Receptor mediated cellular uptake of low molecular weight dendritic polyglycerols

Journal of Biomedical Nanotechnology

Volumn 10, Issue 1, 2014, Pages 92-99

  Calderón, Marcelo ^a   Reichert, Stephanie ^a   Welker, Pia ^b   Licha, Kai ^b   Kratz, Felix ^c   Haag, Rainer ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b Mivenion GmbH   (Germany)

^c TUMOR BIOLOGY CENTER   (Germany)

Author keywords

Active cellular uptake; cRGD; LHRH; Polyglycerol; Polymer therapeutics; Targeting

Indexed keywords

CELLULAR UPTAKE; CRGD; LHRH; POLYGLYCEROLS; POLYMER THERAPEUTICS; TARGETING;

FUNCTIONAL GROUPS; MEDICAL APPLICATIONS; MOLECULAR WEIGHT; SCAFFOLDS (BIOLOGY);

FUNCTIONAL POLYMERS;

FLUORESCENT DYE; GLYCEROL DERIVATIVE; NANOCARRIER; POLYMER;

ARTICLE; CANCER CELL CULTURE; CONJUGATE; CYTOCHEMISTRY; DENDRITE; DENSITY; DRUG DELIVERY SYSTEM; HUMAN; MOLECULAR WEIGHT; POLYMERIZATION; TARGET CELL;

DENDRIMERS; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; FLUORESCENT DYES; GLYCEROL; GONADOTROPIN-RELEASING HORMONE; HUMANS; MALEIMIDES; MOLECULAR TARGETED THERAPY; MOLECULAR WEIGHT; NANOCONJUGATES; OLIGOPEPTIDES; POLYMERS; RECEPTORS, CELL SURFACE; TISSUE DISTRIBUTION; TUMOR CELLS, CULTURED;

EID: 84889066377     PISSN: 15507033     EISSN: 15507041     Source Type: Journal    
DOI: 10.1166/jbn.2014.1697     Document Type: Article

References (47)

1. J. Khandare, M. Calderon, N. M. Dagia, and R. Haag, Multifunctional dendritic polymers in nanomedicine: opportunities and challenges. Chem. Soc. Rev. 41, 2824 (2012).
2. R. Haag and F. Kratz, Polymer therapeutics: concepts and applications. Angew. Chem., Int. Ed. 45, 1198 (2006).
3. M. Calderón, M. A. Quadir, M. Strumia, and R. Haag, Functional dendritic polymer architectures as stimuli-responsive nanocarriers. Biochimie. 92, 1242 (2010).
4. E. Fleige, M. A. Quadir, and R. Haag, Stimuli-responsive polymeric nanocarriers for the controlled transport of active compounds: concepts and applications. Adv. Drug. Deliv. Rev. 64, 866 (2012).
5. M. A. Quadir and R. Haag, Biofunctional nanosystems based on dendritic polymers. J. Control Release 161, 484 (2012).
6. S. Reichert, M. Calderón, K. Licha, and R. Haag, Multifunctional Nanoparticles for Drug Delivery Applications, edited by S. Svenson and R. K. Prud'homme, Springer, US (2012), pp. 315-344.
7. C. C. Lee, E. R. Gillies, M. E. Fox, S. J. Guillaudeu, J. M. J. Fréchet, E. E. Dy, and F. C. Szoka, A single dose of doxorubicin- functionalized bow-tie dendrimer cures mice bearing C-26 colon carcinomas. Proc. Natl. Acad. Sci. U.S.A. 103, 16649 (2006).
8. M. Calderón, M. A. Quadir, S. K. Sharma, and R. Haag, Dendritic Polyglycerols for biomedical applications. Adv. Mater. 22, 190 (2010).
9. M. Calderón and M. Strumia, Hyperbranched and hyperfunctionalized materials from dendritic chemistry. Rev. LatinAm. Metal. Mat. 33, 2 (2013).
10. W. Fischer, M. Calderon, and R. Haag, Hyperbranched polyamines for transfection. Top. Curr. Chem. 296, 95 (2010).
11. Y. Matsumura and H. Maeda, A new concept for macromolecular therapeutics in cancer chemotherapy: mechanism of tumoritropic accumulation of proteins and the antitumor agent smancs. Cancer Research 46, 6387 (1986).
12. K. Yazawa, M. Fujimori, J. Amano, Y. Kano, and S. Taniguchi, Bifidobacterium longum as a delivery system for cancer gene therapy: Selective localization and growth in hypoxic tumors. Cancer. Gene. Ther. 2, 269 (2000).
13. M. Stroh, J. P. Zimmer, D. G. Duda, T. S. Levchenko, K. S. Cohen, E. B. Brown, D. T. Scadden, V. P. Torchilin, M. G. Bawendi, D. Fukumura, and R. K. Jain, Quantum dots spectrally distinguish multiple species within the tumor milieu in vivo. Nat. Med. 11, 678 (2005).
14. Y. Noguchi, J. Wu, R. Duncan, J. Strohalm, K. Ulbrich, T. Akaike, and H. Maeda, Early phase tumor accumulation of macromolecules: A great difference in clearance rate between tumor and normal tissues. Jpn. J. Cancer Res. 89, 307 (1998).
15. R. Haag and F. Kratz, Polymer therapeutics: concepts and applications. Angew. Chem. Int. Ed. Engl. 45, 1198 (2006).
16. C. Gao and D. Yan, Hyperbranched polymers: from synthesis to applications. Prog. Polym. Sci. 29, 183 (2004).
17. A. Sunder, R. Mülhaupt, R. Haag, and H. Frey, Hyperbranched polyether polyols: a modular approach to complex polymer architectures. Adv. Mat. 12, 235 (2000).
18. A. Sunder, R. Hanselmann, H. Frey, and R. Mülhaupt, Controlled synthesis of hyperbranched polyglycerols by ring-opening multibranching polymerization. Macromolecules 32, 4240 (1999).
19. C. C. Lee, J. A. MacKay, J. M. J. Frechet, and F. C. Szoka, Designing dendrimers for biological applications. Nat. Biotech. 23, 1517 (2005).
20. P. Kolhe, J. Khandare, O. Pillai, S. Kannan, M. Lieh-Lai, and R. M. Kannan, Preparation, cellular transport, and activity of polyamidoamine-based dendritic nanodevices with a high drug payload. Biomaterials 27, 660 (2006).
21. R. Haag, A. Sunder, and J.-F. Stumbé, An approach to glycerol dendrimers and pseudo-dendritic polyglycerols. J. Am. Chem. Soc. 122, 2954 (2000).
22. S. Roller, H. Zhou, and R. Haag, High-loading polyglycerol supported reagents for Mitsunobu- and acylation-reactions and other useful polyglycerol derivatives. Molecular diversity 9, 305 (2005).
23. S. Reichert, P. Welker, M. Calderón, J. Khandare, D. Mangoldt, K. Licha, R. K. Kainthan, D. E. Brooks, and R. Haag, Size-dependant cellular uptake of dendritic polyglycerol. Small 7, 820 (2011).
24. C. Fasting, C. A. Schalley, M. Weber, O. Seitz, S. Hecht, B. Koksch, J. Dernedde, C. Graf, E.-W. Knapp, and R. Haag, Multivalency as a chemical organization and action principle. Angew. Chem., Int. Ed. 51, 10472 (2012).
25. S. Malhotra, H. Bauer, A. Tschiche, A. M. Staedtler, A. Mohr, M. Calderon, V. S. Parmar, S. Sharbati, L. Hoeke, R. Einspanier, and R. Haag, Glycine-terminated dendritic amphiphiles for non-viral gene delivery. Biomacromolecules 13, 3087 (2012).
26. A. Barnard, P. Posocco, S. Pricl, M. Calderon, R. Haag, M. E. Hwang, V. W. T. Shum, D. W. Pack, and D. K. Smith, Degradable self-assembling dendrons for gene delivery: experimental and theoretical insights into the barriers to cellular uptake. J. Am. Chem. Soc. 133, 20288 (2011).
27. P. Ofek, W. Fischer, M. Calderon, R. Haag, and R. Satchi-Fainaro, In vivo delivery of small interfering RNA to tumors and their vasculature by novel dendritic nanocarriers. Faseb. J. 24, 3122 (2010).
28. K. Wan, B. Ebert, J. Voigt, Q. Wang, Y. Dai, R. Haag, and W. Kemmner, In vivo tumor imaging using a novel RNAi-based detection mechanism. Nanomedicine 8, 393 (2012).
29. K. Licha, P. Welker, M. Weinhart, N. Wegner, S. Kern, S. Reichert, I. Gemeinhardt, C. Weissbach, B. Ebert, R. Haag, and M. Schirner, Fluorescence imaging with multifunctional polyglycerol sulfates: novel polymeric near-IR Probes targeting inflammation. Bioconjug. Chem. 22, 2453 (2011).
30. I. Papp, C. Sieben, K. Ludwig, M. Roskamp, C. Böttcher, S. Schlecht, A. Herrmann, and R. Haag, Inhibition of influenza virus infection by multivalent sialic-acid-functionalized gold nanoparticles. Small 6, 2900 (2010).
31. I. Papp, J. Dernedde, S. Enders, S. B. Riese, T. C. Shiao, R. Roy, and R. Haag, Multivalent presentation of mannose on hyperbranched polyglycerol and their interaction with concanavalin A lectin. Chembiochem. 12, 1075 (2011).
32. I. Papp, C. Sieben, A. L. Sisson, A. Herrmann, and R. Haag, Inhibition of influenza virus activity by newly designed multivalent glycoarchitectures. J. Controlled Release 148, e114 (2010).
33. M. Weinhart, D. Gröger, S. Enders, S. B. Riese, J. Dernedde, R. K. Kainthan, D. E. Brooks, and R. Haag, The role of dimension in multivalent binding events: structure-activity relationship of dendritic polyglycerol sulfate binding to L-selectin in correlation with size and surface charge density. Macromol. Biosci. 11, 1088 (2011).
34. J. Dernedde, A. Rausch, M. Weinhart, S. Enders, R. Tauber, K. Licha, M. Schirner, U. Zügel, A. V. Bonin, and R. Haag, Dendritic polyglycerol sulfates as multivalent inhibitors of inflammation. Proc. Natl. Acad. Sci. U.S.A. 107, 19679 (2010).
35. J. Khandare, A. Mohr, M. Calderón, P. Welker, K. Licha, and R. Haag, Structure-biocompatibility relationship of dendritic polyglycerol derivatives. Biomaterials 31, 4268 (2010).
36. R. Haag, S. Mecking, and H. Türk, Verfahren zur Herstellung hochverzweigter Polymere. Patent Application DE10211664A1 (2003).
37. H. Türk, R. Haag, and S. Alban, Dendritic polyglycerol sulfates as new heparin analogues and potent inhibitors of the complement system. Bioconjug. Chem. 15, 162 (2003).
38. M. L. Patil, M. Zhang, O. Taratula, O. B. Garbuzenko, H. He, and T. Minko, Internally cationic polyamidoamine PAMAM-OH dendrimers for siRNA delivery: effect of the degree of quaternization and cancer targeting. Biomacromolecules 10, 258 (2009).
39. K. Licha, C. Hessenius, A. Becker, P. Henklein, M. Bauer, S. Wisniewski, B. Wiedenmann, and W. Semmler, Synthesis, characterization, and biological properties of cyanine-labeled somatostatin analogues as receptor-targeted fluorescent probes. Bioconjug. Chem. 12, 44 (2001).
40. R. K. Kainthan, J. Janzen, E. Levin, D. V. Devine, and D. E. Brooks, Biocompatibility testing of branched and linear polyglycidol. Biomacromolecules 7, 703 (2006).
41. M. Calderón, P. Welker, K. Licha, I. Fichtner, R. Graeser, R. Haag, and F. Kratz, Development of efficient acid cleavable multifunctional prodrugs derived from dendritic polyglycerol with a poly(ethylene glycol) shell. J. Controlled Release 151, 295 (2011).
42. S. E. D'Souza, M. H. Ginsberg, and E. F. Plow, Arginyl-glycylaspartic acid (RGD): a cell adhesion motif. Trends Biochem. Sci. 16, 246 (1991).
43. D. Cox, T. Aoki, J. Seki, Y. Motoyama, and K. Yoshida, The pharmacology of the integrins. Med. Res. Reviews 14, 195 (1994).
44. M. Janssen, W. J. Oyen, L. F. Massuger, C. Frielink, I. Dijkgraaf, D. S. Edwards, M. Radjopadhye, F. H. Corstens, and O. C. Boerman, Cancer Biother. Radiopharm. 17, 641 (2002).
45. D. Polyak, C. Ryppa, A. Eldar-Boock, P. Ofek, A. Many, K. Licha, F. Kratz, and R. Satchi-Fainaro, Development of PEGylated doxorubicin-E-[c(RGDfK)2] conjugate for integrin-targeted cancer therapy. Polym. Adv. Technol. 22, 103 (2011).
46. J. Engel and A. V. Schally, edited by A. J. Kastin, Handbook of Biologically Active Peptides. Academic Press, New York (2006).
47. M. Calderón, R. Graeser, F. Kratz, and R. Haag, Development of enzymatically cleavable prodrugs derived from dendritic polyglycerol. Bioorg. Med. Chem. Lett. 19, 3725 (2009).