Recognition-mediated activation of therapeutic gold nanoparticles inside living cells

Nature Chemistry

Volumn 2, Issue 11, 2010, Pages 962-966

  Kim, Chaekyu ^a   Agasti, Sarit S ^a   Zhu, Zhengjiang ^a   Isaacs, Lyle ^b   Rotello, Vincent M ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GOLD; METAL NANOPARTICLE;

ARTICLE; CELL SURVIVAL; CHEMISTRY; HUMAN; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARTICLE SIZE; SURFACE PROPERTY; TRANSMISSION ELECTRON MICROSCOPY; TUMOR CELL LINE; ULTRAVIOLET SPECTROPHOTOMETRY;

CELL LINE, TUMOR; CELL SURVIVAL; GOLD; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; METAL NANOPARTICLES; MICROSCOPY, ELECTRON, TRANSMISSION; PARTICLE SIZE; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET; SURFACE PROPERTIES;

EID: 78049321711     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.858     Document Type: Article

References (47)

1. Lehn, J.-M. Toward self-organization and complex matter. Science 295, 2400-2403 (2002).
2. Lehn, J.-M. From supramolecular chemistry towards constitutional dynamic chemistry and adaptive chemistry. Chem. Soc. Rev. 36, 151-160 (2007).
3. Reinhoudt, D. N. & Crego-Calama, M. Synthesis beyond the molecule. Science 295, 2403-2407 (2002).
4. Yaghi, O. M. et al. Reticular synthesis and the design of new materials. Nature 423, 705-714 (2003)
5. Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives (VCH, 1995).
6. Dankers, P. Y. W., Harmsen, M. C., Brouwer, L. A., Van Luyn, M. J. A. & Meijer, E. W. A modular and supramolecular approach to bioactive scaffolds for tissue engineering. Nature Mater. 4, 568-574 (2005).
7. Hennig, A., Bakirci, H. & Nau, W. M. Label-free continuous enzyme assays with macrocycle fluorescent dye complexes. Nature Methods 4, 629-632 (2007).
8. Klajn, R. et al. Dynamic hook-and-eye nanoparticle sponges. Nature Chem. 1, 733-738 (2009).
9. Angelos, S., Yang, Y.-W., Patel, K., Stoddart, J. F. & Zink, J. I. p H-responsive supramolecular nanovalves based on cucurbit[6]uril pseudorotaxanes. Angew. Chem. Int. Ed. 47, 2222-2226 (2008).
10. Angelos, S. et al. p H clock-operated mechanized nanoparticles. J. Am. Chem. Soc. 131, 12912-12914 (2009).
11. Coti, K. K. et al. Mechanised nanoparticles for drug delivery. Nanoscale 1, 16-39 (2009).
12. Lee, H. K. et al. Vesicle formed by amphiphilc cucurbit[6]uril: versatile, noncovalent modification of the vesicle surface and multivalent binding of sugar-decorated vesicles to lectin. J. Am. Chem. Soc. 127, 5006-5007 (2005).
13. Park, C., Oh, K., Lee, S. C. & Kim, C. Controlled release of guest molecules from mesoporous silica particles based on a p H-responsive polypseudorotaxane motif. Angew. Chem. Int. Ed. 46, 1455-1457 (2007).
14. Du, L., Liao, S., Khatib, H. A., Stoddart, J. F. & Zink, J. I. Controlled-access hollow mechanized silica nanocontainers. J. Am. Chem. Soc. 131, 15136-15142 (2009).
15. Hayashida, O. & Uchiyama, M. Multivalent macrocyclic hosts: histone surface recognition, guest binding and delivery by cyclophane-based resorcinarene oligomers. J. Org. Chem. 72, 610-616 (2007).
16. Sansone, F. et al. DNA condensation and cell transfection properties of guanidinium calixarenes: dependence on macrocycle lipophilicity, size and conformation. J. Am. Chem. Soc. 128, 14528-14536 (2006).
17. Weimann, D. P., Winkler, H. D. F., Falenski, J. A., Koksch, B. & Schalley, C. A. Highly dynamic motion of crown ethers along oligolysine peptide chains. Nature Chem. 1, 573-577 (2009).
18. Darwish, I. A. & Uchegbu, I. F. The evaluation of crown ether based niosomes as cation containing and cation sensitive drug delivery systems. Int. J. Pharm. 159, 207-213 (1997).
19. Lee, J. W., Samal, S., Selvapalam, N., Kim, H.-J. & Kim, K. Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry. Acc. Chem. Res. 36, 621-630 (2003).
20. Kim, K. et al. Functionalized cucurbiturils and their applications. Chem. Soc. Rev. 36, 267-279 (2007).
21. Lagona, J., Mukhopadhyay, P., Chakrabarti, S. & Isaacs, L. The cucurbit[n]uril family. Angew. Chem. Int. Ed. 44, 4844-4870 (2005).
22. Wheate, N. J. et al. Multi-nuclear platinum complexes encapsulated in cucurbit[n]uril as an approach to reduce toxicity in cancer treatment. Chem. Commun. 1424-1425 (2004).
23. Jeon, Y. J. et al. Novel molecular drug carrier: encapsulation of oxaliplatin in cucurbit[7]uril and its effects on stability and reactivity of the drug. Org. Biomol. Chem. 3, 2122-2125 (2005).
24. Wheate, N. J. Improving platinum(II)-based anticancer drug delivery using cucurbit[n]urils. J. Inorg. Biochem. 102, 2060-2066 (2008).
25. Wheate, N. J., Buck, D. P., Day, A. I. & Collins, J. G. Cucurbit[n]uril binding of platinum anticancer complexes. Dalton Trans. 451-458 (2006).
26. Lim, Y. B. et al. Self-assembled ternary complex of cationic dendrimer, cucurbituril and DNA: noncovalent strategy in developing a gene delivery carrier. Bioconjugate Chem. 13, 1181-1185 (2002).
27. Kim, S. K. et al. Galactosylated cucurbituril-inclusion polyplex for hepatocyte-targeted gene delivery. Chem. Commun. 46, 692-694 (2010).
28. Angelos, S., Yang, Y. W., Khashab, N. M., Stoddart, J. F. & Zink, J. I. Dual-controlled nanoparticles exhibiting AND logic. J. Am. Chem. Soc. 131, 11344-11346 (2009).
29. Ghosh, S. & Isaacs, L. Biological catalysis regulated by cucurbit[7]uril molecular containers. J. Am. Chem. Soc. 132, 4445-4454 (2010).
30. Templeton, A. C., Wuelfing, M. P. & Murray, R. W. Monolayer protected cluster molecules. Acc. Chem. Res. 33, 27-36 (2000).
31. Liu, S. M. et al. The cucurbit[n]uril family: prime components for self-sorting systems. J. Am. Chem. Soc. 127, 15959-15967 (2005).
32. Lee, J. W., Ko, Y. H., Park, S. H., Yamaguchi, K. & Kim, K. Novel pseudorotaxane-terminated dendrimers: supramolecular modification of dendrimer periphery. Angew. Chem. Int. Ed. 40, 746-749 (2001). (Pubitemid 32179735)
33. Davies, W. L. et al. Antiviral activity of 1-adamantanamine (amantadine). Science 144, 862-863 (1964).
34. Maassab, H. F. & Cochran, K. W. Rubella virus-inhibition in vitro by amantadine hydrochloride. Science 145, 1443-1444 (1964).
35. Hagan, J. J., Middlemiss, D. N., Sharpe, P. C. & Poste, G. H. Parkinson's disease: prospects for improved drug therapy. Trends Pharmacol. Sci. 18, 156-163 (1997).
36. Zhu, Z. J., Ghosh, P. S., Miranda, O. R., Vachet, R. W. & Rotello, V. M. Multiplexed screening of cellular uptake of gold nanoparticles using laser desorption/ionization mass spectrometry. J. Am. Chem. Soc. 130, 14139-14143 (2008).
37. Kim, C. K. et al. Entrapment of hydrophobic drugs in nanoparticle monolayers with efficient release into cancer cells. J. Am. Chem. Soc. 131, 1360-1361 (2009).
38. Godbey, W. T., Wu, K. K. & Mikos, A. G. Poly(ethylenimine) and its role in gene delivery. J. Controlled Release 60, 149-160 (1999).
39. Leroueil, P. R. et al. Wide varieties of cationic nanoparticles induce defects in supported lipid bilayers. Nano Lett. 8, 420-424 (2008).
40. Fischer, D., Bieber, T., Li, Y. X., Elsasser, H. P. & Kissel, T. A novel non-viral vector for DNA delivery based on low molecular weight, branched polyethylenimine: effect of molecular weight on transfection efficiency and cytotoxicity. Pharm. Res. 16, 1273-1279 (1999).
41. Ghosh, P. S., Kim, C. K., Han, G., Forbes, N. S. & Rotello, V. M. Efficient gene delivery vectors by tuning the surface charge density of amino acid-functionalized gold nanoparticles. ACS Nano 2, 2213-2218 (2008).
42. Lovric, J. et al. Differences in subcellular distribution and toxicity of green and red emitting Cd Te quantum dots. J. Mol. Med. 83, 377-385 (2005).
43. Goodman, C. M., McCusker, C. D., Yilmaz, T. & Rotello, V. M. Toxicity of gold nanoparticles functionalized with cationic and anionic side chains. Bioconjugate Chem. 15, 897-900 (2004).
44. Fuller, J. E. et al. Intracellular delivery of core-shell fluorescent silica nanoparticles. Biomaterials 29, 1526-1532 (2008).
45. Verma, A. et al. Surface-structure-regulated cell-membrane penetration by monolayer-protected nanoparticles. Nature Mater. 7, 588-595 (2008).
46. Taylor, S. K. et al. Triggered release of an active peptide conjugate from a DNA device by an orally administrable small molecule. Angew. Chem. Int. Ed. 48, 4394-4397 (2009).
47. Sarkar, D. et al. Dual cancer-specific targeting strategy cures primary and distant breast carcinomas in nude mice. Proc. Natl Acad. Sci. USA 102, 14034-14039 (2005).