Synthesis, characterization, and antitumor evaluation of the albumin-SN38 conjugate

Anti-Cancer Drugs

Volumn 24, Issue 3, 2013, Pages 270-277

  Yao, Yuqin ^a   Su, Xiaolan ^a   Xie, Yongmei ^a   Wang, Yuxi ^a   Kang, Tairan ^a   Gou, Lantu ^a   Yi, Chen ^a   Yang, Jinliang ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

bovine serum albumin; BSA SN38 conjugate; intraperitoneal chemotherapy; SN38

Indexed keywords

BOVINE SERUM ALBUMIN; CYSTEINE; FIRTECAN; PRODRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER CHEMOTHERAPY; CARCINOMATOUS PERITONITIS; CELL ASSAY; COLORECTAL CANCER; CONTROLLED STUDY; COVALENT BOND; DRUG BINDING SITE; DRUG CONJUGATION; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG PURIFICATION; DRUG SCREENING; DRUG SOLUBILITY; DRUG SYNTHESIS; FEMALE; GEL PERMEATION CHROMATOGRAPHY; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; POLYACRYLAMIDE GEL ELECTROPHORESIS; PRIORITY JOURNAL; TREATMENT DURATION; TUMOR VOLUME; ULTRAVIOLET RADIATION;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CAMPTOTHECIN; CELL LINE, TUMOR; COLORECTAL NEOPLASMS; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HCT116 CELLS; HUMANS; MICE; MICE, INBRED BALB C; PERITONEAL NEOPLASMS; SERUM ALBUMIN, BOVINE; SOLUBILITY; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84873414655     PISSN: 09594973     EISSN: 14735741     Source Type: Journal    
DOI: 10.1097/CAD.0b013e32835c3543     Document Type: Article

References (37)

1. Chabot GG. Clinical pharmacokinetics of irinotecan. Clin Pharmacokinet 1997; 33:245-259
2. Cunningham D, Pyrhönen S, James RD, Punt CJ, Hickish TF, Heikkila R, et al. Randomised trial of irinotecan plus supportive care versus supportive care alone after fluorouracil failure for patients with metastatic colorectal cancer. Lancet 1998; 352:1413-1418
3. Bodurka DC, Levenback C,Wolf JK, Gano J,Wharton JT, Kavanagh JJ, et al. Phase II trial of irinotecan in patients with metastatic epithelial ovarian cancer or peritoneal cancer. J Clin Oncol 2003; 21:291-297
4. Negoro S, Masuda N, Takada Y, Sugiura T, Kudoh S, Katakami N, et al. Randomised phase III trial of irinotecan combined with cisplatin for advanced non-small-cell lung cancer. Br J Cancer 2003; 88:335-341
5. Mathijssen RH, Vanalphen RJ, Verweij J, Loos WJ, Nooter K, Stoter G, et al. Clinical pharmacokinetics and metabolism of irinotecan (CPT-11). Clin Cancer Res 2001; 7:2182-2194
6. Zhao H, Rubio B, Sapra P, Wu D, Reddy P, Sai P, et al. Novel prodrugs of SN38 using multiarm poly(ethylene glycol) linkers. Bioconjugate Chem 2008; 19:849-859
7. Nagano T, Yasunaga M, Goto K, Kenmotsu H, Koga Y, Kuroda J, et al. Antitumor activity of NK012 combined with cisplatin against small cell lung cancer and intestinal mucosal changes in tumor-bearing mouse after treatment. Clin Cancer Res 2009; 15:4348-4355
8. Gottlieb JA, Guarino AM, Call JB, Oliverio VT, Block JB. Preliminary pharmacologic and clinical evaluation of camptothecin sodium (NSC-100880). Cancer Chemother Rep 1970; 54:461-470
9. Saito Y, Yasunaga M, Kuroda J, Koga Y, Matsumura Y. Antitumour activity of NK012, SN-38-incorporating polymeric micelles, in hypovascular orthotopic pancreatic tumour. Eur J Cancer 2010; 46:650-658
10. Koizumi F, Kitagawa M, Negishi T, Onda T, Matsumoto S, Hamaguchi T, et al. Novel SN-38-incorporating polymeric micelles, NK012, eradicate vascular endothelial growth factor-secreting bulky tumors. Cancer Res 2006; 66:10048-10056
11. Sapra P, Zhao H, Mehlig M, Malaby J, Kraft P, Longley C, et al. Novel delivery of SN38 markedly inhibits tumor growth in xenografts, including a camptothecin-11-refractory model. Clin Cancer Res 2008; 14:1888-1896
12. Vijayalakshmi N, Ray A, Malugin A, Ghandehari H. Carboxyl-Terminated PAMAM-SN38 conjugates: Synthesis, characterization, and in vitro evaluation. Bioconjugate Chem 2010; 21:1804-1810
13. Kolhatkar RB, Swaan P, Ghandehari H. Potential oral delivery of 7-Ethyl-10-hydroxyl-camptothecin (SN-38) using poly (amidoamine) dendrimers. Pharm Res 2008; 25:1723-1729
14. Moon SJ, Govindan SV, Cardillo TM, D'Souza CA, Hansen HJ, Goldenberg DM. Antibody conjugates of 7-Ethyl-10-hydroxycamptothecin (SN-38) for targeted cancer chemotherapy. J Med Chem 2008; 51:6916-6926
15. Govindan SV, Cardillo TM, Moon SJ, Hansen HJ, Goldenberg DM. CEACAM5-Targeted therapy of human colonic and pancreatic cancer xenografts with potent labetuzumab-SN-38 immunoconjugates. Clin Cancer Res 2009; 15:6052-6061
16. Cardillo TM, Govindan SV, Sharkey RM, Trisal P, Goldenberg DM. Humanized anti-Trop-2 IgG-SN-38 conjugate for effective treatment of diverse epithelial cancers: Preclinical studies in human cancer xenograft models and monkeys. Clin Cancer Res 2011; 17:3157-3169
17. Lei S, Chien PY, Sheikh S, Zhang A, Ali S, Ahmad I. Enhanced therapeutic efficacy of a novel liposome-based formulation of SN-38 against human tumor models in SCID mice. Anticancer Drugs 2004; 15:773-778
18. Mansour HM, Sohn M, Al-Ghananeem A, Deluca PP. Materials for pharmaceutical dosage forms: Molecular pharmaceutics and controlled release drug delivery aspects. Int J Mol Sci 2010; 11: 3298-3322
19. Wang Y, Jiang J, Jiang X, Cai S, Han H, Li L, et al. Synthesis and antitumor activity evaluations of albumin-binding prodrugs of CC-1065 analog. Bioorg Med Chem 2008; 16:6552-6559
20. Kim I, Kim TH, Ma K, Lee ES, Kim D, Oh KT, et al. Synthesis and evaluation of human serum albumin-modified exendin-4 conjugate via heterobifunctional polyethylene glycol linkage with protracted hypoglycemic efficacy. Bioconjugate Chem 2010; 21:1513-1519
21. Kratz F,Warnecke A, Scheuermann K, Stockmar C, Schwab J, Lazar P, et al. Probing the cysteine-34 position of endogenous serum albumin with thiolbinding doxorubicin derivatives. Improved efficacy of an acid-sensitive doxorubicin derivative with specific albumin-binding properties compared to that of the parent compound. J Med Chem 2002; 45: 5523-5533
22. Hartung G, Stehle G, Sinn H, Wunder A, Schrenk HH, Heeger S, et al. Phase I trial of methotrexate-Albumin in a weekly intravenous bolus regimen in cancer patients. Clin Cancer Res 1999; 5:753-759
23. Wosikowski K, Biedermann E, Rattel B, Breiter N, Jank P, Löser R, et al. In vitro and in vivo antitumor activity of methotrexate conjugated to human serum albumin in human cancer cells. Clin Cancer Res 2003; 9: 1917-1926
24. Kratz F, Drevs J, Bing G, Stockmar C, Scheuermann K, Lazar P, et al. Development and in vitro efficacy of novel MMP2 and MMP9 specific doxorubicin albumin conjugates. Bioorg Med Chem Lett 2001; 11: 2001-2006
25. Kratz F, Mansour A, Soltau J, Warnecke A, Fichtner I, Unger C, et al. Development of albumin-binding doxorubicin prodrugs that are cleaved by prostate-specific antigen. Arch Pharm (Weinheim) 2005; 338:462-472
26. Tanaka T, Kaneo Y, Iguchi S. Properties of mitomycin C-Albumin conjugates in vitro and in vivo. Bioconjugate Chem 1991; 2:261-269
27. Taheri A, Dinarvand R, Atyabi F, Ahadi F, Nouri FS, Ghahremani MH, et al. Enhanced anti-Tumoral activity of methotrexate-human serum albumin conjugated nanoparticles by targeting with luteinizing hormone-releasing hormone (LHRH) peptide. Int J Mol Sci 2011; 12:4591-4608
28. Taheri A, Dinarvand R, Ahadi F, Khorramizadeh MR, Atyabi F. The in vivo antitumor activity of LHRH targeted methotrexate-human serum albumin nanoparticles in 4T1 tumor-bearing Balb/c mice. Int J Pharm 2012; 431:183-189
29. Taheri A, Dinarvand R, Atyabi F, Nouri F, Ahadi F, Ghahremani MH, et al. Targeted delivery of methotrexate to tumor cells using biotin functionalized methotrexate-human serum albumin conjugated nanoparticles. J Biomed Nanotechnol 2011; 7:743-753
30. Taheri A, Dinarvand R, Nouri FS, Khorramizadeh MR, Borougeni AT, Mansoori P, et al. Use of biotin targeted methotrexate-human serum albumin conjugated nanoparticles to enhance methotrexate antitumor efficacy. Int J Nanomedicine 2011; 6:1863-1874
31. Warnecke A, Fichtner I, Garmann D, Jaehde U, Kratz F. Synthesis and biological activity of water-soluble maleimide derivatives of the anticancer drug carboplatin designed as albumin-binding prodrugs. Bioconjugate Chem 2004; 15:1349-1359
32. Yao Y, Li J, Lu Z, Tong A, Wang W, Su X, et al. Proteomic analysis of the interleukin-4 (IL-4) response in hepatitis B virus-positive human hepatocelluar carcinoma cell line HepG2.2.15. Electrophoresis 2011; 32:2004-2012
33. Ishima Y, Akaike T, Kragh-Hansen U, Hiroyama S, Sawa T, Suenaga A, et al. S-Nitrosylated human serum albumin-mediated cytoprotective activity is enhanced by fatty acid binding. J Biol Chem 2008; 283: 34966-34975
34. Yao Y, Cheng Z, Ye H, Xie Y, He J, Tang M, et al. Preparative isolation and purification of anti-Tumor agent ansamitocin P-3 from fermentation broth of Actinosynnema pretiosum using high-performance counter-current chromatography. J Sep Sci 2010; 33:1331-1337
35. Greenwald RB, Pendri A, Conover C, Gilbert C, Yang R, Xia J. Drug delivery systems. 2. Camptothecin 20-O-poly (ethylene glycol) ester transport forms. J Med Chem 1996; 39:1938-1940
36. Zhao H, Lee C, Sai P, Choe YH, Boro M, Pendri A, et al. 20-Oacylcamptothecin derivatives: Evidence for lactone stabilization. J Org Chem 2000; 65:4601-4606
37. Wang Y, Gong C, Yang L,Wu Q, Shi S, Shi H, et al. 5-FU-hydrogel inhibits colorectal peritoneal carcinomatosis and tumor growth in mice. BMC Cancer 2010; 10:402