Fluorinated lipid constructs permit facile passage of molecular cargo into living cells

Journal of the American Chemical Society

Volumn 131, Issue 34, 2009, Pages 12091-12093

  Dafik, Laila ^a   Kalsani, Venkateshwarlu ^a   Leung, Anthony Kar Lun ^b   Kumar, Krishna ^a,c  

^a TUFTS UNIVERSITY   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^c TUFTS MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BOUND PROTEINS; CELL SURFACES; CLATHRINS; ENDOCYTIC PATHWAYS; ENERGY DEPENDENT; LIVING CELL; SHORT INTERFERING RNA;

CELL MEMBRANES; CYTOLOGY; HYDROCARBONS; NANOCAPSULES;

LIPIDS;

CLATHRIN; FLUORESCEIN ISOTHIOCYANATE DEXTRAN; HYDROCARBON; LIPID; MOLECULAR MOTOR; SMALL INTERFERING RNA;

ARTICLE; CELL MEMBRANE; CELL MEMBRANE PERMEABILITY; CELL STRAIN HL 60; CELL SURFACE; ENDOCYTOSIS; ENERGY TRANSFER; FLOW CYTOMETRY; FLUORESCENCE MICROSCOPY; FLUORINATION; HELA CELL; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; INTERNALIZATION; LIPID TRANSPORT; MACROMOLECULE; PROTEIN BINDING; PROTEIN FOLDING; TRANSPORT KINETICS;

BIOLOGICAL TRANSPORT; CELL SURVIVAL; ENDOCYTOSIS; FLOW CYTOMETRY; HALOGENATION; HELA CELLS; HUMANS; MICROSCOPY, FLUORESCENCE; PHOSPHATIDYLETHANOLAMINES;

EID: 69349095898     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja902777d     Document Type: Article

References (40)

1. Conner, S. D.; Schmid, S. L. Nature 2003, 422, 37-44.
2. Smith, D. A.; van de Waterbeemd, H. Curr. Opin. Chem. Biol. 1999, 3, 373-378.
3. Doerr, A. Nat. Methods 2006, 3, 770-771.
4. Kam, N. W. S.; Liu, Z. A.; Dai, H. J. Angew. Chem., Int. Ed. 2006, 45, 577-581.
5. Morris, M. C.; Depollier, J.; Mery, J.; Heitz, F.; Divita, G. Nat. Biotechnol. 2001, 19, 1173-1176.
6. Yan, X. H.; He, Q.; Wang, K. W.; Duan, L.; Cui, Y.; Li, J. B. Angew. Chem., Int. Ed. 2007, 46, 2431-2434.
7. Rothbard, J. B.; Garlington, S.; Lin, Q.; Kirschberg, T.; Kreider, E.; McGrane, P. L.; Wender, P. A.; Khavari, P. A. Nat. Med. 2000, 6, 1253-1257.
8. Okuyama, M.; Laman, H.; Kingsbury, S. R.; Visintin, C.; Leo, E.; Eward, K. L.; Stoeber, K.; Boshoff, C.; Williams, G. H.; Selwood, D. L. Nat. Methods 2007, 4, 153-159.
9. Feazell, R. P.; Nakayama-Ratchford, N.; Dai, H.; Lippard, S. J. J. Am. Chem. Soc. 2007, 129, 8438.
10. Kostarelos, K.; Lacerda, L.; Pastorin, G.; Wu, W.; Wieckowski, S.; Luangsivilay, J.; Godefroy, S.; Pantarotto, D.; Briand, J. P.; Muller, S.; Prato, M.; Bianco, A. Nat. Nanotechnol. 2007, 2, 108-113.
11. Chen, X.; Tam, U. C.; Czlapinski, J. L.; Lee, G. S.; Rabuka, D.; Zettl, A.; Bertozzi, C. R. J. Am. Chem. Soc. 2006, 128, 6292-6293.
12. Kam, N. W. S.; O'Connell, M.; Wisdom, J. A.; Dai, H. J. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 11600-11605.
13. Liu, Z.; Cai, W. B.; He, L. N.; Nakayama, N.; Chen, K.; Sun, X. M.; Chen, X. Y.; Dai, H. J. Nat. Nanotechnol. 2007, 2, 47-52.
14. Jones, M. N. Liposomes, Pt E; Elsevier Academic Press Inc: San Diego, CA, 2005; Vol.391, pp 211-228.
15. Torchilin, V. P. Nat. Rev. Drug Discovery 2005, 4, 145-160.
16. Ng, P. P.; Dela Cruz, J. S.; Sorour, D. N.; Stinebaugh, J. M.; Shin, S. U.; Shin, D. S.; Morrison, S. L.; Penichet, M. L. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 10706-10711.
17. Mayor, S.; Pagano, R. E. Nat. Rev. Mol. Cell Biol. 2007, 8, 603-612.
18. Peterson, B. R. Org. Biomol. Chem. 2005, 3, 3607-3612.
19. Boonyarattanakalin, S.; Martin, S. E.; Dykstra, S. A.; Peterson, B. R. J. Am. Chem. Soc. 2004, 126, 16379-16386.
20. Sun, Q.; Cai, S.; Peterson, B. R. J. Am. Chem. Soc. 2008, 130, 10064-10065.
21. Nabi, I. R.; Le, P. U. J. Cell Biol. 2003, 161, 673-677.
22. Pelkmans, L.; Fava, E.; Grabner, H.; Hannus, M.; Habermann, B.; Krausz, E.; Zerial, M. Nature 2005, 436, 78-86.
23. (a) Yoder, N. C.; Kalsani, V.; Schuy, S.; Vogel, R.; Janshoff, A.; Kumar, K. J. Am. Chem. Soc. 2007, 129, 9037-9043.
24. (b) Yoder, N. C.; Yüksel, D.; Dafik, L.; Kumar, K. Curr. Opin. Chem. Biol. 2006, 10, 576-583.
25. (c) Schuy, S.; Faiss, S.; Yoder, N. C.; Kalsani, V.; Kumar, K.; Janshoff, A.; Vogel, R. J. Phys. Chem. B 2008, 112, 8250-8256.
26. Schuy, S.; Faiss, S.; Yoder, N. C.; Kalsani, V.; Kumar, K.; Janshoff, A.; Vogel, R. J. Phys. Chem. B 2008, 112, 8250-8256.
27. Bilgiçer, B.; Fichera, A.; Kumar, K. J. Am. Chem. Soc. 2001, 123, 4393-4399.
28. Bilgiçer, B.; Kumar, K. Tetrahedron 2002, 58, 4105-4112.
29. Bilgiçer, B.; Kumar, K. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 15324-15329.
30. Bilgiçer, B.; Xing, X.; Kumar, K. J. Am. Chem. Soc. 2001, 123, 11815-11816.
31. Myers, K. E.; Kumar, K. J. Am. Chem. Soc. 2000, 122, 12025-12026.
32. Krafft, M. P. Adv. Drug Delivery Rev. 2001, 47, 209-228.
33. Grant, A. M.; Hanson, P. K.; Nichols, J. W. Traffic 2008, 2, 37-50.
34. Hanson, P. K.; Grant, A. M.; Nichols, J. W. J. Cell Sci. 2002, 115, 2725-2733.
35. Liu, X. Y.; Stocker, B. L.; Seeberger, P. H. J. Am. Chem. Soc. 2006, 128, 3638-3648.
36. Smythe, E.; Warren, G. Eur. J. Biochem. 1991, 202, 689-699.
37. Schmid, S. L.; Carter, L. L. J. Cell Biol. 1990, 111, 2307-2318.
38. Heuser, J. E.; Anderson, R. G. W. J. Cell Biol. 1989, 108, 389-400.
39. Hussey, S. L.; Peterson, B. R. J. Am. Chem. Soc. 2002, 124, 6265-6273.
40. Powers, D. D.; Willard, B. L.; Carbonell, R. G.; Kilpatrick, P. K. Biotechnol. Prog. 1992, 8, 436-453.