Fast dissolving curcumin cocrystals

Crystal Growth and Design

Volumn 11, Issue 9, 2011, Pages 4135-4145

  Sanphui, Palash ^a   Goud, N Rajesh ^a   Khandavilli, U B Rao ^a   Nangia, Ashwini ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS SOLUBILITY; BIOACTIVE PHENOLS; CARBONYL GROUPS; CO-CRYSTALS; CURCUMIN; DISSOLUTION RATES; FT-RAMAN; PHARMACOLOGICAL ACTIVITY; PHENOLIC OH GROUP;

HYDROGEN BONDS; MELTING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHENOLS; STOICHIOMETRY; THERMOANALYSIS; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

DISSOLUTION;

EID: 80052530827     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg200704s     Document Type: Article

References (62)

1. Kola, I.; Landis, J. Can the pharmaceutical industry reduce attrition rates? Nat. Rev. Drug Discovery 2004, 3, 711-715 (Pubitemid 39173511)
2. Stahly, G. P. A Survey of cocrystals reported prior to 2000 Cryst. Growth Des. 2009, 9, 4212-4229
3. Vishweshwar, P.; McMahon, J. A.; Bis, J. A.; Zaworotko, M. J. Pharmaceutical co-crystals (review) J. Pharm. Sci. 2006, 95, 499-516
4. US Food and Drug administration approved GRAS list. EAFUS: A food additive database. http://www.cfsan.fda.gov/-dms/ eafus.html.
5. Remenar, J. F.; Morissette, S. L.; Peterson, M. L.; Moulton, B.; MacPhee, J. M.; Guzmán, H. R.; Almarsson, Ö. Crystal engineering of novel co-crystals of a triazole drug with 1,4-dicarboxylic acids J. Am. Chem. Soc. 2003, 125, 8456-8457 (Pubitemid 36858412)
6. Babu, N. J.; Nangia, A. Solubility advantage of amorphous drugs and pharmaceutical cocrystals Cryst. Growth Des. 2011, 11, 2662-2679
7. Amidon, G. L.; Lennernas, H.; Shah, V. P.; Crison, J. R. Theoretical basis for a biopharmaceutical drug classification: Correlation of in vitro drug product dissolution and in vivo bioavailability Pharm. Res. 1995, 12, 413-420
8. Çkrkç, S.; Mozioglu, E.; Ylmaz, H. Biological activity of curcuminoids isolated from curcuma longa Rec. Nat. Prod. 2008, 2, 19-24 (Pubitemid 351753472)
9. Hatcher, H.; Planalp, R.; Cho, J.; Torti, F. M.; Torti, S. V. Curcumin: From ancient medicine to current clinical trials (review) Cell. Mol. Life Sci. 2008, 65, 1631-1652
10. Mahady, G. B.; Pendland, S. L.; Yun, G; Lu, Z. Z. Turmeric (Curcuma longa) and curcumin inhibit the growth of Helicobacter pylori, a group 1 carcinogen Anticancer Res. 2002, 22, 4179-4181 (Pubitemid 36134453)
11. Sugiyama, Y.; Kawakishi, S.; Osawa, T. Involvement of the beta-diketone moiety in the antioxidative mechanism of tetrahydrocurcumin Biochem. Pharmacol. 1996, 52, 519-525 (Pubitemid 26253384)
12. Ruby, A. J.; Kuttan, G.; Babu, K. D.; Rajasekharan, K. N.; Kuttan, R. Anti-tumour and antioxidant activity of natural curcuminoids Cancer Lett. 1995, 94, 79-83
13. Jordan, W. C.; Drew, C. R. Curcumin-A natural herb with anti-HIV activity J. Natl. Med. Assoc. 1996, 88, 333-335
14. Qureshi, S.; Shah, A. H.; Ageel, A. M. Toxicity studies on Alpinia alangal and Curcuma longa Planta Med. 1992, 58, 124-127
15. Lao, C. D.; Ruffin, M. T.; Normolle, D.; Heath, D. D.; Murray, S. I.; Bailey, J. M.; Boggs, M. E.; Crowell, J.; Rock, C. L.; Brenner, D. E. Dose escalation of a curcuminoid formulation BMC Complement, Altern. Med. 2006, 6, 10
16. Anand, P.; Kunnumakkara, A. B.; Newman, R. A.; Aggarwal, B. B. Bioavailability of curcumin: Problems and promises (review) Mol. Pharmaceutics 2007, 4, 807-818
17. Wang, Y. J.; Pan, M. H.; Cheng, A. L.; Lin, L. I.; Ho, Y. S.; Hsieh, C. Y.; Lin, J. K. Stability of curcumin in buffer solutions and characterization of its degradation products J. Pharm. Biomed. Anal. 1997, 15, 1867-1876
18. Antony, B.; Merina, B.; Iyer, V. S.; Judy, N.; Lennertz, K.; Joyal, S. A. Pilot cross-over study to evaluate human oral bioavailability of BCM-95 CG (Biocurcumax) a novel bioenhanced preparation of curcumin. Ind J. Pharm. Sci. 2008, 445-449
19. Zhang, F.; Koh, G. K.; Jeansonne, D. P.; Hollingworth, J.; Russo, P. S.; Vicente, G.; Stout, R. W.; Liu, Z. A Novel solubility-enhanced curcumin formulation showing stability and maintenance of anticancer activity J. Pharm. Sci. 2011, 100, 2778-2789
20. Gupta, N. K.; Dixit, V. K. Bioavailability enhancement of curcumin by complexation with phosphatidyl choline J. Pharm. Sci. 2011, 100, 1987-1995
21. Schultheiss, N.; Bethune, S.; Henck, J.-O. Nutraceutical cocrystals: Utilizing pterostilbene as a cocrystal former CrystEngComm 2010, 12, 2436-2442
22. Karki, S.; Frişçić, T.; Fábián, L.; Jones, W. New solid forms of artemisinin obtained through cocrystallisation CrystEngComm 2010, 12, 4038-4041
23. Bethune, S. J.; Schultheiss, N.; Henck, J.-O. Improving the poor aqueous solubility of nutraceutical compound pterostilbene through cocrystal formation Cryst. Growth Des. 2011, 11, 2817-2823
24. Schultheiss, N.; Newman, A. Pharmaceutical cocrystals and their physicochemical properties Cryst. Growth Des. 2009, 9, 2950-2967
25. McNamara, D. P.; Childs, S. L.; Giordano, J.; Iarriccio, A.; Cassidy, J.; Shet, M. S.; Mannion, R.; ODonnell, E.; Park, A. Use of a glutaric acid cocrystal to improve oral bioavailability of a low solubility API Pharm. Res. 2006, 23, 1888-1897 (Pubitemid 44200553)
26. Sanphui, P.; Goud, N. R.; Khandavilli, U. B. R.; Bhanoth., S.; Nangia, A. Novel polymorphs of curcumin Chem. Commun. 2011, 47, 5013-5015
27. Mukherjee, A.; Grobelny, P.; Thakur, T. S.; Desiraju, G. R. Polymorphs, pseudopolymorphs and co-crystals of orcinol: Exploring the structural landscape through high throughput crystallography Cryst. Growth Des. 2011, 11, 2637-2653
28. Yang, C. J.; Wang, C. S.; Hung, J. Y.; Huang, H. W.; Chia, Y. C.; Wang, P. H.; Weng, C. F.; Huang, M. S. Pyrogallol induces G2-M arrest in human lung cancer cells and inhibits tumor growth in an animal model Lung Cancer 2009, 66, 162-168
29. Tang, G.; Yang, C. Y.; Nikolovska-Coleska, Z.; Guo, J.; Qiu, S.; Wang, R.; Gao, W.; Wang, G.; Stuckey, J.; Krajewski, K.; Jiang, S.; Roller, P. P.; Wang, S. Pyrogallol based molecules as potent inhibitors of the anti-apoptotic Bcl-2 proteins J. Med. Chem. 2007, 50, 1723-1726 (Pubitemid 46626582)
30. Trask, A. V.; Motherwell, W. D. S.; Jones, W. Solvent-drop grinding: Green polymorph control of cocrystallisation Chem. Commun. 2004, 890-891 (Pubitemid 38530287)
31. Balasubramanian, K. Molecular orbital basis for yellow curry spice curcumins prevention of Alzheimers disease J. Agric. Food Chem. 2006, 54, 3512-3520 (Pubitemid 43844175)
32. Parimita, S. P.; Ramshankar, Y. V.; Suresh, S.; Row, T. N. G. Redetermination of curcumin: (1 E,4 Z,6 E)-5-Hydroxy-1,7-bis(4-hydroxy-3- methoxyphenyl)hepta-1,4,6-trien-3-one Acta Crystallogr. 2007, E63, o860-o862
33. Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Patterns in hydrogen bonding: Functionality and graph set analysis in crystals Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573
34. Cambridge Structural Database, Ver. 5.32, May 2011 update, Cambridge Crystallographic Data Center, UK; www.ccdc.cam.ac.uk.
35. Ermer, O.; Robke, C. Crystal Structure of 2,5-di- tert -butyl-hydroquinone: Polar stacking of nonpolar hydrogen-bonded sheets with trigonal symmetry. Angew. Chem., Int. Ed. Engl. 1994, 33, 1755-1757. [Refcode HESKOF] (Pubitemid 24987141)
36. Dinger, M. B.; Scott, M. J. Extended structures built on a triphenoxymethane platform. C3-symmetric, conformational mimics of calix[ n ]arenes. Eur. J. Org. Chem. 2000, 2467-2478. [Refcode QEXXEW]
37. Parvez, M.; Kurtz, S. K.; Williams, I. Structure of a melanin precursor: 1-Methylindole-5,6-diol. Acta Crystallogr. 1990, C46, 165-167. [Refcode SEFRIE]
38. Andresen, T. L.; Krebs, F. C.; Thorup, N.; Bechgaard, K. Crystal Structures of 2,3,6,7,10,11-oxytriphenylenes. Implications for columnar discotic mesophases. Chem. Mater. 2000, 12, 2428-2433. [Refcode XEFSIK]
39. Ma, Z.; Moulton, B. Supramolecular medicinal chemistry: Mixed-ligand medicinal chemistry Mol. Pharmaceutics 2007, 4, 373-385
40. Aitipamula, S.; Chowa, P. S.; Tan, R. B. H. Trimorphs of a pharmaceutical cocrystal involving two active pharmaceutical ingredients: Potential relevance to combination drugs CrystEngComm 2009, 11, 1823-1827
41. Bhatt, P. M.; Azim, Y.; Thakur, T. S.; Desiraju, G. R. Co-crystals of the anti-HIV drugs lamivudine and zidovudine Cryst. Growth Des. 2009, 9, 951-957
42. Stanton, M. K.; Tufekcic, S.; Morgan, C.; Bak, A. Drug substance and former structure-property relationships in 15 diverse pharmaceutical co-crystals Cryst. Growth Des. 2009, 9, 1344-1352
43. Thakuria, R.; Nangia, A. Highly soluble olanzapinium maleate crystalline salts CrystEngComm. 2011, 13, 1759-1764
44. Remenar, J. F.; Peterson, M. L.; Stephens, P. W.; Zhang, Z.; Zimenkov, Y.; Hickey, M. B. Celecoxib:nicotinamide dissociation: Using excipients to capture the cocrystals potential Mol. Pharmaceutics 2007, 4, 386-400 (Pubitemid 46983955)
45. Li, J.; Bourne, S. A.; Caira, M. R. New polymorphs of nicotinamide and isonicotinamide Chem. Commun. 2011, 47, 1530-1532
46. Elbagerma, M. A.; Edwards, H. G. M.; Munshi, T.; Hargreaves, M. D.; Matousek, P.; Scowen, I. J. Characterization of new cocrystals by Raman spectroscopy, powder X-ray diffraction, differential scanning calorimetry, and transmission Raman spectroscopy Cryst. Growth Des. 2010, 10, 2360-2371
47. Tishmack, P. A.; Bugay, D. E.; Byrn, S. R. Solid-state nuclear magnetic resonance spectroscopy-Pharmaceutical applications (mini review) J. Pharm. Sci. 2002, 92, 441-474
48. Vogt, F. G.; Clawson, J. S.; Strohmeier, M.; Edwards, A. J.; Pham, T. N.; Watson, S. A. Solid-state NMR analysis of organic cocrystals and complexes Cryst. Growth Des. 2009, 9, 921-937
49. Fagerberg, J. H.; Tsinman, O.; Sun, N.; Tsinman, K.; Avdeef, A.; Bergström, C. A. S. Dissolution rate and apparent solubility of poorly soluble drugs in biorelevant dissolution media Mol. Pharmaceutics 2010, 7, 1419-1430
50. Otsuka, M.; Teraoka, R.; Matsuda, Y. Physicochemical properties of nitrofurantoin anhydrate and monohydrate and their dissolution Chem. Pharm. Bull. 1991, 39, 2667-2671
51. Pudipeddi, M.; Serajuddin, A. T. M. Trends in solubility of polymorphs J. Pharm. Sci. 2005, 94, 929-939 (Pubitemid 40780760)
52. Hancock, B. C.; Parks, M. What is the true solubility advantage of amorphous pharmaceuticals? Pharm. Res. 2000, 17, 397-404 (Pubitemid 30395293)
53. Murashima, T.; Tsujimoto, S.; Yamada, T.; Miyazawa, T.; Uno, H.; Ono, N.; Sugimoto, N. Synthesis of water-soluble porphyrin and the corresponding highly planar benzoporphyrin without meso-substituents Tetrahedron Lett. 2005, 46, 113-116 (Pubitemid 39592954)
54. CrysAlis CCD and CrysAlis RED, versions 1.171.33.55; Oxford Diffraction Ltd, Yarnton, Oxfordshire, UK, 2008
55. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: A complete structure solution, refinement and analysis program J. Appl. Crystallogr. 2009, 42, 339-341
56. SMART, version 5.625 and SHELX-TL, version 6.12; Bruker AXS Inc., Madison, WI, 2000.
57. Spek, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University, Utrecht, Netherlands, 2002.
58. Spek, A. L. Single-crystal structure validation with the program PLATON J. Appl. Crystallogr. 2003, 36, 7-13
59. Barbour, L. J. X-Seed, Graphical Interface to SHELX-97 and POV-Ray, a Program for Better Quality of Crystallographic Figures; 1999. University of Missouri-Columbia, Missouri.
60. Kraus, N.; Nolze, G. Powder Cell, Version 2.3. A Program for Structure Visualization, Powder Pattern Calculation and Profile Fitting; Federal Institute for Materials Research and Testing: Berlin, 2000.
61. Glomme, A.; Marz, J.; Dressman, J. B. Comparison of miniaturized shake-flask solubility method with automated potentiometric acid/base titration and calculated solubilities J. Pharm. Sci. 2005, 94, 1-16 (Pubitemid 40116365)
62. Viscomi, G. C.; Campana, M.; Barbanti, M.; Grepioni, F.; Polito, M.; Confortini, D.; Rosini, G.; Righi, P.; Cannata, V.; Braga, D. Crystal forms of rifaximin and their effect on pharmaceutical properties CrystEngComm 2008, 10, 1074-1081