Phenylboronic acid-functionalized polymeric micelles with a HepG2 cell targetability

Biomaterials

Volumn 34, Issue 38, 2013, Pages 10296-10304

  Zhang, Xiaojin ^a   Zhang, Zhenguo ^a   Su, Xin ^a   Cai, Mengmeng ^a   Zhuo, Renxi ^a   Zhong, Zhenlin ^a  

^a WUHAN UNIVERSITY   (China)

Author keywords

Controlled drug release; Copolymer; Pluronics; Polycarbonate; Polymeric micelle

Indexed keywords

3-AMINOPHENYLBORONIC ACID; AMPHIPHILIC BLOCK COPOLYMERS; CONFOCAL LASER SCANNING MICROSCOPY; CONTROLLED DRUG RELEASE; NARROW SIZE DISTRIBUTIONS; PLURONICS; POLYMERIC MICELLE; TARGETED DRUG DELIVERY;

CELL CULTURE; COPOLYMERS; DRUG DELIVERY; HYDROGENATION; ORGANIC ACIDS; POLYCARBONATES; POLYMERS;

MICELLES;

5 METHYL 5 BENZYLOXYCARBONYL 1,3 DIOXAN 2 ONE; BENZENEBORONIC ACID; BENZODIOXAN DERIVATIVE; CARBOXYL GROUP; DOXORUBICIN; FUMARIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CONFOCAL LASER MICROSCOPY; CONTROLLED STUDY; CYTOTOXICITY; DEPROTECTION REACTION; DRUG DELIVERY SYSTEM; DRUG UPTAKE; FUCOSYLATION; HUMAN; HUMAN CELL; HYDROGENATION; IN VITRO STUDY; MICELLE; PARTICLE SIZE; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; SYNTHESIS; TRANSMISSION ELECTRON MICROSCOPY;

CONTROLLED DRUG RELEASE; COPOLYMER; PLURONICS; POLYCARBONATE; POLYMERIC MICELLE;

BORONIC ACIDS; DRUG DELIVERY SYSTEMS; HELA CELLS; HEP G2 CELLS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MICELLES; POLYMERS;

EID: 84885382924     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2013.09.042     Document Type: Article

References (48)

1. Letchford K., Burt H. Areview of the formation and classification of amphiphilic block copolymer nanoparticulate structures: micelles, nanospheres, nanocapsules and polymersomes. Eur J Pharm Biopharm 2007, 65:259-269.
2. Holder S.J., Sommerdijk N.A.J.M. New micellar morphologies from amphiphilic block copolymers: disks, toroids and bicontinuous micelles. Polym Chem 2011, 2:1018-1028.
3. Ma Y.Y., Eisenberg A. Selective localization of preformed nanoparticles in morphologically controllable block copolymer aggregates in solution. Acc Chem Res 2012, 45:1657-1666.
4. Palencia M., Rivas B.L. Metal-ion retention properties of water-soluble amphiphilic block copolymer in double emulsion systems (w/o/w) stabilized by non-ionic surfactants. JColloid Interface Sci 2011, 363:682-689.
5. Yan J.L., Ye Z.Y., Chen M., Liu Z.Z., Xiao Y., Zhang Y., et al. Fine tuning micellar core-forming block of poly(ethylene glycol)-block-poly(ε-caprolactone) amphiphilic copolymers based on chemical modification for the solubilization and delivery of doxorubicin. Biomacromolecules 2011, 12:2562-2572.
6. Leon O., Bordege V., Munoz-Bonilla A., Sanchez-Chaves M., Fernandez-Garcia M. Well-controlled amphiphilic block glycopolymers and their molecular recognition with lectins. JPolym Sci Part A: Polym Chem 2010, 48:3623-3631.
7. Cui C., Xue Y.N., Wu M., Zhang Y., Yu P., Liu L., et al. Cellular uptake, intracellular trafficking, and antitumor efficacy of doxorubicin-loaded reduction-sensitive micelles. Biomaterials 2013, 34:3858-3869.
8. Li X.J., Qian Y.F., Liu T., Hu X.L., Zhang G.Y., You Y.Z., et al. Amphiphilic multiarm star block copolymer-based multifunctional unimolecular micelles for cancer targeted drug delivery and MR imaging. Biomaterials 2011, 32:6595-6605.
9. Xiao Y., You S.S., Yao Y., Zheng T., Lin C., Roth S.V., et al. Generalized synthesis of mesoporous rare earth oxide thin films through amphiphilic ionic block copolymer templating. Eur J Inorg Chem 2013, 8:1251-1257.
10. Goertz M.P., Marks L.E., Montano G.A. Biomimetic mono layer and bilayer membranes made from amphiphilic block copolymer micelles. ACS Nano 2012, 6:1532-1540.
11. Kim Y.R., Jung S., Ryu H., Yoo Y.E., Kim S.M., Jeon T.J. Synthetic biomimetic membranes and their sensor applications. Sensors 2012, 12:9530-9550.
12. van Nostrum C.F. Covalently cross-linked amphiphilic block copolymer micelles. Soft Matter 2011, 7:3246-3259.
13. Gaucher G., Satturwar P., Jones M.C., Furtos A., Leroux J.C. Polymeric micelles for oral drug delivery. Eur J Pharm Biopharm 2010, 76:147-158.
14. Kedar U., Phutane P., Shidhaye S., Kadam V. Advances in polymeric micelles for drug delivery and tumor targeting. Nanomed Nanotechnol Biol Med 2010, 6:714-729.
15. Lee J.S., Feijen J. Polymersomes for drug delivery: design, formation and characterization. JControl Release 2012, 161:473-483.
16. Wang D.R., Wang X.G. Amphiphilic azo polymers: molecular engineering, self-assembly and photoresponsive properties. Prog Polym Sci 2013, 38:271-301.
17. Rosler A., Vandermeulen G.W.M., Klok H.A. Advanced drug delivery devices via self-assembly of amphiphilic block copolymers. Adv Drug Deliver Rev 2012, 64:270-279.
18. Matsumura Y. Preclinical and clinical studies of NK012, an SN-38-incorporating polymeric micelles, which is designed based on EPR effect. Adv Drug Deliver Rev 2011, 63:184-192.
19. Deng C., Jiang Y.J., Cheng R., Meng F.H., Zhong Z.Y. Biodegradable polymeric micelles for targeted and controlled anticancer drug delivery: promises, progress and prospects. Nano Today 2012, 7:467-480.
20. Fujita N., Shinkai S., James T.D. Bronic acids in molecular self-assembly. Chem-Asian J 2008, 3:1076-1091.
21. Severin Kay Boronic acids as building blocks for molecular nanostructures and polymeric materials. Dalton Trans 2009, 27:5254-5264.
22. Nishiyabu R., Kubo Y., James T.D., Fossey J.S. Boronic acid building blocks: tools for sensing and separation. Chem Commun 2011, 47:1106-1123.
23. Nishiyabu R., Kubo Y., James T.D., Fossey J.S. Boronic acid building blocks: tools for self assembly. Chem Commun 2011, 47:1124-1150.
24. Galbraith E., James T.D. Boron based anion receptors as sensors. Chem Soc Rev 2010, 39:3831-3842.
25. Egawa Y., Seki T., Takahashi S., Anzai J. Electrochemical and optical sugar sensors based on phenylboronic acid and its derivatives. Mater Sci Eng C Mater Biol Appl 2011, 31:1257-1264.
26. Hansen J.S., Christensen J.B., Petersen J.F., Hoeg-Jensen T., Norrild J.C. Arylboronic acids: a diabetic eye on glucose sensing. Sens Actuator B-Chem 2012, 161:45-79.
27. Bicker K.L., Sun J., Lavigne J.J., Thompson P.R. Boronic acid functionalized peptidyl synthetic lectins: combinatorial library design, peptide sequencing, and selective glycoprotein recognition. ACS Comb Sci 2011, 13:232-243.
28. Xu G.B., Zhang W., Wei L.M., Lu H.J., Yang P.Y. Boronic acid-functionalized detonation nanodiamond for specific enrichment of glycopeptides in glycoproteome analysis. Analyst 2013, 138:1876-1885.
29. Manju S., Antony M., Sreenivasan K. Synthesis and evaluation of a hydrogel that binds glucose and releases ciprofloxacin. JMater Sci 2010, 45:4006-4012.
30. Cambre J.N., Roy D., Gondi S.R., Sumerlin B.S. Facile strategy to well-defined water-soluble boronic acid (co)polymers. JAm Chem Soc 2007, 129:10348-10349.
31. Hajizadeh S., Ivanov A.E., Jahanshahi M., Sanati M.H., Zhuravleva N.V., Mikhalovska L.I., et al. Glucose sensors with increased sensitivity based on composite gels containing immobilized boronic acid. React Funct Polym 2008, 68:1625-1635.
32. Roy D., Cambre J.N., Sumerlin B.S. Sugar-responsive block copolymers by direct RAFT polymerization of unprotected boronic acid monomers. Chem Commun 2008, 21:2477-2479.
33. Wang B.L., Ma R.J., Liu G., Li Y., Liu X.J., An Y.L., et al. Glucose-responsive micelles from self-assembly of poly(ethylene glycol)-b-poly(acrylic acid-co-acrylamidophenylboronic acid) and the controlled release of insulin. Langmuir 2009, 25:12522-12528.
34. Jin X.J., Zhang X.G., Wu Z.M., Teng D.Y., Zhang X.J., Wang Y.X., et al. Amphiphilic random glycopolymer based on phenylboronic acid: synthesis, characterization, and potential as glucose-sensitive matrix. Biomacromolecules 2009, 10:1337-1345.
35. Chalagalla S., Sun X.L. Synthesis and characterization of biotin chain-end functionalized boronic acid-containing polymer (boropolymer) as functional glyco-affinity macroligand. React Funct Polym 2010, 70:471-476.
36. Zhang L.Z., Lin Y., Wang J.J., Yao W., Wu W., Jiang X.Q. Afacile strategy for constructing boron-rich polymer nanoparticles via a boronic acid-related reaction. Macromol Rapid Commun 2011, 32:534-539.
37. Rzayev Z.M.O., Beskardes O. Boron-containing functional copolymers for bioengineering applications. Collect Czech Chem C 2007, 72:1591-1630.
38. Saito A., Konno T., Ikake H., Kurita K., Ishihara K. Control of cell function on a phospholipid polymer having phenylboronic acid moiety. Biomed Mater 2010, 5:054101.
39. Ivanov A.E., Panahi H.A., Kuzimenkova M.V., Nilsson L., Bergenstahl B., Waqif H.S., et al. Affinity adhesion of carbohydrate particles and yeast cells to boronate-containing polymer brushes grafted onto siliceous supports. Chem-Eur J 2006, 12:7204-7214.
40. Azab A.K., Srebnik M., Doviner V., Rubinstein A. Targeting normal and neoplastic tissues in the rat jejunum and colon with boronated, cationic acrylamide copolymers. JControl Release 2005, 106:14-25.
41. Xiong X.Y., Tam K.C., Gan L.H. Polymeric nanostructures for drug delivery applications based on pluronic copolymer systems. JNanosci Nanotechno 2006, 6:2638-2650.
42. Batrakova E.V., Kabanov A.V. Pluronic block copolymers: evolution of drug delivery concept from inert nanocarriers to biological response modifiers. JControl Release 2008, 130:98-106.
43. Alvarez-Lorenzo C., Sosnik A., Concheiro A. PEO-PPO block copolymers for passive micellar targeting and overcoming multidrug resistance in cancer therapy. Curr Drug Targets 2011, 12:1112-1130.
44. Dehvari K., Lin K.S. Synthesis, characterization and potential applications of multifunctional PEO-PPO-PEO-magnetic drug delivery system. Curr Med Chem 2012, 19:5199-5204.
45. Goodwin A.P., Lam S.S., Fréchet J.M.J. Rapid, efficient synthesis of heterobifunctional biodegradable dendrimers. JAm Chem Soc 2007, 129:6994-6995.
46. Yang W.Q., Gao S.H., Gao X.M., Karnati V.V.R., Ni W.J., Wang B.H., et al. Diboronic acids as fluorescent probes for cells expressing sialyl Lewis X. Bioorg Med Chem Lett 2002, 12:2175-2177.
47. Yang W.Q., Fan H.Y., Gao X.M., Gao S.H., Karnati V.V.R., Ni W.J., et al. The first fluorescent diboronic acid sensor specific for hepatocellular carcinoma cells expressing sialyl Lewis X. Chem Biol 2004, 11:439-448.
48. Moriwaki K., Miyoshi E. Fucosylation and gastrointestinal cancer. World J Hepatol 2010, 2:151-161.