Controlled release from cleavable polymerized liposomes upon redox and pH stimulation

Bioconjugate Chemistry

Volumn 22, Issue 4, 2011, Pages 523-528

  Zhang, Shiyong ^a   Zhao, Yan ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPOUNDS; CROSSLINKING; SULFUR COMPOUNDS; SURFACE REACTIONS;

ANIONIC LIPIDS; AZIDE GROUP; CLICK REACTION; CONTROLLED RELEASE; CROSSLINKER; GALLATE DERIVATIVES; LARGE UNILAMELLAR VESICLES; PHOSPHATIDYL CHOLINE; PHOSPHOETHANOLAMINE; PROPARGYL;

LIPOSOMES;

AZIDE; CLEAVABLE POLYMERIZED LIPOSOME; DISULFIDE; LIPID; LIPOSOME; PALMITOYL OLEOYL PHOSPHATIDYL CHOLINE; PALMITOYL OLEOYL PHOSPHOETHANOLAMINE; THIOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CONTROLLED DRUG RELEASE; CROSS LINKING; HYDROPHOBICITY; OXIDATION REDUCTION REACTION; PH; POLYMERIZATION;

EID: 79954998832     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc1003197     Document Type: Article

References (70)

1. New, R. R. C. (1990) Liposomes: a practical approach; IRL Press; Oxford University Press: Oxford.
2. Philippot, J. R. and Schuber, F. (1995) Liposomes as tools in basic research and industry; CRC Press: Boca Raton.
3. Gregoriadis, G. (2007) Liposome technology, 3 rd ed.; Informa Healthcare: New York.
4. Drummond, D. C., Meyer, O., Hong, K., Kirpotin, D. B., and Papahadjopoulos, D. (1999) Optimizing liposomes for delivery of chemotherapeutic agents to solid tumors Pharmacol. Rev. 51, 691-743
5. Guo, X. and Szoka, F. C., Jr. (2003) Chemical approaches to triggerable lipid vesicles for drug and gene delivery Acc. Chem. Res. 36, 335-341
6. Allen, T. M. and Cullis, P. R. (2004) Drug delivery systems: entering the mainstream Science 303, 1818-22 (Pubitemid 38374867)
7. Drummond, D. C., Noble, C. O., Hayes, M. E., Park, J. W., and Kirpotin, D. B. (2008) Pharmacokinetics and in vivo drug release rates in liposomal nanocarrier development J. Pharm. Sci. 97, 4696-740
8. Yatvin, M. B., Kreutz, W., Horwitz, B. A., and Shinitzky, M. (1980) pH-sensitive liposomes: Possible clinical implications Science 210, 1253-5 (Pubitemid 11178014)
9. Thomas, J. L. and Tirrell, D. A. (1992) Polyelectrolyte-sensitized phospholipid-vesicles Acc. Chem. Res. 25, 336-342
10. Chu, C. -J., Dijkstra, J., Lai, M. -Z., Hong, K., and Szoka, F. C. (1990) Efficiency of cytoplasmic delivery by pH-sensitive liposomes to cells in culture Pharm. Res. 7, 824-34 (Pubitemid 20332534)
11. Kirpotin, D., Hong, K. L., Mullah, N., Papahadjopoulos, D., and Zalipsky, S. (1996) Liposomes with detachable polymer coating: Destabilization and fusion of dioleoylphosphatidylethanolamine vesicles triggered by cleavage of surface-grafted poly(ethylene glycol) FEBS Lett. 388, 115-118 (Pubitemid 26226342)
12. Gerasimov, O. V., Boomer, J. A., Qualls, M. M., and Thompson, D. H. (1999) Cytosolic drug delivery using pH- and light-sensitive liposomes Adv. Drug Delivery Rev. 38, 317-338 (Pubitemid 29376580)
13. Drummond, D. C., Zignani, M., and Leroux, J. -C. (2000) Current status of pH-sensitive liposomes in drug delivery Prog. Lipid Res. 39, 409-60
14. Zhu, J., Munn, R. J., and Nantz, M. H. (2000) Self-cleaving ortho ester lipids: A new class of pH-vulnerable amphiphiles J. Am. Chem. Soc. 122, 2645-2646 (Pubitemid 30211978)
15. Guo, X. and Szoka, F. C., Jr. (2001) Steric stabilization of fusogenic liposomes by a low-pH sensitive PEG-diortho ester-lipid conjugate Bioconjugate Chem. 12, 291-300 (Pubitemid 32235482)
16. Guo, X., MacKay, J. A., and Szoka, F. C., Jr. (2003) Mechanism of pH-triggered collapse of phosphatidylethanolamine liposomes stabilized by an ortho ester polyethyleneglycol lipid Biophys. J. 84, 1784-95 (Pubitemid 36322940)
17. Zhang, J. X., Zalipsky, S., Mullah, N., Pechar, M., and Allen, T. M. (2004) Pharmaco attributes of dioleoylphosphatidylethanolamine/ cholesterylhemisuccinate liposomes containing different types of cleavable lipopolymers Pharmacol. Res. 49, 185-198 (Pubitemid 37485715)
18. Fattal, E., Couvreur, P., and Dubernet, C. (2004) Smart" delivery of antisense oligonucleotides by anionic pH-sensitive liposomes Adv. Drug Delivery Rev. 56, 931-46 (Pubitemid 38520202)
19. Sawant, R. M., Hurley, J. P., Salmaso, S., Kale, A., Tolcheva, E., Levchenko, T. S., and Torchilin, V. P. (2006) SMART" drug delivery systems: Double-targeted pH-responsive pharmaceutical nanocarriers Bioconjugate Chem. 17, 943-949 (Pubitemid 44162612)
20. Meers, P. (2001) Enzyme-activated targeting of liposomes Adv. Drug Delivery Rev. 53, 265-72 (Pubitemid 34026337)
21. Davidsen, J., Jorgensen, K., Andresen, T. L., and Mouritsen, O. G. (2003) Secreted phospholipase A(2) as a new enzymatic trigger mechanism for localised liposomal drug release and absorption in diseased tissue Biochim. Biophys. Acta, Biomembr. 1609, 95-101 (Pubitemid 36044070)
22. Andresen, T. L., Jensen, S. S., Kaasgaard, T., and Jorgensen, K. (2005) Triggered activation and release of liposomal prodrugs and drugs in cancer tissue by secretory phospholipase A2 Curr. Drug Delivery 2, 353-62 (Pubitemid 41277767)
23. Sarkar, N., Banerjee, J., Hanson, A. J., Elegbede, A. I., Rosendahl, T., Krueger, A. B., Banerjee, A. L., Tobwala, S., Wang, R., Lu, X., Mallik, S., and Srivastava, D. K. (2008) Matrix metalloproteinase-assisted triggered release of liposomal contents Bioconjugate Chem. 19, 57-64 (Pubitemid 351213835)
24. Rosoff, M. (1996) Vesicles; Marcel Dekker: New York.
25. Tang, F. and Hughes, J. A. (1998) Introduction of a disulfide bond into a cationic lipid enhances transgene expression of plasmid DNA Biochem. Biophys. Res. Commun. 242, 141-145 (Pubitemid 28412392)
26. Zalipsky, S., Qazen, M., Walker, J. A., 2nd, Mullah, N., Quinn, Y. P., and Huang, S. K. (1999) New detachable poly(ethylene glycol) conjugates: Cysteine-cleavable lipopolymers regenerating natural phospholipid, diacyl phosphatidylethanolamine Bioconjugate Chem. 10, 703-7 (Pubitemid 29456355)
27. Ong, W., Yang, Y., Cruciano, A. C., and McCarley, R. L. (2008) Redox-triggered contents release from liposomes J. Am. Chem. Soc. 130, 14739-44
28. Zhang, Z. -Y. and Smith, B. D. (1999) Synthesis and characterization of NVOC-DOPE, a caged photoactivatable derivative of dioleoylphosphatidylethanolamine Bioconjugate Chem. 10, 1150-2
29. Shum, P., Kim, J. -M., and Thompson, D. H. (2001) Phototriggering of liposomal drug delivery systems Adv. Drug Delivery Rev. 53, 273-84 (Pubitemid 34024910)
30. Bisby, R. H., Mead, C., and Morgan, C. G. (2000) Active uptake of drugs into photosensitive liposomes and rapid release on UV photolysis Photochem. Photobiol. 72, 57-61
31. Bisby, R. H., Mead, C., and Morgan, C. G. (2000) Wavelength-programmed solute release from photosensitive liposomes Biochem. Biophys. Res. Commun. 276, 169-73
32. Kobuke, Y. and Ohgoshi, A. (2000) Supramolecular ion channel containing trans-azobenzene for photocontrol of ionic fluxes Colloids Surf., A 169, 187-197 (Pubitemid 30227399)
33. Huang, Z. and Szoka, F. C., Jr. (2008) Sterol-modified phospholipids: Cholesterol and phospholipid chimeras with improved biomembrane properties J. Am. Chem. Soc. 130, 15702-12
34. Huang, Z., Jaafari, M. R., and Szoka, F. C., Jr. (2009) Disterolphospholipids: Nonexchangeable lipids and their application to liposomal drug delivery Angew. Chem., Int. Ed. 48, 4146-9
35. Lee, S. -M., Chen, H. M., OHalloran, T. V., and Nguyen, S. T. (2009) Clickable" polymer-caged nanobins as a modular drug delivery platform J. Am. Chem. Soc. 131, 9311-9320
36. Mueller, A. and OBrien, D. F. (2002) Supramolecular materials via polymerization of mesophases of hydrated amphiphiles Chem. Rev. 102, 727-57 (Pubitemid 35381632)
37. Ringsdorf, H., Schlarb, B., and Venzmer, J. (1988) Molecular architecture and function of polymeric oriented systems-models for the study of organization, surface recognition, and dynamics of biomembranes Angew. Chem., Int. Ed. Engl. 27, 113-158 (Pubitemid 18043271)
38. Fendler, J. H. and Tundo, P. (1984) Polymerized surfactant aggregates-characterization and utilization Acc. Chem. Res. 17, 3-8
39. Higashi, N., Adachi, T., and Niwa, M. (1990) A novel 2-dimensional photopolymerization at an oriented bilayer surface-effective molecular-weight control using membrane state and chain transfer Macromolecules 23, 1475-1480 (Pubitemid 20659556)
40. Fukuda, H., Diem, T., Stefely, J., Kezdy, F. J., and Regen, S. L. (1986) Polymer-encased vesicles derived from dioctadecyldimethylammonium methacrylate J. Am. Chem. Soc. 108, 2321-2327
41. 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 (Pubitemid 34803480)
42. Kolb, H. C., Finn, M. G., and Sharpless, K. B. (2001) Click chemistry: Diverse chemical function from a few good reactions Angew. Chem., Int. Ed. 40, 2004-2021
43. Finn, M. G., Kolb, H. C., Fokin, V. V., and Sharpless, K. B. (2008) Click chemistry-Definition and aims Prog. Chem. 20, 1-4
44. Link, A. J., Vink, M. K. S., and Tirrell, D. A. (2004) Presentation and detection of azide functionality in bacterial cell surface proteins J. Am. Chem. Soc. 126, 10598-10602 (Pubitemid 39129159)
45. Baskin, J. M., Prescher, J. A., Laughlin, S. T., Agard, N. J., Chang, P. V., Miller, I. A., Lo, A., Codelli, J. A., and Bertozzi, C. R. (2007) Copper-free click chemistry for dynamic in vivo imaging Proc. Natl. Acad. Sci. U.S.A. 104, 16793-7 (Pubitemid 350210944)
46. Iha, R. K., Wooley, K. L., Nyström, A. M., Burke, D. J., Kade, M. J., and Hawker, C. J. (2009) Applications of orthogonal "click" chemistries in the synthesis of functional soft materials Chem. Rev. 109, 5620-5686
47. Wu, P., Feldman, A. K., Nugent, A. K., Hawker, C. J., Scheel, A., Voit, B., Pyun, J., Frechet, J. M., Sharpless, K. B., and Fokin, V. V. (2004) Efficiency and fidelity in a click-chemistry route to triazole dendrimers by the copper(i)-catalyzed ligation of azides and alkynes Angew. Chem., Int. Ed. 43, 3928-32 (Pubitemid 39257472)
48. Helms, B., Mynar, J. L., Hawker, C. J., and Frechet, J. M. (2004) Dendronized linear polymers via "click chemistry J. Am. Chem. Soc. 126, 15020-1 (Pubitemid 39557249)
49. Ornelas, C., Ruiz Aranzaes, J., Cloutet, E., Alves, S., and Astruc, D. (2007) Click assembly of 1,2,3-triazole-linked dendrimers, including ferrocenyl dendrimers, which sense both oxo anions and metal cations Angew. Chem., Int. Ed. 46, 872-7 (Pubitemid 46192034)
50. ONeil, E. J., DiVittorio, K. M., and Smith, B. D. (2007) Phosphatidylcholine-derived bolaamphiphiles via click chemistry Org. Lett. 9, 199-202
51. Hassane, F. S., Frisch, B., and Schuber, F. (2006) Targeted liposomes: Convenient coupling of ligands to preformed vesicles using "click chemistry Bioconjugate Chem. 17, 849-854 (Pubitemid 43794397)
52. Ramakrishnan, B., Boeggeman, E., and Qasba, P. K. (2007) Novel method for in vitro O-glycosylation of proteins: Application for bioconjugation Bioconjugate Chem. 18, 1912-1918 (Pubitemid 350219991)
53. Smith, M. D., Sudhahar, C. G., Gong, D., Stahelin, R. V., and Best, M. D. (2009) Modular synthesis of biologically active phosphatidic acid probes using click chemistry Mol. Biosyst. 5, 962-972
54. Jølck, R. I., Berg, R. H., and Andresen, T. L. (2010) Solid-phase synthesis of PEGylated lipopeptides using click chemistry Bioconjugate Chem. 21, 807-810
55. Frisch, B., Hassane, F. S., and Schuber, F. (2010) Conjugation of ligands to the surface of preformed liposomes by click chemistry Methods Mol. Biol. 605, 267-77
56. New, R. R. C. (1990) Liposomes: A practical approach, pp 131 - 134, Oxford University Press, Oxford.
57. Because the trapping efficiencies for CF by different LUVs were not always the same, the end intensity also differed.
58. Allen, T. M. and Cleland, L. G. (1980) Serum-induced leakage of liposome contents Biochim. Biophys. Acta 597, 418-426 (Pubitemid 10066496)
59. Mönkkönen, J., Liukkonen, J., Taskinen, M., Heath, T. D., and Urtti, A. (1995) Studies on liposome formulations for intraarticular delivery of clodronate J. Controlled Release 35, 145-154
60. Lasic, D. D. and Barenholz, Y. (1996) Handbook of nonmedical applications of liposomes, pp 105 - 111, CRC Press, Boca Raton.
61. Zhang, S. Y. and Zhao, Y. (2010) Facile synthesis of multivalent water-soluble organic nanoparticles via "surface clicking" of alkynylated surfactant micelles Macromolecules 43, 4020-4022
62. Golas, P. L., Tsarevsky, N. V., Sumerlin, B. S., and Matyjaszewski, K. (2006) Catalyst performance in "click" coupling reactions of polymers prepared by ATRP: Ligand and metal effects Macromolecules 39, 6451-6457 (Pubitemid 44555087)
63. Saito, G., Swanson, J. A., and Lee, K.-D. (2003) Drug delivery strategy utilizing conjugation via reversible disulfide linkages: role and site of cellular reducing activities Adv. Drug Delivery Rev. 55, 199-215 (Pubitemid 36135916)
64. Russo, A., DeGraff, W., Friedman, N., and Mitchell, J. B. (1986) Selective modulation of glutathione levels in human normal versus tumor-cells and subsequent differential response to chemotherapy drugs Cancer Res. 46, 2845-2848 (Pubitemid 16074292)
65. Mellman, I., Fuchs, R., and Helenius, A. (1986) Acidification of the endocytic and exocytic pathways Annu. Rev. Biochem. 55, 663-700 (Pubitemid 16070784)
66. Helmlinger, G., Schell, A., Dellian, M., Forbes, N. S., and Jain, R. K. (2002) Acid production in glycolysis-impaired tumors provides new insights into tumor metabolism Clin. Cancer Res. 8, 1284-1291 (Pubitemid 35177386)
67. Trevani, A. S., Andonegui, G., Giordano, M., López, D. H., Gamberale, R., Minucci, F., and Geffner, J. R. (1999) Extracellular acidification induces human neutrophil activation J. Immunol. 162, 4849-4857 (Pubitemid 29314889)
68. Engin, K., Leeper, D. B., Cater, J. R., Thistlethwaite, A. J., Tupchong, L., and Mcfarlane, J. D. (1995) Extracellular pH distribution in human tumors Int. J. Hyperthermia 11, 211-216
69. Smolarsky, M., Teitelbaum, D., Sela, M., and Gitler, C. (1977) Simple fluorescent method to determine complement-mediated liposome immune lysis J. Immunol. Methods 15, 255-265 (Pubitemid 8084150)
70. Ellens, H., Bentz, J., and Szoka, F. C. (1984) pH-Induced destabilization of phosphatidylethanolamine-containing liposomes: role of bilayer contact Biochemistry 23, 1532-8 (Pubitemid 14137550)