Mixed PEG-PE/vitamin E tumor-targeted immunomicelles as carriers for poorly soluble anti-cancer drugs: Improved drug solubilization and enhanced in vitro cytotoxicity

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 70, Issue 1, 2008, Pages 51-57

  Sawant, Rupa R ^a   Sawant, Rishikesh M ^a   Torchilin, Vladimir P ^a  

^a NORTHEASTERN UNIVERSITY   (United States)

Author keywords

Camptothecin; Immunomicelles; Monoclonal antibody; Paclitaxel; Polyethylene glycol phosphatidyl ethanolamine; Polymeric micelles; Vitamin E

Indexed keywords

ALPHA TOCOPHEROL; CAMPTOTHECIN; CARBOXYLIC ACID; DRUG CARRIER; LACTONE; MACROGOL; MACROGOL 2000; MONOCLONAL ANTIBODY 2C5; NUCLEOSOME ANTIBODY; PACLITAXEL; PHOSPHATIDYLETHANOLAMINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CHEMICAL MODIFICATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG MIXTURE; DRUG SOLUBILITY; HYDROLYSIS; IMMUNOMICELLE; IN VITRO STUDY; MICELLE; MICELLIZATION; MOUSE; NONHUMAN; REACTION OPTIMIZATION;

ANIMALS; ANTIBODIES, MONOCLONAL; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CAMPTOTHECIN; CELL LINE, TUMOR; CELL SURVIVAL; CHEMISTRY, PHARMACEUTICAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG CARRIERS; DRUG STABILITY; HYDROLYSIS; MICE; MICELLES; NUCLEOSOMES; PACLITAXEL; PARTICLE SIZE; PHOSPHATIDYLETHANOLAMINES; POLYETHYLENE GLYCOLS; SOLUBILITY; TECHNOLOGY, PHARMACEUTICAL; TIME FACTORS; VITAMIN E;

EID: 50149092136     PISSN: 09396411     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejpb.2008.04.016     Document Type: Article

References (49)

1. Croy S.R., and Kwon G.S. Polymeric micelles for drug delivery. Current Pharmaceutical Design 12 (2006) 4669-4684
2. Torchilin V.P. Structure and design of polymeric surfactant-based drug delivery systems. Journal of Controlled Release 73 (2001) 137-172
3. Torchilin V.P. Micellar nanocarriers: pharmaceutical perspectives. Pharmaceutical Research 24 (2007) 1-16
4. Maeda H., Wu J., Sawa T., Matsumura Y., and Hori K. Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review. Journal of Controlled Release 65 (2000) 271-284
5. Gao Z., Lukyanov A.N., Singhal A., and Torchilin V.P. Diacyl polymer micelles as nanocarriers for poorly soluble anticancer drugs. Nano Letters 2 (2002) 979-982
6. Li M., Chrastina A., Levchenko T., and Torchilin V.P. Micelles from poly(ethylene glycol)-phosphatidyl ethanolamine conjugates (PEG-PE) as pharmaceutical nanocarriers for poorly soluble drug camptothecin. Journal of Biomedical Nanotechnology 1 (2005) 190-195
7. Roby A., Erdogan S., and Torchilin V.P. Solubilization of poorly soluble PDT agent, meso-tetraphenylporphin, in plain or immunotargeted PEG-PE micelles results in dramatically improved cancer cell killing in vitro. European Journal of Pharmaceutics and Biopharmaceutics 62 (2006) 235-240
8. Lukyanov A.N., Gao Z., and Torchilin V.P. Micelles from polyethylene glycol/phosphatidylethanolamine conjugates for tumor drug delivery. Journal of Controlled Release 91 (2003) 97-102
9. Gao Z., Lukyanov A.N., Chakilam A.R., and Torchilin V.P. PEG-PE/phosphatidylcholine mixed immunomicelles specifically deliver encapsulated taxol to tumor cells of different origin and promote their efficient killing. Journal of Drug Targeting 11 (2003) 87-92
10. Roby A., Erdogan S., and Torchilin V.P. Enhanced in vivo antitumor efficacy of poorly soluble PDT agent, meso-tetraphenylporphine, in PEG-PE-based tumor-targeted immunomicelles. Cancer Biology & Therapy 6 (2007) 1136-1142
11. Torchilin V.P. Lipid-core micelles for targeted drug delivery. Current Drug Delivery 2 (2005) 319-327
12. Torchilin V.P., Lukyanov A.N., Gao Z., and Papahadjopoulos-Sternberg B. Immunomicelles: targeted pharmaceutical carriers for poorly soluble drugs. Proceedings of the National Academy of Sciences of the United States of America 100 (2003) 6039-6044
13. Weiss R.B., Donehower R.C., Wiernik P.H., Ohnuma T., Gralla R.J., Trump D.L., Baker Jr. J.R., Van Echo D.A., Von Hoff D.D., and Leyland-Jones B. Hypersensitivity reactions from taxol. Journal of Clinical Oncology 8 (1990) 1263-1268
14. Ruan G., and Feng S.S. Preparation and characterization of poly(lactic acid)-poly(ethylene glycol)-poly(lactic acid) (PLA-PEG-PLA) microspheres for controlled release of paclitaxel. Biomaterials 24 (2003) 5037-5044
15. Stinchcombe T.E. Nanoparticle albumin-bound paclitaxel: a novel Cremophor-EL-free formulation of paclitaxel. Nanomedicine 2 (2007) 415-423
16. Campbell R.B., Balasubramanian S.V., and Straubinger R.M. Influence of cationic lipids on the stability and membrane properties of paclitaxel-containing liposomes. Journal of Pharmaceutical Sciences 90 (2001) 1091-1105
17. Yang T., Choi M.K., Cui F.D., Lee S.J., Chung S.J., Shim C.K., and Kim D.D. Antitumor effect of paclitaxel-loaded PEGylated immunoliposomes against human breast cancer cells. Pharmaceutical Research 24 (2007) 2402-2411
18. Nornoo A.O., Osborne D.W., and Chow D.S. Cremophor-free intravenous microemulsions for paclitaxel: I. Formulation, cytotoxicity and hemolysis. International Journal of Pharmaceutics 349 (2008) 108-116
19. Lee S.C., Huh K.M., Lee J., Cho Y.W., Galinsky R.E., and Park K. Hydrotropic polymeric micelles for enhanced paclitaxel solubility: in vitro and in vivo characterization. Biomacromolecules 8 (2007) 202-208
20. Seow W.Y., Xue J.M., and Yang Y.Y. Targeted and intracellular delivery of paclitaxel using multi-functional polymeric micelles. Biomaterials 28 (2007) 1730-1740
21. You J., Hu F.Q., Du Y.Z., and Yuan H. Polymeric micelles with glycolipid-like structure and multiple hydrophobic domains for mediating molecular target delivery of paclitaxel. Biomacromolecules 8 (2007) 2450-2456
22. Fassberg J., and Stella V.J. A kinetic and mechanistic study of the hydrolysis of camptothecin and some analogues. Journal of Pharmaceutical Sciences 81 (1992) 676-684
23. Hertzberg R.P., Caranfa M.J., Holden K.G., Jakas D.R., Gallagher G., Mattern M.R., Mong S.M., Bartus J.O., Johnson R.K., and Kingsbury W.D. Modification of the hydroxy lactone ring of camptothecin: inhibition of mammalian topoisomerase I and biological activity. Journal of Medicinal Chemistry 32 (1989) 715-720
24. Hsiang Y.H., Hertzberg R., Hecht S., and Liu L.F. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I. Journal of Biological Chemistry 260 (1985) 14873-14878
25. Garcia-Carbonero R., and Supko J.G. Current perspectives on the clinical experience, pharmacology, and continued development of the camptothecins. Clinical Cancer Research 8 (2002) 641-661
26. Gottlieb J.A., Guarino A.M., Call J.B., Oliverio V.T., and Block J.B. Preliminary pharmacologic and clinical evaluation of camptothecin sodium (NSC-100880). Cancer Chemotherapy Reports 54 (1970) 461-470
27. O'Leary J., and Muggia F.M. Camptothecins: a review of their development and schedules of administration. European Journal of Cancer 34 (1998) 1500-1508
28. Conover C.D., Greenwald R.B., Pendri A., and Shum K.L. Camptothecin delivery systems: the utility of amino acid spacers for the conjugation of camptothecin with polyethylene glycol to create prodrugs. Anti-cancer Drug Design 14 (1999) 499-506
29. Dharap S.S., Qiu B., Williams G.C., Sinko P., Stein S., and Minko T. Molecular targeting of drug delivery systems to ovarian cancer by BH3 and LHRH peptides. Journal of Controlled Release 91 (2003) 61-73
30. Dharap S.S., Wang Y., Chandna P., Khandare J.J., Qiu B., Gunaseelan S., Sinko P.J., Stein S., Farmanfarmaian A., and Minko T. Tumor-specific targeting of an anticancer drug delivery system by LHRH peptide. Proceedings of the National Academy of Sciences of the United States of America 102 (2005) 12962-12967
31. Paranjpe P.V., Stein S., and Sinko P.J. Tumor-targeted and activated bioconjugates for improved camptothecin delivery. Anti-cancer Drugs 16 (2005) 763-775
32. Liu X., Lynn B.C., Zhang J., Song L., Bom D., Du W., Curran D.P., and Burke T.G. A versatile prodrug approach for liposomal core-loading of water-insoluble camptothecin anticancer drugs. Journal of the American Chemical Society 124 (2002) 7650-7651
33. Lundberg B.B. Biologically active camptothecin derivatives for incorporation into liposome bilayers and lipid emulsions. Anti-cancer Drug Design 13 (1998) 453-461
34. Ertl B., Platzer P., Wirth M., and Gabor F. Poly(d,l-lactic-co-glycolic acid) microspheres for sustained delivery and stabilization of camptothecin. Journal of Controlled Release 61 (1999) 305-317
35. Tong W., Wang L., and D'Souza M.J. Evaluation of PLGA microspheres as delivery system for antitumor agent-camptothecin. Drug Development and Industrial Pharmacy 29 (2003) 745-756
36. Tyner K.M., Schiffman S.R., and Giannelis E.P. Nanobiohybrids as delivery vehicles for camptothecin. Journal of Controlled Release 95 (2004) 501-514
37. Kawano K., Watanabe M., Yamamoto T., Yokoyama M., Opanasopit P., Okano T., and Maitani Y. Enhanced antitumor effect of camptothecin loaded in long-circulating polymeric micelles. Journal of Controlled Release 112 (2006) 329-332
38. Koo O.M., Rubinstein I., and Onyuksel H. Camptothecin in sterically stabilized phospholipid micelles: a novel nanomedicine. Nanomedicine 1 (2005) 77-84
39. Koo O.M., Rubinstein I., and Onyuksel H. Camptothecin in sterically stabilized phospholipid nano-micelles: a novel solvent pH change solubilization method. Journal of Nanoscience and Nanotechnology 6 (2006) 2996-3000
40. Opanasopit P., Ngawhirunpat T., Chaidedgumjorn A., Rojanarata T., Apirakaramwong A., Phongying S., Choochottiros C., and Chirachanchai S. Incorporation of camptothecin into N-phthaloyl chitosan-g-mPEG self-assembly micellar system. European Journal of Pharmaceutics and Biopharmaceutics 64 (2006) 269-276
41. Yokoyama M., Opanasopit P., Okano T., Kawano K., and Maitani Y. Polymer design and incorporation methods for polymeric micelle carrier system containing water-insoluble anti-cancer agent camptothecin. Journal of Drug Targeting 12 (2004) 373-384
42. Forrest M.L., Won C.Y., Malick A.W., and Kwon G.S. In vitro release of the mTOR inhibitor rapamycin from poly(ethylene glycol)-b-poly(epsilon-caprolactone) micelles. Journal of Controlled Release 110 (2006) 370-377
43. Torchilin V.P., Levchenko T.S., Lukyanov A.N., Khaw B.A., Klibanov A.L., Rammohan R., Samokhin G.P., and Whiteman K.R. p-Nitrophenylcarbonyl-PEG-PE-liposomes: fast and simple attachment of specific ligands, including monoclonal antibodies, to distal ends of PEG chains via p-nitrophenylcarbonyl groups. Biochimica et Biophysica Acta 1511 (2001) 397-411
44. Torchilin V.P., Rammohan R., Weissig V., and Levchenko T.S. TAT peptide on the surface of liposomes affords their efficient intracellular delivery even at low temperature and in the presence of metabolic inhibitors. Proceedings of the National Academy of Sciences of the United States of America 98 (2001) 8786-8791
45. La S.B., Okano T., and Kataoka K. Preparation and characterization of the micelle-forming polymeric drug indomethacin-incorporated poly(ethylene oxide)-poly(beta-benzyl l-aspartate) block copolymer micelles. Journal of Pharmaceutical Sciences 85 (1996) 85-90
46. Dabholkar R.D., Sawant R.M., Mongayt D.A., Devarajan P.V., and Torchilin V.P. Polyethylene glycol-phosphatidylethanolamine conjugate (PEG-PE)-based mixed micelles: some properties, loading with paclitaxel, and modulation of P-glycoprotein-mediated efflux. International Journal of Pharmaceutics 315 (2006) 148-157
47. Mu L., Elbayoumi T.A., and Torchilin V.P. Mixed micelles made of poly(ethylene glycol)-phosphatidylethanolamine conjugate and d-alpha-tocopheryl polyethylene glycol 1000 succinate as pharmaceutical nanocarriers for camptothecin. International Journal of Pharmaceutics 306 (2005) 142-149
48. Lukyanov A.N., and Torchilin V.P. Micelles from lipid derivatives of water-soluble polymers as delivery systems for poorly soluble drugs. Advanced Drug Delivery Reviews 56 (2004) 1273-1289
49. Mi Z., and Burke T.G. Differential interactions of camptothecin lactone and carboxylate forms with human blood components. Biochemistry 33 (1994) 10325-10336