Cocrystals of quercetin with improved solubility and oral bioavailability

Molecular Pharmaceutics

Volumn 8, Issue 5, 2011, Pages 1867-1876

  Smith, Adam J ^a,b   Kavuru, Padmini ^c   Wojtas, Lukasz ^c   Zaworotko, Michael J ^c   Shytle, R Douglas ^a,b  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

^b UNIVERSITY OF SOUTH FLORIDA   (United States)

^c UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

bioavailability; cocrystal; pharmacokinetics; quercetin; solubility

Indexed keywords

CAFFEINE; ISONICOTINAMIDE; METHANOL; QUERCETIN; QUERCETIN CAFFEINE; QUERCETIN CAFFEINE METHANOL; QUERCETIN ISONICOTINAMIDE; QUERCETIN THEOBROMINE DIHYDRATE; THEOBROMINE; THEOBROMINE DIHYDRATE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; COCRYSTAL; CONTROLLED STUDY; CRYSTAL STRUCTURE; CRYSTALLIZATION; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG DISTRIBUTION; DRUG ELIMINATION; DRUG FORMULATION; DRUG HALF LIFE; DRUG SCREENING; DRUG SOLUBILITY; DRUG SYNTHESIS; MALE; MAXIMUM PLASMA CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; RAT; TIME TO MAXIMUM PLASMA CONCENTRATION;

ANIMALS; ANTIOXIDANTS; CAFFEINE; CALORIMETRY, DIFFERENTIAL SCANNING; CRYSTALLOGRAPHY, X-RAY; DIETARY SUPPLEMENTS; HALF-LIFE; INTESTINAL ABSORPTION; MALE; METHANOL; MOLECULAR CONFORMATION; NIACINAMIDE; PHYSICOCHEMICAL PHENOMENA; POWDER DIFFRACTION; QUERCETIN; RATS; RATS, SPRAGUE-DAWLEY; SOLUBILITY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THEOBROMINE;

EID: 80053495707     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp200209j     Document Type: Article

References (52)

1. Hertog, M. G. Epidemiological evidence on potential health properties of flavonoids Proc. Nutr. Soc. 1996, 55, 385-97 (Pubitemid 126795349)
2. Arts, I. C. A review of the epidemiological evidence on tea, flavonoids, and lung cancer J. Nutr. 2008, 138, 1561S-1566S
3. Egert, S.; Wolffram, S.; Bosy-Westphal, A.; Boesch-Saadatmandi, C.; Wagner, A. E.; Frank, J.; Rimbach, G.; Mueller, M. J. Daily quercetin supplementation dose-dependently increases plasma quercetin concentrations in healthy humans J. Nutr. 2008, 138, 1615-21
4. Formica, J. V.; Regelson, W. Review of the biology of Quercetin and related bioflavonoids Food Chem. Toxicol. 1995, 33, 1061-80 (Pubitemid 26009773)
5. Murakami, A.; Ashida, H.; Terao, J. Multitargeted cancer prevention by quercetin Cancer Lett. 2008, 269, 315-25
6. Spencer, J. P.; Kuhnle, G. G.; Williams, R. J.; Rice-Evans, C. Intracellular metabolism and bioactivity of quercetin and its in vivo metabolites Biochem. J. 2003, 372, 173-81 (Pubitemid 36609619)
7. Vargas, A. J.; Burd, R. Hormesis and synergy: pathways and mechanisms of quercetin in cancer prevention and management. Nutr. Rev. 68, 418-28.
8. Bakay, M.; Mucsi, I.; Beladi, I.; Gabor, M. Effect of flavonoids and related substances. II. Antiviral effect of quercetin, dihydroquercetin and dihydrofisetin Acta Microbiol. Acad. Sci. Hung. 1968, 15, 223-7
9. Leopoldini, M.; Russo, N.; Chiodo, S.; Toscano, M. Iron chelation by the powerful antioxidant flavonoid quercetin J. Agric. Food Chem. 2006, 54, 6343-51 (Pubitemid 44375792)
10. Ader, P.; Wessmann, A.; Wolffram, S. Bioavailability and metabolism of the flavonol quercetin in the pig Free Radical Biol. Med. 2000, 28, 1056-67 (Pubitemid 30314704)
11. Cermak, R.; Landgraf, S.; Wolffram, S. The bioavailability of quercetin in pigs depends on the glycoside moiety and on dietary factors J. Nutr. 2003, 133, 2802-7 (Pubitemid 37099763)
12. Erlund, I.; Freese, R.; Marniemi, J.; Hakala, P.; Alfthan, G. Bioavailability of quercetin from berries and the diet Nutr. Cancer 2006, 54, 13-7 (Pubitemid 44141332)
13. Graefe, E. U.; Derendorf, H.; Veit, M. Pharmacokinetics and bioavailability of the flavonol quercetin in humans Int. J. Clin. Pharmacol. Ther. 1999, 37, 219-33 (Pubitemid 29216610)
14. Graefe, E. U.; Wittig, J.; Mueller, S.; Riethling, A. K.; Uehleke, B.; Drewelow, B.; Pforte, H.; Jacobasch, G.; Derendorf, H.; Veit, M. Pharmacokinetics and bioavailability of quercetin glycosides in humans J. Clin. Pharmacol. 2001, 41, 492-9 (Pubitemid 32381866)
15. Hollman, P. C.; van Trijp, J. M.; Buysman, M. N.; van der Gaag, M. S.; Mengelers, M. J.; de Vries, J. H.; Katan, M. B. Relative bioavailability of the antioxidant flavonoid quercetin from various foods in man FEBS Lett. 1997, 418, 152-6 (Pubitemid 27514436)
16. Lesser, S.; Cermak, R.; Wolffram, S. Bioavailability of quercetin in pigs is influenced by the dietary fat content J. Nutr. 2004, 134, 1508-11 (Pubitemid 38720730)
17. Manach, C.; Morand, C.; Demigne, C.; Texier, O.; Regerat, F.; Remesy, C. Bioavailability of rutin and quercetin in rats FEBS Lett. 1997, 409, 12-6 (Pubitemid 27248557)
18. Manach, C.; Texier, O.; Morand, C.; Crespy, V.; Regerat, F.; Demigne, C.; Remesy, C. Comparison of the bioavailability of quercetin and catechin in rats Free Radical Biol. Med. 1999, 27, 1259-66 (Pubitemid 30001487)
19. Gugler, R.; Leschik, M.; Dengler, H. J. Disposition of quercetin in man after single oral and intravenous doses Eur. J. Clin. Pharmacol. 1975, 9, 229-34
20. Reinboth, M.; Wolffram, S.; Abraham, G.; Ungemach, F. R.; Cermak, R. Oral bioavailability of quercetin from different quercetin glycosides in dogs Br. J. Nutr. 2010, 104, 198-203
21. Shan, N.; Zaworotko, M. J. The role of cocrystals in pharmaceutical science Drug Discovery Today 2008, 13, 440-6
22. Sarma, B.; Chen, J.; Hsi, H.-Y.; Myerson, A. S. Solid forms of pharmaceuticals: Polymorphs, salts and cocrystals Korean J. Chem. Eng. 2011, 28, 315-322
23. Basavoju, S.; Bostrom, D.; Velaga, S. P. Indomethacin-saccharin cocrystal: design, synthesis and preliminary pharmaceutical characterization Pharm. Res. 2008, 25, 530-41 (Pubitemid 351357724)
24. Brader, M. L.; Sukumar, M.; Pekar, A. H.; McClellan, D. S.; Chance, R. E.; Flora, D. B.; Cox, A. L.; Irwin, L.; Myers, S. R. Hybrid insulin cocrystals for controlled release delivery Nat. Biotechnol. 2002, 20, 800-4 (Pubitemid 34836756)
25. Cheney, M. L.; Weyna, D. R.; Shan, N.; Hanna, M.; Wojtas, L.; Zaworotko, M. J. Coformer selection in pharmaceutical cocrystal development: A case study of a meloxicam aspirin cocrystal that exhibits enhanced solubility and pharmacokinetics J. Pharm. Sci. 2010, 10.1002/jps.22434
26. 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, 1888-97 (Pubitemid 44200553)
27. Remenar, J. F.; Morissette, S. L.; Peterson, M. L.; Moulton, B.; MacPhee, J. M.; Guzman, H. R.; Almarsson, O. Crystal engineering of novel cocrystals of a triazole drug with 1,4-dicarboxylic acids J. Am. Chem. Soc. 2003, 125, 8456-7 (Pubitemid 36858412)
28. Yadav, A. V.; Dabke, A. P.; Shete, A. S. Crystal engineering to improve physicochemical properties of mefloquine hydrochloride Drug Dev. Ind. Pharm. 2010, 36, 1036-45
29. Childs, S. L.; Chyall, L. J.; Dunlap, J. T.; Smolenskaya, V. N.; Stahly, B. C.; Stahly, G. P. Crystal engineering approach to forming cocrystals of amine hydrochlorides with organic acids. Molecular complexes of fluoxetine hydrochloride with benzoic, succinic, and fumaric acids J. Am. Chem. Soc. 2004, 126, 13335-42 (Pubitemid 39382761)
30. Hickey, M. B.; Peterson, M. L.; Scoppettuolo, L. A.; Morrisette, S. L.; Vetter, A.; Guzman, H.; Remenar, J. F.; Zhang, Z.; Tawa, M. D.; Haley, S.; Zaworotko, M. J.; Almarsson, O. Performance comparison of a co-crystal of carbamazepine with marketed product Eur. J. Pharm. Biopharm. 2007, 67, 112-9 (Pubitemid 46991320)
31. Bak, A.; Gore, A.; Yanez, E.; Stanton, M.; Tufekcic, S.; Syed, R.; Akrami, A.; Rose, M.; Surapaneni, S.; Bostick, T.; King, A.; Neervannan, S.; Ostovic, D.; Koparkar, A. The co-crystal approach to improve the exposure of a water-insoluble compound: AMG 517 sorbic acid co-crystal characterization and pharmacokinetics J. Pharm. Sci. 2008, 97, 3942-56
32. APEX2; Bruker AXS, Inc.: Madison, WI, 2010.
33. SAINT. Data Reduction Software; Bruker AXS Inc.: Madison, WI, 2009.
34. Sheldrick, G. M. SADABS. Program for Empirical Absorption Correction; University of Gottingen: Germany, 2008.
35. Farrugia, L. J. Appl. Crystallogr. 1999, 32, 837-838
36. Sheldrick, G. M. SHELXL-97. program for the Refinement of Crystal, 1997.
37. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-73
38. Srinivas, K.; King, J. W.; Howard, L. R.; Monrad, J. k. Solubility and solution thermodynamic properties of quercetin and quercetin dihydrate in subcritical water J. Food Eng. 2010, 100, 208-218
39. Lambert, J. D.; Lee, M. J.; Diamond, L.; Ju, J.; Hong, J.; Bose, M.; Newmark, H. L.; Yang, C. S. Dose-dependent levels of epigallocatechin-3-gallate in human colon cancer cells and mouse plasma and tissues Drug Metab. Dispos. 2006, 34, 8-11 (Pubitemid 43042639)
40. Wang, L.; Morris, M. E. Liquid chromatography-tandem mass spectroscopy assay for quercetin and conjugated quercetin metabolites in human plasma and urine J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 2005, 821, 194-201 (Pubitemid 40827027)
41. Wang, M.; Miksa, I. R. Multi-component plasma quantitation of anti-hyperglycemic pharmaceutical compounds using liquid chromatography-tandem mass spectrometry J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 2007, 856, 318-27 (Pubitemid 47302935)
42. Wang, Z.; Hop, C. E.; Leung, K. H.; Pang, J. Determination of in vitro permeability of drug candidates through a caco-2 cell monolayer by liquid chromatography/tandem mass spectrometry J Mass Spectrom 2000, 35, 71-6 (Pubitemid 30060154)
43. Sparidans, R. W.; Lagas, J. S.; Schinkel, A. H.; Schellens, J. H.; Beijnen, J. H. Liquid chromatography-tandem mass spectrometric assays for salinomycin in mouse plasma, liver, brain and small intestinal contents and in OptiMEM cell culture medium J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 2007, 855, 200-10 (Pubitemid 47225053)
44. Etter, M. C.; MacDonald, J. C.; Bernstein, J. Graph-set analysis of hydrogen-bond patterns in organic crystals. Acta Crystallogr., B 1990, 46 (Part 2), 256-62.
45. Clarke, H. D.; Arora, K. K.; Bass, H.; Kavuru, P.; Ong, T. T.; Pujari, T.; Wojtas, L.; Zaworotko, M. J. Structure-Stability Relationships in Cocrystal Hydrates: Does the Promiscuity of Water Make Crystalline Hydrates the Nemesis of Crystal Engineering? Cryst. Growth Des. 2010, 10, 2152-2167
46. Mullen, W.; Rouanet, J. M.; Auger, C.; Teissedre, P. L.; Caldwell, S. T.; Hartley, R. C.; Lean, M. E.; Edwards, C. A.; Crozier, A. Bioavailability of [2-(14)C]quercetin-4′-glucoside in rats J. Agric. Food Chem. 2008, 56, 12127-37
47. Khaled, K. A.; El-Sayed, Y. M.; Al-Hadiya, B. M. Disposition of the flavonoid quercetin in rats after single intravenous and oral doses Drug Dev. Ind. Pharm. 2003, 29, 397-403 (Pubitemid 36528607)
48. Morand, C.; Manach, C.; Crespy, V.; Remesy, C. Respective bioavailability of quercetin aglycone and its glycosides in a rat model Biofactors 2000, 12, 169-74 (Pubitemid 32107403)
49. Piskula, M.; Terao, J. Quercetins Solubility Affects Its Accumulation in Rat Plasma after Oral Administration J. Agric. Food Chem. 1998, 46, 4313-4317 (Pubitemid 128488535)
50. Kim, M. K.; Park, K. S.; Yeo, W. S.; Choo, H.; Chong, Y. In vitro solubility, stability and permeability of novel quercetin-amino acid conjugates Bioorg. Med. Chem. 2009, 17, 1164-71
51. Biasutto, L.; Marotta, E.; De Marchi, U.; Zoratti, M.; Paradisi, C. Ester-based precursors to increase the bioavailability of quercetin J. Med. Chem. 2007, 50, 241-53 (Pubitemid 46147705)
52. Jung, M. S.; Kim, J. S.; Kim, M. S.; Alhalaweh, A.; Cho, W.; Hwang, S. J.; Velaga, S. P. Bioavailability of indomethacin-saccharin cocrystals J. Pharm. Pharmacol. 2010, 62, 1560-8