Peripheral functionalization of dendrimers regulates internalization and intracellular trafficking in living cells

Bioconjugate Chemistry

Volumn 23, Issue 5, 2012, Pages 1059-1068

  Albertazzi, Lorenzo ^a,b,d   Fernandez Villamarin, Marcos ^c   Riguera, Ricardo ^c   Fernandez Megia, Eduardo ^c  

^a ISTITUTO NANOSCIENZE CNR   (Italy)

^b CENTER FOR NANOTECHNOLOGY INNOVATION NEST   (Italy)

^c UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^d EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CELL CULTURE; CELL PROLIFERATION; CONTROLLED DRUG DELIVERY; MEDICAL APPLICATIONS; TARGETED DRUG DELIVERY;

BIOMEDICAL APPLICATIONS; BIOMEDICAL FIELDS; CELL POPULATIONS; FUNCTIONALIZATIONS; GALLIC ACIDS; IMAGING AGENT; INTRACELLULAR TRAFFICKING; LIVING CELL; PHYSICOCHEMICAL PROPERTY; TRIETHYLENE GLYCOL;

DENDRIMERS;

DENDRIMER; GALLIC ACID DERIVATIVE; LIGAND; NANOMATERIAL; TRIETHYLENE GLYCOL;

ARTICLE; CELL POPULATION; CELL STRAIN HEPG2; CELL STRAIN MCF 7; CELLULAR DISTRIBUTION; CONFOCAL MICROSCOPY; DRUG DELIVERY SYSTEM; HELA CELL; INTERNALIZATION; INTRACELLULAR TRANSPORT; LYSOSOME; PH; PHYSICAL CHEMISTRY; REGULATORY MECHANISM; SURFACE PROPERTY;

CELL LINE, TUMOR; CELL MEMBRANE PERMEABILITY; DELAYED-ACTION PREPARATIONS; DENDRIMERS; DRUG DELIVERY SYSTEMS; GALLIC ACID; HUMANS; HYDROGEN-ION CONCENTRATION; LYSOSOMES; MICROSCOPY, CONFOCAL; PEPTIDES; POLYETHYLENE GLYCOLS;

EID: 84861125786     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc300079h     Document Type: Article

References (49)

1. Menjoge, A. R., Kannan, R. M., and Tomalia, D. A. (2010) Dendrimer-based drug and imaging conjugates: design considerations for nanomedical applications Drug Discovery Today 15, 171-185
2. Gillies, E. R. and Fréchet, J. M. J. (2005) Dendrimers and dendritic polymers in drug delivery Drug Discovery Today 10, 35-43
3. Lee, C. C., MacKay, J. A., Fréchet, J. M. J., and Szoka, F. C. (2005) Designing dendrimers for biological applications Nat. Biotechnol. 23, 1517-1526
4. Shcharbin, D., Pedziwiatr, E., Blasiak, J., and Bryszewska, M. (2010) How to study dendriplexes II: Transfection and cytotoxicity J. Controlled Release 141, 110-127
5. Rolland, O., Turrin, C.-O., Caminade, A.-M., and Majoral, J.-P. (2009) Dendrimers and nanomedicine: multivalency in action New J. Chem. 33, 1809-1824
6. Tekade, R. K., Kumar, P. V., and Jain, N. K. (2009) Dendrimers in oncology: an expanding horizon Chem. Rev. 109, 49-87
7. Villaraza, A. J. L., Bumb, A., and Brechbiel, M. W. (2010) Macromolecules, dendrimers, and nanomaterials in magnetic resonance imaging: the interplay between size, function, and pharmacokinetics Chem. Rev. 110, 2921-2959
8. Sakadžić, S., Roussakis, E., Yaseen, M. A., Mandeville, E. T., Srinivasan, V. J., Arai, K., Ruvinskaya, S., Devor, A., Lo, E. H., Vinogradov, S. A., and Boas, D. A. (2010) Two-photon high-resolution measurement of partial pressure of oxygen in cerebral vasculature and tissue Nat. Methods 7, 755-759
9. Albertazzi, L., Brondi, M., Pavan, G. M., Sato, S. S., Signore, G., Storti, B., Ratto, G. M., and Beltram, F. (2011) Dendrimer-based fluorescent indicators: in vitro and in vivo applications PLoS ONE 6, e28450
10. Buhleier, E., Wehner, W., and Vögtle, F. (1978) "Cascade"- and "nonskid-chain-like" syntheses of molecular cavity topologies Synthesis 155-158
11. Tomalia, D. A., Baker, H., Dewald, J., Hall, M., Kallos, G., Martin, S., Roeck, J., Ryder, J., and Smith, P. (1985) A new class of polymers: starburst-dendritic macromolecules Polym. J. 17, 117-132
12. Newkome, G. R., Yao, Z.-q., Baker, G. R., and Gupta, V. K. (1985) Cascade molecules: a new approach to micelles. A [27]-arborol J. Org. Chem. 50, 2003-2004
13. Hawker, C. J. and Fréchet, J. M. J. (1990) Preparation of polymers with controlled molecular architecture. A new convergent approach to dendritic macromolecules J. Am. Chem. Soc. 112, 7638-7647
14. Astruc, D., Boisselier, E., and Ornelas, C. (2010) Dendrimers designed for functions: from physical, photophysical, and supramolecular properties to applications in sensing, catalysis, molecular electronics, photonics, and nanomedicine Chem. Rev. 110, 1857-1959
15. Vögtle, F., Richardt, G., and Werner, N. (2009) Dendrimer Chemistry, Wiley-VCH, Weinheim,.
16. Dendrimers and Other Dendritic Polymers, John Wiley & Sons, Ltd., Chichester, 2001.
17. Fernandez-Megia, E., Correa, J., and Riguera, R. (2006) "Clickable" PEG-dendritic block copolymers Biomacromolecules 7, 3104-3111
18. Fernandez-Megia, E., Correa, J., Rodríguez-Meizoso, I., and Riguera, R. (2006) A click approach to unprotected glycodendrimers Macromolecules 39, 2113-2120
19. Amaral, S. P., Fernandez-Villamarin, M., Correa, J., Riguera, R., and Fernandez-Megia, E. (2011) Efficient multigram synthesis of the repeating unit of gallic acid-triethylene glycol dendrimers Org. Lett. 13, 4522-4525
20. Meunier, S. J., Wu, Q., Wang, S.-N., and Roy, R. (1997) Synthesis of hyperbranched glycodendrimers incorporating α-thiosialosides based on a gallic acid core Can. J. Chem. 75, 1472-1482
21. Tornøe, C. W., Christensen, C., and Meldal, M. (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 67, 3057-3064
22. Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless, K. B. (2002) A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes Angew. Chem., Int. Ed. 41, 2596-2599
23. Harris, J. M. and Chess, R. B. (2003) Effect of pegylation on pharmaceuticals Nat. Rev. Drug Discovery 2, 214-221
24. Joralemon, M. J., McRae, S., and Emrick, T. (2010) PEGylated polymers for medicine: from conjugation to self-assembled systems Chem. Commun. 46, 1377-1393
25. Munoz, E. M., Correa, J., Fernandez-Megia, E., and Riguera, R. (2009) Probing the relevance of lectin clustering for the reliable evaluation of multivalent carbohydrate recognition J. Am. Chem. Soc. 131, 17765-17767
26. Novoa-Carballal, R., Säwén, E., Fernandez-Megia, E., Correa, J., Riguera, R., and Widmalm, G. (2010) The dynamics of GATG glycodendrimers by NMR diffusion and quantitative 13C relaxation Phys. Chem. Chem. Phys. 12, 6587-6589
27. Sousa-Herves, A., Fernandez-Megia, E., and Riguera, R. (2008) Synthesis and supramolecular assembly of clicked anionic dendritic polymers into polyion complex micelles Chem. Commun. 3136-3138
28. Raviña, M., de la Fuente, M., Correa, J., Sousa-Herves, A., Pinto, J., Fernandez-Megia, E., Riguera, R., Sanchez, A., and Alonso, M. J. (2010) Core-shell dendriplexes with sterically induced stoichiometry for gene delivery Macromolecules 43, 6953-6961
29. Fernández-Trillo, F., Pacheco-Torres, J., Correa, J., Ballesteros, P., Lopez-Larrubia, P., Cerdán, S., Riguera, R., and Fernandez-Megia, E. (2011) Dendritic MRI contrast agents: an efficient prelabeling approach based on CuAAC Biomacromolecules 12, 2902-2907
30. Doménech, R., Abian, O., Bocanegra, R., Correa, J., Sousa-Herves, A., Riguera, R., Mateu, M. G., Fernandez-Megia, E., Velázquez-Campoy, A., and Neira, J. L. (2010) Dendrimers as potential inhibitors of the dimerization of the capsid protein of HIV-1 Biomacromolecules 11, 2069-2078
31. Ikeda, M., Minari, J., Shimada, N., Numata, M., Sakurai, K., and Shinkai, S. (2007) Complex formation between cationic β-1,3-glucan and hetero-sequence oligodeoxynucleotide and its delivery into macrophage-like cells to induce cytokine secretion Org. Biomol. Chem. 5, 2219-2224
32. Perumal, O. P., Inapagolla, R., Kannan, S., and Kannan, R. M. (2008) The effect of surface functionality on cellular trafficking of dendrimers Biomaterials 29, 3469-3476
33. Albertazzi, L., Serresi, M., Albanese, A., and Beltram, F. (2010) Dendrimer internalization and intracellular trafficking in living cells Mol. Pharmaceutics 7, 680-688
34. Hong, S., Bielinska, A. U., Mecke, A., Keszler, B., Beals, J. L., Shi, X., Balogh, L., Orr, B. G., Baker, J. R., Jr., and Banaszak Holl, M. M. (2004) Interaction of poly(amidoamine) dendrimers with supported lipid bilayers and cells: hole formation and the relation to transport Bioconjugate Chem. 15, 774-782
35. Albertazzi, L., Storti, B., Marchetti, L., and Beltram, F. (2010) Delivery and subcellular targeting of dendrimer-based fluorescent pH sensors in living cells J. Am. Chem. Soc. 132, 18158-18167
36. Kiessling, L. L., Young, T., Gruber, T. D., and Mortell, K. H. (2008) In Glycoscience (Fraser-Reid, Tatsuta, and Thiem, Eds.) pp 2483-2523, Springer, Berlin.
37. Dam, T. K. and Brewer, C. F. (2008) Effects of clustered epitopes in multivalent ligand-receptor interactions Biochemistry 47, 8470-8476
38. Lundquist, J. J. and Toone, E. J. (2002) The cluster glycoside effect Chem. Rev. 102, 555-578
39. Imberty, A., Chabre, Y. M., and Roy, R. (2008) Glycomimetics and glycodendrimers as high affinity microbial anti-adhesins Chem. - Eur. J. 14, 7490-7499
40. Vrasidas, I., de Mol, N. J., Liskamp, R. M. J., and Pieters, R. J. (2001) Synthesis of lactose dendrimers and multivalency effects in binding to the cholera toxin B subunit Eur. J. Org. Chem. 2001, 4685-4692
41. Arima, H., Yamashita, S., Mori, Y., Hayashi, Y., Motoyama, K., Hattori, K., Takeuchi, T., Jono, H., Ando, Y., Hirayama, F., and Uekama, K. (2010) In vitro and in vivo gene delivery mediated by lactosylated dendrimer/α- cyclodextrin conjugates (G2) into hepatocytes J. Controlled Release 146, 106-117
42. Hynes, R. O. (2002) Integrins: bidirectional, allosteric signaling machines Cell 110, 673-687
43. Desgrosellier, J. S. and Cheresh, D. A. (2010) Integrins in cancer: biological implications and therapeutic opportunities Nat. Rev. Cancer 10, 9-22
44. Welsh, D. J. and Smith, D. K. (2011) Comparing dendritic and self-assembly strategies to multivalency-RGD peptide-integrin interactions Org. Biomol. Chem. 9, 4795-4801 and references therein.
45. Burke, P. A., DeNardo, S. J., Miers, L. A., Lamborn, K. R., Matzku, S., and DeNardo, G. L. (2002) Cilengitide targeting of αvβ3 integrin receptor synergizes with radioimmunotherapy to increase efficacy and apoptosis in breast cancer xenografts Cancer Res. 62, 4263-4272
46. Mas-Moruno, C., Rechenmacher, F., and Kessler, H. (2010) Cilengitide: the first anti-angiogenic small molecule drug candidate. design, synthesis and clinical evaluation Anti-Cancer Agents Med. Chem. 10, 753-768
47. Reardon, D. A., Neyns, B., Weller, M., Tonn, J. C., Nabors, L. B., and Stupp, R. (2011) Cilengitide: an RGD pentapeptide αÎ1/2β3 and αÎ1/2β5 integrin inhibitor in development for glioblastoma and other malignancies Future Oncol. 7, 339-354
48. Rajendran, L., Knölker, H.-J., and Simons, K. (2010) Subcellular targeting strategies for drug design and delivery Nat. Rev. Drug Discovery 9, 29-42
49. Ulbrich, K. and Subr, V. (2004) Polymeric anticancer drugs with pH-controlled activation Adv. Drug Delivery Rev. 56, 1023-1050