Therapeutic efficacy of a lipid-based prodrug of mitomycin C in pegylated liposomes: Studies with human gastro-entero-pancreatic ectopic tumor models

Journal of Controlled Release

Volumn 160, Issue 2, 2012, Pages 245-253

  Gabizon, Alberto ^a,b   Amitay, Yasmine ^c   Tzemach, Dina ^a   Gorin, Jenny ^a   Shmeeda, Hilary ^a   Zalipsky, Samuel ^d  

^a SHAARE ZEDEK MEDICAL CENTER   (Israel)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^c Lipomedix Pharmaceuticals Ltd   (Israel)

^d Independent Consultant   (United States)

Author keywords

Cancer; Chemotherapy; Liposome; Mitomycin C; Prodrug

Indexed keywords

ANTI-TUMOR ACTIVITIES; CA MODEL; CANCER; CLINICAL SETTINGS; CO-INJECTION; DRUG LEAKAGE; EFFECTIVE TOOL; GASTRIC CARCINOMA; GEMCITABINE; HALF LIVES; IN-VIVO; IRINOTECAN; MITOMYCIN C; MOLE RATIO; MOUSE MODELS; MOUSE TUMORS; MYELOSUPPRESSION; N-ACETYLCYSTEINE; NUDE MICE; PEGYLATED LIPOSOMES; PHARMACOKINETIC STUDIES; PHOSPHATIDYLCHOLINE; PLASMA LEVELS; PRODRUG ACTIVATION; PRODRUGS; RADIOLABEL; REDUCED TOXICITY; THERAPEUTIC DOSE; THERAPEUTIC EFFICACY; THIOLYSIS; TUMOR GROWTH; TUMOR MODELS; TUMOR REGRESSION; VESICLE SIZE; WHOLE BLOOD;

CALCIUM; CHEMICAL ACTIVATION; CHEMOTHERAPY; DISEASES; DRUG PRODUCTS; LIPOSOMES; MAMMALS; PHARMACOKINETICS; PHOSPHOLIPIDS; PLASMA STABILITY; PLASMAS; REDUCING AGENTS; TUMORS;

C (PROGRAMMING LANGUAGE);

ACETYLCYSTEINE; CHOLESTEROL; GEMCITABINE; IRINOTECAN; LIPOSOME; MITOMYCIN C LIPID BASED PRODRUG; PEGYLATED LIPOSOME; PHOSPHATIDYLCHOLINE; PRODRUG; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; BONE MARROW SUPPRESSION; CANCER CELL CULTURE; CANCER CHEMOTHERAPY; CANCER CONTROL; CANCER TRANSPLANTATION; COLON CARCINOMA; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DELIVERY SYSTEM; DRUG EFFICACY; DRUG FORMULATION; DRUG HALF LIFE; DRUG RELEASE; DRUG SAFETY; DRUG STABILITY; DRUG SYNTHESIS; FEMALE; GASTROENTEROPANCREATIC ECTOPIC TUMOR; GASTROINTESTINAL TUMOR; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH THROUGHPUT SCREENING; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; IN VIVO STUDY; MAXIMUM TOLERATED DOSE; MOUSE; NONHUMAN; PANCREAS CARCINOMA; PRIORITY JOURNAL; STOMACH CARCINOMA; TUMOR GROWTH; TUMOR REGRESSION; TUMOR VOLUME;

ANIMALS; ANTIBIOTICS, ANTINEOPLASTIC; CHOLESTEROL; COLONIC NEOPLASMS; DRUG CARRIERS; DRUG STABILITY; FEMALE; HUMANS; LIPIDS; LIPOSOMES; MICE; MICE, INBRED BALB C; MICE, NUDE; MICROSCOPY, ELECTRON, TRANSMISSION; MITOMYCIN; PANCREATIC NEOPLASMS; PARTICLE SIZE; PHOSPHATIDYLCHOLINES; POLYETHYLENE GLYCOLS; PRODRUGS; STOMACH NEOPLASMS; SURFACE PROPERTIES; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84861658483     PISSN: 01683659     EISSN: 18734995     Source Type: Journal    
DOI: 10.1016/j.jconrel.2011.11.019     Document Type: Article

References (29)

1. M. Tomasz Mitomycin C: small, fast and deadly (but very selective) Chem. Biol. 2 9 1995 575 579
2. A.C. Sartorelli, W.F. Hodnick, M.F. Belcourt, M. Tomasz, B. Haffty, J.J. Fischer, and S. Rockwell Mitomycin C: a prototype bioreductive agent Oncol. Res. 6 10-11 1994 501 508
3. R.T. Dorr New findings in the pharmacokinetic, metabolic, and drug-resistance aspects of mitomycin C Semin. Oncol. 15 3 Suppl 4 1988 32 41
4. P.A. Lambert, Y. Kang, B. Greaves, and R.R. Perry The importance of DT-diaphorase in mitomycin C resistance in human colon cancer cell lines J. Surg. Res. 80 2 1998 177 181
5. R. Valavaara, and E. Nordman Renal complications of mitomycin C therapy with special reference to the total dose Cancer 55 1 1985 47 50
6. A.A. Gabizon, D. Tzemach, A.T. Horowitz, H. Shmeeda, J. Yeh, and S. Zalipsky Reduced toxicity and superior therapeutic activity of a mitomycin C lipid-based prodrug incorporated in pegylated liposomes Clin. Cancer Res. 12 6 2006 1913 1920
7. P.D. Senter, W.E. Pearce, and R.S. Greenfield Development of a drug-release strategy based on the reductive fragmentation of benzyl carbamate disulfides J. Org. Chem. 55 1990 2975 2978
8. S. Zalipsky, M. Saad, R. Kiwan, E. Ber, N. Yu, and T. Minko Antitumor activity of new liposomal prodrug of mitomycin C in multidrug resistant solid tumor: insights of the mechanism of action J. Drug Target. 15 7-8 2007 518 530
9. M.L. Immordino, F. Dosio, and L. Cattel Stealth liposomes: review of the basic science, rationale, and clinical applications, existing and potential Int. J. Nanomedicine 1 3 2006 297 315
10. G. Powis, and W.R. Montfort Properties and biological activities of thioredoxins Annu. Rev. Pharmacol. Toxicol. 41 2001 261 295
11. G. Powis, and D.L. Kirkpatrick Thioredoxin signaling as a target for cancer therapy Curr. Opin. Pharmacol. 7 4 2007 392 397
12. G.R. Bartlett Phosphorus assay in column chromatography J. Biol. Chem. 234 3 1959 466 468
13. A. Gabizon, H. Shmeeda, and Y. Barenholz Pharmacokinetics of pegylated liposomal Doxorubicin: review of animal and human studies Clin. Pharmacokinet. 42 5 2003 419 436
14. T. Kojima, M. Hashida, S. Muranishi, and H. Sezaki Mitomycin C-dextran conjugate: a novel high molecular weight pro-drug of mitomycin C J. Pharm. Pharmacol. 32 1 1980 30 34
15. Y. Song, H. Onishi, and T. Nagai Pharmacokinetic characteristics and antitumor activity of the N-succinyl-chitosan-mitomycin C conjugate and the carboxymethyl-chitin-mitomycin C conjugate Biol. Pharm. Bull. 16 1 1993 48 54
16. L.W. Seymour, H. Soyez, A. De Marre, M.A. Shoaibi, and E.H. Schacht Polymeric prodrugs of mitomycin C designed for tumour tropism and sustained activation Anticancer Drug Des. 11 5 1996 351 365
17. H. Sasaki, T. Kakutani, M. Hashida, and H. Sezaki Characterization of liposomes and an emulsion containing mitomycin C or lipophilic mitomycin C prodrugs J. Pharm. Sci. 75 12 1986 1166 1170
18. Y. Tokunaga, T. Iwasa, J. Fujisaki, S. Sawai, and A. Kagayama Liposomal sustained-release delivery systems for intravenous injection. I. Physicochemical and biological properties of newly synthesized lipophilic derivatives of mitomycin C Chem. Pharm. Bull.(Tokyo) 36 8 1988 3060 3069
19. Y. Tokunaga, T. Iwasa, J. Fujisaki, S. Sawai, and A. Kagayama Liposomal sustained-release delivery systems for intravenous injection. II. Design of liposome carriers and blood disposition of lipophilic mitomycin C prodrug-bearing liposomes Chem. Pharm. Bull.(Tokyo) 36 9 1988 3557 3564
20. Y. Tokunaga, T. Iwasa, J. Fujisaki, S. Sawai, and A. Kagayama Liposomal sustained-release delivery systems for intravenous injection. III. Antitumor activity of lipophilic mitomycin C prodrug-bearing liposomes Chem. Pharm. Bull.(Tokyo) 36 9 1988 3565 3573
21. G. Bachar, K. Cohen, R. Hod, R. Feinmesser, A. Mizrachi, T. Shpitzer, O. Katz, and D. Peer Hyaluronan-grafted particle clusters loaded with Mitomycin C as selective nanovectors for primary head and neck cancers Biomaterials 32 21 2011 4840 4848
22. J.A. Reddy, E. Westrick, I. Vlahov, S.J. Howard, H.K. Santhapuram, and C.P. Leamon Folate receptor specific anti-tumor activity of folate-mitomycin conjugates Cancer Chemother. Pharmacol. 58 2 2006 229 236
23. K.P. Olive, M.A. Jacobetz, C.J. Davidson, A. Gopinathan, D. McIntyre, D. Honess, B. Madhu, M.A. Goldgraben, M.E. Caldwell, D. Allard, K.K. Frese, G. Denicola, C. Feig, C. Combs, S.P. Winter, H. Ireland-Zecchini, S. Reichelt, W.J. Howat, A. Chang, M. Dhara, L. Wang, F. Ruckert, R. Grutzmann, C. Pilarsky, K. Izeradjene, S.R. Hingorani, P. Huang, S.E. Davies, W. Plunkett, M. Egorin, R.H. Hruban, N. Whitebread, K. McGovern, J. Adams, C. Iacobuzio-Donahue, J. Griffiths, and D.A. Tuveson Inhibition of Hedgehog signaling enhances delivery of chemotherapy in a mouse model of pancreatic cancer Science 324 5933 2009 1457 1461
24. T.M. Allen, and F.J. Martin Advantages of liposomal delivery systems for anthracyclines Semin. Oncol. 31 6 Suppl 13 2004 5 15
25. A. Soderberg, B. Sahaf, and A. Rosen Thioredoxin reductase, a redox-active selenoprotein, is secreted by normal and neoplastic cells: presence in human plasma Cancer Res. 60 8 2000 2281 2289
26. E.S. Arner, and A. Holmgren The thioredoxin system in cancer Semin. Cancer Biol. 16 6 2006 420 426
27. S. Kakolyris, A. Giatromanolaki, M. Koukourakis, G. Powis, J. Souglakos, E. Sivridis, V. Georgoulias, K.C. Gatter, and A.L. Harris Thioredoxin expression is associated with lymph node status and prognosis in early operable non-small cell lung cancer Clin. Cancer Res. 7 10 2001 3087 3091
28. J. Raffel, A.K. Bhattacharyya, A. Gallegos, H. Cui, J.G. Einspahr, D.S. Alberts, and G. Powis Increased expression of thioredoxin-1 in human colorectal cancer is associated with decreased patient survival J. Lab. Clin. Med. 142 1 2003 46 51
29. A.F. Baker, T. Dragovich, W.R. Tate, R.K. Ramanathan, D. Roe, C.H. Hsu, D.L. Kirkpatrick, and G. Powis The antitumor thioredoxin-1 inhibitor PX-12 (1-methylpropyl 2-imidazolyl disulfide) decreases thioredoxin-1 and VEGF levels in cancer patient plasma J. Lab. Clin. Med. 147 2 2006 83 90