Crystal engineering of an anti-HIV drug based on the recognition of assembling molecular frameworks

Crystal Growth and Design

Volumn 9, Issue 12, 2009, Pages 5283-5292

  Martins, Felipe T ^a   Paparidis, Nikolas ^a   Doriguetto, Antônio C ^b   Ellena, Javier ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FEDERAL UNIVERSITY OF ALFENAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 75249105047     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg900790f     Document Type: Article

References (39)

1. Lu, J.; Wang, X.-J.; Yang, X.; Ching, C.-B. Cryst. Growth Des. 2007, 7, 1590-1598.
2. Grant, D. J. W. In Polymorphism in Pharmaceutical Solids; Brittain, H. G., Ed.; Dekker: New York, 1999; Vol.95, pp 1-33.
3. Bond, A. D. CrystEngComm 2007, 9, 833-834.
4. Lara-Ochoa, F.; Espinosa-Pérez, G. Cryst. Growth Des. 2007, 7, 1213-1215.
5. Miroshnyk, I.; Mirza, S.; Sandlert, N. Expert Opin. Drug Delivery 2009, 6, 333-341.
6. Almarsson, Ö.; Zaworotko, M. J. Chem. Commun. 2004, 1889-1896.
7. Cheney, M. L.; McManus, G. J.; Perman, J. A.; Wang, Z.; Zaworotko, M. J. Cryst. Growth Des. 2007, 7, 616-617.
8. Banerjee, R.; Bhatt, P. M.; Ravindra, N. V; Desiraju, G. R. Cryst. Growth Des. 2005, 5, 2299-2309.
9. Bhatt, P. M.; Azim, Y.; Thakur, T. S.; Desiraju, G. R. Cryst. Growth Des. 2009, 9, 951-957.
10. Greene, W. C.; Debyser, Z.; Ikeda, Y.; Freed, E. O.; Stephens, E.; Yonemoto, W.; Buckheit, R. W.; Este, J. A.; Cihlar, T. Antiviral Res. 2008, 80, 251-265.
11. Coates, J. A.; Cammack, N.; Jenkinson, H. J.; Mutton, I. M.; Pearson, B. A.; Storer, R.; Cameron, J. M.; Penn, C. R. Antimicrob. Agents Chemother. 1992, 36, 202-205.
12. Belleau, B.; Nguyen-Ba, N. U.S. Patent US5047407, October 9, 1991.
13. Chang, C. N.; Skalskiv, V.; Zhou, J. H.; Cheng, Y. C. J. Biol. Chem. 1992, 267, 22414-22420.
14. Harris, R. K.; Yeung, R. R.; Lamont, R. B.; Lancaster, R. W.; Lynn, S. M.; Staniforth, S. E. J. Chem. Soc., Perkin Trans. 2 1997, 2653-2659.
15. Jozwiakowski, M. J.; Nguyen, N. T.; Sisco, J. M.; Spancake, C. W. J. Pharm. Sci. 1996, 85, 193-199.
16. Singh, G. P.; Srivastava, D.; Saini, M. B.; Upadhyay, P. R. Int. Patent WO2007119248, October 25, 2007.
17. Martins, F. T.; Doriguetto, A. C.; Ellena, J. Cryst. Growth Des. [Online early access]. DOI: 10.1021/cg901103r. Published Online October 15, 2009.
18. Takahashi, S.; Inoue, K.; Yanagida, Y.; Ohashi, T.; Watanabe, K. European Patent EP215335, March 25, 1987.
19. Eswaraiah, S.; Reddy, G. M.; Reddy, J. M.; Rambabu, K. V.; Bhaskar, B. V. U. S. Patent US2007004783, January 4, 2007.
20. Hu, M.; Paliwal, S.; Shih, N.; Guenter, F.; Mergelsberg, I. International Patent WO2007114922, October 11, 2007.
21. COLLECT Data Collection Software; Nonius: Delft, The Netherlands, 1998.
22. Otwinowski, Z.; Minor, W. In Methods in Enzymology: Macromolecular Crystallography, Part A; Carter, C. W., Jr., Sweet, R. M., Eds.; Academic Press: New York, 1997; Vol.276, pp 307-326.
23. Sheldrick, G. M. SHELXS-97: Program for Crystal Structure Resolution; University of Göttingen: Göttingen, Germany, 1997.
24. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838.
25. Sheldrick, G. M. SHELXL-97: Program for Crystal Structure Analysis; University of Göttingen: Göttingen, Germany, 1997.
26. Bruno, I. J.; Cole, J. C.; Edgington, P. R.; Kessler, M. K.; Macrae, C. F.; McCabe, P.; Pearson, J.; Taylor, R. Acta Crystallogr., Sect. B 2002, 58, 389-397.
27. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.
28. Kraus, W.; Nolze, G. PowderCell for Windows, version 2.3; Federal Institute for Materials Research and Testing: Berlin, Germany, 1999.
29. The United States Pharmacopeia XXXI and National Formulary XXVI; The United States Pharmacopeial Convention, Inc.: Rockville, MD, 2008; pp 2498-2499.
30. Glomme, A.; Marz, J.; Dressman, J. B. J. Pharm. Sci. 2005, 94, 1-16.
31. Kroner, M.; Schornick, G.; Feindt, H.; Meyer, T.; Ludwig, A.; Metzmann, U. U. S. Patent US5830985, November 3, 1998.
32. Kütt, A.; Leito, I.; Kaljurand, I.; Sooväli, L.; Vlasov, V. M.; Yagupolskii, L. M.; Koppel, I. A. J. Org. Chem. 2006, 71, 2829-2838.
33. Dossi, N.; Toniolo, R.; Susmel, S.; Pizzariello, A.; Bontempelli, G. Chromatographia 2006, 63, 557-562.
34. Cooke, C. L.; Davey, R. J. Cryst. Growth Des. 2008, 8, 3483-3485.
35. Serajuddin, A. T. M. Adv. Drug Delivery Rev. 2007, 59, 603-616.
36. Anderson, B. D.; Conradi, R. A. J. Pharm. Sci. 1985, 74, 815-820.
37. Galcera, J.; Molins, E. Cryst. Growth Des. 2009, 9, 327-334.
38. Lide, D. R., Ed. In CRC Handbook of Chemistry and Physics, 89th Edition (Internet Version 2009): Aqueous Solubility and Henry's Law Constants of Organic Compounds, Section 8; CRC Press/Taylor and Francis: Boca Raton, FL, 2009.
39. McKinnon, J. J.; Spackman, M. A.; Mitchell, A. S. Acta Crystallogr., Sect. B 2004, 60, 627-668.