The Use of Amino Acid Linkers in the Conjugation of Paclitaxel with Hyaluronic Acid as Drug Delivery System: Synthesis, Self-Assembled Property, Drug Release, and In Vitro Efficiency (original) (raw)
Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT. Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc. 1971;93:2325–7. ArticleCASPubMed Google Scholar
Schiff PB, Fant J, Horwitz SB. Promotion of microtubule assembly in vitro by taxol. Nature. 1979;277:665–7. ArticleCASPubMed Google Scholar
Rowinsky EK, Donehower RC, Jones RJ, Tucker RW. Microtubule changes and cytotoxicity in leukemic cell lines treated with taxol. Cancer Res. 1988;48:4093–100. CASPubMed Google Scholar
Weiss RB, Donehower RC, Wiernik PH, Ohnuma T, Gralla RJ, Trump DL, et al. Hypersensitivity reactions from taxol. J Clin Oncol. 1990;8:1263–8. CASPubMed Google Scholar
Singla AK, Garg A, Aggarwal D. Paclitaxel and its formulations. Int J Pharm. 2002;235:179–92. ArticleCASPubMed Google Scholar
Francesco MV, Oddone S, Gianfranco P, Raniero M, Ruth D. PEG-doxorubicin conjugates: influence of polymer structure on drug release, in vitro cytotoxicity, biodistribution, and antitumor activity. Bioconjugate Chem. 2005;16:775–84. Article Google Scholar
Hsiangfa L, Sungching C, Meichin C, Powei L, Chiungtong C, Hsingwen S. Paclitaxel-loaded poly (γ-glutamic acid)-poly(lactide) nanoparticles as a targeted drug delivery system against cultured HepG2 cells. Bioconjugate Chem. 2006;17:291–9. Article Google Scholar
Shu-ichi S, Masahiro K, Hiroshi K, To-ru K. Complete regression of xenografted human carcinomas by a paclitaxel-carboxymethyl dextran conjugate (AZ10992). J Control Release. 2007;117:40–50. Article Google Scholar
Crosasso P, Ceruti M, Brusa P, Arpicco S, Dosio F, Cattel L. Preparation, characterization and properties of sterically stabilized paclitaxel-containing liposomes. J Controlled Release. 2000;63:19–30. ArticleCAS Google Scholar
Tarr BD, Sambandan TG, Yalkowsky SH. A new parenteral emulsion for the administration of taxol. Pharm Res. 1987;4:162–5. ArticleCASPubMed Google Scholar
Bae KH, Lee Y, Park TG. Oil-encapsulating PEO-PPO-PEO shell crosslinked nanocapsules for target-specific delivery of paclitaxel. Biomacromolecules. 2007;8:650–6. ArticleCASPubMed Google Scholar
Maeda H, Seymour LW, Miyamoto Y. Conjugates of anticancer agents and polymers: advantages of macromolecular therapeutics in vivo. Bioconjugate Chem. 1992;3:351–62. ArticleCAS Google Scholar
Jian Y, Fu-Qiang H, Yong ZD, Hong Y. Polymeric micelles with glycolipid-like structure and multiple hydrophobic domains for mediating molecular target delivery of paclitaxel. Biomacromolecules. 2007;8:2450–6. Article Google Scholar
Shuliang L, Belinda B, JoEllen W, Andre FP. Self-assembled poly (butadiene)-b-poly (ethylene oxide) polymersomes as paclitaxel carriers. Biotechnol Prog. 2007;23:278–85. Article Google Scholar
Hyun JL, Hye YN, Byung HL, Dae JK, Jai YK, Jong-sang P. A novel technique for loading of paclitaxel-PLGA nanoparticles onto ePTFE vascular grafts. Biotechnol Prog. 2007;23:693–7. Article Google Scholar
Hosseinkhani H, Hosseinkhani M, Khademhosseini A, Kobayashi H. Bone regeneration through controlled release of bone morphogenetic protein-2 from 3-D tissue engineered nano-scaffold. J Controlled Release. 2007;117:380–6. ArticleCAS Google Scholar
Hosseinkhani H, Hosseinkhani M, Tian F, Kobayashi H, Tabata Y. Osteogenic differentiation of mesenchymal stem cells in self-assembled peptide-amphiphile nanofibers. Biomaterials. 2006;27:4079–86. ArticleCASPubMed Google Scholar
Hosseinkhani H, Hosseinkhani M, Tian F, Kobayashi H, Tabata Y. Ectopic bone formation in collagen sponge self-assembled peptide-amphiphile nanofibers hybrid scaffold in a perfusion culture bioreactor. Biomaterials. 2006;27:5089–98. ArticleCASPubMed Google Scholar
Hosseinkhani H, Hosseinkhani M, Khademhosseini A, Kobayashi H, Tabata Y. Enhanced angiogenesis through controlled release of basic fibroblast growth factor from peptide amphiphile for tissue regeneration. Biomaterials. 2006;27:5836–44. ArticleCASPubMed Google Scholar
Hosseinkhani H, Hosseinkhani M, Kobayashi H. Design of tissue-engineered nanoscaffold through self-assembly of peptide amphiphile. J Bioact Compat Polym. 2006;21:277–96. ArticleCAS Google Scholar
Entwistle J, Hall CL, Turley EA. HA receptors: regulators of signalling to the cytoskeleton. J Cell Biochem. 1996;61:569–77. ArticleCASPubMed Google Scholar
Stern R. Association between cancer and “acid mucopolysaccharides”: an old concept comes of age, finally. Semin Cancer Biol. 2008;18:238–43. ArticleCASPubMed Google Scholar
Hua Q, Knudson CB, Knudson WJ. Internalization of hyaluronan by chondrocytes occurs via receptor-mediated endocytosis. J Cell Sci. 1993;106:365–75. CASPubMed Google Scholar
Day AJ, Prestwich GD. Hyaluronan-binding proteins: tying up the giant. J Biol Chem. 2002;277:4585–8. ArticleCASPubMed Google Scholar
Toole BP, Slomiany MG. Hyaluronan: a constitutive regulator of chemoresistance and malignancy in cancer cells. Semin Cancer Biol. 2008;18:244–50. ArticleCASPubMed Google Scholar
Coradini D, Pellizzaro C, Miglierini G, Daidone MG, Perbellini A. Hyaluronic acid as drug delivery for sodium butyrate: improvement of the anti-proliferative activity on a breast-cancer cell line. Int J Cancer. 1999;81:411–6. ArticleCASPubMed Google Scholar
Coradini D, Zorzet S, Rossin R, Scarlata I, Pellizzaro C, Turrin C, et al. Inhibition of hepatocellular carcinomas in vitro and hepatic metastases in vivo in mice by the histone deacetylase inhibitor HA-But. Clin Cancer Res. 2004;10:4822–30. ArticleCASPubMed Google Scholar
Speranzaa A, Pellizzaroa C, Coradini D. Hyaluronic acid butyric esters in cancer therapy. Anticancer Drug Des. 2005;16:373–9. Article Google Scholar
Luo Y, Bernshaw NJ, Lu Z, Kopecek J, Prestwich GD. Targeted delivery of doxorubicin by HPMA copolymer-hyaluronan bioconjugates. Pharm Res. 2002;19:396–402. ArticleCASPubMed Google Scholar
Luo Y, Prestwich GD. Synthesis and selective cytotoxicity of a hyaluronic acid-antitumor bioconjugate. Bioconjugate Chem. 1999;10:755–63. ArticleCAS Google Scholar
Luo Y, Ziebell MR, Prestwich GD. A hyaluronic acid-taxol antitumor bioconjugate targeted to cancer cells. Biomacromolecules. 2000;1:208–18. ArticleCASPubMed Google Scholar
Wang Y, Xin D, Liu K, Xiang J. Heparin-paclitaxel conjugates using mixed anhydride as intermediate: synthesis, influence of polymer structure on drug release, anticoagulant activity and in vitro efficiency. Pharm Res. 2009;26:785–93. ArticlePubMed Google Scholar
Coradini D, Pellizzaro C, Abolafio G, Bosco M, Scarlata I, Cantoni S, et al. Hyaluronic-acid butyric esters as promising antineoplastic agents in human lung carcinoma: A preclinical study. Invest New Drug. 2004;22:207–17. ArticleCAS Google Scholar
Shu-ichi S, Masahiro K, Hiroshi K, To-ru K. Paclitaxel delivery systems: the use of amino acid linkers in the conjugation of paclitaxel with carboxymethyldextran to create prodrugs. Biol Pharm Bull. 2002;25:632–41. Article Google Scholar
Peniche C, Arguelles-Monal W, Davidenko N, Sastre R, Gallardo A, Roman J. Self-curing membranes of chitosan/ PAA IPNs obtained by radical polymerization: preparation, characterization and interpolymer complexation. Biomaterials. 1999;20:1869–78. ArticleCASPubMed Google Scholar
Chun L, Dong-fang Y, Robert AN, Fernando CL, Clifton S, Nancy H, et al. Complete regression of well-established tumors using a novel water-soluble Poly(l-Glutamic acid)-paclitaxel conjugate. Cancer Res. 1998;58:2404–9. Google Scholar
Rosler A, Vandermeulen GWM, Klok HA. Advanced drug delivery devices via self-assembly of amphiphilic block copolymers. Adv Drug Deliv Rev. 2001;53:95–108. ArticleCASPubMed Google Scholar
Hosseinkhani H, Aoyama T, Yamamoto S, Ogawa O, Tabata Y. In vitro transfection of plasmid DNA by amine derivatives of gelatin accompanied with ultrasound irradiation. Pharm Res. 2002;19:1471–9. ArticleCASPubMed Google Scholar
Hosseinkhani H, Aoyama T, Ogawa O, Tabata Y. Tumor targeting of gene expression through metal-coordinated conjugation with dextran. J Controlled Release. 2003;88:297–312. ArticleCAS Google Scholar
Hosseinkhani H, Tabata Y. PEGylation enhances tumor targeting of plasmid DNA by an artificial cationized protein with repeated RGD sequences, Pronectin. J Controlled Release. 2004;97:157–71. ArticleCAS Google Scholar
Hosseinkhani H, Azzam T, Tabata Y, Domb AJ. Dextran-spermine polycation: an efficient nonviral vector for in vitro and in vivo gene transfection. Gene Ther. 2004;11:194–203. ArticleCASPubMed Google Scholar
Hosseinkhani H, Tabata Y. Ultrasound enhances in vivo tumor expression of plasmid DNA by PEG-introduced cationized dextran. J Controlled Release. 2005;108:540–56. ArticleCAS Google Scholar
Nicolaou KC, Rlemer C, Kerr MA, Rideout D, Wrasidlo E. Design, synthesis and biological activity of protaxols. Nature. 1993;364:464–6. ArticleCASPubMed Google Scholar
Schiff PB, Horwitz SB. Taxol stabilizes microtubules in mouse fibroblast cells. Proc Natl Acad Sci. 1980;77:1561–5. ArticleCASPubMed Google Scholar
Jordan MA, Wendll K, Gardiner S, Derry WB, Copp H, Wilson L. Mitotic block induced in HeLa cells by low concentrations of paclitaxel (Taxol) results in abnormal mitotic exit and apoptotic cell death. Cancer Res. 1996;56:816–25. CASPubMed Google Scholar