Solid dispersions containing ursolic acid in Poloxamer 407 and PEG 6000: A comparative study of fusion and solvent methods

Powder Technology

Volumn 253, Issue , 2014, Pages 98-106

  Eloy, Josimar Oliveira ^a   Marchetti, Juliana Maldonado ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Fusion method; PEG 6000; Poloxamer 407; Solid dispersion; Solvent method; Ursolic acid

Indexed keywords

FUSION METHODS; POLOXAMER 407; SOLID DISPERSION; SOLVENT METHOD; URSOLIC ACID;

BIOCHEMISTRY; CRYSTALLINE MATERIALS; DIFFERENTIAL SCANNING CALORIMETRY; DISPERSIONS; DISSOLUTION; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROGEN BONDS; MIXTURES; PARTICLE SIZE; SCANNING ELECTRON MICROSCOPY; SOLUBILITY; SOLVENTS; X RAY DIFFRACTION ANALYSIS;

CARBOXYLIC ACIDS;

BUFFER; MACROGOL 6000; PHOSPHATE; POLOXAMER; SOLVENT; URSOLIC ACID; WATER;

ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; DISPERSION; FUSION METHOD; HOT STAGE MICROSCOPY; HYDROGEN BOND; HYDROPHILICITY; IN VITRO STUDY; INFRARED SPECTROSCOPY; INTERMETHOD COMPARISON; MICROSCOPY; PARTICLE SIZE; POWDER; SCANNING ELECTRON MICROSCOPY; SOLID DISPERSION; SOLUBILITY; SOLVENT METHOD; X RAY DIFFRACTION;

EID: 84888771571     PISSN: 00325910     EISSN: 1873328X     Source Type: Journal    
DOI: 10.1016/j.powtec.2013.11.017     Document Type: Article

References (48)

1. Li G., Zhang X., You J., Song C., Sun Z., Xia L., Suo Y. Highly sensitive and selective pre-column derivatization high-performance liquid chromatographic approach for rapid determination of triterpenes oleanolic and ursolic acids and application to Swertia species: optimization of triterpene acids extraction and pre-column derivatization using response surface methodology. Anal. Chim. Acta. 2011, 4:208-218.
2. Saravanan R., Viswanathan P., Pugalendi K.V. Protective effect of ursolic acid on ethanol-mediated experimental liver damage in rats. Life Sci. 2006, 78:713-718.
3. Bonaccorsi I., Altieri F., Sciamanna I., Oricchio E., Grillo C., Contartese G., Galati E.M. Endogenous reverse transcriptase as a mediator of ursolic acid's anti-proliferative and differentiating effects in human cancer cell lines. Cancer Lett. 2008, 263:130-139.
4. Resende F.A., Barcala C.A.M.A., Faria M.C.S., Kato F.H., Cunha W.R., Tavares D.C. Antimutagenicity of ursolic acid and oleanolic acid against doxorubicin-induced clastrogenisis in Balb/c mice. Life Sci. 2006, 79:1268-1273.
5. Crespo F.A., Galicia J.V., Molina R.V., Guerrero J.J.R., Vázquez G.N., Soto S.E. Ursolic acid mediates the vasorelaxant activity in Lepechinia causlescens via NO release in isolated rat thoracic aorta. Life Sci. 2006, 79:1062-1268.
6. Somova L.A., Nadar A., Rammanan P., Shode F.O. Cardiovascular, antihyperlipidemic and antioxidant effects of oleanolic and ursolic acids in experimental hypertension. Phytomedicine 2003, 10:115-121.
7. Raphael T.J., Kuttan G. Effect of naturally occurring triterpenoids glycyrrhizic acid, ursolic acid, oleanolic acid and nomilin on the immune system. Phytomedicine 2003, 10:483-489.
8. Ramachandran S., Prasad N.R. Effect of ursolic acid, a triterpenoid antioxidant, on ultraviolet-B-radiation-induced cytotoxicity, lipid peroxidation and DNA damage in human lymphocytes. Chem. Biol. Interact. 2008, 176:99-107.
9. Ferreira D.S., Esperandim V.R., Toldo M.P.A., Saraiva J., Cunha W.R., Albuquerque S. Trypanocidal activity and acute toxicity assessment of triterpene acids. Parasitol. Res. 2010, 106:985-989.
10. Wang Z.H., Hsu C.C., Huang C.N., Yin M.C. Anti-glycative effects of oleanolic acid and ursolic acid in kidney of diabetic mice. Eur. J. Pharmacol. 2010, 628:255-260.
11. Lee J., Yee S.T., Kim J.J., Choi M.S., Kwon E.Y., Seo K.I., Lee M.K. Ursolic acid ameliorates thymic atrophy and hyperglycemia in streptozotocin-nicotinamide-induced diabetic mice. Chem. Biol. Interact. 2010, 108:635-642.
12. Jang S.M., Yee S.T., Choi J., Choi M.S., Do G.M., Jeon S.M., Yeo J., Kim M.J., Seo K.I., Lee M.K. Ursolic acid enhances the cellular immune system and pancreatic β-cell function in streptozotocin-induced diabetic mice fed a high-fat diet. Int. Immunopharmacol. 2009, 9:113-119.
13. Takada K., Nakane T., Masuda K., Ishii H. Ursolic acid and oleanolic acid, members of pentacyclic triterpenoids acids, suppress TNF-α-induced E-selectin expression by cultured umbilical vein endothelial cells. Phytomedicine 2010, 17:1114-1119.
14. Lee S.H., Park S.J., Kwak H.B., Oh J., Min Y.K., Kim S.H. Anabolic activity of ursolic acid in bone: stimulating osteoblast differentiation in vitro and inducing new bone formation in vivo. Pharmacol. Res. 2008, 58:290-296.
15. Du H., Chen C. CD-MEKC method to analyse triterpene acids in traditional Chinese medicines. J. Braz. Chem. Soc. 2009, 20:1268-1274.
16. Liu J. Oleanolic acid and ursolic acid: research prospectives. J. Ethnopharmacol. 2005, 100:92-94.
17. Maulvi F.A., Dalwadi S.J., Thakkar V.T., Soni T.G., Gohel M.C., Gandhi T.R. Improvement of dissolution rate of aceclofenac by solid dispersion technique. Powder Technol. 2011, 207:47-54.
18. Both D.M., Goodtsova K., Yarosh D.B., Brown D.A. Liposome-encapsulated ursolic acid increases ceramides and collagen in human skin cells. Arch. Dermatol. Res. 2002, 293:569-575.
19. Li R. The influence of cosolvent on the complexation of HP-beta-cyclodextrins with oleanolic acid and ursolic acid. AAPS PharmSciTech 2009, 40:1137-1144.
20. Almeida M.A., Bou-Chacra N.A., Conte J.D., Kaneko T.M., Baby A.R., Velasco M.V.R. Evaluation of physical and chemical stability of nanostructured lipid carriers containing ursolic acid in cosmetic formulation. J App Pharm Sci 2013, 3:5-8.
21. Vasconcelos T., Sarmento B., Costa P. Solid dispersions as strategy to improve oral bioavailability of poor water soluble drugs. Drug Discov. Today 2007, 12:1068-1075.
22. Craig Q.M.D. The mechanisms of drug release from solid dispersions in water-soluble polymer. Int. J. Pharm. 2002, 231:131-144.
23. Frizon F., Eloy J.O., Donaduzzi C.M., Mitsui M.L., Marchetti J.M. Dissolution rate enhancement of loratadine in polyvinylpyrrolidone K-30 solid dispersions by solvent methods. Powder Technol. 2013, 235:532-539.
24. Sekiguchi K., Obi N. Studies on absorption of eutectic mixture. absorption of fused conglomerates of chloramphenicol and urea in rabbits. Chem. Pharm. Bull. 1961, 12:134-144.
25. Leuner C., Dressman J. Improving drug solubility for oral delivery using solid dispersions. Eur. J. Pharm. Biopharm. 2000, 50:47-60.
26. Tachibana T., Nakamura A. A method for preparing an aqueous colloidal dispersion of organic materials by using water-soluble polymers: dispersion of beta-carotene by polyvinylpyrrolidone. Kolloid-Z. Polym 1965, 203:130-133.
27. Won D.A., Kim M.S., Lee S., Park J.S., Hwang S.J. Improved physicochemical characteristics of felodipine solid dispersions particles by supercritical anti-solvent precipitation properties. Int. J. Pharm. 2005, 301:199-208.
28. Dehghan M.H.G., Saifee M., Hanwate R.M. Comparative dissolution study of glipizide by solid dispersion technique. J. Pharm. Sci. Technol. 2010, 2:293-297.
29. Poovi G., Umamaheswari M., Sharmila S., Kumar S., Rajalakshmi A.N. Development of domperidone solid dispersion powders using sodium alginate as carrier. Eur. J. Appl. Sci. 2013, 5:36-42.
30. Patel T., Patel L.D., Patel T., Makawana S., Patel T. Enhancement of dissolution of fenofibrate by solid dispersion technique. Int. J. Res.Pharm. 2010, 1:127-132.
31. Verheyen S., Blaton N., Kinget R., Van den Mooter G. Mechanisms of increased dissolution of diazepam and temazepam from polyethylene glycol 6000 solid dispersion. Int. J. Pharm. 2002, 249:45-58.
32. Bley H., Fussnegger B., Bodmeir R. Characterization and stability of solid dispersions based on PEG/polymer blends. Int. J. Pharm. 2010, 390:165-173.
33. Goddeeris C., Van Den Mooter G. Free flowing solid dispersions of the anti-HIV drug UC 781 with Poloxamer 407 and a maximum amount of TPGS 1000: investigating the relationship between physicochemical characteristics and dissolution behavior. Eur. J. Pharm. Sci. 2008, 35:104-113.
34. Newa M., Bhandari K.H., Li D.X., Kwon T.H., Kim J.A., Yoo B.K., Woo J.S., Lyoo W.S., Yong C.S., Choi H.G. Preparation, characterization and in vivo evaluation of ibuprofen binary solid dispersions with Poloxamer 188. Int. J. Pharm. 2007, 343:228-237.
35. Chen Y., Zhang G.G.Z., Neilly J., Marsh K., Mawhinney D., Sanzgiri Y.D. Enhancing the bioavailability of ABT-963 using solid dispersion containing Pluronic F-68. Int. J. Pharm. 2004, 286:69-80.
36. Nepal P.R., Han H.K., Choi H.K. Enhancement of solubility and dissolution of Coenzyme Q10 using solid dispersion formulation. Int. J. Pharm. 2010, 383:147-153.
37. Ali W., Williams A.C., Rawlinson C.F. Stochiometrically governed molecular interactions in drug: poloxamer solid dispersions. Int. J. Pharm. 2010, 391:162-168.
38. Chutimaworapan S., Ritthidej G.C., Yonemochi E., Oguchi T., Yananiti K. Effect of water soluble carriers on dissolution characteristics of nifedipine solid dispersions. Drug Dev. Ind. Pharm. 2000, 26:1141-1450.
39. Eloy J.O., Saraiva J., Albuquerque S., Marchetti J.M. Solid dispersion of ursolic acid in gelucire 50/13: a strategy to enhance drug release and trypanocidal activity. AAPS PharmSciTech 2012, 13:1436-1445.
40. Papageogeou G.Z., Bikiaris D., Karavas E., Politis S., Docoslis A., Park Y., Stergiou A., Geogarakis E. Effect of physical state and particle size distribution on dissolution enhancement of nimodipine/PEG solid dispersions prepared by melt mixing and solvent evaporation. AAPS J. 2006, 8:623-663.
41. Marin M.T., Margarit M.V., Salcedo G.E. Characterization and solubility study of solid dispersions of flunarizine and polyvinylpyrrolidone. Farmaco 2002, 57:723-727.
42. Eloy J.O., Oliveira E.C.V., Marotta-Oliveira S.S., Saraiva J., Marchetti J.M. Desenvolvimento e validação de um método analítico por CLAE para quantificação de ácido ursólico em dispersões sólidas. Quim. Nova 2012, 35:1036-1040.
43. Chauhan B., Shimpi S., Paradkar A. Preparation and characterization of etoricoxib solid dispersions using lipid carriers by spray drying technique. AAPS PharmSciTech 2005, 6:405-412.
44. Naima Z., Siro T., Juan-Manual G.D., Chantal C., René C.J. Interactions between carbamazepine and polyethylene glycol (PEG) 6000: characterizations of the physical, solid dispersed and eutectic mixtures. Eur. J. Pharm. Sci. 2007, 12:395-404.
45. Dhirendra K., Lewis S., Udupa N., Atik K. Solid dispersions: a review. Pak. J. Pharm. Sci. 2009, 22:234-246.
46. Kabanov K.V., Batrakova E.V., Alakhov V.Y. Pluronic block copolymers as novel polymer therapeutics for drug and gene delivery. J. Control. Release 2002, 82:189-12.
47. Jones M.C., Leroux J.C. Polymeric micelles-a new generation of colloidal drug carriers. Eur. J. Pharm. Biopharm. 1999, 48:101-111.
48. Taylor L.S., Zografi G. Spectroscopic characterization of interactions between PVP and indomethacin in amorphous molecular dispersions. Pharm. Res. 1997, 14:1691-1698.