Improving the poor aqueous solubility of nutraceutical compound pterostilbene through cocrystal formation

Crystal Growth and Design

Volumn 11, Issue 7, 2011, Pages 2817-2823

  Bethune, Sarah J ^a   Schultheiss, Nate ^a   Henck, Jan Olav ^a  

^a Aptuit Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS CONCENTRATIONS; AQUEOUS SOLUBILITY; CO-CRYSTAL FORMATION; CO-CRYSTALS; GLUTARIC ACID; MOLAR RATIO; NUTRACEUTICAL COMPOUNDS; PARTIAL TRANSFORMATION; PHYSICAL STABILITY; RELATIVE HUMIDITIES; SINGLE CRYSTAL X-RAY DIFFRACTION;

ATMOSPHERIC HUMIDITY; DIFFRACTION; DISSOLUTION; X RAY DIFFRACTION; X RAY POWDER DIFFRACTION;

SOLUBILITY;

EID: 79960035458     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg1016092     Document Type: Article

References (37)

1. A "nutraceutical" compound can be defined as, "a food (or part of a food) that provides medical or health benefits, including the prevention and/or treatment of a disease and possesses a physiological benefit or reduces the risk of chronic disease". Kalra, E. K. AAPS Pharm. Sci. 2003, 3 25
2. Rimando, A. M.; Kalt, W.; Magee, J. B.; Dewey, J.; Ballington, J. R. J. Agric. Food Chem. 2004, 52, 4713-4719
3. Adrian, M.; Jeandet, P.; Douillet-Breuil, A. C.; Tesson, L.; Bessis, R. J. Agric. Food Chem. 2002, 48, 6103-6105
4. Langcake, P. Physiol. Plant Pathol. 1981, 18, 213-226
5. Rimando, A. M.; Cuendet, M.; Desmarchelier, C.; Mehta, R. G.; Pezzuto, J. M.; Duke, S. O. J. Agric. Food Chem. 2002, 50, 3453-3457
6. Cichocki, M.; Paluszczak, J.; Szaefer, H.; Piechowiak, A.; Rimando, A. M.; Baer-Dubowska, W. Mol. Nutr. Food Res. 2008, 52, 62-70
7. Suh, N.; Paul, S.; Hao, X.; Simi, B.; Xiao, H.; Rimando, A. M.; Reddy, B. S. Clin. Cancer Res. 2007, 13, 350-355
8. Lin, H.-S.; Yue, B.-D.; Ho, P. C. Biomed. Chromatogr. 2009, 23, 1308-1315
9. Das, S.; Lin, H.-S.; Ho, P. C.; Ng, K.-Y. Pharm. Res. 2008, 25, 2593-2600
10. Ivanisevic, I.; Andres, M. C.; Stephens, K.; Bethune, S.; Bower, M.; Wolfe, S.; Smit, J.; Gilkinson, A.; Roe, M. manuscript in preparation, 2011.
11. Etter, M. C. Acc. Chem. Res. 1990, 23, 120-126
12. Aakeröy, C. B.; Salmon, D. J. CrystEngComm 2005, 7, 439-448
13. MacGillivray, L. CrystEngComm 2004, 6, 77-78
14. Desiraju, G. R. Acc. Chem. Res. 2002, 35, 565-573
15. Moulton, B.; Zaworotko, M. Chem. Rev. 2001, 101, 1629-1658
16. Lehn, J.-M. Science 2002, 295, 2400-2403
17. Grepioni, F.; Braga, D. Making Crystals by Design-From Molecules to Molecular Materials, Methods, Techniques, Applications; Wiley-VCH: Weinheim, Germany, 2007; Chapter 2.5 and references therein.
18. Crystal Growth and Design virtual issue on Pharmaceutical Cocrystals, http://pubs.acs.org/page/cgdefu/vi/1, and references therein.
19. Good, D. J.; Rodríguez-Hornedo, N. Cryst. Growth Des. 2009, 9 (5) 2252-2264
20. Childs, S. L.; Chyall, L. J.; Dunlap, J. T.; Smolenskaya, V. N.; Stahly, B. C.; Stahly, G. P. J. Am. Chem. Soc. 2004, 126, 13335-13342
21. Shiraki, K.; Takata, N.; Takano, R.; Hayashi, Y.; Terada, K. Pharm. Res. 2008, 25, 2581-2592
22. Childs, S. L.; Rodríguez-Hornedo, N.; Reddy, L. S.; Jayasankar, A.; Maheshwari, C.; McCausland, L.; Shipplett, R.; Stahly, B. C. CrystEngComm 2008, 10, 856-864
23. Schultheiss, N.; Bethune, S.; Henck, J. O. CrystEngComm 2010, 12, 2436-2442
24. Coformers were selected for the screen if they possessed estimated aqueous solubilities of 30 mg/mL or greater.
25. Handbook of Pharmaceutical Salts: Properties, Selection and Use; Stahl, P. H.; Wermuth, C. G., Eds.; Verlag Helvetica Chimica Acta: Zürich, 2002.
26. Generally Regarded as Safe: http://www.cfsan.fda.gov/-rdb/opa-gras.html and http://www.cfsan.fda.gov/-dms/grasguid.html
27. Everything Added to Food Stuff in the United States: Http://vm.cfsan.fda. gov/-dms/eafus.html.
28. APEXII, v1.27; Bruker Analytical X-ray Systems, Madison, WI, 2005.
29. SAINT, v6.02; Bruker Analytical X-ray Systems, Madison, WI, 1997-1999.
30. SHELXTL, v5.10; Bruker Analytical X-ray Systems, Madison, WI, 1997.
31. Figure generated using proprietary in-house Pattern Match software: Ivanisevic, I.; Bugay, D. E.; Bates, S. J. Phys. Chem. B 2005, 109, 7781-7787
32. Images created using Mercury 2.1.
33. CSD refcodes: AYISIK, DIVCUH, DIVDOC, DOSJOK, FEKQOC, HIBFED, JESMEA, LAKMOA, LOHNOM, MUPPUI, OGEZIJ, QAMRAY, RAWFAW, TICFOA, and XOKBOO.
34. Oswald, I. D. H.; Allan, D. R.; McGregor, P. A.; Motherwell, W. D. S.; Parsons, S.; Pulham, C. R. Acta Crystallogr. 2002, B58, 1057-1066
35. Tian, Y.; Cui, D. Acta Crystallogr. 2008, E64, 2334-2335
36. Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256-262
37. Approximate aqueous solubilities were calculated based on the total solvent used to produce a solution; actual solubilities may be greater due to the slow rate of dissolution.