Stability and solution concentration enhancement of resveratrol by solid dispersion in cellulose derivative matrices

Cellulose

Volumn 20, Issue 3, 2013, Pages 1249-1260

  Li, Bin ^a   Wegiel, Lindsay A ^b   Taylor, Lynne S ^b   Edgar, Kevin J ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^b PURDUE UNIVERSITY   (United States)

Author keywords

Amorphous solid dispersion; Bioavailability; CAAdP; CMCAB; Dissolution; HPMCAS; Resveratrol; Solubility; Stability

Indexed keywords

AMORPHOUS SOLID DISPERSIONS; BIOAVAILABILITY; CAADP; CMCAB; HPMCAS;

AMORPHOUS MATERIALS; BIOCHEMISTRY; CELLULOSIC RESINS; CONVERGENCE OF NUMERICAL METHODS; DIFFERENTIAL SCANNING CALORIMETRY; DISSOLUTION; ESTERS; FLAVONOIDS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; RESVERATROL; SOLUBILITY; VOLATILE FATTY ACIDS; X RAY DIFFRACTION;

DISPERSIONS;

EID: 84877600122     PISSN: 09690239     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10570-013-9889-3     Document Type: Article

References (30)

1. Amri A, Chaumeil JC, Sfar S, Charrueau C (2012) Administration of resveratrol: what formulation solutions to bioavailability limitations? J Contr Rel 158: 182-193. doi: 10. 1016/j. jconrel. 2011. 09. 083.
2. Baird JA, Taylor LS (2012) Evaluation of amorphous solid dispersion properties using thermal analysis techniques. Adv Drug Del Rev 64(5): 396-421. doi: 10. 1016/j. addr. 2011. 07. 009.
3. Commodari F, Khiat A, Ibrahimi S, Brizius AR, Kalkstein N (2005) Comparison of the phytoestrogen trans-resveratrol (3, 4′, 5-trihydroxystilbene) structures from X-ray diffraction and solution NMR. Magn Reson Chem 43: 567-572. doi: 10. 1002/mrc. 1583.
4. Das S, Lin HS, Ho PC, Ng KY (2008) The impact of aqueous solubility and dose on the pharmacokinetic profiles of resveratrol. Pharm Res 25(11): 2593-2600. doi: 10. 1007/s11095-008-9677-1.
5. Friesen DT, Shanker R, Crew M, Smithey DT, Curatolo WJ, Nightingale JA (2008) Hydroxypropyl methylcellulose acetate succinate-based spray-dried dispersions: an overview. Mol Pharm 5(6): 1003-1019. doi: 10. 1021/mp8000793.
6. Ilevbare GA, Liu H, Edgar KJ, Taylor LS (2012) Understanding polymer properties important for crystal growth inhibition: impact of chemically diverse polymers on solution crystal growth of ritonavir. Cryst Growth Des 12(6): 3133-3143. doi: 10. 1021/cg300325p.
7. Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF, Beecher CWW, Fong HHS, Farnsworth NR, Kinghorn AD, Mehta RG, Moon RC, Pezzuto JM (1997) Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 275(5297): 218-220. doi: 10. 1126/science. 275. 5297. 218.
8. Kar N, Liu H, Edgar KJ (2011) Synthesis of cellulose adipate derivatives. Biomacromolecules 12(4): 1106-1115. doi: 10. 1021/bm101448f.
9. Konno H, Taylor LS (2006) Influence of different polymers on the crystallization tendency of molecularly dispersed amorphous felodipine. J Pharm Sci 95(12): 2692-2705. doi: 10. 1002/jps. 20697.
10. Kopp P (1998) Resveratrol, a phytoestrogen found in red wine. A possible explanation for the conundrum of the 'French paradox'? Eur J Endocrinol 138(6): 619-620. doi: 10. 1530/eje. 0. 1380619.
11. Krayz GT, Averbuch M, Berman A, Zalcenstein A, Jaffe I (2009) Oral delivery with novel solid dispersions: stable self-assembled formulations of lipophilic drugs with improved bioperformance. Drug Delivery Technol 9(36): 38-43.
12. Kumpugdee-Vollrath M, Ibold Y (2012) Increasing solubility of poorly water soluble drug resveratrol by surfactants and cyclodextrins. Adv Mater Res 418-420: 2231-2234. doi: 10. 4028, http://www. scientific. net/AMR. 418-420. 2231.
13. Leuner C, Dressman JB (2000) Improving drug solubility for oral delivery using solid dispersions. Eur J Pharm Biopharm 50(1): 47-60.
14. Lucas-Abellán C, Fortea I, López-Nicolás JM, Núñez-Delicado E (2007) Cyclodextrins as resveratrol carrier system. Food Chem 104(1): 39-44. doi: 10. 1016/j. foodchem. 2006. 10. 068.
15. Maier-Salamon A, Hagenauer B, Wirth M, Gabor F, Szekeres T, Jäger W (2006) Increased transport of resveratrol across monolayers of the human intestinal caco-2 cells is mediated by inhibition and saturation of metabolites. Pharm Res 23(9): 2107-2115. doi: 10. 1007/s11095-006-9060-z.
16. Miller JM, Beig A, Carr RA, Spence JK, Dahan A (2012) A win-win solution in oral delivery of lipophilic drugs: supersaturation via amorphous solid dispersions increases apparent solubility without sacrifice of intestinal membrane permeability. Mol Pharm 9(7): 2009-2016. doi: 10. 1021/mp300104s.
17. Ndiaye M, Kumar R, Ahmad N (2011) Resveratrol in cancer management: where are we and where we go from here? Ann NY Acad Sci 1215(1): 144-149. doi: 10. 1111/j. 1749-6632. 2010. 05851. x.
18. Park S-J, Ahmad F, Philp A, Baar K, Williams T, Luo H, Ke H, Rehmann H, Taussig R, Brown Alexandra L, Kim Myung K, Beaven Michael A, Burgin Alex B, Manganiello V, Chung Jay H (2012) Resveratrol ameliorates aging-related metabolic phenotypes by inhibiting cAMP phosphodiesterases. Cell 148(3): 421-433. doi: 10. 1016/j. cell. 2012. 01. 017.
19. Patel KR, Scott E, Brown VA, Gescher AJ, Steward WP, Brown K (2011) Clinical trials of resveratrol. Ann NY Acad Sci 1215(1): 161-169. doi: 10. 1111/j. 1749-6632. 2010. 05853. x.
20. Posey-Dowty JD, Watterson TL, Wilson AK, Edgar KJ, Shelton MC, Lingerfelt LR (2007) Zero-order release formulations using a novel cellulose ester. Cellulose 14(1): 73-83. doi: 10. 1007/s10570-006-9079-7.
21. Qian F, Huang J, Hussain MA (2010) Drug-polymer solubility and miscibility: stability consideration and practical challenges in amorphous solid dispersion development. J Pharm Sci 99(7): 2941-2947. doi: 10. 1002/jps. 22074.
22. Roberti M, Pizzirani D, Simoni D, Rondanin R, Baruchello R, Bonora C, Buscemi F, Grimaudo S, Tolomeo M (2003) Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents. J Med Chem 46(16): 3546-3554. doi: 10. 1021/jm030785u.
23. Rumondor AC, Stanford LA, Taylor LS (2009) Effects of polymer type and storage relative humidity on the kinetics of felodipine crystallization from amorphous solid dispersions. Pharm Res 26(12): 2599-2606. doi: 10. 1007/s11095-009-9974-3.
24. Santos AC, Veiga F, Ribeiro AJ (2011) New delivery systems to improve the bioavailability of resveratrol. Expert Opin Drug Deliv 8: 973-990. doi: 10. 1517/17425247. 2011. 581655.
25. Sapino S, Carlotti M, Caron G, Ugazio E, Cavalli R (2009) In silico design, photostability and biological properties of the complex resveratrol/hydroxypropyl-β-cyclodextrin. J Incl Phenom Macro 63(1): 171-180. doi: 10. 1007/s10847-008-9504-7.
26. Savouret JF, Quesne M (2002) Resveratrol and cancer: a review. Biomed Pharmacother 56(2): 84-87. doi: 10. 1016/S0753-3322(01)00158-5.
27. Shelton MC, Posey-Dowty JD, Lingerfelt LR, Kirk SK, Klein S, Edgar KJ (2009) Enhanced dissolution of poorly soluble drugs from solid dispersions in carboxymethylcellulose acetate butyrate matrices. In: Edgar KJ, Heinze T, Liebert T (eds) Polysaccharide materials: performance by design, vol 1017. American Chemical Society, Washington, pp 93-113.
28. Simonelli AP, Mehta SC, Higuchi WI (1976) Dissolution rates of high energy sulfathiazole-povidone coprecipitates II: characterization of form of drug controlling its dissolution rate via solubility studies. J Pharm Sci 65(3): 355-361. doi: 10. 1002/jps. 2600650310.
29. Trela BC, Waterhouse AL (1996) Resveratrol: isomeric molar absorptivities and stability. J Agr Food Chem 44(5): 1253-1257. doi: 10. 1021/jf9504576.
30. Walle T, Hsieh F, DeLegge MH, Oatis JE, Walle UK (2004) High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab Dispos 32(12): 1377-1382. doi: 10. 1124/dmd. 104. 000885.