Fabrication of novel hepatoma-targeting microdisks by hydrogen bond-assisted self-assembly of an azacitidine-conjugating amphiphilic random copolymer

Acta Biomaterialia

Volumn 6, Issue 2, 2010, Pages 511-518

  Li, Xia ^a   Guo, Hui ^a   Wang, Junliang ^a   Wu, Qi ^a   Lin, Xianfu ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Azacitidine; Disk; Random copolymer; Self assembly; Targeting

Indexed keywords

ATOMIC FORCE MICROSCOPY; FABRICATION; FLUORESCENCE SPECTROSCOPY; HIGH RESOLUTION TRANSMISSION ELECTRON MICROSCOPY; HYDROGEN BONDS; SCANNING ELECTRON MICROSCOPY;

AMPHIPHILICS; AZACITIDINE; DISK; MICRODISKS; RANDOM COPOLYMER; SYNTHETIC ROUTES; TARGETING; THIN DISK; ULTRAVIOLET FLUORESCENCE SPECTROSCOPY; ULTRAVIOLET-VISIBLE SPECTROSCOPY;

SELF ASSEMBLY;

3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; AMPHOPHILE; AZACITIDINE; COPOLYMER; GALACTOSE;

ARTICLE; ATOMIC FORCE MICROSCOPY; CELL FUNCTION; CELL STRAIN HEPG2; CONFOCAL LASER MICROSCOPY; CONTROLLED STUDY; CYTOTOXICITY TEST; DRUG CONJUGATION; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG TARGETING; FLUORESCENCE SPECTROSCOPY; HEPATOMA CELL; HUMAN; HUMAN CELL; HYDROGEN BOND; HYDROPHOBICITY; INFRARED RADIATION; INTERNALIZATION; LIVER CELL CARCINOMA; MICROMORPHOLOGY; PRIORITY JOURNAL; SCANNING ELECTRON MICROSCOPY; THICKNESS; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET RADIATION;

EID: 72049113078     PISSN: 17427061     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.actbio.2009.07.002     Document Type: Article

References (35)

1. Haag R., and Kratz F. Polymer therapeutics: concepts and applications. Angew Chem Int Ed 45 (2006) 1198-1215
2. Duncan R. Polymer conjugates as anticancer nanomedicines. Nat Rev Cancer 6 (2006) 688-701
3. Yuan Q., Venkatasubramanian R., Hein S., and Misra R.D.K. A stimulus-responsive magnetic nanoparticle drug carrier: magnetite encapsulated by chitosan-grafted-copolymer. Acta Biomater 4 (2008) 1024-1037
4. Nishiyama N., and Kataoka K. Current state, achievements, and future prospects of polymeric micelles as nanocarriers for drug and gene delivery. Pharmacol Ther 112 (2006) 630-648
5. Wolinsky J.B., and Grinstaff M.W. Therapeutic and diagnostic applications of dendrimers for cancer treatment. Adv Drug Delivery Rev 60 (2008) 1037-1055
6. Casadei M.A., Pitarresi G., Calabrese R., Paolicelli P., and Giammona G. Biodegradable and pH-sensitive hydrogels for potential colon-specific drug delivery: characterization and in vitro release studies. Biomacromolecules 9 (2008) 43-49
7. Sun C., Lee J.S.H., and Zhang M.Q. Magnetic nanoparticles in MR imaging and drug delivery. Adv Drug Delivery Rev 60 (2008) 1252-1265
8. Xu X.L., Chen X.S., Xu X.Y., Lu T.C., Wang X., Yang L.X., et al. BCNU-loaded PEG-PLLA ultrafine fibers and their in vitro antitumor activity against glioma C6 cells. J Control Release 114 (2006) 307-316
9. Maeda H., Sawa T., and Konno T. Mechanism of tumor-targeted delivery of macromolecular drugs, including the EPR effect in solid tumor and clinical overview of the prototype polymeric drug SMANCS. J Control Release 74 (2001) 47-61
10. McCarron P.A., Marouf W.M., Quinn D.J., Fay F., Burden R.E., Olwill S.A., et al. Antibody targeting of camptothecin-loaded PLGA nanoparticles to tumor cells. Bioconjugate Chem 19 (2008) 1561-1569
11. Nasongkla N., et al. Multifunctional polymeric micelles as cancer-targeted, MRI-ultrasensitive drug delivery systems. Nano Lett 6 (2006) 2427-2430
12. Lin A.H., Liu Y.M., Huang Y., Sun J.B., Wu Z.F., Zhang M., et al. Glycyrrhizin surface-modified chitosan nanoparticles for hepatocyte-targeted delivery. Int J Pharm 359 (2008) 247-253
13. Kim D., Lee E.S., Oh K.T., Gao Z.G., and Bae Y.H. Doxorubicin-loaded polymeric micelle overcomes multidrug resistance of cancer by double-targeting folate receptor and early endosomal pH. Small 4 (2008) 2043-2050
14. Zeng F.Q., Lee H., and Allen C. Epidermal growth factor-conjugated poly(ethylene glycol)-block-poly(delta-valerolactone) copolymer micelles for targeted delivery of chemotherapeutics. Bioconjugate Chem 17 (2006) 399-409
15. Edmonds W.F., Li Z.B., Hillmyer M.A., and Lodge T.P. Disk micelles from nonionic coil-coil diblock copolymers. Macromolecules 39 (2006) 4526-4530
16. Azzam T., and Eisenberg A. Control of vesicular morphologies through hydrophobic block length. Angew Chem Int Ed 45 (2006) 7443-7447
17. Fu J., et al. Self-assembly of crystalline-coil diblock copolymer in solvents with varying selectivity: from spinodal-like aggregates to spheres, cylinders, and lamellae. Macromolecules 37 (2004) 976-986
18. Zhu J.T., Yu H.Z., and Jiang W. Morphological transition of aggregates from ABA amphiphilic triblock copolymer induced by hydrogen bonding. Macromolecules 38 (2005) 7492-7501
19. Ilhan F., Galow T.H., Gray M., Clavier G., and Rotello V.M. Giant vesicle formation through self-assembly of complementary random copolymers. J Am Chem Soc 122 (2000) 5895-5896
20. Chebotareva N., Bomans P.H.H., Frederik P.M., Sommerdijk N.A.J.M., and Sijbesma R.P. Morphological control and molecular recognition by bis-urea hydrogen bonding in micelles of amphiphilic tri-block copolymers. Chem Commun 39 (2005) 4967-4969
21. Kaminskas E., et al. Approval summary: azacitidine for treatment of myelodysplastic syndrome subtypes. Clin Cancer Res 11 (2005) 3604-3608
22. Rudek M.A., et al. Pharmacokinetics of 5-azacitidine administered with phenylbutyrate in patients with refractory solid tumors or hematologic malignancies. J Clin Oncol 23 (2005) 3906-3911
23. Mi F.L., et al. Synthesis of a novel glycoconjugated chitosan and preparation of its derived nanoparticles for targeting hepG2 cells. Biomacromolecules 8 (2007) 892-898
24. Ying L., Yin C., Zhuo R.X., Leong K.W., Mao H.Q., Kang E.T., et al. Immobilization of galactose ligands on acrylic acid graft-copolymerized poly(ethylene terephthalate) film and its application to hepatocyte culture. Biomacromolecules 4 (2003) 157-165
25. Hiratsuka T., Goto M., Kondo Y., Cho C.S., and Akaike T.R. Copolymers for hepatocyte-specific targeting carrying galactose and hydrophobic alkyl groups. Macromol Biosci 8 (2008) 231-238
26. Li B.S., Cheuk K.K.L., Yang D.L., Lam J.W.Y., Wan L.J., Bai C.L., et al. Self-assembling of an amphiphilic polyacetylene carrying l-leucine pendants: a homopolymer case. Macromolecules 36 (2003) 5447-5450
27. Wu Q., Wang N., Xiao Y.M., Lu D.S., and Lin X.F. Regiospecific alkaline protease-catalyzed divinyl acyl transesterifications of primary hydroxyl groups of mono- and di-saccharides in pyridine. Carbohydr Res 339 (2004) 2059-2067
28. Lu M., Gong X.G., Lu Y.W., Guo J.J., Wang C.H., and Pan Y.J. Molecular cloning and functional characterization of a cell-permeable superoxide dismutase targeted to lung adenocarcinoma cells-inhibition cell proliferation through the Akt/p27(kip1) pathway. J Bio Chem 281 (2006) 13620-13627
29. Ferrero M., and Gotor V. Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides, and C-nucleosides. Chem Rev 100 (2000) 4319-4347
30. Soyez H., Schacht E., and Vanderkerken S. The crucial role of spacer groups in macromolecular prodrug design. Adv Drug Delivery Rev 21 (1996) 81-106
31. David A., Kopečková P., Rubinstein A., and Kopeček J. Enhanced biorecognition and internalization of HPMA copolymers containing multiple or multivalent carbohydrate side-chains by human hepatocarcinoma cells. Bioconjugate Chem 12 (2001) 890-899
32. Savariar E.N., Aathimanikandan S.V., and Thayumanavan S. Supramolecular assemblies from amphiphilic homopolymers: testing the scope. J Am Chem Soc 128 (2006) 16224-16230
33. Dong D.C., and Winnik M.A. The Py scale of solvent polarities. Can J Chem 62 (1984) 2560-2565
34. Kalyanasundaram K., and Thomas J.K. Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems. J Am Chem Soc 99 (1977) 2039-2044
35. Li Z.B., Chen Z.Y., Cui H.G., Hales K., Qi K., Wooley K.L., et al. Disk morphology and disk-to-cylinder tunability of poly(acrylic acid)-b-poly(methyl acrylate)-b-polystyrene triblock copolymer solution-state assemblies. Langmuir 21 (2005) 7533-7539