Is an Alternative Drug Delivery System Needed for Docetaxel? the Role of Controlling Epimerization in Formulations and beyond

Pharmaceutical Research

Volumn 30, Issue 10, 2013, Pages 2675-2693

  Manjappa, Arehalli S ^a,b   Goel, Peeyush N ^c   Vekataraju, Makam P ^a   Rajesh, Kesarla S ^d   Makwana, Kinjal ^a   Ukawala, Mukesh ^a   Nikam, Yuvraj ^c   Gude, Rajiv P ^c   Murthy, Rayasa S Ramachandra ^a,e  

^a M S UNIVERSITY OF BARODA   (India)

^b Tatyasaheb Kore College of Pharmacy Warananagar   (India)

^c TATA MEMORIAL HOSPITAL   (India)

^d Parul Institute of Pharmacy and Research   (India)

^e ISF COLLEGE OF PHARMACY   (India)

Author keywords

7 epidocetaxel; adenocarcinoma cell line; docetaxel; mouse melanoma cell line; PEGylated liposome; Taxotere

Indexed keywords

DOCETAXEL;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DIFFERENTIAL SCANNING CALORIMETRY; DRUG CYTOTOXICITY; DRUG DEGRADATION; DRUG DELIVERY SYSTEM; DRUG DETERMINATION; DRUG DOSAGE FORM COMPARISON; DRUG EFFICACY; DRUG FORMULATION; DRUG RELEASE; DRUG STRUCTURE; DRUG UPTAKE; EPIMERIZATION; HUMAN; HUMAN CELL; IN VITRO STUDY; LIPOSOMAL DELIVERY; LIPOSOMAL GENE DELIVERY SYSTEM; MOUSE; NONHUMAN; PREDICTION; PRIORITY JOURNAL; SINGLE DRUG DOSE; TRANSMISSION ELECTRON MICROSCOPY;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; CHEMISTRY, PHARMACEUTICAL; DRUG CARRIERS; FEMALE; HUMANS; LIPOSOMES; MELANOMA, EXPERIMENTAL; MICE; MICE, INBRED C57BL; MOLECULAR STRUCTURE; POLYETHYLENE GLYCOLS; SOLUBILITY; STEREOISOMERISM; SURFACE PROPERTIES; TAXOIDS;

EID: 84883893887     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-013-1093-5     Document Type: Article

References (56)

1. Gueritte-Voegelein F, Guenard D, Lavelle F, Le Goff MT, Mangatal L, Potier P. Relationships between the structure of taxol analogues and their antimitotic activity. J Med Chem. 1991;34(3):992-8.
2. Sandoz AG. Pharmaceutical Composition of Improved Stability Containing Taxane Derivatives. European Patent 2008, EP 1 946 747 A1.
3. Vasu Dev R, Moses Babu J, Vyas K, Sai Ram P, Ramachandra P, Sekhar NM, et al. Isolation and characterization of impurities in docetaxel. J Pharm Biomed Anal. 2006;40(3):614-22.
4. Czejka M, Greil R, Ulsperger E, Schnait H, Kienesberger K, Brumnik T, et al. Evidence for the conversion of docetaxel into 7′-epidocetaxel in patients receiving Taxotere-based conventional chemotherapy. Int J Clin Pharmacol Ther. 2010;48(7):483-4.
5. Machado A, Fora JD, Maranduba A, Guimaraes E, Machado L, Marcio Santiago JR, Silva M. Pharmaceutical Compositions Containing Docetaxel and a Degradation Inhibitor and a Process for Obtaining the Same. US Patent 2009, US 20090221688 A1.
6. Bournique B, Lemarie A. Docetaxel (Taxotere®) is not metabolized by recombinant human CYP1B1 in vitro, but acts as an effector of this isozyme. Drug Metab Dispos. 2002;30(11):1149-52.
7. McFadyen MC, McLeod HL, Jackson FC, Melvin WT, Doehmer J, Murray GI. Cytochrome P450 CYP1B1 protein expression: a novel mechanism of anticancer drug resistance. Biochem Pharmacol. 2001;62(2):207-12.
8. Du W, Hong L, Yao T, Yang X, He Q, Yang B, et al. Synthesis and evaluation of water-soluble docetaxel prodrugs-docetaxel esters of malic acid. Bioorg Med Chem. 2007;15(18):6323-30.
9. Wang L, Liu Z, Liu D, Liu C, Juan Z, Zhang N. Docetaxel-loaded-lipid- based-nanosuspensions (DTX-LNS): preparation, pharmacokinetics, tissue distribution and antitumor activity. Int J Pharm. 2011;413(1-2):194-201.
10. Chu CY, Yang CH, Yang CY, Hsiao GH, Chiu HC. Fixed erythrodysaesthesia plaque due to intravenous injection of docetaxel. Br J Dermatol. 2000;142(4):808-11.
11. Naik S, Patel D, Surti N, Misra A. Preparation of PEGylated liposomes of docetaxel using supercritical fluid technology. J Supercrit Fluids. 2010;54(1):110-9.
12. Zhai G, Wu J, Yu B, Guo C, Yang X, Lee RJ. A transferrin receptor-targeted liposomal formulation for docetaxel. J Nanosci Nanotechnol. 2010;10(8):5129-36.
13. Grosse PY, Bressolle F, Pinguet F. In vitro modulation of doxorubicin and docetaxel antitumoral activity by methyl-beta-cyclodextrin. Eur J Cancer. 1998;34(1):168-74.
14. Hwang HY, Kim IS, Kwon IC, Kim YH. Tumor targetability and antitumor effect of docetaxel-loaded hydrophobically modified glycol chitosan nanoparticles. J Control Release. 2008;128(1):23-31.
15. Li X, Li R, Qian X, Ding Y, Tu Y, Guo R, et al. Superior antitumor efficiency of cisplatin-loaded nanoparticles by intratumoral delivery with decreased tumor metabolism rate. Eur J Pharm Biopharm. 2008;70(3):726-34.
16. Xu Z, Chen L, Gu W, Gao Y, Lin L, Zhang Z, et al. The performance of docetaxel-loaded solid lipid nanoparticles targeted to hepatocellular carcinoma. Biomaterials. 2009;30(2):226-32.
17. Li X, Wang D, Zhang J, Pan W. Preparation and pharmacokinetics of docetaxel based on nanostructured lipid carriers. J Pharm Pharmacol. 2009;61(11):1485-92.
18. Chen J, Ping QN, Guo JX, Chu XZ, Song MM. Effect of phospholipid composition on characterization of liposomes containing 9-nitrocamptothecin. Drug Dev Ind Pharm. 2006;32(6):719-26.
19. Kan P, Tsao CW, Wang AJ, Su WC, Liang HF. A liposomal formulation able to incorporate a high content of Paclitaxel and exert promising anticancer effect. J Drug Deliv, 2011, Article ID 629234, 9 pages.
20. Bangham AD, Standish MM, Watkins JC. Diffusion of univalent ions across the lamellae of swollen phospholipids. J Mol Biol. 1965;13(1):238-52.
21. Kumar D, Tomar RS, Deolia SK, Mitra M, Mukherjee R, Burman AC. Isolation and characterization of degradation impurities in docetaxel drug substance and its formulation. J Pharm Biomed Anal. 2007;43(4):1228-35.
22. Rao BM, Chakraborty A, Srinivasu MK, Devi ML, Kumar PR, Chandrasekhar KB, et al. A stability-indicating HPLC assay method for docetaxel. J Pharm Biomed Anal. 2006;41(2):676-81.
23. Nanjwade BK, Manjappa AS, Murthy RSR, Pol YD. A novel pH-triggered in situ gel for sustained ophthalmic delivery of Ketorolac tromethamine. Asian J Pharm Sci. 2009;4(3):189-99.
24. Manjappa AS, Nanjwade BK, Manvi FV, Murthy RSR. Sustained ophthalmic in situ gel of ketorolac tromethamine: rheology and in vivo studies. Drug Dev Res. 2009;70(6):417-24.
25. Stewart JC. Colorimetric determination of phospholipids with ammonium ferrothiocyanate. Anal Biochem. 1980;104(1):10-4.
26. Ishida T, Ichihara M, Wang X, Yamamoto K, Kimura J, Majima E, et al. Injection of PEGylated liposomes in rats elicits PEG-specific IgM, which is responsible for rapid elimination of a second dose of PEGylated liposomes. J Control Release. 2006;112(1):15-25.
27. Chonn A, Semple SC, Cullis PR. Association of blood proteins with large unilamellar liposomes in vivo. Relation to circulation lifetimes. J Biol Chem. 1992;267(26):18759-65.
28. Yang T, Cui FD, Choi MK, Cho JW, Chung SJ, Shim CK, et al. Enhanced solubility and stability of PEGylated liposomal paclitaxel: in vitro and in vivo evaluation. Int J Pharm. 2007;338(1-2):317-26.
29. Zhang C, Qineng P, Zhang H. Self-assembly and characterization of paclitaxel-loaded N-octyl-O-sulfate chitosan micellar system. Colloids Surf B Biointerfaces. 2004;39(1-2):69-75.
30. Koziara JM, Lockman PR, Allen DD, Mumper RJ. Paclitaxel nanoparticles for the potential treatment of brain tumors. J Control Release. 2004;99(2):259-69.
31. Twentyman PR, Luscombe M. A study of some variables in a tetrazolium dye (MTT) based assay for cell growth and chemosensitivity. Br J Cancer. 1987;56(3):279-85.
32. Goel PN, Gude RP. Unravelling the antimetastatic potential of pentoxifylline, a methylxanthine derivative in human MDA-MB-231 breast cancer cells. Mol Cell Biochem. 2011;358(1-2):141-51.
33. Sharma A, Sharma US, Straubinger RM. Paclitaxel-liposomes for intracavitary therapy of intraperitoneal P388 leukemia. Cancer Lett. 1996;107(2):265-72.
34. Hwang PH, Yi HK, Kim DS, Nam SY, Kim JS, Lee DY. Suppression of tumorigenicity and metastasis in B16F10 cells by PTEN/MMAC1/TEP1 gene. Cancer Lett. 2001;172(1):83-91.
35. Gautam A, Waldrep JC, Densmore CL, Koshkina N, Melton S, Roberts L, et al. Growth inhibition of established B16-F10 lung metastases by sequential aerosol delivery of p53 gene and 9-nitrocamptothecin. Gene Ther. 2002;9(5):353-7.
36. Chen L, Lu Y, Wu JM, Xu B, Zhang LJ, Gao M, et al. Ligustrazine inhibits B16F10 melanoma metastasis and suppresses angiogenesis induced by Vascular Endothelial Growth Factor. Biochem Biophys Res Commun. 2009;386(2):374-9.
37. Dora CL, Alvarez-Silva M, Trentin AG, de Faria TJ, Fernandes D, da Costa R, et al. Evaluation of antimetastatic activity and systemic toxicity of camptothecin-loaded microspheres in mice injected with B16-F10 melanoma cells. J Pharm Pharm Sci. 2006;9(1):22-31.
38. Chen Y, Zhu X, Zhang X, Liu B, Huang L. Nanoparticles modified with tumor-targeting scFv deliver siRNA and miRNA for cancer therapy. Mol Ther. 2010;18(9):1650-6.
39. Javeri I, Andover MA, Kaliappanadar N, Lexington MA. Methods for the Preparation of Liposomes Comprising Docetaxel. US Patent 2011, US 201 10070293A1.
40. Malleswara Reddy A, Banda N, Govind Dagdu S, Venugopala Rao D, Kocherlakota CS, Krishnamurthy V. Evaluation of the pharmaceutical quality of docetaxel injection using new stability indicating chromatographic methods for assay and impurities. Sci Pharm. 2010;78(2):215-31.
41. Drummond DC, Meyer O, Hong K, Kirpotin DB, Papahadjopoulos D. Optimizing liposomes for delivery of chemotherapeutic agents to solid tumors. Pharmacol Rev. 1999;51(4):691-743.
42. Hinrichs WLJ, Manceñido FA, Sanders NN, Braeckmans K, De Smedt SC, Demeester J, et al. The choice of a suitable oligosac-charide to prevent aggregation of PEGylated nanoparticles during freeze thawing and freeze drying. Int J Pharm. 2006;311:237-44.
43. Thomas LC. Use of multiple heating rate DSC and modulated temperature DSC to detect and analyze temperature-time-dependent transitions in materials. Am Lab. 2001;33(1):26-31.
44. Lee JW, Thomas LC, Schmidt SJ. Effects of heating conditions on the glass transition parameters of amorphous sucrose produced by melt-quenching. J Agric Food Chem. 2011;59(7):3311-9.
45. Grest GS, Cohen MH. Liquid-glass transition: dependence of the glass transition on heating and cooling rates. Phys Rev B. 1980;21:4113-7.
46. Bonte F, Juliano RL. Interacion of liposomes with serum proteins. Chem Phys Lipids. 1986;40(2-4):359-72.
47. Kessler RJ, Fanestil DD. Interference by lipids in the determination of protein using bicinchoninic acid. Anal Biochem. 1986;159(1):138-42.
48. Feng SS, Mei L, Anitha P, Gan CW, Zhou W. Poly(lactide)-vitamin E derivative/montmorillonite nanoparticle formulations for the oral delivery of Docetaxel. Biomaterials. 2009;30(19):3297-306.
49. Montero A, Fossella F, Hortobagyi G, Valero V. Docetaxel for treatment of solid tumours: a systematic review of clinical data. Lancet Oncol. 2005;6(4):229-39.
50. Yanasarn N, Sloat BR, Cui Z. Nanoparticles engineered from lecithin-in-water emulsions as a potential delivery system for docetaxel. Int J Pharm. 2009;379(1):174-80.
51. Wong HL, Rauth AM, Bendayan R, Manias JL, Ramaswamy M, Liu Z, et al. A new polymer-lipid hybrid nanoparticle system increases cytotoxicity of doxorubicin against multidrug-resistant human breast cancer cells. Pharm Res. 2006;23(7):1574-85.
52. Serpe L, Catalano MG, Cavalli R, Ugazio E, Bosco O, Canaparo R, et al. Cytotoxicity of anticancer drugs incorporated in solid lipid nanoparticles on HT-29 colorectal cancer cell line. Eur J Pharm Biopharm. 2004;58(3):673-80.
53. Manjappa AS, Chaudhari KR, Venkataraju MP, Dantuluri P, Nanda B, Sidda C, et al. Antibody derivatization and conjugation strategies: application in preparation of stealth immunoliposome to target chemotherapeutics to tumor. J Control Release. 2011;150(1):2-22.
54. Snodin DJ, McCrossen SD. Guidelines and pharmacopoeial standards for pharmaceutical impurities: overview and critical assessment. Regul Toxicol Pharmacol. 2012;63(2):298-312.
55. Tannock IF, Rotin D. Acid pH in tumors and its potential for therapeutic exploitation. Cancer Res. 1989;49(16):4373-84.
56. Mahoney BP, Raghunand N, Baggett B, Gillies RJ. Tumor acidity, ion trapping and chemotherapeutics. I. Acid pH affects the distribution of chemotherapeutic agents in vitro. Biochem Pharmacol. 2003;66(7):1207-18.