Investigation of aqueous stability of taxol in different release media

Drug Development and Industrial Pharmacy

Volumn 40, Issue 4, 2014, Pages 519-526

  Amini Fazl, Mohammad Sadegh ^a   Mobedi, Hamid ^a   Barzin, Jalal ^a  

^a IRAN POLYMER AND PETROCHEMICAL INSTITUTE   (Iran)

Author keywords

Epimerization; HPLC; Hydrolysis; Paclitaxel; Stability

Indexed keywords

10 DEACETYLBACCATIN III; 10 DEACETYLTAXOL; 2 HYDROXYPROPYL BETA CYCLODEXTRIN; 7 EPI 10 DEACETYLTAXOL; 7 EPITAXOL; ACETIC ACID ETHYL ESTER; ALCOHOL; BACCATIN III; CHLOROFORM; CITRATE SODIUM; DICHLOROMETHANE; DRUG CARRIER; HYDROXYL GROUP; METHANOL; OCTANOL; PACLITAXEL; PHOSPHATE BUFFERED SALINE; POLYSORBATE 80; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; DRUG DEGRADATION; DRUG DELIVERY SYSTEM; DRUG HYDROLYSIS; DRUG RELEASE; DRUG RESEARCH; DRUG SOLUBILITY; DRUG STABILITY; EPIMERIZATION; EQUILIBRIUM CONSTANT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; IN VITRO STUDY;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG STABILITY; HYDROGEN BONDING; HYDROLYSIS; PACLITAXEL; WATER;

EID: 84896708443     PISSN: 03639045     EISSN: 15205762     Source Type: Journal    
DOI: 10.3109/03639045.2013.771646     Document Type: Article

References (67)

1. Wani MC, Taylor HL, Wall ME, et al. Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc 1971;93: 2325-7.
2. Safavy A, Raisch KP, Khazaeli MB, et al. Paclitaxel derivatives for targeted therapy of cancer: toward the development of smart taxanes. J Med Chem 1999;42:4919-24.
3. Pazdur R, Kudelka AP, Kavanagh JK, et al. The taxoids: paclitaxel (taxol) and docetaxel (taxotere). Cancer Treat Rev 1993;19:351-86.
4. Li J, Strobel G, Sidhu R, et al. Endophytic taxol-producing fungi from bald cypress - Taxodium distichum. Microbiology 1996;142: 2223-6.
5. Fang GF, Chang BS, Kim CN, et al. Loop domain is necessary for taxol-induced mobility shift and phosphorylation of Bcl-2 as well as for inhibiting taxol-induced cytosolic accumulation of cytochrome c and apoptosis. Cancer Res 1998;58:3202-8.
6. Rodi DJ, Janes RW, Sanganee HJ, et al. Screening of a library of phage-displayed peptides identifies human Bcl-2 as a taxolbinding protein. J Mol Biol 1999;285:197-203.
7. Schiff PB, Fant J, Horwitz SB. Promotion of microtubule assembly in vitro by Taxol. Nature 1979;227:665-7.
8. Manfredi JJ, Horwitz SB. Taxol: an antimitotic agent with a new mechanism of action. Pharmacol Therapeut 1984;25:83-125.
9. Wenz F, Greiner S, Germa F, et al. Radiochemotherapy with paclitaxel: synchronization effects and the role of p53. Strahlenther Onkol 1999;175:2-6.
10. Supiot S, Gouard S, Charrier J, et al. Mechanisms of cell sensitization to a radioimmunotherapy by doxorubicin or paclitaxel in multiple myeloma cell lines. Clin Cancer Res 2005;11:7047s-52s.
11. Tiwari SB, Amiji MM. Improved oral delivery of paclitaxel following administration in nanoemulsion formulations. J Nanosci Nanotechnol 2006;6:3215-21.
12. Ganta S, Amiji M. Co administration of paclitaxel and curcumin in nanoemulsion formulations to overcome multidrug resistance in tumor cells. Mol Pharmacol 2009;6:928-39.
13. Lo JT, Chen BH, Lee TM, et al. Self-emulsifying O/W formulations of paclitaxel prepared from mixed nonionic surfactants. J Pharm Sci 2010;99:2320-32.
14. Alkan-Onyuksel H, Ramakrishnan S, Chai HB, Pezzuto JM. A mixed micellar formulation suitable for the parenteral administration of taxol. Pharmacol Res 1994;11:206-12.
15. Campbell RB, Balasubramanian SV, Straubinger RM. Influence of cationic lipids on the stability and membrane properties of paclitaxel-containing liposomes. J Pharm Sci 2001;90:1091-105.
16. Yang T, Choi M-K, Cui F-D, et al. Preparation and evaluation of paclitaxel-loaded PEGylated immunoliposome. J Control Release 2007;120:169-77.
17. Cho YW, Lee J, Lee SC, et al. Hydrotropic agents for study of in vitro paclitaxel release from polymeric micelles. J Control Release 2004;97:249-57.
18. Huh KM, Min HS, Lee SC, et al. A new hydrotropic block copolymer micelle system for aqueous solubilization of paclitaxel. J Control Release 2008;126:122-9.
19. Liang H, Yang Q, Deng L, et al. Phospholipid-Tween 80 mixed micelles as an intravenous delivery carrier for paclitaxel. Drug Dev Ind Pharm 2011;37:597-605.
20. Nsereko S, Amiji M. Localized delivery of paclitaxel in solid tumors from biodegradable chitin microparticle formulations. Biomaterials 2002;23:2723-31.
21. Hamoudeh M, Diab R, Fessi H, et al. Paclitaxel-loaded microparticles for intratumoral administration via the TMT technique: preparation, characterization, and preliminary antitumoral evaluation. Drug Dev Ind Pharm 2008;34:698-707.
22. Burt HM, Jackson JK, Sarvjeet BK, et al. Controlled delivery of taxol from microspheres composed of a blend of ethylene-vinyl acetate copolymer and poly(D,L-lactic acid). Cancer Lett 1995;88: 73-9.
23. Liggins RT, Burt HM. Paclitaxel loaded poly(L-lactic acid) microspheres: properties of microspheres made with low molecular weight polymers. Int J Pharm 2001;222:19-33.
24. Li KW, Dang W, Tyler BM, et al. Polilactofate microspheres for paclitaxel delivery to central nervous system malignancies. Clin Cancer Res 2003;9:3441-7.
25. Ibrahim NK, Desai N, Legha S, et al. Phase I and pharmacokinetic study of ABI-007, a cremophor-free, protein-stabilized, nanoparticle formulation of paclitaxel. Clin Cancer Res 2002;8:1038-44.
26. Lim HJ, Nam HY, Lee BH, et al. A novel technique for loading of paclitaxel-PLGA nanoparticles onto ePTFE vascular grafts. Biotechnol Progr 2007;23:693-7.
27. Yang R, Yang SG, Shim WS, et al. Lung-specific delivery of Paclitaxel by chitosan-modified PLGA nanoparticles via transient formation of microaggregates. J Pharm Sci 2009;98:970-84.
28. Wu L, Tang C, Yin C. Folate-mediated solid-liquid lipid nanoparticles for paclitaxel-coated poly(ethylene glycol). Drug Dev Ind Pharm 2010;36:439-48.
29. Kollipara S, Bende G, Movva S, Saha R. Application of rotatable central composite design in the preparation and optimization of poly(lactic-co-glycolic acid) nanoparticles for controlled delivery of paclitaxel. Drug Dev Ind Pharm 2010;36:1377-87.
30. Wang Y, Jiang G, Qiu T, Ding F. Preparation and evaluation of paclitaxel-loaded nanoparticle incorporated with galactose-carrying polymer for hepatocyte targeted delivery. Drug Dev Ind Pharm 2012;38:1039-46.
31. Yegin BA, Beno?t J-P, Lamprecht A. Paclitaxel-loaded lipid nanoparticles prepared by solvent injection or ultrasound emulsification. Drug Dev Ind Pharm 2006;32:1089-94.
32. Bartoli HM, Boitard M, Fessi H, et al. In vitro and in vivo antitumoral activity of free and encapsulated taxol. J Microencapsul 1990;7:191-7.
33. Suh H, Jeong B, Rathi R, Kim SW. Regulation of smooth muscle cell proliferation using Paclitaxel-loaded poly(ethylene oxide)- poly(lactide/ glycolide) nanospheres. J Biomed Mater Res 1998;42: 331-8.
34. Khandavilli S, Panchagnula R. Nanoemulsions as versatile formulations for paclitaxel delivery: peroral and dermal delivery studies in rats. J Invest Dermatol 2007;127:154-62.
35. Hosmer JM, Shin SH, Nornoo A, et al. Influence of internal structure and composition of liquid crystalline phases on topical delivery of paclitaxel. J Pharm Sci 2011;100:1444-55.
36. Finkelstein A, McClean D, Kar S, et al. Local drug delivery via a coronary stent with programmable release pharmacokinetics. Circulation 2003;107:777-84.
37. Alexis F, Venkatraman SS, Rath SK, Boey F. In vitro study of release mechanisms of paclitaxel and rapamycin from drugincorporated biodegradable stent matrices. J Control Release 2004; 98:67-74.
38. Shin YM, Lim KS, Jin JY, et al. In vitro and in vivo characterization of a coronary stent coated with an elastic biodegradable polymer for the sustained release of paclitaxel. Macromol Res 2009;17:1039-42.
39. Bege N, Steinmuller SO, Kalinowskic M, et al. Drug eluting stents based on poly(ethylene carbonate): optimization of the stent coating process. Eur J Pharm Biopharm 2012;80:562-70.
40. Tailor J, Raval A, Engineer C, et al. Development and validation of a reversed-phase HPLC method for in-vitro loading and release analysis of paclitaxel coated stent. Trends Biomater Artif Organs 2008;22:79-86.
41. Washington C. Drug release from microdisperse systems: a critical review. Int J Pharm 1990;58:1-12.
42. Dordunoo SK, Jackson JK, Arsenault LA, et al. Taxol encapsulation in poly("-caprolactone) microspheres. Cancer Chemoth Pharm 1995;36:279-82.
43. Springate CM, Jackson JK, Gleave ME, Burt HM. Efficacy of an intratumoral controlled release formulation of clusterin antisense oligonucleotide complexed with chitosan containing paclitaxel or docetaxel in prostate cancer xenograft models. Cancer Chemoth Pharm 2005;56:239-47.
44. Song D, Hsu LF, Au JL. Binding of taxol to plastic and glass containers and protein under in vitro conditions. J Pharm Sci 1996; 85:29-31.
45. Montaseri H, Jamali F, Rogers JA, et al. The effect of temperature, pH, and different solubilizing agents on stability of taxol. Iran J Pharm Sci 2004;1:43-51.
46. Hamada H, Ishihara K, Masuoka N, et al. Enhancement of watersolubility and bioactivity of paclitaxel using modified cyclodextrins. J Biosci Bioeng 2006;102:369-71.
47. Winternitz CI, Jackson JK, Oktaba AM, Burt HM. Development of a polymeric surgical paste formulation for taxol. Pharmacol Res 1996; 13:368-75.
48. Lee SC, Huh KM, Lee J, et al. Hydrotropic polymeric micelles for enhanced paclitaxel solubility: in vitro and in vivo characterization. Biomacromolecules 2007;8:202-8.
49. Baek N, Lee J, Park J. Aqueous N,N-diethylnicotinamide (DENA) solution as a medium for accelerated release study of Paclitaxel. J Biomater Sci Polym Ed 2004;15:527-42.
50. Harper E, Dang W, Lapidus Jr. RG, Garver RI. Enhanced efficacy of a novel controlled release paclitaxel formulation (PACLIMER delivery system) for local-regional therapy of lung cancer tumor nodules in mice. Clin Cancer Res 1999;5:4242-8.
51. Jackson JK, Skinner KC, Burgess L, et al. Paclitaxel-loaded crosslinked hyaluronic acid films for the prevention of postsurgical adhesions. Pharm Res 2002;19:411-17.
52. Ringel I, Horwitz SB. Taxol is converted to 7-epitaxol, a biologically active isomer, in cell culture medium. J Pharmacol Exp Ther 1987;242:692-8.
53. Nguyen T, Eshraghi J, Gonyea G, et al. Studies on factors influencing stability and recovery of paclitaxel from suspension media and cultures of Taxus cuspidata cv Densiformis by high-performance liquid chromatography. J Chromatogr A 2001;911:55-61.
54. Tian J, Stella VJ. Degradation of paclitaxel and related compounds in aqueous solutions I: epimerization. J Pharm Sci 2008;97:1224-35.
55. Samaranayake G, Magri NF, Jitrangsri C, Kingston DGI. Modified taxols. 5. Reaction of taxol with electrophilic reagents and preparation of a rearranged taxol derivative with tubulin assembly activity. J Org Chem 1991;56:5114-19.
56. Tian J, Stella VJ. Degradation of paclitaxel and related compounds in aqueous solutions II: nonepimerization degradation under neutral to basic pH conditions. J Pharm Sci 2008;97:3100-8.
57. Tian J, Stella VJ. Degradation of paclitaxel and related compounds in aqueous solutions III: degradation under acidic pH conditions and overall kinetics. J Pharm Sci 2010;99:1288-98.
58. Lee J, Lee SC, Acharya G, et al. Hydrotropic solubilization of paclitaxel: analysis of chemical structures for hydrotropic property. Pharm Res 2003;20:1022-30.
59. Huang CHO, Kingston DGI, Magri NF, et al. New taxanes from Taxus brevifolia, 2. J Nat Prod 1986;49:665-9.
60. Castellano EE, Hodder OJR. Crystal and molecular structure of the diterpenoid baccatin V, a naturally occurring oxetane with a taxane skeleton. Acta Crystallogr Sect B: Struct Crystallogr Cryst Chem 1973;29:2566-70.
61. Miller RW, Powell RG, Smith Jr CR, et al. Antileukemic alkaloids from Taxus wallichiana Zucc. J Org Chem 1981;46:1469-73.
62. Williams HJ, Scott AL, Dieden RA, et al. NMR and molecular modeling study of the conformations of taxol and its side chain methyl ester in aqueous and nonaqueous solution. Tetrahedron 1993; 49:6545-60.
63. McLaughlin JL, Miller RW, Powell RG, Smith Jr CR. 19-Hydroxybaccatin III, 10-deacetylcephalomannine, and 10-deacetyltaxol: New antitumor taxanes from Taxus wallichiana. J Nat Prod 1981;44:312-19.
64. MacEachern-Keith GJ, Butterfield LJ, Mattina IMJ. Paclitaxel stability in solution. Anal Chem 1997;69:72-7.
65. Dordunoo SK, Burt HM. Solubility and stability of taxol: effects of buffers and cyclodextrins. Int J Pharm 1996;133:191-201.
66. Richheimer SL, Tinnermeier DM, Timmons DW. Highperformance liquid chromatographic assay of taxol. Anal Chem 1992;64:2323-6.
67. Kuh H-J, Jang SH, Wientjes MG, et al. Determinants of paclitaxel penetration and accumulation in human solid tumor. J Pharmacol Exp Ther 1999;290:871-80.