A quantitative structure activity relationship approach to probe the influence of the functionalization on the drug encapsulation of porous metal-organic frameworks

Microporous and Mesoporous Materials

Volumn 157, Issue , 2012, Pages 124-130

  Gaudin, C ^a,b   Cunha, D ^b   Ivanoff, E ^a   Horcajada, P ^b   Cheve G ^c   Yasri, A ^c   Loget, O ^c   Serre, C ^b   Maurin, G ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

^c OriBase Pharma   (France)

Author keywords

Caffeine; Drug encapsulation; Functionalization; MOFs; QSAR

Indexed keywords

CAFFEINE; DRUG ENCAPSULATION; FUNCTIONALIZATIONS; MOFS; QSAR;

BROMINE; CARBOXYLATION; COMPUTATIONAL CHEMISTRY; FUNCTIONAL GROUPS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IRON COMPOUNDS; LINEAR REGRESSION; MOLECULAR GRAPHICS; MOLECULES; THERMOGRAVIMETRIC ANALYSIS;

ENCAPSULATION;

EID: 84861192162     PISSN: 13871811     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.micromeso.2011.06.011     Document Type: Article

References (67)

1. G. Férey, C. Serre, T. Devic, G. Maurin, H. Jobic, P.L. Llewellyn, G. De Weireld, A. Vimont, M. Daturi, and J.-S. Chang Chem. Soc. Rev. 40 2011 550 562
2. L.J. Murray, M. Dinca, and J.R. Long Chem. Soc. Rev. 38 2009 1294 1314
3. J.-R. Li, R.J. Kuppler, and H.-C. Zhou Chem. Soc. Rev. 38 2009 1477 1504
4. J. Lee, O.K. Farha, J. Roberts, K.A. Scheidt, S.T. Nguyen, and J.T. Hupp Chem. Soc. Rev. 38 2009 1450 1459
5. L. Ma, C. Abney, and W. Lin Chem. Soc. Rev. 38 2009 1248 1256
6. F. Millange, C. Serre, N. Guillou, G. Férey, and R. Walton Angew. Chem. Int. Ed. 47 2008 4100 4105
7. A.C. McKinlay, R.E. Morris, P. Horcajada, G. Férey, R. Gref, P. Couvreur, and C. Serre Angew. Chem. Int. Ed. 49 2010 6260 6266
8. R.C. Huxford Curr. Opin. Chem. Biol. 14 2010 262 268
9. R.E. Morris, and X. Bu Nat. Chem. 2 2010 353 361
10. N.J. Hinks, A.C. McKinlay, B. Xiao, P.S. Wheatley, and R.E. Morris Micropor. Mesopor. Mater. 129 2010 330 334
11. K.M.L. Taylor-Pashow, J.D. Rocca, Z. Xie, S. Tran, and W. Lin J. Am. Chem. Soc. 131 2009 14261 14263
12. W.J. Rieter, K.M.L. Taylor, H. An, W. Lin, and W. Lin J. Am. Chem. Soc. 128 2006 9024 9025
13. P. Horcajada, C. Serre, M. Vallet-Regí, M. Sebban, F. Taulelle, and G. Férey Angew. Chem. Int. Ed. 45 2006 5974 5978
14. P. Horcajada, C. Serre, G. Maurin, N.A. Ramsahye, F. Balas, M.a. Vallet-Regí, M. Sebban, F. Taulelle, and G. Férey J. Am. Chem. Soc. 130 2008 6774 6780
15. L.O. Cinteza, T.Y. Ohulchanskyy, Y. Sahoo, E.J. Bergey, R.K. Pandey, and P.N. Prasad Mol. Pharm. 3 2006 415 423
16. Y. Chen, A. Bose, and G.D. Bothun ACS Nano 4 2010 3215 3221
17. R. Liu, X. Zhao, T. Wu, and P. Feng J. Am. Chem. Soc. 130 2008 14418 14419
18. P. Horcajada, T. Chalati, C. Serre, B. Gillet, C. Sebrie, T. Baati, J.F. Eubank, D. Heurtaux, P. Clayette, C. Kreuz, J.-S. Chang, Y.K. Hwang, V. Marsaud, P.-N. Bories, L. Cynober, S. Gil, G. Férey, P. Couvreur, and R. Gref Nat. Mater. 9 2010 172 178
19. M. Vallet-Regi, M. Colilla, and B. Gonzalez Chem. Soc. Rev. 40 2011 596 607
20. T. Devic, P. Horcajada, C. Serre, F. Salles, and G. Maurin J. Am. Chem. Soc. 132 2010 1127 1136
21. J. Gascon, U. Aktay, M.D. Hernandez-Alonso, G.P.M. van Klink, and F. Kapteijn J. Catal. 261 2009 75 87
22. P. Horcajada, D. Heurtaux, F. Salles, S. Wuttke, C. Serre, T. Devic, G. Maurin, A. Vimont, G. Clet, M. Maturi, O. David, E. Magnier, N. Stock, Y. Filinchuk, D. Popov, C. Rieckel, G. Férey, submitted for publication.
23. A. Nehlig, J.-L. Daval, and G. Debry Brain Res. Rev. 17 1992 139 170
24. G. Zheng, K. Sayama, T. Okubo, L.R. Juneja, and I. Oguni In Vivo 18 2004 55 62
25. T.W. Fischer, U.C. Hipler, and P. Elsner Int. J. Dermatol. 46 2007 27 35
26. E. Burello, and G. Rothenberg Int. J. Mol. Sci. 7 2006 375 404
27. C. Obiol-Pardo, J. Gomis-Tena, F. Sanz, J. Saiz, and M. Pastor J. Chem. Inf. Model. 51 2011 483 492
28. A. Varnek, C. Gaudin, G. Marcou, I. Baskin, A.K. Pandey, and I.V. Tetko J. Chem. Inf. Model. 49 2009 133 144
29. H. Zhu, A. Tropsha, D. Fourches, A. Varnek, E. Papa, P. Gramatica, T. Oberg, P. Dao, A. Cherkasov, and I.V. Tetko J. Chem. Inf. Model. 48 2008 766 784
30. J.P. Brincat, E. Carosati, S. Sabatini, G. Manfroni, A. Fravolini, J.L. Raygada, D. Patel, G.W. Kaatz, and G. Cruciani J. Med. Chem. 54 2010 354 365
31. D.Q. Do, R.C. Rowe, and P. York Int. J. Pharm. 351 2008 194 200
32. A. Niazi, S. Jameh-Bozorghi, and D. Nori-Shargh Chin. Chem. Lett. 18 2007 621 624
33. D. Fourches, D. Pu, C. Tassa, R. Weissleder, S.Y. Shaw, R.J. Mumper, and A. Tropsha ACS Nano 4 2010 5703 5712
34. A.A. Toropov, and J. Leszczynski Chem. Phys. Lett. 433 2006 125 129
35. S. Giraudet, P. Pré, H. Tezel, and P. Le Cloirec Carbon 44 2006 1873 1883
36. C. Brasquet, and P. Le Cloirec Water Res. 33 1999 3603 3608
37. P. Leflaive, G.D. Pirngruber, A. Faraj, P. Martin, G.V. Baron, and J.F.M. Denayer Micropor. Mesopor. Mater. 132 2010 246 257
38. A. Goulon, A. Faraj, G. Pirngruber, M. Jacquin, F. Porcheron, P. Leflaive, P. Martin, G.V. Baron, and J.F.M. Denayer Catal. Today 159 2011 74 83
39. D. Kim, J. Kim, D.H. Jung, T.B. Lee, S.B. Choi, J.H. Yoon, J. Kim, K. Choi, and S.-H. Choi Catal. Today 120 2007 317 323
40. T.A. Halgren J. Comput. Chem. 17 1996 490 519
41. Molecular Operational Environment; Chemical Computing Group Inc.: Montreal, Canada,Version 2009.10, 2009.
42. M. Hall, E. Frank, G. Holmes, B. Pfahringer, P. Reutemann, I.H. Witten, The WEKA Data Mining Software: An Update, 3.6.2 ed., 2009.
43. A.S. Reddy, S. Kumar, and R. Garg J. Mol. Graph. Model. 28 2010 852 862
44. J. Shen, F. Cheng, Y. Xu, W. Li, and Y. Tang J. Chem. Inf. Model. 50 2010 1034 1041
45. A.R. Katritzky, M. Kuanar, S. Slavov, C.D. Hall, M. Karelson, I. Kahn, and D.A. Dobchev Chem. Rev. 110 2010 5714 5789
46. F.R. Burden, M.G. Ford, D.C. Whitley, and D.A. Winkler J. Chem. Inf. Comput. Sci. 40 2000 1423 1430
47. M. Hewitt, M.T.D. Cronin, S.J. Enoch, J.C. Madden, D.W. Roberts, and J.C. Dearden J. Chem. Inf. Model. 49 2009 2572 2587
48. R.G. Karki, and V.M. Kulkarni Biorg. Med. Chem. 9 2001 3153 3160
49. M. Hewitt, M.T.D. Cronin, J.C. Madden, P.H. Rowe, C. Johnson, A. Obi, and S.J. Enoch J. Chem. Inf. Model. 47 2007 1460 1468
50. W. Tong, W. Xie, H. Hong, L. Shi, H. Fang, and R. Perkins Environ. Health Perspect. 112 2004 1249 1254
51. M. Ganguly, N. Brown, A. Schuffenhauer, P. Ertl, V.J. Gillet, and P.A. Greenidge J. Chem. Inf. Model. 46 2006 2110 2124
52. P. Gramatica, E. Giani, and E. Papa J. Mol. Graph. Model. 25 2007 755 766
53. J.R. Votano, M. Parham, L.H. Hall, L.B. Kier, S. Oloff, A. Tropsha, Q. Xie, and W. Tong Mutagenesis 19 2004 365 377
54. P. Gramatica, P. Pilutti, and E. Papa J. Chem. Inf. Comput. Sci. 44 2004 1794 1802
55. R. Todeschini, V. Consonni, and M. Pavan Chemometr. Intell. Lab. Syst. 70 2004 55 61
56. M. Manzano, V. Aina, C.O. Areán, F. Balas, V. Cauda, M. Colilla, M.R. Delgado, and M. Vallet-Regí Chem. Eng. J. 137 2008 30 37
57. J.G. Topliss, and R.P. Edwards J. Med. Chem. 22 1979 1238 1244
58. A. Doweyko, and J. Comput Aided Mol. Des. 22 2008 81 89
59. S. Funar-Timofei, T. Suzuki, J.A. Paier, A. Steinreiber, K. Faber, and W.M.F. Fabian J. Chem. Inf. Comput. Sci. 43 2003 934 940
60. T.I. Oprea, C.M.W. Ho, and G.R. Marshall C.H. Reynolds, M.K. Holloway, H.K. Cox, Computer-Aided Molecular Design - Applications in Agrochemicals, Materials, and Pharmaceuticals vol. 589 1995 Amer Chemical Soc Washington 64 81
61. P. Labute J. Mol. Graph. Model. 18 2000 464 477
62. T. Chalati, P. Horcajada, P. Couvreur, C. Serre, G. Maurin, R. Gref, Nanomedicine in press.
63. A.A. Toropov, and E. Benfenati Biorg. Med. Chem. 16 2008 4801 4809
64. S. Weaver, and M.P. Gleeson J. Mol. Graph. Model. 26 2008 1315 1326
65. D. Horvath, G. Marcou, and A. Varnek J. Chem. Inf. Model. 49 2009 1762 1776
66. I. Billard, G. Marcou, A. Ouadi, and A. Varnek J. Phys. Chem. B 115 2010 93 98
67. F. Li, X. Li, J. Shao, P. Chi, J. Chen, and Z. Wang Chem. Res. Toxicol. 23 2010 1349 1355