Construction and cellular uptake behavior of redox-sensitive docetaxel prodrug-loaded liposomes

References

• Bekkara-Aounallah F, Gref R, Othman M, Reddy LH, Pili B, Allain V, Bourgaux C, Hillaireau H, Lepêtre-Mouelhi S, Desmaële D. Novel PEGylated nanoassemblies made of self-assembled squalenoyl nucleoside analogues. Adv Funct Mater. 2008;18:3715–3725.
   Web of Science ®Google Scholar
• Brandenberger C, Muhlfeld C, Ali Z, Lenz AG, Schmid O, Parak WJ, Gehr P, Rothen-Rutishauser B. Quantitative evaluation of cellular uptake and trafficking of plain and polyethylene glycol-coated gold nanoparticles. Small. 2010;6:1669–1678.
   PubMed Web of Science ®Google Scholar
• Chang J, Jallouli Y, Kroubi M, Yuan XB, Feng W, Kang CS, Pu PY, Betbeder D. Characterization of endocytosis of transferrin-coated PLGA nanoparticles by the blood-brain barrier. Int J Pharm. 2009;379:285–292.
   PubMed Web of Science ®Google Scholar
• Chang M, Lu S, Zhang F, Zuo T, Guan Y, Wei T, Shao W, Lin G. RGD-modified pH-sensitive liposomes for docetaxel tumor targeting. Colloids Surf B Biointerfaces. 2015;129:175–182.
   PubMed Web of Science ®Google Scholar
• Chen H, Wang Z, Zong S, Wu L, Chen P, Zhu D, Wang C, Xu S, Cui Y. SERS-fluorescence monitored drug release of a redox-responsive nanocarrier based on graphene oxide in tumor cells. ACS Appl Mater Interfaces. 2014;6:17526–17533.
   PubMed Web of Science ®Google Scholar
• Duan X, Xiao J, Yin Q, Zhang Z, Yu H, Mao S, Li Y. Smart pH-sensitive and temporal-controlled polymeric micelles for effective combination therapy of doxorubicin and disulfira. ACS Nano. 2013;7:5858–5869.
   PubMed Web of Science ®Google Scholar
• Duangjit S, Opanasopit P, Rojanarata T, Takayama J, Takayama K, Ngawhirunpat T. Bootstrap resampling technique to evaluate the reliability of the optimal liposome formulation: skin permeability and stability response variables. Biol Pharm Bull. 2014;37:1543–1549.
   PubMed Web of Science ®Google Scholar
• Ganesh T. Improved biochemical strategies for targeted delivery of taxoids. Bioorg Med Chem. 2007;15:3597–3623.
   PubMed Web of Science ®Google Scholar
• Huynh L, Leroux JC, Allen C. Enhancement of docetaxel solubility via conjugation of formulation-compatible moieties. Org Biomol Chem. 2009;7:3437–3446.
   PubMed Web of Science ®Google Scholar
• Immordino ML, Brusa P, Arpicco S, Stella B, Dosio F, Cattel L. Preparation, characterization, cytotoxicity and pharmacokinetics of liposomes containing docetaxel. J Control Release. 2003;91:417–429.
   PubMed Web of Science ®Google Scholar
• Jahnke JP, Bazan GC, Sumner JJ. Effect of modified phospholipid bilayers on the electrochemical activity of a membrane-spanning conjugated oligoelectrolyte. Langmuir. 2015;31:11613–11620.
   PubMed Web of Science ®Google Scholar
• Kastantin M, Missirlis D, Black M, Ananthanarayanan B, Peters D, Tirrell M. Thermodynamic and kinetic stability of DSPE-PEG(2000) micelles in the presence of bovine serum albumin. J Phys Chem B. 2010;114:12632–12640.
   PubMed Web of Science ®Google Scholar
• Kim H, Lee Y, Lee IH, Kim S, Kim D, Saw PE, Lee J, Choi M, Kim YC, Jon S. Synthesis and therapeutic evaluation of an aptide-docetaxel conjugate targeting tumor-associated fibronectin. J Control Release. 2014;178:118–124.
   PubMed Web of Science ®Google Scholar
• Kim JS, Yoon TJ, Yu KN, Noh MS, Woo M, Kim BG, Lee KH, Sohn BH, Park SB, Lee JK. Cellular uptake of magnetic nanoparticle is mediated through energy-dependent endocytosis in A549 cells. J Vet Sci. 2006;7:321–326.
   PubMed Web of Science ®Google Scholar
• Kratz F, Muller IA, Ryppa C, Warnecke A. Prodrug strategies in anticancer chemotherapy. ChemMedChem. 2008;3:20–53.
   PubMed Web of Science ®Google Scholar
• Li Y, Liu R, Yang J, Ma G, Zhang Z, Zhang X. Dual sensitive and temporally controlled camptothecin prodrug liposomes codelivery of siRNA for high efficiency tumor therapy. Biomaterials. 2014;35:9731–9745.
   PubMed Web of Science ®Google Scholar
• Lian H, Zhang TH, Sun J, Liu XH, Ren GL, Kou LF, Zhang YX, Han XP, Ding WY, Ai XY. Enhanced oral delivery of paclitaxel using acetylcysteine functionalized chitosan-vitamin E succinate nanomicelles based on a mucus bioadhesion and penetration mechanism. Mol Pharm. 2013;10:3447–3458.
   PubMed Web of Science ®Google Scholar
• Lu J, Liu C, Wang P, Ghazwani M, Xu J, Huang Y, Ma X, Zhang P, Li S. The self-assembling camptothecin-tocopherol prodrug: An effective approach for formulating camptothecin. Biomaterials. 2015;62:176–187.
   PubMed Web of Science ®Google Scholar
• Mackiewicz N, Nicolas J, Handké N, Noiray M, Mougin J, Daveu C, Lakkireddy HR, Bazile D, Couvreur P. Precise engineering of multifunctional PEGylated polyester nanoparticles for cancer cell targeting and imaging. Chem Mater. 2014;26:1834–1847.
   Web of Science ®Google Scholar
• Mannock DA, Lewis RNAH, McMullen TPW, McElhaney RN. The effect of variations in phospholipid and sterol structure on the nature of lipid–sterol interactions in lipid bilayer model membranes. Chem Phys Lipids. 2010;163:403–448.
   PubMed Web of Science ®Google Scholar
• Meng F, Hennink WE, Zhong Z. Reduction-sensitive polymers and bioconjugates for biomedical applications. Biomaterials. 2009;30:2180–2198.
   PubMed Web of Science ®Google Scholar
• Meyer FJM, Benjamini A, Rodgers JM, Misteli Y, Smit B. Molecular simulation of the DMPC-cholesterol phase diagram. J Phys Chem B. 2010;114:10451–10461.
   Google Scholar
• Mo R, Sun Q, Li N, Zhang C. Intracellular delivery and antitumor effects of pH-sensitive liposomes based on zwitterionic oligopeptide lipids. Biomaterials. 2013;34:2773–2786.
   PubMed Web of Science ®Google Scholar
• Monti DM, Guarnieric D, Napolitanod G, Piccoli R, Nettic P, Fuscoc S, Arciello A. Biocompatibility, uptake and endocytosis pathways of polystyrene nanoparticles in primary human renal epithelial cells. J Biotechnol. 2015;193:3–10.
   PubMed Web of Science ®Google Scholar
• Ohnishi N, Tomida H, Ito Y, Tahara K, Takeuchi H. Characterization of a doxorubicin liposome formulation by a novel in vitro release test methodology using column-switching high-performance liquid chromatography. Chem Pharm Bull. 2014;62:538–544.
   PubMed Web of Science ®Google Scholar
• Park MH, Keum CG, Song JY, Kim D, Cho CW. A novel aqueous parenteral formulation of docetaxel using prodrugs. Int J Pharm. 2014;462:1–7.
   PubMed Web of Science ®Google Scholar
• Ren G, Liu D, Guo W, Wang M, Wu C, Guo M, Ai X, Wang Y, He Z. Docetaxel prodrug liposomes for tumor therapy: characterization, in vitro and in vivo evaluation. Drug Deliv. 2016;23:1272–1281.
   PubMed Web of Science ®Google Scholar
• Song Q, Wang X, Wang Y, Liang Y, Zhou Y, Song X, He B, Zhang H, Dai W, Wang X. Reduction responsive self-assembled nanoparticles based on disulfide-linked drug-drug conjugate with high drug loading and antitumor efficacy. Mol Pharm. 2016;13:190–201.
   PubMed Web of Science ®Google Scholar
• Swansona JA, Wattsb C. Macropinocytosis. Trends Cell Biol. 1995;5:424–428.
   PubMed Web of Science ®Google Scholar
• Varshosaz J, Minayian M, Ahmadi M, Ghassami E. Enhancement of solubility and antidiabetic effects of Repaglinide using spray drying technique in STZ-induced diabetic rats. Pharm Dev Technol. 2016. [Epub ahead of print]. doi: http://dx.doi.org/10.3109/10837450.2016.1143001
   Web of Science ®Google Scholar
• Wang J, Li L, Du Y, Sun J, Han X, Luo C, Ai X, Zhang Q, Wang Y, Fu Q. Improved oral absorption of doxorubicin by amphiphilic copolymer of lysine-linked ditocopherol polyethylene glycol 2000 succinate: in vitro characterization and in vivo evaluation. Mol Pharm. 2015;12:463–473.
   PubMed Web of Science ®Google Scholar
• Wang Y, Liu D, Zheng Q, Zhao Q, Zhang H, Ma Y, Fallon JK, Fu Q, Haynes MT, Lin G. Disulfide bond bridge insertion turns hydrophobic anticancer prodrugs into self-assembled nanomedicines. Nano Lett. 2014;14:5577–5583.
   PubMed Web of Science ®Google Scholar
• Wu G, Fang YZ, Yang S, Lupton JR, Turner ND. Glutathione metabolism and its implications for health. J Nutr. 2003;134:489–492.
   Web of Science ®Google Scholar
• Yang C, Hu T, Cao H, Zhang L, Zhou P, He G, Song X, Tong A, Guo G, Yang F. Facile construction of chloroquine containing PLGA-based pDNA delivery system for efficient tumor and pancreatitis targeting in vitro and in vivo. Mol Pharm. 2015;12:2167–2179.
   PubMed Web of Science ®Google Scholar
• Zhang H, Li RY, Lu X, Mou ZZ, Lin GM. Docetaxel-loaded liposomes: preparation, pH sensitivity, pharmacokinetics, and tissue distribution. J Zhejiang Univ Sci B. 2012;13:981–989.
   PubMed Web of Science ®Google Scholar
• Zhang JA, Anyarambhatla G, Ma L, Ugwu S, Xuan T, Sardone T, Ahmad I. Development and characterization of a novel Cremophor EL free liposome-based paclitaxel (LEP-ETU) formulation. Eur J Pharm Biopharm. 2005;59:177–187.
   PubMed Web of Science ®Google Scholar
• Zhang W, Li Y, Liu L, Sun Q, Shuai X, Zhu W, Chen Y. Amphiphilic toothbrushlike copolymers based on poly(ethylene glycol) and poly(ɛ-caprolactone) as drug carriers with enhanced properties. Biomacromolecules. 2010;11:1331–1338.
   PubMed Web of Science ®Google Scholar
• Zhang W, Sun J, Liu Y, Tao M, Ai X, Su X, Cai C, Tang Y, Feng Z, Yan X. PEG-stabilized bilayer nanodisks as carriers for doxorubicin delivery. Mol Pharm. 2014;11:3279–3290.
   PubMedGoogle Scholar
• Zhigaltsev IV, Winters G, Srinivasulu M, Crawford J, Wong M, Amankwa L, Waterhouse D, Masin D, Webb M, Harasym N. Development of a weak-base docetaxel derivative that can be loaded into lipid nanoparticles. J Control Release. 2010;144:332–340.
   PubMed Web of Science ®Google Scholar