Acid-triggered release via dePEGylation of fusogenic liposomes mediated by heterobifunctional phenyl-substituted vinyl ethers with tunable pH-sensitivity

Bioconjugate Chemistry

Volumn 23, Issue 10, 2012, Pages 2071-2077

  Kim, Hee Kwon ^a   Van Den Bossche, Jeroen ^a   Hyun, Seok Hee ^a   Thompson, David H ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIFICATION; BLENDING; COUPLING AGENTS; ETHERS; ETHYLENE; ETHYLENE GLYCOL; LIPOSOMES;

ACID SENSITIVITIES; ACIDIC CONDITIONS; CALCEIN; FUSOGENIC LIPOSOMES; LIPO-POLYMER; PH-SENSITIVITY; PHOSPHOETHANOLAMINE; TRIGGERED RELEASE; TUNABLES; VINYL ETHERS;

HYDROLYSIS;

CALCEIN; ETHER DERIVATIVE; ETHYLENE GLYCOL; GLYCEROL; LIPID; LIPOSOME; MACROGOL; PHENYL GROUP; PHENYL SUBSTITUTED VINYL ETHER; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ACIDIFICATION; ARTICLE; CONTROLLED STUDY; ELECTRON; HYDROLYSIS; PH;

EID: 84867541874     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc300266y     Document Type: Article

References (38)

1. Mellman, I., Fuchs, R., and Helenius, A. (1986) Acidification of the endocytic and exocytic pathways Annu. Rev. Biochem. 55, 663-700 (Pubitemid 16070784)
2. Gerweck, L. E. (1998) Tumor pH: Implications for treatment and novel drug design Semin. Radiat. Oncol. 8, 176-182 (Pubitemid 28323476)
3. Watson, P., Jones, A. T., and Stephens, D. J. (2005) Intracellular trafficking pathways and drug delivery: fluorescence imaging of living and fixed cells Adv. Drug Delivery Rev. 57, 43-61 (Pubitemid 39424063)
4. Benjaminsen, R. V., Sun, H. H., Henriksen, J. R., Christensen, N. M., Almdal, K., and Andresen, T. L. (2011) Evaluating nanoparticle sensor design for intracellular pH measurements ACS Nano 5, 5864-5873
5. Brune, K. and Graf, P. (1978) Non-steroid anti-inflammatory drugs-influence of extracellular pH on biodistribution and pharmacological effects Biochem. Pharmacol. 27, 525-530 (Pubitemid 8276863)
6. Rofstad, E. K., Mathiesen, B., Kindem, K., and Galappathi, K. (2006) Acidic extracellular pH promotes experimental metastasis of human melanoma cells in athymic nude mice Cancer Res. 66, 6699-6707 (Pubitemid 44085627)
7. Yatvin, M. B., Kreutz, W., Horwitz, B. A., and Shinitzky, M. (1980) pH-Sensitive liposomes: possible clinical implications Science 210, 1253-1255 (Pubitemid 11178014)
8. Shin, J., Shum, P., and Thompson, D. H. (2003) Acid-triggered release via dePEGylation of DOPE liposomes containing acid-labile vinyl ether PEG-lipids J. Controlled Release 91, 187-200 (Pubitemid 37288890)
9. Yeo, Y., Xu, P. S., Bajaj, G., Shugg, T., and Van Alstine, W. G. (2010) Zwitterionic chitosan derivatives for pH-sensitive stealth coating Biomacromolecules 11, 2352-2358
10. Gillies, E. R., Goodwin, A. P., and Frechet, J. M. J. (2004) Acetals as pH-sensitive linkages for drug delivery Bioconjugate Chem. 15, 1254-1283
11. Knorr, V., Allmendinger, L., Walker, G. F., Paintner, F. F., and Wagner, E. (2007) An acetal-based PEGylation reagent for pH-sensitive shielding of DNA polyplexes Bioconjugate Chem. 18, 1218-1225 (Pubitemid 47122645)
12. Knorr, V., Russ, V., Allmendinger, L., Ogris, M., and Wagner, E. (2008) Acetal linked oligoethyleneimines for use as pH-sensitive gene carriers Bioconjugate Chem. 19, 1625-1634
13. Guo, X. and Szoka, F. C. (2001) Steric stabilization of fusogenic liposomes by a low-pH sensitive PEG-diortho ester-lipid conjugate Bioconjugate Chem. 12, 291-300 (Pubitemid 32235482)
14. Guo, X., MacKay, J. A., and Szoka, F. C. (2003) Mechanism of pH-triggered collapse of phosphatidylethanolamine liposomes stabilized by an ortho ester polyethyleneglycol lipid Biophys. J. 84, 1784-1795 (Pubitemid 36322940)
15. Masson, C., Garinot, M., Mignet, N., Wetzer, B., Mailhe, P., Scherman, D., and Bessodes, M. (2004) pH-Sensitive PEG lipids containing orthoester linkers: new potential tools for nonviral gene delivery J. Controlled Release 99, 423-434 (Pubitemid 39296911)
16. Huang, Z. H., Guo, X., Li, W. J., MacKay, J. A., and Szoka, F. C. (2006) Acid-triggered transformation of diortho ester phosphocholine liposome J. Am. Chem. Soc. 128, 60-61 (Pubitemid 43100848)
17. Chen, H. G., Zhang, H. Z., McCallum, C. M., Szoka, F. C., and Guo, X. (2007) Unsaturated cationic ortho esters for endosome permeation in gene delivery J. Med. Chem. 50, 4269-4278 (Pubitemid 47378827)
18. Bruyere, H., Westwell, A. D., and Jones, A. T. (2010) Tuning the pH sensitivities of orthoester based compounds for drug delivery applications by simple chemical modification Bioorg. Med. Chem. Lett. 20, 2200-2203
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. Kale, A. A. and Torchilin, V. P. (2007) Design, synthesis, and characterization of pH-sensitive PEG-PE conjugates for stimuli-sensitive pharmaceutical nanocarriers: the effect of substitutes at the hydrazone linkage on the pH stability of PEG-PE conjugates Bioconjugate Chem. 18, 363-370 (Pubitemid 46493506)
21. Shen, W. C. and Ryser, H. J. P. (1981) Cis-aconityl spacer between daunomycin and macromolecular carriers-a model of pH-sensitive linkage releasing drug from a lysosomotropic conjugate Biochem. Biophys. Res. Commun. 102, 1048-1054 (Pubitemid 12213826)
22. Alshamkhani, A. and Duncan, R. (1995) Synthesis, controlled release properties and antitumor activity of alginate-cis-aconityl-daunomycin conjugates Int. J. Pharm. 122, 107-119
23. Remenyi, J., Balazs, B., Toth, S., Falus, A., Toth, G., and Hudecz, F. (2003) Isomer-dependent daunomycin release and in vitro antitumour effect of cis-aconityl-daunomycin Biochem. Biophys. Res. Commun. 303, 556-561 (Pubitemid 36349205)
24. Parrott, M. C., Luft, J. C., Byrne, J. D., Fain, J. H., Napier, M. E., and DeSimone, J. M. (2010) Tunable bifunctional silyl ether cross-linkers for the design of acid-sensitive biomaterials J. Am. Chem. Soc. 132, 17928-17932
25. Boomer, J. A., Inerowicz, H. D., Zhang, Z.-Y., Bergstrand, N., Edwards, K., Kim, J.-M., and Thompson, D. H. (2003) Acid-triggered release from sterically-stabilized fusogenic vesicles via a hydrolytic dePEGylation strategy Langmuir 19, 6408-6415
26. Boomer, J. A., Qualls, M. M., Inerowicz, H. D., Haynes, R. H., Patri, G. V. S., Kim, J.-M., and Thompson, D. H. (2009) Cytoplasmic delivery of liposomal contents mediated by an acid-labile cholesterol-vinyl ether-PEG conjugate Bioconjugate Chem. 20, 47-59
27. Gerasimov, O., Schwan, A., and Thompson, D. H. (1997) Acid-catalyzed plasmenylcholine hydrolysis and its effect on bilayer permeability: a quantitative study Biochim. Biophys. Acta 1324, 200-214 (Pubitemid 27117827)
28. Shin, J., Shum, P., Grey, J., Fujiwara, S., Malhotra, G. S., González-Bonet, A. M., Hyun, S. H., Moase, E., Allen, T. M., and Thompson, D. H. (2012) Mol. Pharm., DOI: 10.1021/mp300326z.
29. Kresge, A. J. (1987) Unusual reactivity of prostacyclin: rational drug design through physical organic chemistry Acc. Chem. Res. 20, 364-370
30. Keeffe, J. R. and Kresge, A. J. (1990) in The Chemistry of Enols (Rappoport, Z., Ed.) p 437, John Wiley & Sons, New York.
31. Shin, J. (2002) Synthesis and acid-triggered release activity of PEG lipid conjugates in DOPE liposomes, Ph.D. Thesis, Purdue University
32. Becke, A. D. (1993) Density-functional thermochemistry. 3. The role of exact exchange J. Chem. Phys. 98, 5648-5652
33. Lee, C. T., Yang, W. T., and Parr, R. G. (1988) Development of the Colle-Salvetti correlation energy formula into a functional of the electron density Phys. Rev. B 37, 785-789
34. Kendall, R. A., Dunning, T. H., and Harrison, R. J. (1992) Electron affinities of the 1st row atoms revisited-systematic basis sets and wave functions J. Chem. Phys. 96, 6796-6806
35. Allen, T. M., Hong, K., and Papahadjopoulos, D. (1990) Membrane contact, fusion and hexagonal (HII) transitions in phosphatidylethanolamine liposomes Biochemistry 29, 2976-2985 (Pubitemid 20119293)
36. Patel, V. F., Hardin, J. N., Mastro, J. M., Law, K. L., Zimmermann, J. L., Ehlhardt, W. J., Woodland, J. M., and Starling, J. J. (1996) Novel acid labile COL1 trityl-linked difluoronucleoside immunoconjugates: Synthesis, characterization, and biological activity Bioconjugate Chem. 497-510 (Pubitemid 26312141)
37. Kong, S. D., Luong, A., Manorek, G., Howell, S. B., and Yang, J. (2007) Acidic hydrolysis of N-ethoxybenzylimidazoles (NEBIs): potential applications as pH-sensitive linkers for drug delivery Bioconjugate Chem. 18, 293-296 (Pubitemid 46493497)
38. Berrien, J. F., Raymond, M. N., Moskowitz, H., and Mayrargue, J. (1999) Selective gamma-1,4 addition of methoxyallylcopper to enone Tetrahedron Lett. 40, 1313-1314 (Pubitemid 29062173)