Examination of structure-activity relationship of viologen-based dendrimers as cxcr4 antagonists and gene carriers

Bioconjugate Chemistry

Volumn 25, Issue 5, 2014, Pages 907-917

  Li, Jing ^a   Lepadatu, Ana Maria ^b   Zhu, Yu ^a   Ciobanu, Marius ^b   Wang, Yan ^a   Asaftei, Simona C ^b   Oupický, David ^a  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

^b UNIVERSITY OF OSNABRÜCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DISEASES; GENE THERAPY; GENE TRANSFER; LIGANDS; MOLECULAR BIOLOGY;

CANCER CELLS; DUAL FUNCTION; GENE CARRIER; MOLECULAR ARCHITECTURE; PHYSICOCHEMICAL PROPERTY; POLYPLEXES; POSITIVE CHARGES; STRUCTURE-ACTIVITY RELATIONSHIPS; VIOLOGEN-BASED DENDRIMERS; VIOLOGENS;

DENDRIMERS;

CHEMOKINE RECEPTOR CXCR4; CHEMOKINE RECEPTOR CXCR4 ANTAGONIST; DENDRIMER; PLASMID DNA; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; VIOLOGEN; VIOLOGEN DENDRIMER; ANTINEOPLASTIC AGENT; CXCR4 PROTEIN, HUMAN;

ARTICLE; CANCER CELL DESTRUCTION; CANCER INHIBITION; COMPLEX FORMATION; CONTROLLED STUDY; DNA CONDENSATION; DNA STRUCTURE; DNA TRANSFECTION; DRUG ANTAGONISM; DRUG DNA BINDING; DRUG SCREENING; HEPG2 CELL LINE; HUMAN; HUMAN CELL; MOLECULAR WEIGHT; NONVIRAL GENE DELIVERY SYSTEM; PARTICLE SIZE; PHYSICAL CHEMISTRY; RECEPTOR BLOCKING; STRUCTURE ACTIVITY RELATION; SURFACE CHARGE; TUMOR INVASION; U2OS CELL LINE; ANTAGONISTS AND INHIBITORS; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; GENE THERAPY; GENE TRANSFER; GENETICS; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DENDRIMERS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; GENE TRANSFER TECHNIQUES; GENETIC THERAPY; HEP G2 CELLS; HUMANS; MODELS, MOLECULAR; RECEPTORS, CXCR4; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR NECROSIS FACTOR-ALPHA; VIOLOGENS;

EID: 84901054431     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc500191q     Document Type: Article

References (53)

1. Davis, M. E. (2002) Non-viral gene delivery systems Curr. Opin. Biotechnol. 13, 128-31
2. Leong, K. W., Mao, H. Q., Truong-Le, V. L., Roy, K., Walsh, S. M., and August, J. T. (1998) DNA-polycation nanospheres as non-viral gene delivery vehicles J. Controlled Release 53, 183-93
3. Merdan, T., Kopecek, J., and Kissel, T. (2002) Prospects for cationic polymers in gene and oligonucleotide therapy against cancer Adv. Drug Delivery Rev. 54, 715-58
4. Pack, D. W., Hoffman, A. S., Pun, S., and Stayton, P. S. (2005) Design and development of polymers for gene delivery Nat. Rev. Drug Discovery 4, 581-93
5. Navarro, G. and Tros de Ilarduya, C. (2009) Activated and non-activated PAMAM dendrimers for gene delivery in vitro and in vivo Nanomedicine 5, 287-97
6. Dufes, C., Keith, W. N., Bilsland, A., Proutski, I., Uchegbu, I. F., and Schatzlein, A. G. (2005) Synthetic anticancer gene medicine exploits intrinsic antitumor activity of cationic vector to cure established tumors Cancer Res. 65, 8079-84
7. Lim, Y. B., Kim, T., Lee, J. W., Kim, S. M., Kim, H. J., Kim, K., and Park, J. S. (2002) Self-assembled ternary complex of cationic dendrimer, cucurbituril, and DNA: noncovalent strategy in developing a gene delivery carrier Bioconjugate Chem. 13, 1181-5
8. Luo, D., Haverstick, K., Belcheva, N., Han, E., and Saltzman, W. M. (2002) Poly(ethylene glycol)-conjugated PAMAM dendrimer for biocompatible, high-efficiency DNA delivery Macromolecules 35, 3456-3462
9. Merkel, O. M., Mintzer, M. A., Sitterberg, J., Bakowsky, U., Simanek, E. E., and Kissel, T. (2009) Triazine dendrimers as nonviral gene delivery systems: effects of molecular structure on biological activity Bioconjugate Chem. 20, 1799-806
10. Chen, Y., Sen, J., Bathula, S. R., Yang, Q., Fittipaldi, R., and Huang, L. (2009) Novel cationic lipid that delivers siRNA and enhances therapeutic effect in lung cancer cells Mol. Pharmaceutics 6, 696-705
11. Martin, M. E. and Rice, K. G. (2008) A novel class of intrinsic proteasome inhibitory gene transfer peptides Bioconjugate Chem. 19, 370-6
12. Li, J., Zhu, Y., Hazeldine, S. T., Li, C., and Oupický, D. (2012) Dual-function CXCR4 antagonist polyplexes to deliver gene therapy and inhibit cancer cell invasion Angew. Chem., Int. Ed. Engl. 51, 8740-3
13. Li, J. and Oupicky, D. (2014) Effect of biodegradability on CXCR4 antagonism, transfection efficacy and antimetastatic activity of polymeric Plerixafor Biomaterials 35, 5572-5579
14. Balkwill, F. R. (2012) The chemokine system and cancer J. Pathol. 226, 148-157
15. Rajagopal, S., Kim, J., Ahn, S., Craig, S., Lam, C. M., Gerard, N. P., Gerard, C., and Lefkowitz, R. J. (2010) o-arrestin-but not G protein-mediated signaling by the "decoy" receptor CXCR7 Proc. Natl. Acad. Sci. U.S.A. 107, 628-632
16. Sun, X. Q., Cheng, G. C., Hao, M. G., Zheng, J. H., Zhou, X. M., Zhang, J. A., Taichman, R. S., Pienta, K. J., and Wang, J. H. (2010) CXCL12/CXCR4/CXCR7 chemokine axis and cancer progression Cancer Met. Rev. 29, 709-722
17. Chang, L. and Karin, M. (2001) Mammalian MAP kinase signalling cascades Nature 410, 37-40
18. Zlotnik, A., Burkhardt, A. M., and Homey, B. (2011) Homeostatic chemokine receptors and organ-specific metastasis Nat. Rev. Immunol. 11, 597-606
19. Burger, M., Glodek, A., Hartmann, T., Schmitt-Graff, A., Silberstein, L. E., Fujii, N., Kipps, T. J., and Burger, J. A. (2003) Functional expression of CXCR4 (CD184) on small-cell lung cancer cells mediates migration, integrin activation, and adhesion to stromal cells Oncogene 22, 8093-8101
20. Spoo, A. C., Lubbert, M., Wierda, W. G., and Burger, J. A. (2007) CXCR4 is a prognostic marker in acute myelogenous leukemia Blood 109, 786-91
21. Holm, N. T., Byrnes, K., Li, B. D., Turnage, R. H., Abreo, F., Mathis, J. M., and Chu, Q. D. (2007) Elevated levels of chemokine receptor CXCR4 in HER-2 negative breast cancer specimens predict recurrence J. Surg. Res. 141, 53-9
22. Chu, Q. D., Panu, L., Holm, N. T., Li, B. D., Johnson, L. W., and Zhang, S. (2010) High chemokine receptor CXCR4 level in triple negative breast cancer specimens predicts poor clinical outcome J. Surg. Res. 159, 689-95
23. Wald, O., Shapira, O. M., and Izhar, U. (2013) CXCR4/CXCL12 axis in non small cell lung cancer (NSCLC) pathologic roles and therapeutic potential Theranostics 3, 26-33
24. Spano, J.-P., Andre, F., Morat, L., Sabatier, L., Besse, B., Combadiere, C., Deterre, P., Martin, A., Azorin, J., Valeyre, D., Khayat, D., Le Chevalier, T., and Soria, J.-C. (2004) Chemokine receptor CXCR4 and early-stage non-small cell lung cancer: pattern of expression and correlation with outcome Ann. Oncol. 15, 613-617
25. Oonakahara, K.-i., Matsuyama, W., Higashimoto, I., Kawabata, M., Arimura, K., and Osame, M. (2004) Stromal-Derived Factor-1α/CXCL12-CXCR 4 Axis Is Involved in the Dissemination of NSCLC Cells into Pleural Space Am. J. Respir. Cell Mol. Biol. 30, 671-677
26. Gangadhar, T., Nandi, S., and Salgia, R. (2010) The role of chemokine receptor CXCR4 in lung cancer Cancer Biol. Ther. 9, 409-416
27. Wald, O., Izhar, U., Amir, G., Avniel, S., Bar-Shavit, Y., Wald, H., Weiss, I. D., Galun, E., and Peled, A. (2006) CD4+CXCR4highCD69+ T cells accumulate in lung adenocarcinoma J. Immunol. 177, 6983-6990
28. Wald, O., Izhar, U., Amir, G., Kirshberg, S., Shlomai, Z., Zamir, G., Peled, A., and Shapira, O. M. (2011) Interaction between neoplastic cells and cancer-associated fibroblasts through the CXCL12/CXCR4 axis: Role in non-small cell lung cancer tumor proliferation J. Thorac. Cardiovasc. Surg. 141, 1503-1512
29. Bleul, C. C., Wu, L., Hoxie, J. A., Springer, T. A., and Mackay, C. R. (1997) The HIV coreceptors CXCR4 and CCR5 are differentially expressed and regulated on human T lymphocytes Proc. Natl. Acad. Sci. U. S. A. 94, 1925-30
30. Alkhatib, G. (2009) The biology of CCR5 and CXCR4 Curr. Opin. HIV AIDS 4, 96-103
31. Yamada, M., Kubo, H., Kobayashi, S., Ishizawa, K., He, M., Suzuki, T., Fujino, N., Kunishima, H., Hatta, M., Nishimaki, K., Aoyagi, T., Tokuda, K., Kitagawa, M., Yano, H., Tamamura, H., Fujii, N., and Kaku, M. (2011) The increase in surface CXCR4 expression on lung extravascular neutrophils and its effects on neutrophils during endotoxin-induced lung injury Cell. Mol. Immunol. 8, 305-14
32. Lukacs, N. W., Berlin, A., Schols, D., Skerlj, R. T., and Bridger, G. J. (2002) AMD3100, a CxCR4 antagonist, attenuates allergic lung inflammation and airway hyperreactivity Am. J. Pathol. 160, 1353-60
33. Gonzalo, J. A., Lloyd, C. M., Peled, A., Delaney, T., Coyle, A. J., and Gutierrez-Ramos, J. C. (2000) Critical involvement of the chemotactic axis CXCR4/stromal cell-derived factor-1 alpha in the inflammatory component of allergic airway disease J. Immunol. 165, 499-508
34. Danese, S. and Gasbarrini, A. (2005) Chemokines in inflammatory bowel disease J. Clin. Pathol. 58, 1025-7
35. Rhodes, L. V., Short, S. P., Neel, N. F., Salvo, V. A., Zhu, Y., Elliott, S., Wei, Y., Yu, D., Sun, M., Muir, S. E., Fonseca, J. P., Bratton, M. R., Segar, C., Tilghman, S. L., Sobolik-Delmaire, T., Horton, L. W., Zaja-Milatovic, S., Collins-Burow, B. M., Wadsworth, S., Beckman, B. S., Wood, C. E., Fuqua, S. A., Nephew, K. P., Dent, P., Worthylake, R. A., Curiel, T. J., Hung, M. C., Richmond, A., and Burow, M. E. (2011) Cytokine receptor CXCR4 mediates estrogen-independent tumorigenesis, metastasis, and resistance to endocrine therapy in human breast cancer Cancer Res. 71, 603-13
36. Lapteva, N., Yang, A. G., Sanders, D. E., Strube, R. W., and Chen, S. Y. (2005) CXCR4 knockdown by small interfering RNA abrogates breast tumor growth in vivo Cancer Gene Ther. 12, 84-9
37. Liang, Z., Yoon, Y., Votaw, J., Goodman, M. M., Williams, L., and Shim, H. (2005) Silencing of CXCR4 blocks breast cancer metastasis Cancer Res. 65, 967-71
38. Brave, M., Farrell, A., Lin, S. C., Ocheltree, T., Miksinski, S. P., Lee, S. L., Saber, H., Fourie, J., Tornoe, C., Booth, B., Yuan, W. S., He, K., Justice, R., and Pazdur, R. (2010) FDA review summary: mozobil in combination with granulocyte colony-stimulating factor to mobilize hematopoietic stem cells to the peripheral blood for collection and subsequent autologous transplantation Oncology 78, 282-288
39. Asaftei, S., Huskens, D., and Schols, D. (2012) HIV-1 X4 activities of polycationic viologen based dendrimers by interaction with the chemokine receptor CXCR4: study of structure-activity relationship J. Med. Chem. 55, 10405-13
40. Germershaus, O., Mao, S., Sitterberg, J., Bakowsky, U., and Kissel, T. (2008) Gene delivery using chitosan, trimethyl chitosan or polyethylenglycol- graft-trimethyl chitosan block copolymers: establishment of structure-activity relationships in vitro J. Controlled Release 125, 145-54
41. Fischer, D., Li, Y., Ahlemeyer, B., Krieglstein, J., and Kissel, T. (2003) In vitro cytotoxicity testing of polycations: influence of polymer structure on cell viability and hemolysis Biomaterials 24, 1121-31
42. Morgan, D. M., Clover, J., and Pearson, J. D. (1988) Effects of synthetic polycations on leucine incorporation, lactate dehydrogenase release, and morphology of human umbilical vein endothelial cells J. Cell Sci. 91 (Pt 2) 231-8
43. Morgan, D. M., Larvin, V. L., and Pearson, J. D. (1989) Biochemical characterisation of polycation-induced cytotoxicity to human vascular endothelial cells J. Cell Sci. 94 (Pt 3) 553-9
44. Hong, S., Leroueil, P. R., Janus, E. K., Peters, J. L., Kober, M. M., Islam, M. T., Orr, B. G., Baker, J. R., Jr., and Banaszak Holl, M. M. (2006) Interaction of polycationic polymers with supported lipid bilayers and cells: nanoscale hole formation and enhanced membrane permeability Bioconjugate Chem. 17, 728-34
45. van Horssen, R., Ten Hagen, T. L., and Eggermont, A. M. (2006) TNF-alpha in cancer treatment: molecular insights, antitumor effects, and clinical utility Oncologist 11, 397-408
46. Waters, J. P., Pober, J. S., and Bradley, J. R. (2013) Tumour necrosis factor and cancer J. Pathol. 230, 241-8
47. Rostasy, K., Gorgun, G., Kleyner, Y., Garcia, A., Kramer, M., Melanson, S. M., Mathys, J. M., Yiannoutsos, C., Skolnik, P. R., and Navia, B. A. (2005) Tumor necrosis factor alpha leads to increased cell surface expression of CXCR4 in SK-N-MC cells J. Neurovirol. 11, 247-55
48. Kulbe, H., Hagemann, T., Szlosarek, P. W., Balkwill, F. R., and Wilson, J. L. (2005) The inflammatory cytokine tumor necrosis factor-alpha regulates chemokine receptor expression on ovarian cancer cells Cancer Res. 65, 10355-62
49. Zhao, C., Lu, X., Bu, X., Zhang, N., and Wang, W. (2010) Involvement of tumor necrosis factor-alpha in the upregulation of CXCR4 expression in gastric cancer induced by Helicobacter pylori BMC Cancer 10, 419
50. Asaftei, S. and De Clercq, E. (2010) Viologen dendrimers as antiviral agents: the effect of charge number and distance J. Med. Chem. 53, 3480-8
51. Asaftei, S. (2008) New hybrid compounds of nucleobases and organic redox molecules and their use, PCT/EP 2008/004527, WO2008/148560 A1, 1-56
52. Asaftei, S., Lepadatu, A. M., and Ciobanu, M. (2011) Novel compounds with a viologen skeleton and N-heterocycles on the peripheries: electrochemical and spectroscopic properties Helv. Chim. Acta 94, 1091-1101
53. Bongard, D. (2008) PhD Thesis, University of Osnabrück.