Kinetic entrapment of a hidden curcumin cocrystal with phloroglucinol

Crystal Growth and Design

Volumn 14, Issue 10, 2014, Pages 5079-5089

  Chow, Shing Fung ^a   Shi, Limin ^b   Ng, Wai Wing ^a   Leung, Kari Hoi Yan ^a   Nagapudi, Karthik ^c   Sun, Changquan Calvin ^b   Chow, Albert H L ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

^b UNIVERSITY OF MINNESOTA   (United States)

^c AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CO-CRYSTALS; CURCUMIN; PHLOROGLUCINOL;

EID: 84907484354     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg5007007     Document Type: Article

References (47)

1. Desiraju, G. R. Crystal and co-crystal CrystEngComm 2003, 5, 466-467
2. Nair, R. Cocrystals: Molecular design of pharmaceutical materials Mol. Pharmaceutics 2007, 4 (3) 299-300
3. Sun, C. C. Cocrystallization for successful drug delivery Expert Opin. Drug Delivery 2013, 10 (2) 201-213
4. Aitipamula, S.; Banerjee, R.; Bansal, A. K.; Biradha, K.; Cheney, M. L.; Choudhury, A. R. Polymorphs, salts, and cocrystals: what's in a name? Cryst. Growth Des. 2012, 12 (5) 2147-2152
5. Shan, N.; Zaworotko, M. J. The role of cocrystals in pharmaceutical science Drug Discovery Today. 2008, 13 (9-10) 440-446
6. Good, D. J.; Rodriguez-Hornedo, N. Solubility advantage of pharmaceutical cocrystals Cryst. Growth Des. 2009, 9 (5) 2252-2264
7. Sun, C. C.; Hou, H. Improving mechanical properties of caffeine and methyl gallate crystals by cocrystallization Cryst. Growth Des. 2008, 8 (5) 1575-1579
8. Jones, W.; Motherwell, W. D. S.; Trask, A. V. Pharmaceutical cocrystals: an emerging approach to physical property enhancement MRS Bull. 2006, 31 (11) 875-879
9. Trask, A. V.; Jones, W. Crystal engineering of organic cocrystals by the solid-state grinding approach. Organic Solid State Reactions; Springer: Berlin Heidelberg, 2005; pp 41-70.
10. Trask, A. V.; Motherwell, W. D. S.; Jones, W. Solvent-drop grinding: green polymorph control of cocrystallisation Chem. Commun. 2004, 7, 890-891
11. Rodriguez-Hornedo, N.; Nehm, S. J.; Seefeldt, K. F.; Pagan-Torres, Y.; Falkiewicz, C. J. Reaction crystallization of pharmaceutical molecular complexes Mol. Pharmaceutics 2006, 3 (3) 362-367
12. Berry, D. J.; Seaton, C. C.; Clegg, W.; Harrington, R. W.; Coles, S. J.; Horton, P. N. Applying hot-stage microscopy to co-crystal screening: a study of nicotinamide with seven active pharmaceutical ingredients Cryst. Growth Des. 2008, 8 (5) 1697-1712
13. Takata, N.; Shiraki, K.; Takano, R.; Hayashi, Y.; Terada, K. Cocrystal screening of stanolone and mestanolone using slurry crystallization Cryst. Growth Des. 2008, 8 (8) 3032-3037
14. Pedireddi, V. R.; Jones, W.; Chorlton, A. P.; Docherty, R. Creation of crystalline supramolecular arrays: a comparison of co-crystal formation from solution and by solid-state grinding Chem. Commun. 1996, 8, 987-988
15. Horst, J. H. T.; Cains, P. W. Co-crystal polymorphs from a solvent-mediated transformation Cryst. Growth Des. 2008, 8 (7) 2537-2542
16. Jayasankar, A.; Reddy, L. S.; Bethune, S. J.; Rodriguez-Hornedo, N. Role of cocrystal and solution chemistry on the formation and stability of cocrystals with different stoichiometry Cryst. Growth Des. 2009, 9 (2) 889-897
17. Grant, K. L.; Schneider, C. D. Turmeric Am. J. Health Syst. Pharm. 2000, 57 (12) 1121-1122
18. Chan, M. M.; Huang, H.; Fenton, M. R.; Fong, D. In vivo inhibition of nitric oxide synthase gene expression by curcumin, a cancer preventive natural product with anti-inflammatory properties Biochem. Pharmacol. 1998, 55 (12) 1955-1962
19. Joe, B.; Lokesh, B. R. Role of capsaicin, curcumin and dietary n-3 fatty acids in lowering the generation of reactive oxygen species in rat peritoneal macrophages Biochim. Biophys. Acta, Mol. Cell Res. 1994, 1224 (2) 255-263
20. Yang, F.; Lim, G. P.; Begum, A. N.; Ubeda, O. J.; Simmons, M. R.; Ambegaokar, S. S. Curcumin inhibits formation of amyloid β oligomers and fibrils, binds plaques, and reduces amyloid in vivo J. Biol. Chem. 2005, 280 (7) 5892-5901
21. Kelloff, G. J.; Boone, C. W.; Crowell, J. A.; Steele, V. E.; Lubet, R.; Sigman, C. C. Chemopreventive drug development: perspectives and progress Cancer Epidemiol. Biomarkers Prev. 1994, 3 (1) 85-98
22. Ireson, C.; Orr, S.; Jones, D. J. L.; Verschoyle, R.; Lim, C.; Luo, J. Characterization of metabolites of the chemopreventive agent curcumin in human and rat hepatocytes and in the rat in vivo, and evaluation of their ability to inhibit phorbol ester-induced prostaglandin E2 production Cancer Res. 2001, 61 (3) 1058-1064
23. Baum, L.; Cheung, S. K. K.; Mok, V. C. T.; Lam, L. C. W.; Leung, V. P. Y.; Hui, E. Curcumin effects on blood lipid profile in a 6-month human study Pharmacol. Res. 2007, 56 (6) 509-514
24. Tonnesen, H. H.; Masson, M.; Loftsson, T. Studies of curcumin and curcuminoids. XXVII. Cyclodextrin complexation: solubility, chemical and photochemical stability Int. J. Pharm. 2002, 244 (1-2) 127-135
25. Ireson, C. R.; Jones, D. J. L.; Orr, S.; Coughtrie, M. W. H.; Boocock, D. J.; Williams, M. L. Metabolism of the cancer chemopreventive agent curcumin in human and rat intestine Cancer Epidemiol. Biomarkers Prev. 2002, 11 (1) 105-111
26. Anand, P.; Kunnumakkara, A. B.; Newman, R. A.; Aggarwal, B. B. Bioavailability of curcumin: problems and promises Mol. Pharmaceutics 2007, 4 (6) 807-818
27. Sanphui, P.; Goud, N. R.; Khandavilli, U. B. R.; Nangia, A. Fast dissolving curcumin cocrystals Cryst. Growth Des. 2011, 11 (9) 4135-4145
28. Bag, P. P.; Patni, M.; Reddy, C. M. A kinetically controlled crystallization process for identifying new co-crystal forms: fast evaporation of solvent from solutions to dryness CrystEngComm 2011, 13 (19) 5650-5652
29. Chow, S. F.; Chen, M.; Shi, L.; Chow Albert, H. L.; Sun, C. C. Simultaneously improving the mechanical properties, dissolution performance, and hygroscopicity of ibuprofen and flurbiprofen by cocrystallization with nicotinamide Pharm. Res. 2012, 29 (7) 1854-1865
30. Singh, I. P.; Bharate, S. B. Phloroglucinol compounds of natural origin Nat. Prod. Rep. 2006, 23 (4) 558-591
31. Li, N.; Luo, X.; Zhang, Y.; He, L.; Liu, Y.; Peng, J. Phloroglucinol protects gastric mucosa against ethanol-induced injury through regulating myeloperoxidase and catalase activities Fundam. Clin. Pharmacol. 2011, 25 (4) 462-468
32. Kang, K. A.; Lee, K. H.; Chae, S.; Zhang, R.; Jung, M. S.; Ham, Y. M. Cytoprotective effect of phloroglucinol on oxidative stress induced cell damage via catalase activation J. Cell Biochem. 2006, 97 (3) 609-620
33. Sun, C.; Grant, D. J. W. Influence of crystal shape on the tableting performance of l -lysine monohydrochloride dihydrate J. Pharm. Sci. 2001, 90 (5) 569-579
34. Sun, C.; Grant, D. J. W. Effects of initial particle size on the tableting properties of l -lysine monohydrochloride dihydrate powder Int. J. Pharm. 2001, 215 (1-2) 221-228
35. Childs, S. L.; Rodriguez-Hornedo, N.; Reddy, L. S.; Jayasankar, A.; Maheshwari, C.; McCausland, L. Screening strategies based on solubility and solution composition generate pharmaceutically acceptable cocrystals of carbamazepine CrystEngComm 2008, 10 (7) 856-864
36. Gu, C.; Young, V.; Grant, D. J. W. Polymorph screening: influence of solvents on the rate of solvent-mediated polymorphic transformation J. Pharm. Sci. 2001, 90 (11) 1878-1890
37. Nardo, L.; Paderno, R.; Andreoni, A.; Masson, M.; Haukvik, T.; Toennesen, H. H. Role of H-bond formation in the photoreactivity of curcumin Spectroscopy 2008, 22 (2,3) 187-198
38. Tomren, M. A.; Masson, M.; Loftsson, T.; Tonnesen, H. H. Studies on curcumin and curcuminoids XXXI. Symmetric and asymmetric curcuminoids: stability, activity and complexation with cyclodextrin Int. J. Pharm. 2007, 338 (1-2) 27-34
39. Braun, D. E.; Tocher, D. A.; Price, S. L.; Griesser, U. J. The complexity of hydration of phloroglucinol: a comprehensive structural and thermodynamic characterization J. Phys. Chem. B 2012, 116 (13) 3961-3972
40. Joseph, J.; Jemmis, E. D. Red-, blue-, or no-shift in hydrogen bonds: a unified explanation J. Am. Chem. Soc. 2007, 129 (15) 4620-4632
41. Trask, A. V.; Motherwell, W. D. S.; Jones, W. Physical stability enhancement of theophylline via cocrystallization Int. J. Pharm. 2006, 320 (1-2) 114-123
42. Perumalla, S. R.; Sun, C. C. Improved solid-state stability of salts by cocrystallization between conjugate acid-base pairs CrystEngComm 2013, 15 (29) 5756-5759
43. Schultheiss, N.; Newman, A. Pharmaceutical cocrystals and their physicochemical properties Cryst. Growth Des. 2009, 9 (6) 2950-2967
44. Basavoju, S.; Bostrom, D.; Velaga, S. P. Indomethacin-saccharin cocrystal: design, synthesis and preliminary pharmaceutical characterization Pharm. Res. 2008, 25 (3) 530-541
45. Sun, C. C.; Hou, H.; Gao, P.; Ma, C.; Medina, C.; Alvarez, F. J. Development of a high drug load tablet formulation based on assessment of powder manufacturability: moving towards quality by design J. Pharm. Sci. 2009, 98 (1) 239-247
46. Chattoraj, S.; Shi, L.; Sun, C. C. Understanding the relationship between crystal structure, plasticity and compaction behaviour of theophylline, methyl gallate, and their 1:1 co-crystal CrystEngComm 2010, 12 (8) 2466-2472
47. Sun, C. C. Decoding powder tabletability: roles of particle adhesion and plasticity J. Adhes. Sci. Technol. 2011, 25 (4-5) 483-499