
43. Zhang Z., and Grigorov M.G. Proteins 62 (2006) 470
44. Bonchev D., and Buck G.A. J. Chem. Inf. Model. 47 (2007) 909
45. Ivanciuc O., Ivanciuc T., and Klein D.J. SAR QSAR Environ. Res. 12 (2001) 1
46. Ivanciuc O., Ivanciuc T., Klein D.J., Seitz W.A., and Balaban A.T. J. Chem. Inf. Comput. Sci. 41 (2001) 536
47. Ivanciuc O. J. Chem. Inf. Comput. Sci. 40 (2000) 1412
48. Gupta N., Mangal N., and Biswas S. Proteins 59 (2005) 196
49. Gan H.H., Pasquali S., and Schlick T. Nucleic Acids Res. 31 (2003) 2926
50. Marrero-Ponce Y., Nodarse D., González-Díaz H., Ramos de Armas R., Romero-Zaldivar V., Torrens F., and Castro E.A. Int. J. Mol. Sci. 5 (2004) 276
51. González-Díaz H., Agüero-Chapin G., Varona J., Molina R., Delogu G., Santana L., Uriarte E., and Gianni P. J. Comput. Chem. 28 (2007) 1049
52. Rose A., Schraegle S.J., Stahlberg E.A., and Meier I. BMC Evol. Biol. 5 (2005) 66
53. Estrada E., and Rodriguez-Velazquez J.A. Phys. Rev. E 71 (2005) 056103
54. Yu X., Lin J., Masuda T., Esumi N., Zack D.J., and Qian J. Nucleic Acids Res. 34 (2006) 917
55. Guido N.J., Wang X., Adalsteinsson D., McMillen D., Hasty J., Cantor C.R., Elston T.C., and Collins J.J. Nature 439 (2006) 856
56. Williams R.J., Berlow E.L., Dunne J.A., Barabasi A.L., and Martinez N.D. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 12913
57. Marrero-Ponce Y., Castillo-Garit J.A., and Nodarse D. Bioorg. Med. Chem. 13 (2005) 3397
58. González-Díaz H., de Armas R.R., and Molina R. Bioinformatics 19 (2003) 2079
59. Vullo A., and Frasconi P. J. Bioinform. Comput. Biol. 1 (2003) 411
60. Lange B.M., and Ghassemian M. Phytochemistry 66 (2005) 413
61. Chou K.C., and Cai Y.D. J. Proteome Res. 5 (2006) 316
62. Yu X., Lin J., Zack D.J., and Qian J. Nucleic Acids Res. 34 (2006) 4925
63. Margolin A.A., Nemenman I., Basso K., Wiggins C., Stolovitzky G., Dalla Favera R., and Califano A. BMC Bioinformatics 7 (2006) S7
64. Estrada E. J. Proteome Res. 5 (2006) 2177
65. Newman M.E. Phys. Rev. E: Stat. Nonlin. Soft Matter Phys. 74 (2006) 036104
66. Kleinberg J.M. Nature 406 (2000) 845
67. González-Díaz H., and Prado-Prado F. J. Comput. Chem. 29 (2008) 656
68. Hill, T.; Lewicki, P. STATISTICS Methods and Applications; Tulsa: StatSoft, 2006.
69. Lilien R.H., Farid H., and Donald B.R. J. Comput. Biol. 10 (2003) 925
70. Vilar S., Estrada E., Uriarte E., Santana L., and Gutierrez Y. J. Chem. Inf. Model. 45 (2005) 502
71. Bisquerra Alzina, R. Introducción conceptual al análisis multivariante: Un enfoque informático con los paquetes SPSS-X, BMDP, LISREL y SPAD; Barcelona: PPU, 1989.
72. Stewart J., and Gill L. Econometrics (1998), Prentice Hall, London
73. Dillon W.R., and Goldstein M. Multivariate Analysis: Methods and Applications (1984), Wiley, N.Y.
74. James A., and Hanley B.J.M. Radiology 143 (1982) 29
75. Helguera A.M., Rodríguez-Borges J.E., García-Mera X., Fernández F., and Cordeiro M.N. J. med. chem. (2007) 50, 1537
76. Gómez G., Rivera H., García I., Estévez L., and Fall Y. Tetrahedron Lett. 46 (2005) 5819
77. Boccaletti S., Latora V., Moreno Y., Chavez M., and Hwang D.U. Phys. Rep. 424 (2006) 175
78. Bianconi G., and Barabasi A.L. Phys. Rev. Lett. 86 (2001) 5632
79. Bornholdt S., and Schuster H.G. Handbook of Graphs and Complex Networks (2003), Wiley-VCH GmbH & Co. KGa, Wheinheim
80. Kuroda M., and Endo A. Biochim. Biophys. Acta 486 (1977) 70
81. Turabi N., DiPietro R.A., Mantha S., Ciosek C., Rich L., and Tu J.I. Bioorg. Med. Chem. 3 (1995) 1479
82. Watanabe M., Koike H., Ishiba T., Okada T., Seo S., and Hirai K. Bioorg. Med. Chem. 5 (1997) 437
83. Romo D., Harrison P.H., Jenkins S.I., Riddoch R.W., Park K., Yang H.W., Zhao C., and Wright G.D. Bioorg. Med. Chem. 6 (1998) 1255
84. Colle S., Taillefumier C., Chapleur Y., Liebl R., and Schmidt A. Bioorg. Med. Chem. 7 (1999) 1049
85. Suzuki M., Iwasaki H., Fujikawa Y., Kitahara M., Sakashita M., and Sakoda R. Bioorg. Med. Chem. 9 (2001) 2727
86. Taillefumiera C., Fornelb D., and Chapleur Y. Bioorg. Med. Chem. Lett. 6 (1996) 615
87. Alali F., Zeng L., Zhang Y., Ye Q., Hopp D.C., Schwedler J.T., and McLaughlin J.L. Bioorg. Med. Chem. 5 (1997) 549
88. Schroepfer Jr. G.J., Parish E.J., Chen H.W., and Kandutsch A.A. J. Biol. Chem. 252 (1977) 8975
89. Beck G., Kesseler K., Baader E., Bartmann W., Bergmann A., Granzer E., Jendralla H., von Kerekjarto B., Krause R., Paulus E., et al. J. Med. Chem. 33 (1990) 52
90. Zhang Q.Y., Wan J., Xu X., Yang G.F., Ren Y.L., Liu J.J., Wang H., and Guo Y. J. Comb. Chem. 9 (2007) 131
91. Grabley S., Granzer E., Hutter K., Ludwig D., Mayer M., Thiericke R., Till G., Wink J., Philipps S., and Zeeck A. J. Antibiot. (Tokyo) 45 (1992) 56
92. Gohrt A., Zeeck A., Hutter K., Kirsch R., Kluge H., and Thiericke R. J. Antibiot. (Tokyo) 45 (1992) 66
93. Grabley S., Hammann P., Hutter K., Kirsch R., Kluge H., Thiericke R., Mayer M., and Zeeck A. J. Antibiot. (Tokyo) 45 (1992) 1176
94. Chan C., Bailey E.J., Hartley C.D., Hayman D.F., Hutson J.L., Inglis G.G.A., Jones P.S., Keeling S.E., Kirk B.E., Lamont R.B., Lester M.G., Pritchard J.M., ROSS B.C., Scicinski J.J., Spooner S.J., Smith G., Steeples I.P., and Watson N.S. J. Med. Chem. 36 (1993) 3646
95. StatSoft, Inc., 2002.
96. Microsoft Corp., Microsoft Excel, 2002.
97. Zhang W. Environ. Monit. Assess. 124 (2007) 253