Crystal engineering of pharmaceutical co-crystals: Application of methyl paraben as molecular hook

Journal of the American Chemical Society

Volumn 132, Issue 14, 2010, Pages 5254-5263

  Khan, Mujeeb ^a   Enkelmann, Volker ^a   Brunklaus, Gunther ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM CHEMISTRY; QUANTUM THEORY;

CO-CRYSTALS; MOLECULAR SPECIFICITY; MULTINUCLEAR SOLID STATE NMR; NMR DATA; QUANTUM CHEMICAL COMPUTATIONS; SELECTIVE SEPARATION; TREE BARKS;

PARABENS;

ANTIMALARIAL AGENT; CINCHONA BARK; EXCIPIENT; HYDROGEN; METHYL PARABEN; NITROGEN; OXYGEN; QUINIDINE; QUININE;

ARTICLE; BARK; CINCHONA; CONFORMATION; CRYSTAL; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; DRUG SYNTHESIS; HYDROGEN BOND; MOLECULAR MECHANICS; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; SOLID STATE; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

EID: 77950848543     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja100146f     Document Type: Article

References (127)

1. Blagden, N., De Metas, M., Gavan, P. T., and York, P. Adv. Drug Delivery Rev. 2007, 59, 617 - 630
2. Huang, L. F. and Tong, W. Q. Adv. Drug Delivery Rev. 2004, 56, 321 - 324
3. Amin, K., Dannenfelser, R. M., Zielinski, J., and Wang, B. J. Pharm. Sci. 2004, 93, 2244 - 2249
4. Torchillin, V. P. Pharm. Res. 2007, 24, 1 - 16
5. Humberstone, A. J. and Charman, W. N. Adv. Drug Delivery Rev. 1997, 25, 103 - 128
6. Jeong, S. H., Takaishi, Y., Fu, Y., and Park, K. J. Mater. Chem. 2008, 18, 3527 - 3535
7. Fu, Y., Yang, S., Jeong, S. H., Kimura, S., and Park, K. Crit. Rev. Ther. Drug 2004, 21, 433 - 475
8. Schultheiss, N. and Newman, A. Cryst. Growth Des. 2009, 9, 2950 - 2967
9. Datta, S. and Grant, D. J. W. Nat. Rev. Drug Discovery 2004, 3, 42 - 57
10. Chow, K., Tong, H. H. Y., Lum, S., and Chow, A. H. L. J. Pharm. Sci. 2008, 97, 2855 - 2877
11. Khan, M., Enkelmann, V., and Brunklaus, G. J. Org. Chem. 2009, 74, 2261 - 2270
12. Khan, M., Enkelmann, V., and Brunklaus, G. CrystEngComm 2009, 11, 1001 - 1005
13. Desiraju, G. R. Angew. Chem., Int. Ed. 2007, 46, 8342 - 8356
14. Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311 - 2327
15. Desiraju, G. R. Nat. Mater. 2002, 1, 77 - 79
16. Desiraju, G. R. Nature (London) 2001, 412, 397 - 400
17. Desiraju, G. R. Chem. Commun. 1997, 16, 1474 - 1482
18. Lehn, J. M. Angew. Chem., Int. Ed. Engl. 1990, 29, 1304 - 1319
19. Childs, S. L., Chyall, L. J., Dunlap, J. T., Smolenskaya, V. N., Stahly, B. C., and Stahly, G. P. J. Am. Chem. Soc. 2004, 126, 13335 - 13342
20. Remenar, J. F., Morissette, S. L., Peterson, M. L., Moulton, B., MacPhee, J. M., Guzman, H. R., and Almarsson, O. J. Am. Chem. Soc. 2003, 125, 8456 - 8457
21. Reddy, L. S., Jagadeesh, N. B., and Nangia, A. Chem. Commun. 2006, 1369 - 1371
22. Fleischman, S. G., Srinivasan, S. K., McMahon, J. A., Moulton, B., Rosa, D., Walsh, B., Rodrguez-Hornedo, N., and Zaworotko, M. J. Cryst. Growth Des. 2003, 3, 909 - 919
23. Walsh, R. D. B., Bradner, M. W., Fleischman, S., Morales, L. A., Moulton, B., Rodriguez-Hornedo, N., and Zaworotko, M. J. Chem. Commun. 2003, 186 - 187
24. Almarsson, O. and Zaworotko, M. J. Chem. Commun. 2004, 1889 - 1896
25. McMahon, J. A., Bis, J. A., Vishweshwar, P., Shattock, T. R., McLaughlin, O. L., and Zaworotko, M. J. Z. Kristallogr. 2005, 220, 340 - 350
26. Gohel, M. C. and Jogani, P. D. J. Pharm. Pharm. Sci. 2005, 8, 76 - 93
27. Childs, S. L. and Zaworotko, M. J. Cryst. Growth Des. 2009, 9, 4208 - 4211
28. Shan, N. and Zaworotko, M. J. Drug Discovery Today 2008, 13, 440 - 446
29. Weyna, D. R., Shattock, T., Vishweshwar, P., and Zaworotko, M. J. Cryst. Growth Des. 2009, 9, 1106 - 1123
30. Bis, J. A., Vishweshwar, P., Weyna, D., and Zaworotko, M. J. Mol. Pharmacol. 2007, 4, 401 - 416
31. Veber, D. F., Stephen, R. J., Cheng, H. Y., Smith, B. R., Ward, K. W., and Kopple, K. D. J. Med. Chem. 2002, 45, 2615 - 2623
32. Stanton, M. K., Tufekcic, S., Morgan, C., and Bak, A. Cryst. Growth Des. 2009, 9, 1344 - 1352
33. Jones, W., Motherwell, W. D. S., and Trask, A. V. MRS Bull. 2006, 31, 875 - 879
34. Good, D. J. and Rodriguez-Hornedo, N. Cryst. Growth Des. 2009, 5, 2252 - 2264
35. Morissette, S. L., Almarsson, O., Peterson, M. L., Remenar, J. F., Read, M. J., Lemmo, A. V., Ellis, S., Cima, M. J., and Gardner, C. R. Adv. Drug Delivery Rev. 2004, 56, 275 - 300
36. Trask, A. V. Mol. Pharmaceutics 2007, 4, 301 - 309
37. Desiraju, G. R. CrystEngComm 2003, 5, 466 - 467
38. Dunitz, J. D. CrystEngComm 2003, 5, 506 - 507
39. Zuckerman-Schpector, J. and Tiekink, E. R. T. Z. Kristalogr. 2008, 223, 233 - 234
40. Aakeroy, C. B., Fasulo, M. E., and Desper, J. Mol. Pharmaceutics 2007, 4, 317 - 322
41. Childs, S. L., Stahly, G. P., and Park, A. Mol. Pharmaceutics 2007, 4, 323 - 338
42. Vogt, M., Kunath, K., and Dressman, J. B. Eur. J. Pharm. Biopharm. 2008, 68, 330 - 337
43. Shakhtshneider, T. P., Vasiltchenko, M. A., Politov, A. A., and Boldyrev, V. V. Int. J. Pharm. 1996, 130, 25 - 32
44. Handbook of Pharmaceutical Salts: Properties, Selection and Use; Sthal, P. H. and Wermuth, C. G., Eds.; Verlag Helvetica Chimica Acta: ZuÌrich, 2002. GRAS Notices: http://www.cfsan.fda.gov/∼rdb/opa -gras.html. Food Additive status list: http://www.cfsan.fda.gov/∼dms/opa-appa.html.
45. Chow, K., Tong, H. H. Y., Lum, S., and Chow, A. H. L. J. Pharm. Sci. 2008, 97, 2855 - 2877
46. Khan, M., Enkelmann, V., and Brunklaus, G. Cryst. Growth Design 2009, 9, 2354 - 2362
47. Soni, M. G., Carabin, I. G., and Burdoc, G. A. Food Chem. Toxicol. 2005, 43, 985 - 1015
48. Wahbi, A. M., Moneed, M. S., Hewala, I. I., and Bahnasy, M. F. Chem. Pharm. Bull. 2008, 56, 787 - 79
49. Kashino, S. and Haisa, M. Acta Crystallogr. 1983, C39, 310 - 312
50. Pniewska, B. and Suszko-Purzycka, A. Acta Crystallogr. 1989, C45, 638 - 642
51. Smith, R. A. Exp. Opin. Pharmacother. 2006, 7, 2581 - 2591
52. Dijkstra, G. D. H., Kellog, R. M., Wynberg, H., Svendsen, J. S., Marko, I., and Sharpless, K. B. J. Am. Chem. Soc. 1989, 111, 8069 - 8076
53. Silva, T. H. A., Oliveira, A. B., and De Almeida, W. B. Bioorg. Med. Chem. 1997, 5, 353 - 361
54. Mortison, J. D., Kittendorf, J. D., and Sherman, D. H. J. Am. Chem. Soc. 2009, 131, 15784 - 15793
55. Doyon, J. B., Synder, T. M., and Liu, D. R. J. Am. Chem. Soc. 2003, 125, 12372 - 12373
56. Reichert, D. Annu. Rep. NMR Spectrosc. 2005, 55, 159 - 203
57. Ashbrook, S. E. and Smith, M. E. Chem. Soc. Rev. 2006, 35, 718 - 735
58. Brown, S. P. Prog. Nucl. Magn. Reson. 2007, 50, 199 - 251
59. Vogt, F. G., Clawson, J. S., Strohmeier, M., Edwards, A. J., Pham, T. N., and Watson, S. A. Cryst. Growth Des. 2009, 9, 921 - 937
60. Vogt, F. G., Vena, J. A., Chavda, M., Clawson, J. S., Strohmeier, M., and Barnett, M. E. J. Mol. Struct. 2009, 932, 16 - 30
61. Li, Z. J., Abramov, Y., Bordner, J., Leonard, J., Medek, A., and Trask, A. V. J. Am. Chem. Soc. 2006, 128, 8199 - 8210
62. Terakita, A., Matsunaga, H., Ueda, T., Eguchi, T., Echigoya, M., Umemoto, K., and Godo, M. Chem. Pharm. Bull. 2004, 52, 546 - 551
63. Orendt, A. M. and Facelli, J. C. Annu. Rep. NMR Spectrosc. 2007, 62, 115 - 178
64. Harris, R. K. Solid State Sci. 2004, 6, 1025 - 1037
65. Senker, J., Seyfarth, L., and Voll, J. Solid State Sci. 2004, 6, 1039 - 1052
66. Chierotti, M. R. and Gobetto, R. Chem. Commun. 2008, 1621 - 1634
67. Limbach, H. H. In Hydrogen Transfer Reactions; Hynes, J. T., Klinman, J. P., Limbach, H. H., and Schowen, R. L., Eds.; Wiley-VCH: Weinheim, 2007.
68. Brown, S. P. and Spiess, H. W. Chem. Rev. 2001, 101, 4125 - 4155
69. Schulz-Dobrick, M., Metzroth, T., Spiess, H. W., Gauss, J., and Schnell, I. Chem. Phys. Chem. 2005, 6, 315 - 327
70. Schnell, I., Langer, B., SoÌntjens, S. H. M., Sijbesma, R. P., van Genderen, M. H. P., and Spiess, H. W. Phys. Chem. Chem. Phys. 2002, 4, 3750 - 3758
71. Bolz, I., Moon, C., Enkelmann, V., Brunklaus, G., and Spange, S. J. Org. Chem. 2008, 73, 4783 - 4793
72. Schulz-Dobrick, M. and Schnell, I. Central Eur. J. Chem. 2005, 3, 245 - 251
73. Lazzeretti, P. Prog. Nucl. Magn. Reson. Spectrosc. 2000, 36, 1 - 88
74. Gomes, J. A. N. F. and Mallion, R. B. Chem. Rev. 2001, 101, 1301 - 1315
75. SaalwaÌchter, K. and Schnell, I. Solid State Nucl. Magn. Reson. 2002, 22, 154 - 187
76. Geerlings, P., De Proft, F., and Langenaeker, W. Chem. Rev. 2003, 103, 1793 - 1873 Parr, R. G. and Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, 1989.
77. Elena, B., Pintacuda, G., Mifsud, N., and Emsley, L. J. Am. Chem. Soc. 2006, 128, 9555 - 9560
78. Pickard, C. J., Salager, E., Pintacuda, G., Elena, B., and Emsley, L. J. Am. Chem. Soc. 2007, 129, 8932 - 8933
79. Taulelle, F. Solid State Sci. 2004, 6, 1053 - 1057
80. Seyfarth, L., Seyfarth, J., Lotsch, B. V., Schnick, W., and Senker, J. Phys. Chem. Chem. Phys. 2007, 12, 2227 - 2237
81. Harris, R. K. J. Pharm. Pharmacol. 2007, 59, 225 - 239
82. Harris, R. K. Analyst 2006, 131, 351 - 373
83. Hamaed, H., Pawlowski, J. M., Cooper, B. F. T., Fu, R., Eichhorn, S. H., and Schurko, R. W. J. Am. Chem. Soc. 2008, 130, 11056 - 11065
84. Salanger, E., Stein, R. S., Pickard, C. J., Elena, B., and Emsley, L. Phys. Chem. Chem. Phys. 2009, 11, 2610 - 2621
85. Aakeroy, C. B. and Beatty, A. M. Aust. J. Chem. 2001, 54, 409 - 421
86. Desiraju, G. R. Acc. Chem. Res. 2002, 35, 565 - 573
87. Harris, K. D. M. and Cheung, E. Y. Chem. Soc. Rev. 2004, 33, 526 - 538
88. Frey, P. A. Magn. Reson. Chem. 2001, 39, S190 - S198
89. Khan, M., Brunklaus, G., Enkelmann, V., and Spiess, H. W. J. Am. Chem. Soc. 2008, 130, 1741 - 1748
90. Gobetto, R., Nervi, C., ValfreÌε, E., Chierotti, M. R., Braga, D., Maini, L., Grepioni, F., Harris, R. K., and Ghi, P. Y. Chem. Mater. 2005, 17, 1457 - 1466
91. Leskes, M., Madhu, P. K., and Vega, S. J. Chem. Phys. 2008, 128, 052309/1 - 052309/11
92. Leskes, M., Madhu, P. K., and Vega, S. J. Chem. Phys. 2006, 125, 124506/1 - 124506/18
93. Lesage, A., Sakellariou, D., Hediger, S., Elena, B., Charmont, P., Steuernagel, S., and Emsley, L. J. Magn. Reson. 2003, 163, 105 - 113
94. Brown, S. P., Lesage, A., Elena, B., and Emsley, L. J. Am. Chem. Soc. 2004, 126, 13230 - 13231
95. Bradley, J. P., Tripon, C., Filip, C., and Brown, S. P. Phys. Chem. Chem. Phys. 2009, 11, 6941 - 6952
96. Friedrich, U., Schnell, I., Brown, S. P., Lupulescu, A., Demco, D. E., and Spiess, H. W. Mol. Phys. 1998, 95, 1209 - 1227
97. Goward, G. R., Sebastiani, D., Schnell, I., Spiess, H. W., Kim, H. D., and Ishida, H. J. Am. Chem. Soc. 2003, 125, 5792 - 5800
98. Brown, S. P., Schnell, I., Brand, J. D., MuÌllen, K., and Spiess, H. W. J. Am. Chem. Soc. 1999, 121, 6712 - 6718
99. Holland, G. P., Cherry, B. R., and Alam, T. M. J. Magn. Reson. 2004, 167, 161 - 167
100. Foces-Foces, C., Echevarria, A., Jagerovic, N., Alkorta, I., Elguero, J., Langer, U., Klein, O., Minguet-Bonvehi, M., and Limbach, H.-H. J. Am. Chem. Soc. 2001, 123, 7898 - 7906
101. Lorente, P., Shenderovich, I. G., Golubev, N. S., Denisov, G. S., Buntkowsky, G., and Limbach, H.-H. Magn. Reson. Chem. 2001, 39, S18 - S29
102. Sarotti, A. M. and Pellegrinet, S. C. J. Org. Chem. 2009, 74, 7254 - 7260
103. Zurek, E., Pickard, C. J., and Autschbach, J. J. Am. Chem. Soc. 2007, 129, 4430 - 4439
104. Uldry, A. C., Griffin, J. M., Yates, J. R., Perez-Torralba, M., Maria, M. D. S., Webber, A. L., Beaumont, M. L. L., Samoson, A., Claramunt, R. M., Pickard, C. J., and Brown, S. P. J. Am. Chem. Soc. 2008, 130, 945 - 954
105. Harris, R. K., Ghi, P. Y., Hammond, R. B., Ma, C. Y., Roberts, K. J., Yates, J. R., and Pickard, C. J. Magn. Reson. Chem. 2006, 44, 325 - 333
106. Yates, J. R., Dobbins, S. E., Pickard, C. J., Mauri, F., Ghi, P. Y., and Harris, R. K. Phys. Chem. Chem. Phys. 2005, 7, 1402 - 1407
107. Zheng, A., Liu, S.-B., and Deng, F. J. Comput. Chem. 2009, 30, 222 - 235
108. Vujovic, D. and Nassimbeni, L. R. Cryst. Growth Des. 2006, 6, 1595 - 1597
109. Lin, X. and Chin, T. J. Struct. Chem. 1983, 2, 213 - 215
110. Harris, R. K. Analyst 2006, 131, 351 - 373
111. Masuda, K., Tabata, S., Kono, H., Sakata, Y., Hyyase, T., Yonemochi, E., and Tarada, K. Int. J. Pharm. 2006, 318, 146 - 153
112. Brus, J. and Jegorov, A. J. Phys. Chem. A 2004, 108, 3955 - 3964
113. Taylor, S. V., Kast, P., and Hilvert, D. Angew. Chem., Int. Ed. 2001, 40, 3310 - 3335
114. Lin, H. and Cornish, V. W. Angew. Chem., Int. Ed. 2002, 41, 4402 - 4425
115. McCalley, D. V. Analyst 1990, 115, 1355 - 1358
116. Gatti, R., Gioia, M. G., and Cavrini, V. Anal. Chim. Acta 2004, 512, 85 - 91
117. Geen, J., Titman, J., Gottwald, J., and Spiess, H. W. Chem. Phys. Lett. 1994, 227, 79 - 86
118. Gottwald, J., Demco, D. E., Graf, R., and Spiess, H. W. Chem. Phys. Lett. 1995, 243, 314 - 323
119. Sommer, W., Gottwald, J., Demco, D. E., and Spiess, H. W. J. Magn. Reson. 1995, A 113, 131 - 134
120. Feike, M., Demco, D. E., Graf, R., Gottwald, J., Hafner, S., and Spiess, H. W. J. Magn. Reson. 1996, A122, 214 - 221
121. SaalwaÌchter, K., Graf, R., and Spiess, H. W. J. Magn. Reson. 1999, 140, 471 - 476
122. SaalwaÌchter, K., Graf, R., and Spiess, H. W. J. Magn. Reson. 2001, 148, 398 - 418
123. Marion, D., Ikura, M., Tschudin, R., and Bax, A. J. Magn. Reson. 1989, 85, 393 - 399
124. Krishnan, R., Binkley, J. S., Seger, R., and Pople, J. A. J. Chem. Phys. 1980, 72, 650 - 654
125. Frisch, M. J.; et al. Gaussian 03, Revision D.02; Gaussian, Inc.: Wallingford, CT, 2004.
126. Sheldrick, G. M. SHELXS-86, Program package for crystal structure solution and refinement; UniveristaÌt GoÌttingen: Germany, 1986.
127. Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K., and Watkin, D. J. J. Appl. Crystallogr. 2003, 36, 1487 - 1487