PH-Sensitive nano-systems for drug delivery in cancer therapy

Biotechnology Advances

Volumn 32, Issue 4, 2014, Pages 693-710

  Liu, Juan ^a   Huang, Yuran ^a   Kumar, Anil ^a,b   Tan, Aaron ^c   Jin, Shubin ^a   Mozhi, Anbu ^a   Liang, Xing Jie ^a  

^a NATIONAL CENTER FOR NANOSCIENCE AND TECHNOLOGY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Controlled drug release; Drug delivery system; Nanomedicine; PH Sensitive nanoparticles

Indexed keywords

BIOLOGICAL MATERIALS; DISEASES; ENZYME ACTIVITY; HISTOLOGY; MATERIALS PROPERTIES; MEDICAL NANOTECHNOLOGY; NANOSYSTEMS; ONCOLOGY; TUMORS;

CLINICAL APPLICATION; CONTROLLED DRUG RELEASE; DRUG DELIVERY SYSTEM; FOOD AND DRUG ADMINISTRATION; INTRACELLULAR DRUG DELIVERY; PH SENSITIVE; STIMULUS-RESPONSIVE MATERIALS; TUMOR MICROENVIRONMENT;

DRUG DELIVERY;

BIOTECHNOLOGY; CANCER; DISEASE TREATMENT; DRUG; MEDICINE; NANOTECHNOLOGY; PH; TECHNOLOGICAL DEVELOPMENT; TUMOR;

ANTINEOPLASTIC AGENT; DRUG; DRUG CARRIER; MICELLE; PEPTIDE;

ANIMAL; CHEMISTRY; DRUG DELIVERY SYSTEM; DRUG EFFECTS; HUMAN; MICELLE; NANOMEDICINE; NANOTECHNOLOGY; NEOPLASMS; PH; PROCEDURES; TRENDS; TUMOR MICROENVIRONMENT;

ANIMALS; ANTINEOPLASTIC AGENTS; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; HUMANS; HYDROGEN-ION CONCENTRATION; MICELLES; NANOMEDICINE; NANOTECHNOLOGY; NEOPLASMS; PEPTIDES; PHARMACEUTICAL PREPARATIONS; TUMOR MICROENVIRONMENT;

EID: 84901983377     PISSN: 07349750     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biotechadv.2013.11.009     Document Type: Review

References (175)

1. Agostini A., Mondragon L., Bernardos A., Martinez-Manez R., Marcos M.D., Sancenon F., et al. Targeted cargo delivery in senescent cells using capped mesoporous silica nanoparticles. Angew Chem Int Edit 2012, 51:10556-10560.
2. Aryal S., Hu C.M., Zhang L. Polymer-cisplatin conjugate nanoparticles for acid-responsive drug delivery. Acs Nano 2010, 4:251-258.
3. Aznar E., Casasus R., Garcia-Acosta B., Marcos M.D., Martinez-Manez R. Photochemical and chemical two-channel control of functional nanogated hybrid architectures. Adv Mater 2007, 19:2228.
4. Aznar E., Marcos M.D., Martinez-Manez R., Sancenon F., Soto J., Amoros P., et al. pH- and photo-switched release of guest molecules from mesoporous silica supports. J Am Chem Soc 2009, 131:6833-6843.
5. Bae Y.M., Park Y.I., Nam S.H., Kim J.H., Lee K., Kim H.M., et al. Endocytosis, intracellular transport, and exocytosis of lanthanide-doped upconverting nanoparticles in single living cells. Biomaterials 2012, 33:9080-9086.
6. Bailey A.L., Monck M.A., Cullis P.R. pH-Induced destabilization of lipid bilayers by a lipopeptide derived from influenza hemagglutinin. Bba-Biomembranes 1997, 1324:232-244.
7. Bajaj I., Singhal R. Poly (glutamic acid)-an emerging biopolymer of commercial interest. Bioresour Technol 2011, 102:5551-5561.
8. Banerjee S.S., Roy M., Bose S. pH tunable fluorescent calcium phosphate nanocomposite for sensing and controlled drug delivery. Adv Eng Mater 2011, 13:B10-B17.
9. Barick K., Nigam S., Bahadur D. Nanoscale assembly of mesoporous ZnO: a potential drug carrier. J Mater Chem 2010, 20:6446-6452.
10. Batrakova E.V., Kabanov A.V. Pluronic block copolymers: evolution of drug delivery concept from inert nanocarriers to biological response modifiers. J Control Release 2008, 130:98-106.
11. Berndt I., Popescu C., Wortmann F.J., Richtering W. Mechanics versus thermodynamics: swelling in multiple-temperature-sensitive core-shell microgels. Angew Chem 2006, 45:1081-1085.
12. Bhattarai N., Gunn J., Zhang M. Chitosan-based hydrogels for controlled, localized drug delivery. Adv Drug Deliv Rev 2010, 62:83-99.
13. Calderon M., Welker P., Licha K., Fichtner I., Graeser R., Haag R., et al. Development of efficient acid cleavable multifunctional prodrugs derived from dendritic polyglycerol with a poly(ethylene glycol) shell. J Control Release 2011, 151:295-301.
14. Chen F., Zhu Y.C. Chitosan enclosed mesoporous silica nanoparticles as drug nano-carriers: sensitive response to the narrow pH range. Microporous Mesoporous Mater 2012, 150:83-89.
15. Chen W., Meng F., Cheng R., Zhong Z. pH-Sensitive degradable polymersomes for triggered release of anticancer drugs: a comparative study with micelles. J Control Release 2010, 142:40-46.
16. Chen H., Moore T., Qi B., Colvin D.C., Jelen E.K., Hitchcock D.A., et al. Monitoring pH-triggered drug release from radioluminescent nanocapsules with X-ray excited optical luminescence. Acs Nano 2013, 7:1178-1187.
17. Collins L., Parker A.L., Gehman J.D., Eckley L., Perugini M.A., Separovic F., et al. Self-assembly of peptides into spherical nanoparticles for delivery of hydrophilic moieties to the cytosol. Acs Nano 2010, 4:2856-2864.
18. Cui J., Yan Y., Wang Y., Caruso F. Templated assembly of pH-labile polymer-drug particles for intracellular drug delivery. Adv Funct Mater 2012, 22:4718-4723.
19. Das M., Mardyani S., Chan W.C.W., Kumacheva E. Biofunctionalized pH-responsive microgels for cancer cell targeting: rational design. Adv Mater 2006, 18:80-83.
20. Determan M.D., Cox J.P., Mallapragada S.K. Drug release from pH-responsive thermogelling pentablock copolymers. J Biomed Mater Res 2007, 81:326-333.
21. Dhar S., Gu F.X., Langer R., Farokhzad O.C., Lippard S.J. Targeted delivery of cisplatin to prostate cancer cells by aptamer functionalized Pt(IV) prodrug-PLGA-PEG nanoparticles. Proc Natl Acad Sci U S A 2008, 105:17356-17361.
22. Ding C.X., Gu J.X., Qu X.Z., Yang Z.Z. Preparation of multifunctional drug carrier for tumor-specific uptake and enhanced intracellular delivery through the conjugation of weak acid labile linker. Bioconjugs Chem 2009, 20:1163-1170.
23. Ding M., Song N., He X., Li J., Zhou L., Fu Q., et al. Toward the next-generation nanomedicines: design of multifunctional multiblock polyurethanes for effective cancer treatment. Acs Nano 2013, 7:1918-1928.
24. Drummond D.C., Zignani M., Leroux J. Current status of pH-sensitive liposomes in drug delivery. Prog Lipid Res 2000, 39:409-460.
25. Du J.Z., Du X.J., Mao C.Q., Wang J. Tailor-made dual pH-sensitive polymer-doxorubicin nanoparticles for efficient anticancer drug delivery. J Am Chem Soc 2011, 133:17560-17563.
26. Du C., Deng D., Shan L., Wan S., Cao J., Tian J., et al. A pH-sensitive doxorubicin prodrug based on folate-conjugated BSA for tumor-targeted drug delivery. Biomaterials 2013, 34:3087-3097.
27. Duncan R. Polymer conjugates as anticancer nanomedicines. Nat Rev Cancer 2006, 6:688-701.
28. Engin K., Leeper D.B., Cater J.R., Thistlethwaite A.J., Tupchong L., McFarlane J.D. Extracellular pH distribution in human tumours. Int J Hyperth 1995, 11:211-216.
29. Ercole F., Davis T.P., Evans R.A. Photo-responsive systems and biomaterials: photochromic polymers, light-triggered self-assembly, surface modification, fluorescence modulation and beyond. Polym Chem-Uk 2010, 1:37-54.
30. Etrych T., Sirova M., Starovoytova L., Rihova B., Ulbrich K. HPMA copolymer conjugates of paclitaxel and docetaxel with pH-controlled drug release. Mol Pharm 2010, 7:1015-1026.
31. Fang C., Kievit F.M., Veiseh O., Stephen Z.R., Wang T., Lee D., et al. Fabrication of magnetic nanoparticles with controllable drug loading and release through a simple assembly approach. J Control Release 2012, 162:233-241.
32. Felber A.E., Dufresne M.H., Leroux J.C. pH-sensitive vesicles, polymeric micelles, and nanospheres prepared with polycarboxylates. Adv Drug Deliver Rev 2012, 64:979-992.
33. Futaki S., Masui Y., Nakase I., Sugiura Y., Nakamura T., Kogure K., et al. Unique features of a pH-sensitive fusogenic peptide that improves the transfection efficiency of cationic liposomes. J Gene Med 2005, 7:1450-1458.
34. Gan Q., Lu X., Dong W., Yuan Y., Qian J., Li Y., et al. Endosomal pH-activatable magnetic nanoparticle-capped mesoporous silica for intracellular controlled release. J Mater Chem 2012, 22:15960-15968.
35. Gao G.H., Li Y., Lee D.S. Environmental pH-sensitive polymeric micelles for cancer diagnosis and targeted therapy. J Control Release 2013, 169:180-184.
36. Gillies E.R., Frechet J.M. A new approach towards acid sensitive copolymer micelles for drug delivery. Chem Commun 2003, 1640-1641.
37. Gottschalk S., Sparrow J.T., Hauer J., Mims M.P., Leland F.E., Woo S.L., et al. A novel DNA-peptide complex for efficient gene transfer and expression in mammalian cells. Gene Ther 1996, 3:448-457.
38. Green J.J., Langer R., Anderson D.G. A combinatorial polymer library approach yields insight into nonviral gene delivery. Acc Chem Res 2008, 41:749-759.
39. Guo S., Huang Y., Jiang Q., Sun Y., Deng L., Liang Z., et al. Enhanced gene delivery and siRNA silencing by gold nanoparticles coated with charge-reversal polyelectrolyte. Acs Nano 2010, 4:5505-5511.
40. Guo X.D., Zhang L.J., Chen Y., Qian Y. Core/shell pH-sensitive micelles self-assembled from cholesterol conjugated oligopeptides for anticancer drug delivery. Aiche J 2010, 56:1922-1931.
41. Guo X.D., Zhang L.J., Wu Z.M., Qian Y. Dissipative particle dynamics studies on microstructure of pH-sensitive micelles for sustained drug delivery. Macromolecules 2010, 43:7839-7844.
42. Guo X.D., Wiradharma N., Liu S.Q., Zhang L.J., Khan M, Qian Y., et al. Oligomerized alpha-helical KALA peptides with pendant arms bearing cell-adhesion, DNA-binding and endosome-buffering domains as efficient gene transfection vectors. Biomaterials 2012, 33:6284-6291.
43. Gurski L.A., Jha A.K., Zhang C., Jia X.Q., Farach-Carson M.C. Hyaluronic acid-based hydrogels as 3D matrices for in vitro evaluation of chemotherapeutic drugs using poorly adherent prostate cancer cells (vol 30, pg 6076, 2009). Biomaterials 2010, 31:4248-48.
44. Han L., Zhao J., Zhang X., Cao W., Hu X, Duan X., et al. Enhanced siRNA delivery and silencing gold-chitosan nanosystem with surface charge-reversal polymer assembly and good biocompatibility. Acs Nano 2012, 6:7340-7351.
45. Hatakeyama H., Ito E., Akita H., Oishi M., Nagasaki Y., Futaki S., et al. A pH-sensitive fusogenic peptide facilitates endosomal escape and greatly enhances the gene silencing of siRNA-containing nanoparticles in vitro and in vivo. J Control Release 2009, 139:127-132.
46. Heffernan M.J., Murthy N. Polyketal nanoparticles: a new pH-sensitive biodegradable drug delivery vehicle. Bioconjug Chem 2005, 16:1340-1342.
47. Heller J., Penhale D.W.H., Helwing R.F. Preparation of polyacetals by the reaction of divinyl ethers and polyols. J Polym Sci Pol Lett 1980, 18:293-297.
48. Heller J., Barr J., Ng S.Y., Abdellauoi K.S., Gurny R. Poly(ortho esters): synthesis, characterization, properties and uses. Adv Drug Deliv Rev 2002, 54:1015-1039.
49. Hruby M., Konak C., Ulbrich K. Polymeric micellar pH-sensitive drug delivery system for doxorubicin. J Control Release 2005, 103:137-148.
50. Hu F.Q., Zhang Y.Y., You J., Yuan H., Du Y.Z. pH triggered doxorubicin delivery of PEGylated glycolipid conjugate micelles for tumor targeting therapy. Mol Pharm 2012, 9:2469-2478.
51. Hu X., Hao X., Wu Y., Zhang J., Zhang X., Wang P.C., et al. Multifunctional hybrid silica nanoparticles for controlled doxorubicin loading and release with thermal and pH dual response. J Mater Chem B 2013, 1:1109-1118.
52. Huh K.M., Kang H.C., Lee Y.J., Bae Y.H. pH-sensitive polymers for drug delivery. Macromol Res 2012, 20:224-233.
53. Iversen T.G., Skotland T., Sandvig K. Endocytosis and intracellular transport of nanoparticles: present knowledge and need for future studies. Nano Today 2011, 6:176-185.
54. Jeong J.H., Kim S.W., Park T.G. Novel intracellular delivery system of antisense oligonucleotide by self-assembled hybrid micelles composed of DNA/PEG conjugate and cationic fusogenic peptide. Bioconjug Chem 2003, 14:473-479.
55. Ju X.J., Liu L., Xie R., Niu C.H., Chu L.Y. Dual thermo-responsive and ion-recognizable monodisperse microspheres. Polymer 2009, 50:922-929.
56. Kakinoki A., Kaneo Y., Ikeda Y., Tanaka T., Fujita K. Synthesis of poly(vinyl alcohol)-doxorubicin conjugates containing cis-aconityl acid-cleavable bond and its isomer dependent doxorubicin release. Biol Pharm Bull 2008, 31:103-110.
57. Kamada H., Tsutsumi Y., Yoshioka Y., Yamamoto Y., Kodaira H., Tsunoda S., et al. Design of a pH-sensitive polymeric carrier for drug release and its application in cancer therapy. Clin Cancer Res 2004, 10:2545-2550.
58. Kang S.I., Bae Y.H. A sulfonamide based glucose-responsive hydrogel with covalently immobilized glucose oxidase and catalase. J Control Release 2003, 86:115-121.
59. Kang H.C., Bae Y.H. Co-delivery of small interfering RNA and plasmid DNA using a polymeric vector incorporating endosomolytic oligomeric sulfonamide. Biomaterials 2011, 32:4914-4924.
60. Kavitha T., Haider Abdi S.I., Park S.Y. pH-Sensitive nanocargo based on smart polymer functionalized graphene oxide for site-specific drug delivery. Phys Chem Chem Phys 2013, 15:5176-5185.
61. Ke C.J., Su T.Y., Chen H.L., Liu H.L., Chiang W.L., Chu P.C., et al. Smart multifunctional hollow microspheres for the quick release of drugs in intracellular lysosomal compartments. Angew Chem 2011, 50:8086-8089.
62. Ke C.J., Lin Y.J., Hu Y.C., Chiang W.L., Chen K.J., Yang W.C., et al. Multidrug release based on microneedle arrays filled with pH-responsive PLGA hollow microspheres. Biomaterials 2012, 33:5156-5165.
63. Ke C.J., Chiang W.L., Liao Z.X., Chen H.L., Lai P.S., Sun J.S., et al. Real-time visualization of pH-responsive PLGA hollow particles containing a gas-generating agent targeted for acidic organelles for overcoming multi-drug resistance. Biomaterials 2013, 34:1-10.
64. Kester M., Heakal Y., Fox T., Sharma A., Robertson G.P, Morgan T.T., et al. Calcium phosphate nanocomposite particles for in vitro imaging and encapsulated chemotherapeutic drug delivery to cancer cells. Nano letters 2008, 8:4116-4121.
65. Khandare J.J., Jalota-Badhwar A., Taneja N., Mascarenhas R.R., Vadodaria K., Zope K.R., et al. Fabrication of pH-tunable calcium phosphate nanocapsules via dendrimer-templated assembly for intracellular lysosomal release of drugs. Part Part Syst Charact 2013, 30:494-500.
66. Kikuchi A., Okano T. Intelligent thermoresponsive polymeric stationary phases for aqueous chromatography of biological compounds. Prog Polym Sci 2002, 27:1165-1193.
67. Kim A., Szoka F.C. Amino acid side-chain contributions to free energy of transfer of tripeptides from water to octanol. Pharm Res 1992, 9:504-514.
68. Kim Y.H., Park J.H., Lee M., Kim Y.H., Park T.G., Kim S.W. Polyethylenimine with acid-labile linkages as a biodegradable gene carrier. J Control Release 2005, 103:209-219.
69. Kim M.S., Hwang S.J., Han J.K., Choi E.K., Park H.J., Kim J.S., et al. pH-Responsive PEG-poly(beta-amino ester) block copolymer micelles with a sharp transition. Macromol Rapid Commun 2006, 27:447-451.
70. Kim D., Lee E.S., Oh K.T., Gao Z.G., Bae Y.H. Doxorubicin-loaded polymeric micelle overcomes multidrug resistance of cancer by double-targeting folate receptor and early endosomal pH. Small 2008, 4:2043-2050.
71. Kim J.O., Kabanov A.V., Bronich T.K. Polymer micelles with cross-linked polyanion core for delivery of a cationic drug doxorubicin. J Control Release 2009, 138:197-204.
72. Kim J.K., Garripelli V.K., Jeong U.H., Park J.S., Repka M.A., Jo S. Novel pH-sensitive polyacetal-based block copolymers for controlled drug delivery. Int J Pharm 2010, 401:79-86.
73. Knorr V., Russ V., Allmendinger L., Ogris M., Wagner E. Acetal linked oligoethylenimines for use as pH-sensitive gene carriers. Bioconjug Chem 2008, 19:1625-1634.
74. Kratz F. DOXO-EMCH (INNO-206): the first albumin-binding prodrug of doxorubicin to enter clinical trials. Expert Opin Investig Drug 2007, 16:855-866.
75. Kuhn W., Hargitay B., Katchalsky A., Eisenberg H. Reversible dilation and contraction by changing the state of ionization of high-polymer acid networks. Nature 1950, 165:514-516.
76. Langer R. Where a pill won't reach. Sci Am 2003, 288:50-57.
77. Lee E.S., Na K., Bae Y.H. Polymeric micelle for tumor pH and folate-mediated targeting. J Control Release 2003, 91:103-113.
78. Lee E.S., Shin H.J., Na K., Bae Y.H. Poly(l-histidine)-PEG block copolymer micelles and pH-induced destabilization. J Control Release 2003, 90:363-374.
79. Lee E.S., Na K., Bae Y.H. Doxorubicin loaded pH-sensitive polymeric micelles for reversal of resistant MCF-7 tumor. J Control Release 2005, 103:405-418.
80. Lee E.S., Na K., Bae Y.H. Super pH-sensitive multifunctional polymeric micelle. Nano letters 2005, 5:325-329.
81. Lee E.S., Oh K.T., Kim D., Youn Y.S., Bae Y.H. Tumor pH-responsive flower-like micelles of poly(l-lactic acid)-b-poly(ethylene glycol)-b-poly(l-histidine). J Control Release 2007, 123:19-26.
82. Lee S.H., Kim S.H., Park T.G. Intracellular siRNA delivery system using polyelectrolyte complex micelles prepared from VEGF siRNA-PEG conjugate and cationic fusogenic peptide. Biochem Bioph Res Co 2007, 357:511-516.
83. Lee E.S., Gao Z., Kim D., Park K., Kwon I.C., Bae Y.H. Super pH-sensitive multifunctional polymeric micelle for tumor pH(e) specific TAT exposure and multidrug resistance. J Control Release 2008, 129:228-236.
84. Lee J.E., Lee N., Kim T., Kim J., Hyeon T. Multifunctional mesoporous silica nanocomposite nanoparticles for theranostic applications. Acc Chem Res 2011, 44:893-902.
85. Lim E.K., Huh Y.M., Yang J., Lee K., Suh J.S., Haam S. pH-triggered drug-releasing magnetic nanoparticles for cancer therapy guided by molecular imaging by MRI. Adv Mater 2011, 23:2436-2442.
86. Lin Y.L., Jiang G.H., Birrell L.K., El-Sayed M.E.H. Degradable, pH-sensitive, membrane-destabilizing, comb-like polymers for intracellular delivery of nucleic acids. Biomaterials 2010, 31:7150-7166.
87. Liu R., Zhang Y., Zhao X., Agarwal A., Mueller L.J., Feng P. pH-responsive nanogated ensemble based on gold-capped mesoporous silica through an acid-labile acetal linker. J Am Chem Soc 2010, 132:1500-1501.
88. Liu J., Ma H., Wei T., Liang X.J. CO2 gas induced drug release from pH-sensitive liposome to circumvent doxorubicin resistant cells. Chem commun 2012, 48:4869-4871.
89. Liu T., Li X., Qian Y., Hu X., Liu S. Multifunctional pH-disintegrable micellar nanoparticles of asymmetrically functionalized beta-cyclodextrin-based star copolymer covalently conjugated with doxorubicin and DOTA-Gd moieties. Biomaterials 2012, 33:2521-2531.
90. Lu D.X., Wen X.T., Liang J., Gu Z.W., Zhang X.D., Fan Y.J. A pH-sensitive nano drug delivery system derived from pullulan/doxorubicin conjugate. J Biomed Mater Res B 2009, 89B:177-183.
91. Lu T.L., Wang Z., Ma Y.F., Zhang Y., Chen T. Influence of polymer size, liposomal composition, surface charge, and temperature on the permeability of pH-sensitive liposomes containing lipid-anchored poly(2-ethylacrylic acid). Int J Nanomedicine 2012, 7:4917-4926.
92. Luo Z., Cai K.Y., Hu Y., Zhao L., Liu P., Duan L., et al. Mesoporous silica nanoparticles end-capped with collagen: redox-responsive nanoreservoirs for targeted drug delivery. Angew Chem Int Edit 2011, 50:640-643.
93. Lynn D.M., Anderson D.G., Putnam D., Langer R. Accelerated discovery of synthetic transfection vectors: parallel synthesis and screening of degradable polymer library. J Am Chem Soc 2001, 123:8155-8156.
94. Makhlof A., Tozuka Y., Takeuchi H. pH-Sensitive nanospheres for colon-specific drug delivery in experimentally induced colitis rat model. Eur J Pharm Biopharm 2009, 72:1-8.
95. Meng H., Xue M., Xia T., Zhao Y.L., Stoddart J.F., Tamanoi F., et al. Autonomous in vitro anticancer drug release from mesoporous silica nanoparticles by pH-sensitive nanovalves. J Am Chem Soc 2010, 132:12690-12697.
96. Midoux P., Pichon C., Yaouanc J.J., Jaffres P.A. Chemical vectors for gene delivery: a current review on polymers, peptides and lipids containing histidine or imidazole as nucleic acids carriers. Brit J Pharmacol 2009, 157:166-178.
97. Morgan T.T., Muddana H.S., Altinoglu E.I., Rouse S.M., Tabakovic A., Tabouillot T., et al. Encapsulation of organic molecules in calcium phosphate nanocomposite particles for intracellular imaging and drug delivery. Nano letters 2008, 8:4108-4115.
98. Morishita M., Lowman A.M., Takayama K., Nagai T., Peppas N.A. Elucidation of the mechanism of incorporation of insulin in controlled release systems based on complexation polymers. J Control Release 2002, 81:25-32.
99. Muhammad F., Guo M., Guo Y., Qi W., Qu F., Sun F., et al. Acid degradable ZnO quantum dots as a platform for targeted delivery of an anticancer drug. J Mater Chem 2011, 21:13406-13412.
100. Murthy N., Campbell J., Fausto N., Hoffman A.S., Stayton P.S. Design and synthesis of pH-responsive polymeric carriers that target uptake and enhance the intracellular delivery of oligonucleotides. J Control Release 2003, 89:365-374.
101. Na K., Lee K.H., Bae Y.H. pH-sensitivity and pH-dependent interior structural change of self-assembled hydrogel nanoparticles of pullulan acetate/oligo-sulfonamide conjugate. J Control Release 2004, 97:513-525.
102. Ossipov D.A., Yang X., Varghese O., Kootala S., Hilborn J. Modular approach to functional hyaluronic acid hydrogels using orthogonal chemical reactions. Chem Commun 2010, 46:8368-8370.
103. Park S.Y., Bae Y.H. Novel pH-sensitive polymers containing sulfonamide groups. Macromol Rapid Commun 1999, 20:269-273.
104. Patenaude M., Hoare T. Injectable, mixed natural-synthetic polymer hydrogels with modular properties. Biomacromolecules 2012, 13:369-378.
105. Peng H., Dong R., Wang S., Zhang Z., Luo M., Bai C., et al. A pH-responsive nano-carrier with mesoporous silica nanoparticles cores and poly(acrylic acid) shell-layers: fabrication, characterization and properties for controlled release of salidroside. Int J Pharm 2013, 446:153-159.
106. Plank C., Zatloukal K., Cotten M., Mechtler K., Wagner E. Gene-transfer into hepatocytes using asialoglycoprotein receptor mediated endocytosis of DNA complexed with an artificial tetra-antennary galactose ligand. Bioconjug Chem 1992, 3:533-539.
107. Prabaharan M., Grailer J.J., Pilla S., Steeber D.A., Gong S. Gold nanoparticles with a monolayer of doxorubicin-conjugated amphiphilic block copolymer for tumor-targeted drug delivery. Biomaterials 2009, 30:6065-6075.
108. Prabaharan M., Grailer J.J., Pilla S., Steeber D.A., Gong S.Q. Amphiphilic multi-arm-block copolymer conjugated with doxorubicin via pH-sensitive hydrazone bond for tumor-targeted drug delivery. Biomaterials 2009, 30:5757-5766.
109. Quan C.Y., Chen J.X., Wang H.Y., Li C., Chang C., Zhang X.Z., et al. Core-shell nanosized assemblies mediated by the alpha-beta cyclodextrin dimer with a tumor-triggered targeting property. Acs Nano 2010, 4:4211-4219.
110. Rao N.V., Mane S.R., Kishore A., Das Sarma J., Shunmugam R. Norbornene derived doxorubicin copolymers as drug carriers with pH responsive hydrazone linker. Biomacromolecules 2012, 13:221-230.
111. Rihova B., Etrych T., Pechar M., Jelinkova M., Stastny M., Hovorka O., et al. Doxorubicin bound to a HPMA copolymer carrier through hydrazone bond is effective also in a cancer cell line with a limited content of lysosomes. J Control Release 2001, 74:225-232.
112. Rim H.P., Min K.H., Lee H.J., Jeong S.Y., Lee S.C. pH-Tunable calcium phosphate covered mesoporous silica nanocontainers for intracellular controlled release of guest drugs. Angew Chem 2011, 50:8853-8857.
113. Risbud M.V., Hardikar A.A., Bhat S.V., Bhonde R.R. pH-sensitive freeze-dried chitosan-polyvinyl pyrrolidone hydrogels as controlled release system for antibiotic delivery. J Control Release 2000, 68:23-30.
114. Rittner K., Benavente A., Bompard-Sorlet A., Heitz F., Divita G., Brasseur R., et al. New basic membrane-destabilizing peptides for plasmid-based gene delivery in vitro and in vivo. Mol Ther 2002, 5:104-114.
115. Sakurai Y., Hatakeyama H., Sato Y., Akita H., Takayama K., Futaki S., et al. Endosomal escape and the knockdown efficiency of liposomal-siRNA by the fusogenic peptide shGALA. Biomaterials 2011, 32:5733-5742.
116. Savla R., Taratula O., Garbuzenko O., Minko T. Tumor targeted quantum dot-mucin 1 aptamer-doxorubicin conjugate for imaging and treatment of cancer. J Control Release 2011, 153:16-22.
117. Sethuraman V.A., Lee M.C., Bae Y.H. A biodegradable pH-sensitive micelle system for targeting acidic solid tumors. Pharm Res 2008, 25:657-666.
118. She W., Li N., Luo K., Guo C., Wang G., et al. Dendronized heparin-doxorubicin conjugate based nanoparticle as pH-responsive drug delivery system for cancer therapy. Biomaterials 2013, 34:2252-2264.
119. Shen Y., Zhuo Z., Sui M., Tang J., Xu P., Van Kirk E.A., et al. Charge-reversal polyamidoamine dendrimer for cascade nuclear drug delivery. Nanomedicine 2010, 5:1205-1217.
120. Shen M., Huang Y., Han L., Qin J., Fang X., Wang J., et al. Multifunctional drug delivery system for targeting tumor and its acidic microenvironment. J Control Release 2012, 161:884-892.
121. Shieh Y.A., Yang S.J., Wei M.F., Shieh M.J. Aptamer-based tumor-targeted drug delivery for photodynamic therapy. Acs Nano 2010, 4:1433-1442.
122. Shim M.S., Kwon Y.J. Ketalized poly(amino ester) for stimuli-responsive and biocompatible gene delivery. Polym Chem Uk 2012, 3:2570-2577.
123. Siegel R.A., Falamarzian M., Firestone B.A., Moxley B.C. pH-Controlled release from hydrophobic poly-electrolyte copolymer hydrogels. J Control Release 1988, 8:179-182.
124. Song W., Tang Z., Li M., Lv S., Yu H., Ma L., et al. Tunable pH-sensitive poly (β-amino ester) s synthesized from primary amines and diacrylates for intracellular drug delivery. Macromol Biosci 2012, 12:1375-1383.
125. Song L., Ho V.H., Chen C., Yang Z., Liu D., Chen R., et al. Efficient, pH-triggered drug delivery using a pH-responsive DNA-conjugated gold nanoparticle. Adv Healthc mater 2013, 2:275-280.
126. Stuart M.A.C., Huck W.T., Genzer J., Müller M., Ober C., Stamm M., et al. Emerging applications of stimuli-responsive polymer materials. Nat Mater 2010, 9:101-113.
127. Stubbs M., McSheehy P.M., Griffiths J.R., Bashford C.L. Causes and consequences of tumour acidity and implications for treatment. Mol Med Today 2000, 6:15-19.
128. Su S., Wang H., Liu X., Wu Y., Nie G. iRGD-coupled responsive fluorescent nanogel for targeted drug delivery. Biomaterials 2013, 34:3523-3533.
129. Subbarao N.K., Parente R.A., Szoka F.C., Nadasdi L., Pongracz K. pH-Dependent bilayer destabilization by an amphipathic peptide. Biochemistry US 1987, 26:2964-2972.
130. Sun J.T., Hong C.Y., Pan C.Y. Fabrication of PDEAEMA-coated mesoporous silica nanoparticles and pH-responsive controlled release. J Phys Chem C 2010, 114:12481-12486.
131. Takahashi S. Conformation of membrane fusion-active 20-residue peptides with or without lipid bilayers. Implication of alpha-helix formation for membrane fusion. Biochemistry 1990, 29:6257-6264.
132. Tang R.P., Ji W.H., Panus D., Palumbo R.N., Wang C. Block copolymer micelles with acid-labile ortho ester side-chains: synthesis, characterization, and enhanced drug delivery to human glioma cells. J Control Release 2011, 151:18-27.
133. Thambi T., Deepagan V.G., Yoo C.K., Park J.H. Synthesis and physicochemical characterization of amphiphilic block copolymers bearing acid-sensitive orthoester linkage as the drug carrier. Polymer 2011, 52:4753-4759.
134. Tomita S., Sato K., Anzai J. Layer-by-layer assembled thin films composed of carboxyl-terminated poly(amidoamine) dendrimer as a pH-sensitive nano-device. J Colloid Interface Sci 2008, 326:35-40.
135. Tomlinson R., Heller J., Brocchini S., Duncan R. Polyacetal-doxorubicin conjugates designed for pH-dependent degradation. Bioconjug Chem 2003, 14:1096-1106.
136. Toncheva V., Schacht E., Ng S.Y., Barr J., Heller J. Use of block copolymers of poly(ortho esters) and poly (ethylene glycol) micellar carriers as potential tumour targeting systems. J Drug Target 2003, 11:345-353.
137. Toriyabe N., Hayashi Y., Harashima H. The transfection activity of R8-modified nanoparticles and siRNA condensation using pH sensitive stearylated-octahistidine. Biomaterials 2013, 34:1337-1343.
138. Traitel T., Goldbart R., Kost J. Smart polymers for responsive drug-delivery systems. J Biomater Sci Polym Ed 2008, 19:755-767.
139. Tu C., Zhu L., Qiu F., Wang D., Su Y., Zhu X., et al. Facile PEGylation of Boltorn® H40 for pH-responsive drug carriers. Polymer 2013, 54:2020-2027.
140. Ulbrich K., Etrych T., Chytil P., Jelinkova M., Rihova B. Antibody-targeted polymer-doxorubicin conjugates with pH-controlled activation. J Drug Target 2004, 12:477-489.
141. Ulijn R.V. Enzyme-responsive materials: a new class of smart biomaterials. J Mater Chem 2006, 16:2217-2225.
142. Van Rossenberg S.M., Sliedregt-Bol K.M., Meeuwenoord N.J., Van Berkel T.J., Van Boom J.H., Van Der Marel G.A., et al. Targeted lysosome disruptive elements for improvement of parenchymal liver cell-specific gene delivery. J Biol Chem 2002, 277:45803-45810.
143. Vogel K., Wang S., Lee R.J., Chmielewski J., Low P.S. Peptide-mediated release of folate-targeted liposome contents from endosomal compartments. J Am Chem Soc 1996, 118:1581-1586.
144. Wagner E. Application of membrane-active peptides for nonviral gene delivery. Adv Drug Deliv Rev 1999, 38:279-289.
145. Wang X.Q., Zhang Q. pH-Sensitive polymeric nanoparticles to improve oral bioavailability of peptide/protein drugs and poorly water-soluble drugs. Eur J Pharm Biopharm 2012, 82:219-229.
146. Wang C.-H., Wang C.-H., Hsiue G.-H. Polymeric micelles with a pH-responsive structure as intracellular drug carriers. J Control Release 2005, 108:140-149.
147. Wang C., Wang G., Wang Z., Zhang X. A pH-responsive superamphiphile based on dynamic covalent bonds. Chemistry 2011, 17:3322-3325.
148. Wang F., Wang Y.C., Dou S., Xiong M.H., Sun T.M., Wang J. Doxorubicin-tethered responsive gold nanoparticles facilitate intracellular drug delivery for overcoming multidrug resistance in cancer cells. Acs Nano 2011, 5:3679-3692.
149. Wang J., Chen B., Zhao D., Peng Y., Zhuo R.X., Cheng S.X. Peptide decorated calcium phosphate/carboxymethyl chitosan hybrid nanoparticles with improved drug delivery efficiency. Int J Pharm 2013, 446:205-210.
150. Wu H., Zhu L., Torchilin V.P. pH-Sensitive poly(histidine)-PEG/DSPE-PEG co-polymer micelles for cytosolic drug delivery. Biomaterials 2013, 34:1213-1222.
151. Wu S., Huang X., Du X. Glucose- and pH-responsive controlled release of cargo from protein-gated carbohydrate-functionalized mesoporous silica nanocontainers. Angew Chem 2013, 52:5580-5584.
152. Wyman T.B., Nicol F., Zelphati O., Scaria P.V., Plank C., Szoka F.C. Design, synthesis, and characterization of a cationic peptide that binds to nucleic acids and permeabilizes bilayers. Biochemistry US 1997, 36:3008-3017.
153. Xie Z., Guan H., Chen X., Lu C., Chen L., Hu X., et al. A novel polymer-paclitaxel conjugate based on amphiphilic triblock copolymer. J Control Release 2007, 117:210-216.
154. Yamada Y., Shinohara Y., Kakudo T., Chaki S., Futaki S., Kamiya H., et al. Mitochondrial delivery of mastoparan with transferrin liposomes equipped with a pH-sensitive fusogenic peptide for selective cancer therapy. Int J Pharm 2005, 303:1-7.
155. Yamada Y., Hashida M., Hayashi Y., Tabata M., Hyodo M., Kamiya H., et al. An approach to transgene expression in liver endothelial cells using a liposome-based gene vector coated with hyaluronic acid. J Pharm Sci 2013, 102:3119-3127.
156. Yan F., Li L., Deng Z., Jin Q., Chen J., Yang W., et al. Paclitaxel-liposome-microbubble complexes as ultrasound-triggered therapeutic drug delivery carriers. J Control Release 2013, 166:246-255.
157. Yang X., Hong H., Grailer J.J., Rowland I.J., Javadi A., Hurley S.A., et al. cRGD-functionalized, DOX-conjugated, and (6)(4)Cu-labeled superparamagnetic iron oxide nanoparticles for targeted anticancer drug delivery and PET/MR imaging. Biomaterials 2011, 32:4151-4160.
158. Yavuz M.S., Cheng Y.Y., Chen J.Y., Cobley C.M., Zhang Q., Rycenga M., et al. Gold nanocages covered by smart polymers for controlled release with near-infrared light. Nat Mater 2009, 8:935-939.
159. Yin H.Q., Kang H.C., Huh K.M., Bae Y.H. Biocompatible, pH-sensitive AB(2) miktoarm polymer-based polymersomes: preparation, characterization, and acidic pH-activated nanostructural transformation. J Mater Chem 2012, 22:19168-19178.
160. Yoo H.S., Lee E.A., Park T.G. Doxorubicin-conjugated biodegradable polymeric micelles having acid-cleavable linkages. J Control Release 2002, 82:17-27.
161. Yuan H., Luo K., Lai Y.S., Pu Y.J., He B, Wang G., et al. A novel poly(l-glutamic acid) dendrimer based drug delivery system with both pH-sensitive and targeting functions. Mol Pharm 2010, 7:953-962.
162. Yuan Q., Hein S., Misra R.D. New generation of chitosan-encapsulated ZnO quantum dots loaded with drug: synthesis, characterization and in vitro drug delivery response. Acta Biomater 2010, 6:2732-2739.
163. Yuan Z., Huang J., Liu J., Cheng S., Zhuo R., Li F. PEG-detachable and acid-labile cross-linked micelles based on orthoester linked graft copolymer for paclitaxel release. Nanotechnology 2011, 22.
164. Yuba E., Kojima C., Sakaguchi N., Harada A., Koiwai K., Kono K. Gene delivery to dendritic cells mediated by complexes of lipoplexes and pH-sensitive fusogenic polymer-modified liposomes. J Control Release 2008, 130:77-83.
165. Yue Y.M., Sheng X., Wang P.X. Fabrication and characterization of microstructured and pH sensitive interpenetrating networks hydrogel films and application in drug delivery field. Eur Polym J 2009, 45:309-315.
166. Yui N., Okano T., Sakurai Y. Inflammation responsive degradation of cross-linked hyaluronic-acid gels. J Control Release 1992, 22:105-116.
167. Zhan F.X., Chen W., Wang Z.J., Lu W.T., Cheng R, Deng C., et al. Acid-activatable prodrug nanogels for efficient intracellular doxorubicin release. Biomacromolecules 2011, 12:3612-3620.
168. Zhang W.L., Choi H.J. Fast and facile fabrication of a graphene oxide/titania nanocomposite and its electro-responsive characteristics. Chem Commun 2011, 47:12286-12288.
169. Zhang X., Li Y., Chen X., Wang X., Xu X., Liang Q., et al. Synthesis and characterization of the paclitaxel/MPEG-PLA block copolymer conjugate. Biomaterials 2005, 26:2121-2128.
170. Zhang L., Gu F.X., Chan J.M., Wang A.Z., Langer R.S., Farokhzad O.C. Nanoparticles in medicine: therapeutic applications and developments. Clin Pharmacol Ther 2008, 83:761-769.
171. Zhang Z.Y., Xu Y.D., Ma Y.Y., Qiu L.L., Wang Y., Kong J.L., et al. Biodegradable ZnO@polymer core-shell nanocarriers: pH-triggered release of doxorubicin in vitro. Angew Chem 2013, 52:4127-4131.
172. Zhou Z., Shen Y., Tang J., Fan M., Van Kirk E.A., Murdoch W.J., et al. Charge-reversal drug conjugate for targeted cancer cell nuclear drug delivery. Adv Funct Mater 2009, 19:3580-3589.
173. Zhou L., Cheng R., Tao H., Ma S., Guo W., Meng F., et al. Endosomal pH-activatable poly(ethylene oxide)-graft-doxorubicin prodrugs: synthesis, drug release, and biodistribution in tumor-bearing mice. Biomacromolecules 2011, 12:1460-1467.
174. Zhou L., Liang D., He X., Li J., Tan H., Li J., et al. The degradation and biocompatibility of pH-sensitive biodegradable polyurethanes for intracellular multifunctional antitumor drug delivery. Biomaterials 2012, 33:2734-2745.
175. Zignani M., Drummond D.C., Meyer O., Hong K., Leroux J.C. In vitro characterization of a novel polymeric-based pH-sensitive liposome system. BBA Biomembranes 2000, 1463:383-394.