Reduction-sensitive liposomes from a multifunctional lipid conjugate and natural phospholipids: Reduction and release kinetics and cellular uptake

Langmuir

Volumn 27, Issue 17, 2011, Pages 10820-10829

  Goldenbogen, Björn ^a   Brodersen, Nicolai ^a   Gramatica, Andrea ^a   Loew, Martin ^a   Liebscher, Jürgen ^a   Herrmann, Andreas ^a   Egger, Holger ^b   Budde, Bastian ^b   Arbuzova, Anna ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

^b BAYER AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE TARGETING; ANTI-CANCER THERAPIES; BIOTIN MOIETY; BREAST CANCER CELLS; CALCEIN; CELLULAR UPTAKE; DELIVERY SYSTEMS; DISULFIDE BONDS; DISULFIDE BRIDGE; DITHIOTHREITOL; ENVIRONMENTAL SENSITIVITIES; FUNCTIONALIZED; GLUTATHIONES; L-CYSTEINE; RELEASE KINETICS; RESONANCE ENERGY TRANSFER; STREPTAVIDIN; SUBSEQUENT REDUCTION; TRIS(2-CARBOXYETHYL) PHOSPHINE;

AMINO ACIDS; CELL CULTURE; COENZYMES; COVALENT BONDS; ENERGY TRANSFER; LIPOSOMES; PHOSPHORUS COMPOUNDS; PROTEINS;

PHOSPHOLIPIDS;

BIOTIN; CALCEIN; DISULFIDE; DOXORUBICIN; FLUORESCEIN DERIVATIVE; LIPID; LIPOSOME;

ARTICLE; BREAST TUMOR; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DELIVERY SYSTEM; DRUG EFFECT; FEMALE; FLUORESCENCE MICROSCOPY; HUMAN; KINETICS; MACROPHAGE; METABOLISM; OXIDATION REDUCTION REACTION; PARTICLE SIZE; SURFACE PROPERTY; TISSUE DISTRIBUTION; TUMOR CELL LINE;

BIOTIN; BREAST NEOPLASMS; CELL LINE, TUMOR; DISULFIDES; DOXORUBICIN; DRUG DELIVERY SYSTEMS; FEMALE; FLUORESCEINS; HUMANS; KINETICS; LIPIDS; LIPOSOMES; MACROPHAGES; MICROSCOPY, FLUORESCENCE; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PARTICLE SIZE; SURFACE PROPERTIES; TISSUE DISTRIBUTION;

EID: 80052219412     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la201160y     Document Type: Article

References (58)

1. Allen, T. M.; Cullis, P. R. Science 2004, 303, 1818-1822
2. Guo, X.; Szoka, F. C., Jr. Acc. Chem. Res. 2003, 36, 335-341
3. Torchilin, V. Eur. J. Pharm. Biopharm. 2009, 71, 431-444
4. Riehemann, K.; Schneider, S. W.; Luger, T. A.; Godin, B.; Ferrari, M.; Fuchs, H. Angew. Chem., Int. Ed. 2009, 48, 872-897
5. Davis, M. E.; Chen, Z. G.; Shin, D. M. Nat. Rev. Drug Discovery 2008, 7, 771-782
6. Leonard, R. C.; Williams, S.; Tulpule, A.; Levine, A. M.; Oliveros, S. Breast 2009, 18, 218-224
7. Tai, W.; Mahato, R.; Cheng, K. J. Controlled Release 2010, 146, 264-275
8. Maeda, T.; Fujimoto, K. Colloids Surf., B 2006, 49, 15-21
9. Chen, Z. G. Trends Mol. Med. 2010, 16, 594-602
10. Farokhzad, O. C.; Langer, R. ACS Nano 2009, 3, 16-20
11. Davidsen, J.; Jorgensen, K.; Andresen, T. L.; Mouritsen, O. G. Biochim. Biophys. Acta 2003, 1609, 95-101
12. Kirpotin, D.; Hong, K.; Mullah, N.; Papahadjopoulos, D.; Zalipsky, S. FEBS Lett. 1996, 388, 115-118
13. Zalipsky, S.; Qazen, M.; Walker, J. A., II; Mullah, N.; Quinn, Y. P.; Huang, S. K. Bioconjugate Chem. 1999, 10, 703-707
14. Zhang, J.; Chua, L. S.; Lynn, D. M. Langmuir 2004, 20, 8015-8021
15. Oumzil, K.; Khiati, S.; Grinstaff, M. W.; Barthélémy, P. J. Controlled Release 2011, 151, 123-130
16. Cerritelli, S.; Velluto, D.; Hubbell, J. A. Biomacromolecules 2007, 8, 1966-1972
17. Sun, Y.; Yan, X.; Yuan, T.; Liang, J.; Fan, Y.; Gu, Z.; Zhang, X. Biomaterials 2010, 31, 7124-7131
18. Ryu, J. H.; Roy, R.; Ventura, J.; Thayumanavan, S. Langmuir 2010, 26, 7086-7092
19. Ong, W.; Yang, Y.; Cruciano, A. C.; McCarley, R. L. J. Am. Chem. Soc. 2008, 130, 14739-14744
20. Ganta, S.; Devalapally, H.; Shahiwala, A.; Amiji, M. J. Controlled Release 2008, 126, 187-204
21. Saito, G.; Swanson, J. A.; Lee, K. D. Adv. Drug Delivery Rev. 2003, 55, 199-215
22. Zelikin, A. N.; Quinn, J. F.; Caruso, F. Biomacromolecules 2006, 7, 27-30
23. Meng, F.; Hennink, W. E.; Zhong, Z. Biomaterials 2009, 30, 2180-2198
24. Kim, E.; Kim, D.; Jung, H.; Lee, J.; Paul, S.; Selvapalam, N.; Yang, Y.; Lim, N.; Park, C. G.; Kim, K. Angew. Chem., Int. Ed. 2010, 49, 4405-4408
25. Yang, J.; Chen, H.; Vlahov, I. R.; Cheng, J. X.; Low, P. S. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 13872-13877
26. West, K. R.; Otto, S. Curr. Drug Discovery Technol. 2005, 2, 123-160
27. Ballatori, N.; Krance, S. M.; Notenboom, S.; Shi, S.; Tieu, K.; Hammond, C. L. Biol. Chem. 2009, 390, 191-214
28. Arner, E. S.; Holmgren, A. Semin. Cancer Biol. 2006, 16, 420-426
29. Arbuzova, A.; Schwarz, G. Biochim. Biophys. Acta 1999, 1420, 139-152
30. Kurz, A.; Bunge, A.; Windeck, A. K.; Rost, M.; Flasche, W.; Arbuzova, A.; Strohbach, D.; Müller, S.; Liebscher, J.; Huster, D.; Herrmann, A. Angew. Chem., Int. Ed. 2006, 45, 4440-4444
31. Loew, M.; Springer, R.; Scolari, S.; Altenbrunn, F.; Seitz, O.; Liebscher, J.; Huster, D.; Herrmann, A.; Arbuzova, A. J. Am. Chem. Soc. 2010, 132, 16066-16072
32. Pescador, P.; Brodersen, N.; Scheidt, H. A.; Loew, M.; Holland, G.; Bannert, N.; Liebscher, J.; Herrmann, A.; Huster, D.; Arbuzova, A. Chem. Commun. 2010, 46, 5358-5360
33. Rigler, P.; Meier, W. J. Am. Chem. Soc. 2006, 128, 367-373
34. Lin, J. J.; Ghoroghchian, P. P.; Zhang, Y.; Hammer, D. A. Langmuir 2006, 22, 3975-3979
35. Verderone, G.; Van Craynest, N.; Boussif, O.; Santaella, C.; Bischoff, R.; Kolbe, H. V.; Vierling, P. J. Med. Chem. 2000, 43, 1367-1379
36. Shirude, P.; Kumar, V.; Ganesh, K. Eur. J. Org. Chem. 2005, 2005, 5207-5215
37. Hope, M. J.; Bally, M. B.; Webb, G.; Cullis, P. R. Biochim. Biophys. Acta 1985, 812, 55-65
38. Allen, T. M.; Cleland, L. G. Biochim. Biophys. Acta 1980, 597, 418-426
39. Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 3 rd ed.; Springer: New York, 2006.
40. Stryer, L. Annu. Rev. Biochem. 1978, 47, 819-846
41. Smith, C. V.; Jones, D. P.; Guenthner, T. M.; Lash, L. H.; Lauterburg, B. H. Toxicol. Appl. Pharmacol. 1996, 140, 1-12
42. Hynes, N. E.; Lane, H. A. Nat. Rev. Cancer 2005, 5, 341-354
43. Slamon, D. J.; Godolphin, W.; Jones, L. A.; Holt, J. A.; Wong, S. G.; Keith, D. E.; Levin, W. J.; Stuart, S. G.; Udove, J.; Ullrich, A. Science 1989, 244, 707-712
44. Jones, K. L.; Buzdar, A. U. Lancet Oncol. 2009, 10, 1179-1187
45. Press, M. F.; Cordon-Cardo, C.; Slamon, D. J. Oncogene 1990, 5, 953-962
46. Park, J. W.; Hong, K.; Kirpotin, D. B.; Colbern, G.; Shalaby, R.; Baselga, J.; Shao, Y.; Nielsen, U. B.; Marks, J. D.; Moore, D.; Papahadjopoulos, D.; Benz, C. C. Clin. Cancer Res. 2002, 8, 1172-1181
47. Burks, S. R.; Macedo, L. F.; Barth, E. D.; Tkaczuk, K. H.; Martin, S. S.; Rosen, G. M.; Halpern, H. J.; Brodie, A. M.; Kao, J. P. Breast Cancer Res. Treat. 2010, 124, 121-131
48. Müller, C. E.; Roth, H. J. Arch. Pharm. (Weinheim) 1989, 322, 343-350
49. Lewis Phillips, G. D.; Li, G.; Dugger, D. L.; Crocker, L. M.; Parsons, K. L.; Mai, E.; Blattler, W. A.; Lambert, J. M.; Chari, R. V.; Lutz, R. J.; Wong, W. L.; Jacobson, F. S.; Koeppen, H.; Schwall, R. H.; Kenkare-Mitra, S. R.; Spencer, S. D.; Sliwkowski, M. X. Cancer Res. 2008, 68, 9280-9290
50. Müller, C. E.; Daniel, P. T.; Holzschuh, J.; Roth, H. J. Int. J. Pharm. 1989, 57, 41-47
51. Liem, A. A.; Appleyard, M. V.; O'Neill, M. A.; Hupp, T. R.; Chamberlain, M. P.; Thompson, A. M. Br. J. Cancer 2003, 88, 1281-1284
52. Cullis, P. R.; de Kruijff, B. Biochim. Biophys. Acta 1979, 559, 399-420
53. Cullis, P. R.; de Kruijff, B. Biochim. Biophys. Acta 1978, 513, 31-42
54. Gawrisch, K.; Parsegian, V. A.; Hajduk, D. A.; Tate, M. W.; Graner, S. M.; Fuller, N. L.; Rand, R. P. Biochemistry 1992, 31, 2856-2864
55. Goni, F. M.; Alonso, A. Prog. Lipid Res. 1999, 38, 1-48
56. Connor, J.; Yatvin, M. B.; Huang, L. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 1715-1718
57. Boomer, J. A.; Inerowicz, H. D.; Zhang, Z.-Y.; Bergstrand, N.; Edwards, K.; Kim, J.-M.; Thompson, D. H. Langmuir 2003, 19, 6408-6415
58. Whitesides, G. M.; Lilburn, J. E.; Szajewski, R. P. J. Org. Chem. 1977, 42, 332-338