Conjugate (MTC-220) of muramyl dipeptide analogue and paclitaxel prevents both tumor growth and metastasis in mice

Journal of Medicinal Chemistry

Volumn 54, Issue 8, 2011, Pages 2767-2777

  Ma, Yao ^a   Zhao, Nan ^a   Liu, Gang ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMETASTATIC AGENT; ANTINEOPLASTIC AGENT; GELATINASE B; MONOCYTE CHEMOTACTIC PROTEIN 1; MTC 220; MURAMYL DIPEPTIDE DERIVATIVE; PACLITAXEL; PACLITAXEL DERIVATIVE; TRANSFORMING GROWTH FACTOR BETA; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CARCINOMA; BREAST METASTASIS; CANCER INHIBITION; CONJUGATE; CONTROLLED STUDY; CYTOKINE PRODUCTION; DRUG CONJUGATION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; LEWIS CARCINOMA; LUNG METASTASIS; MALE; METASTASIS INHIBITION; MOUSE; NONHUMAN; SUPPRESSOR CELL; TUMOR XENOGRAFT;

ACETYLMURAMYL-ALANYL-ISOGLUTAMINE; ANIMALS; BONE MARROW CELLS; BREAST NEOPLASMS; CARCINOMA, LEWIS LUNG; CELL DIVISION; CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOKINES; FEMALE; HUMANS; INFLAMMATION MEDIATORS; MICE; MICE, NUDE; NEOPLASM METASTASIS; PACLITAXEL;

EID: 79955425013     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101577z     Document Type: Article

References (50)

1. Gupta, G. P.; Massagué, J. Cancer metastasis: building a framework Cell 2006, 127, 679-695 (Pubitemid 44781029)
2. Steeg, P. S. Tumor metastasis: mechanistic insights and clinical challenges Nat. Med. 2006, 12, 895-904 (Pubitemid 44175140)
3. Meyers, P. A. Muramyl tripeptide (mifamurtide) for the treatment of osteosarcoma Expert Rev Anticancer Ther. 2009, 9, 1035-1049
4. Meyers, P. A.; Schwartz, C. L.; Krailo, M.; Kleinerman, E. S.; Betcher, D.; Bernstein, M. L.; Conrad, E.; Ferguson, W.; Gebhardt, M.; Goorin, A. M.; Harris, M. B.; Healey, J.; Huvos, A.; Link, M.; Montebello, J.; Nadel, H.; Nieder, M.; Sato, J.; Siegal, G.; Weiner, M.; Wells, R.; Wold, L.; Womer, R.; Grier, H. Osteosarcoma: a randomized, prospective trial of the addition of ifosfamide and/or muramyl tripeptide to cisplatin, doxorubicin, and high-dose methotrexate J. Clin. Oncol. 2005, 23, 2004-2011 (Pubitemid 46211380)
5. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. Plant antitumor agents. VI. Isolation and structure of Taxol, a novel antileukemic and antitumor agent from Taxus brevifolia J. Am. Chem. Soc. 1971, 93, 2325-2327
6. Schiff, P. B.; Horwitz, S. B. Taxol stabilizes microtubules in mouse fibroblast cells Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 1561-1565 (Pubitemid 10073801)
7. Kawasaki, K.; Akashi, S.; Shimazu, R.; Yoshida, T.; Miyake, K.; Nishijima, M. Mouse Toll-like receptor 4. MD-2 complex mediates lipopolysaccharide-mimetic signal transduction by Taxol J. Biol. Chem. 2000, 275, 2251-2254 (Pubitemid 30081977)
8. Ding, A. H.; Porteu, F.; Sanchez, E.; Nathan, C. F. Shared actions of endotoxin and Taxol on TNF receptors and TNF release Science 1990, 248, 370-372
9. Kim, S.; Takahashi, H; Lin, W. W.; Descargues, P.; Grivennikov, S.; Kim, Y.; Luo, J. L.; Karin, M. Carcinoma-produced factors activate myeloid cells through TLR2 to stimulate metastasis Nature 2009, 457, 102-106
10. Balkwill, F. TNF-α in promotion and progression of cancer Cancer Metastasis Rev. 2006, 25, 409-416
11. Allen, J. N.; Moore, S. A.; Wewers, M. D. Taxol enhances but does not induce interleukin 1 beta and tumor necrosis factor alpha production J. Lab. Clin. Med. 1993, 122, 374-381 (Pubitemid 23346771)
12. Wang, J.; Kobayashi, M.; Han, M.; Choi, S.; Takano, M.; Hashino, S.; Tanaka, J.; Kondoh, T.; Kawamura, K.; Hosokawa, M. MyD88 is involved in the signalling pathway for Taxol induced apoptosis and TNF-α expression in human myelomonocytic cells Br. J. Haematol. 2002, 118, 638-645 (Pubitemid 34994676)
13. Lee, L. F.; Schuerer-Maly, C. C.; Lofquist, A. K.; van Haaften-Day, C.; Ting, J. P.; White, C. M.; Martin, B. K.; Haskill, J. S. Taxol dependent transcriptional activation of IL-8 expression in a subset of human ovarian cancer Cancer Res. 1996, 56, 1303-1308 (Pubitemid 26080973)
14. Wang, A. C.; Su, Q. B.; Wu, F. X.; Zhang, X. L.; Liu, P. S. Role of TLR4 for paclitaxel chemotherapy in human epithelial ovarian cancer cells Eur. J. Clin. Invest. 2009, 39, 157-164
15. Szajnik, M.; Szczepanski, M. J.; Czystowska, M.; Elishaev, E.; Mandapathil, M.; Nowak-Markwitz, E.; Spaczynski, M.; Whiteside, T. L. TLR4 signaling induced by lipopolysaccharide or paclitaxel regulates tumor survival and chemoresistance in ovarian cancer Oncogene 2009, 28, 4353-4363
16. He, W.; Liu, Q.; Wang, L.; Chen, W.; Li, N.; Cao, X. TLR4 signaling promotes immune escape of human lung cancer cells by inducing immunosuppressive cytokines and apoptosis resistance Mol. Immunol. 2007, 44, 2850-2859 (Pubitemid 46412506)
17. Tsavaris, N.; Kosmas, C.; Vadiaka, M.; Kanelopoulos, P.; Boulamatsis, D. Immune changes in patients with advanced breast cancer undergoing chemotherapy with taxanes Br. J. Cancer 2002, 87, 21-27
18. Ellouz, F.; Adam, A.; Ciorbaru, R.; Lederer, E. Minimal structural requirements for adjuvant activity of bacterial peptidoglycan derivatives Biochem. Biophys. Res. Commun. 1974, 59, 1317-1325
19. Adam, A.; Ciorbaru, R.; Ellouz, F.; Petit, J. F.; Lederer, E. Adjuvant activity of monomeric bacterial cell wall peptidoglycans Biochem. Biophys. Res. Commun. 1974, 56, 561-567
20. Parant, M. A.; Audibert, F. M.; Chedid, L. A.; Level, M. R.; Lefrancier, P. L.; Choay, J. P.; Lederer, E. Immunostimulant activities of a lipophilic muramyl dipeptide derivative and of desmuramyl peptidolipid analogs Infect. Immun. 1980, 27, 826-831 (Pubitemid 10147215)
21. Riveau, G. J.; Brunel-Riveau, B. G.; Audibert, F. M.; Chedid, L. A. Influence of a muramyl dipeptide on human blood leukocyte functions and their membrane antigens Cell. Immunol. 1991, 134, 147-156
22. Li, X.; Yu, J.; Xu, S; Wang, N.; Yang, H.; Yan, Z.; Cheng, G.; Liu, G. Chemical conjugation of muramyl dipeptide and paclitaxel to explore the combination of immunotherapy and chemotherapy for cancer Glycoconjugate J. 2008, 25, 415-425
23. Liu, G; Cheng, G; Wang, N; Li, X; Yu, J; Xu, S; Fang, Q. Conjugation of Muramyl Dipeptide and Paclitaxel. P. R. China Patent ZL200510081265.X, 2005.
24. Joyce, J. A.; Pollard, J. W. Microenvironmental regulation of metastasis Nat. Rev. Cancer 2009, 9, 239-252
25. Grown, J.; O' Leary, M. The taxanes: an update Lancet 2000, 355, 1176-1178
26. Horwitz, S. B.; Lothstein, L.; Manfredi, J. J.; Mellado, W.; Parness, J.; Roy, S. N.; Schiff, P. B.; Sorbara, L.; Zeheb, R. Taxol: mechanisms of action and resistance Ann. N.Y. Acad. Sci. 1986, 466, 733-744 (Pubitemid 16012884)
27. Bhalla, K.; Ibrado, A. M.; Tourkina, E.; Tang, C.; Mahoney, M. E.; Huang, Y. Taxol induces internucleosomal DNA fragmentation associated with programmed cell Leukemia 1993, 7, 563-568 (Pubitemid 23139860)
28. Byrd-Leifer, C. A.; Block, E. F.; Takeda, K.; Akira, S.; Ding, A. The role of MyD88 and TLR4 in the LPS-mimetic activity of Taxol Eur. J. Immunol. 2001, 31, 2448-2457 (Pubitemid 32785364)
29. Fitzpatrick, F. A.; Wheeler, R. The immunopharmacology of paclitaxel (Taxol), docetaxel (Taxotere), and related agents Int. Immunopharmacol. 2003, 3, 1699-1714 (Pubitemid 37421260)
30. Manthey, C. L.; Qureshi, N.; Stutz, P. L.; Vogel, S. N. Lipopolysaccharide antagonists block Taxol-induced signaling in murine macrophages J. Exp. Med. 1993, 178, 695-702 (Pubitemid 23218219)
31. Cassidy, P. B.; Moos, P. J.; Kelly, R. C.; Fitzpatrick, F. A. Cyclooxygenase-2 induction by paclitaxel, docetaxel and taxane analogs in human monocytes and murine macrophages: structure-activity relationships and their implications Clin. Cancer Res. 2002, 8, 846-855 (Pubitemid 34742117)
32. Moos, P. J.; Muskardin, D. T.; Fitzpatrick, F. A. Effect of Taxol and taxotere on gene expression in macrophages: induction of the prostaglandin H synthase-2 isoenzyme J. Immunol. 1999, 162, 467-473 (Pubitemid 29018955)
33. Watson, J. M.; Kingston, D. G.; Chordia, M. D.; Chaudhary, A. G.; Rinehart, C. A.; Haskill, J. S. Identification of the structural region of Taxol that may be responsible for cytokine gene induction and cytotoxicity in human ovarian cancer cells Cancer Chemother. Pharmacol. 1998, 41, 391-397 (Pubitemid 28095755)
34. Subbaramaiah, K.; Hart, J. C.; Norton, L.; Dannenberg, A. J. Microtubule-interfering agents stimulate the transcription of cyclooxygenase-2. Evidence for involvement of ERK1/2 and p38 mitogen-activated protein kinase pathways J. Biol. Chem. 2000, 275, 14838-14845 (Pubitemid 30337196)
35. Zaks-Zilberman, M.; Zaks, T. Z.; Vogel, S. N. Induction of proinflammatory and chemokine genes by lipopolysaccharide and paclitaxel (Taxol) in murine and human breast cancer cell lines Cytokine 2001, 15, 156-165 (Pubitemid 34587497)
36. Liu, G.; Zhang, S. D.; Xia, S. Q.; Ding, Z. K. Solid-phase synthesis of of muramyl dipeptide (MDP) derivatives using a multipin method Bioorg. Med. Chem. Lett. 2000, 10, 1361-1363 (Pubitemid 30391969)
37. 6- trans -(m -nitrocinnamoyl)- l -lysine (MDP-C), and its adjuvancy on the hepatitis B surface antigen J. Med. Chem. 2005, 48, 5112-5122
38. Mehlen, P.; Puisieux, A. Metastasis: a question of life or death Nat Rev. Cancer 2006, 6, 449-458
39. Wu, Y.; Zhou, B. P. Inflammation: a driving force speeds cancer metastasis Cell Cycle 2009, 8, 3267-3273
40. Mantovani, A.; Garlanda, C.; Allavena, P. Molecular pathways and targets in cancer-related inflammation Ann. Med. 2010, 42, 161-170
41. Almand, B.; Clark, J. I.; Nikitina, E.; van Beynen, J.; English, N. R.; Knight, S. C.; Carbone, D. P.; Gabrilovi, D. I. Increased production of immature myeloid cells in cancer patients: a mechanism of immunosuppression in cancer J. Immunol. 2001, 166, 678-689 (Pubitemid 32038493)
42. Young, M. R.; Lathers, D. M. Myeloid progenitor cells mediate immune suppression in patients with head and neck cancers Int. J. Immunopharmacol. 1999, 21, 241-252 (Pubitemid 29241776)
43. Diaz-Montero, C. M.; Salem, M. L.; Nishimura, M. I.; Garrett-Mayer, E.; Cole, D. J.; Montero, A. J. Increased circulating myeloid-derived suppressor cells correlate with clinical cancer stage, metastatic tumor burden and doxorubicin-cyclophosphamide chemotherapy Cancer Immunol. Immunother. 2009, 58, 49-59
44. Huang, B.; Lei, Z.; Zhao, J.; Gong, W.; Liu, J.; Chen, Z.; Liu, Y.; Li, D.; Yuan, Y.; Zhang, G. M.; Feng, Z. H. CCL2/CCR2 pathway mediates recruitment of myeloid suppressor cells to cancers Cancer Lett. 2007, 252, 86-92 (Pubitemid 46734559)
45. Sinha, P.; Clements, V. K.; Bunt, S. K.; Albelda, S. M.; Ostrand-Rosenberg, S. Cross-talk between myeloid-derived suppressor cells and macrophages subverts tumor immunity toward a type 2 response J. Immunol. 2007, 179, 977-983
46. Yang, L.; DeBusk, L. M.; Fukuda, K.; Fingleton, B.; Green-Jarvis, B.; Shyr, Y.; Matrisian, L. M.; Carbone, D. P.; Lin, P. C. Expansion of myeloid immune suppressor Gr+CD11b+ cells in tumor-bearing host directly promotes tumor angiogenesis Cancer Cell 2004, 6, 409-421 (Pubitemid 39361441)
47. Yang, L.; Huang, J.; Ren, X.; Gorska, A. E.; Chytil, A.; Aakre, M.; Carbone, D. P.; Matrisian, L. M.; Richmond, A.; Lin, P. C.; Moses, H. L. Abrogation of TGF-β signaling in mammary carcinomas recruits Gr-1+CD11b+ myeloid cells that promote metastasis Cancer Cell 2008, 13, 23-35 (Pubitemid 350309741)
48. Wu, Y.; Zhou, B. P. TNF-a/NF-kB/Snail pathway in cancer cell migration and invasion Br. J. Cancer 2010, 102, 639-644
49. Deutsch, H. M.; Glinski, J. A.; Hernandez, M.; Haugwitz, R. D.; Narayanan, V. L.; Suffness, M.; Zalkow, L. H. Synthesis of congeners and prodrugs. 3. Water-soluble prodrugs of Taxol with potent antitumor activity J. Med. Chem. 1989, 32, 788-792 (Pubitemid 19100192)
50. Shoemaker, R. H. The NCI60 human tumour cell line anticancer drug screen Nat. Rev. Cancer 2006, 6, 813-823 (Pubitemid 44450469)