Cell-specific delivery of polymeric nanoparticles to carbohydrate-tagging cells

Biomacromolecules

Volumn 8, Issue 10, 2007, Pages 3162-3168

  Iwasaki, Yasuhiko ^a   Maie, Haruki ^b   Akiyoshi, Kazunari ^b  

^a KANSAI UNIVERSITY   (Japan)

^b TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CELLS; DRUG DELIVERY; FREE RADICAL POLYMERIZATION; SYNTHESIS (CHEMICAL);

HUMAN CERVICAL CARCINOMA CELL; METHACRYLOYLOXYETHYL PHOSPHORYLCHOLINE (MPC); POLYMER BEARING HYDRAZIDE GROUPS;

NANOPARTICLES;

2 METHACRYLOYLOXYETHYLPHOSPHORYLCHOLINE; CARBOHYDRATE; DOXORUBICIN; DRUG CARRIER; EMULSIFYING AGENT; HYDRAZIDE; KETONE; NANOCARRIER; PACLITAXEL; PHOSPHORYLCHOLINE; POLYMER; SOLVENT; WATER;

ARTICLE; CELL SPECIFICITY; CELL SURFACE; CELL VIABILITY; CONTROLLED STUDY; DRUG COATING; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG SOLUBILITY; EVAPORATION; HELA CELL; HUMAN; HUMAN CELL; IMMOBILIZED CELL; POLYMERIZATION; PRIORITY JOURNAL; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CARBOHYDRATES; CELL MEMBRANE; CHEMISTRY, PHARMACEUTICAL; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; HELA CELLS; HUMANS; METHACRYLATES; MICROSCOPY, FLUORESCENCE; MICROSCOPY, PHASE-CONTRAST; NANOPARTICLES; PHOSPHORYLCHOLINE; POLYMERS; SPECTROMETRY, X-RAY EMISSION;

EID: 35548962352     PISSN: 15257797     EISSN: None     Source Type: Journal    
DOI: 10.1021/bm700606z     Document Type: Article

References (48)

1. Shive, M. S.; Anderson, J. M. Biodegradation and biocompatibility of PLA and PLGA microspheres. Adv. Drug Delivery Rev. 1997, 28, 5-24.
2. Moghimi, S. M.; Hunter, A. C.; Murray, J. C. Long-circulating and target-specific nanoparticles: theory to practice. Pharmacol. Rev. 2001, 53, 283-318.
3. Gao, X.; Cui, Y.; Levenson, R. M.; Chung, L. W.; Nie, S. In vivo cancer targeting and imaging with semiconductor quantum dots. Nat. Biotechnol. 2004, 22, 969-976.
4. Harada, A.; Kataoka, K. Supramolecular assemblies of block copolymers in aqueous media as nanocontainers relevant to biological applications. Prog. Polym. Sci. 2006, 31, 949-982.
5. Dutta, R. C. Drug carriers in pharmaceutical design: promises and progress. Curr. Pharm. Des. 2007, 13, 761-769.
6. Nagasaki, Y.; Ishii, T.; Sunaga, Y.; Watanabe, Y.; Otsuka, H.; Kataoka, K. Novel molecular recognition via fluorescent resonance energy transfer using a biotin-PEG/polyamine stabilized CdS quantum dot. Langmuir 2004, 20, 6396-6400.
7. Arnida, A.; Nishiyama, N.; Kanayama, N.; Jang, W. D.; Yamasaki, Y.; Kataoka, K. PEGylated gene nanocarriers based on block catiomers bearing ethylenediamine repeating units directed to remarkable enhancement of photochemical transfection. J. Controlled Release 2006, 115, 208-215.
8. Lemarchand, C.; Gref, R.; Lesieur, S.; Hommel, H.; Vacher B.; Besheer, A.; Maeder, K.; Couvreur, P. Physico-chemical characterization of polysaccharide-coated nanoparticles. J. Controlled Release 2005, 108, 97-111.
9. Martwiset, S.; Koh, A. E.: Chen, W. Nonfouling characteristics of dextran-containing surfaces. Langmuir 2006, 22, 8192-8196.
10. Dwek, R. A. Glycobiology: Toward understanding the function of sugars. Chem. Rev. 1996, 96, 683-720.
11. Kayser, H.; Zeitler, R.; Kannicht, C.; Grunow. D.; Nuck, R.; Reutter, W. Biosynthesis of a nonphysiological sialic acid in different rat organs, using N-propanoyl-D-hexosamines as precursors. J. Biol. Chem. 1992, 267, 16934-16938.
12. Keppler, O. T.; Stehling, P.; Herrmann, M.; Kayser, H.; Grunow, D.; Reutter, W.; Pawlita, M. Biosynthetic modulation of sialic acid-dependent virus-receptor interactions of two primate polyoma viruses. J. Biol. Chem. 1995, 270, 1308-1314.
13. Mahal, L. K.; Yarema, K. J.; Bertozzi, C. R. Engineering chemical reactivity on cell surfaces through oligosaccharide biosynthesis. Science 1997, 276, 1125-1128.
14. Yarema, K. J.; Mahal, L. K.; Bruehl, R. E.; Rodriguez, E. C.; Bertozzi, C. R. Metabolic delivery of ketone groups to sialic acid residues. Application to cell surface glycoform engineering. J. Biol. Chem. 1998, 273, 31168-31179.
15. Saxon, E.; Bertozzi, C. R. Cell surface engineering by a modified Staudinger reaction. Science 2000, 287, 2007-2010.
16. Yarema, K. J.; Bertozzi, C. R. Characterizing glycosylation pathways. Genome Biol. 2001, 2, 0004.1-0004.10
17. Lemieux, G. A.; Yarema, K. J.; Jacobs, C. L.; Bertozzi, C. R. Exploiting differences in sialoside expression for selective targeting of MRI contrast reagents. J. Am. Chem. Soc. 1999, 121, 4278-4279.
18. Lee, J. H.; Baker, T. J.; Mahal, L. K.; Zabner, J.; Bertozzi, C. R.; Wiemer, D. F.; Welsh, M. J. Engineering novel cell surface receptors for virus-mediated gene transfer. J. Biol. Chem. 1999, 274, 21878-21884.
19. Keppler, O. T.; Horstkorte, R.; Pawlita, M.; Schmidt, C.; Reutter, W. Biochemical engineering of the N-acyl side chain of sialic acid: biological implications. Glycobiology 2001, 11, 11R-18R.
20. Prescher, J. A.; Duhe, D. H.; Bertozzi, C. R. Chemical remodelling of cell surfaces in living animals. Nature 2004, 430, 873-877.
21. Ishihara, K.; Nomura, H.; Mihara, T.; Kurita, K.; Iwasaki. Y.; Nakabayashi, N. Why do phospholipid polymers reduce protein adsorption? J. Biomed. Mater. Res. 1998, 39, 323-330.
22. Iwasaki, Y.; Mikami, A.; Kurita, K.; Yui, N.; Ishihara, K.; Nakabayashi, N. Reduction of surface-induced platelet activation on phospholipid polymer. J. Biomed. Mater. Res. 1997, 36, 508-515.
23. Konno, T.; Watanabe, J.; Ishihara, K. Enhanced solubility of paclitaxel using water-soluble and biocompatible 2-methacryloyloxyethyl phosphorylcholine polymers. J. Biomed. Mater. Res. A 2003, 65, 209-214.
24. Konno, T.; Kurita, K.; Iwasaki, Y.; Nakabayashi, N.; Ishihara, K. Preparation of nanoparticles composed with bioinspired 2-methacryloyloxyethyl phosphorylcholine polymer. Biomaterials 2001, 22, 1883-1889.
25. Konno, T.; Ishihara, K. Blood compatible nanoparticles immobilized with 2-methacryloyloxyethyl phosphorylcholine polymer. Trans. Mater. Res. Soc. Jpn. 2001, 26, 897-900.
26. Liu, T.; Guo, Z.; Yang, Q.; Sad, S.; Jennings, H. J. Biochemical engineering of surface alpha 2-8 polysialic acid for immunotargeting tumor cells. J. Biol. Chem. 2000, 275, 32832-32836.
27. Ishihara, K.; Ueda, T.; Nakabayashi, N. Preparation of phospholipid polymers and their properties as polymer hydrogel membranes. Polym. J. 1990, 22, 355-360.
28. Iwasaki, Y.; Tabata, E.; Akiyoshi, K. Selective cell attachment to a biomimetic polymer surface through the recognition of cell-surface tags. Bioconjugate Chem. 2005, 16, 567-575.
29. Qi, X. Y.; Keyhani, N. O.; Lee, Y. C. Spectrophotometric determination of hydrazine, hydrazides, and their mixtures with trinitrobenzenesulfonic acid. Anal. Biochem. 1988, 175, 139-144.
30. Campbell, C. T.; Sampathkumar, S. G.; Yarema, K. J. Metabolic oligosaccharide engineering: perspectives, applications, and future directions. Mol. Biosyst. 2007, 3, 187-194.
31. Sampathkumar, S. G.; Li, A. V.; Yarema, K. J. Synthesis of nonnatural ManNAc analogs for the expression of thiols on cell-surface sialic acids. Nat. Protoc. 2006, 1, 2377-2385.
32. Nauman, D. A.; Bertozzi, C. R. Kinetic parameters for small-molecule drug delivery by covalent cell surface targeting. Biochim. Biophys. Acta 2001, 1568, 147-154.
33. Gruenberg, J. The endocytic pathway: a mosaic of domains. Nat. Rev. Mol. Cell Biol. 2001, 2, 721-730.
34. Chithrani, B. D.; Ghazani, A. A.; Chan, W. C. W. Determining the size and shape dependence of gold nanoparticle uptake into mammalian cells. Nano Lett. 2006, 6, 662-668.
35. Fjallskog, M. L.; Frii, L.; Bergh, J. Is Cremophor EL, solvent for paclitaxel, cytotoxic? Lancet 1993, 342, 873.
36. Panchagnula, R. Pharmaceutical aspects of paclitaxel. Int. J. Pharm. 1998, 172, 1-15.
37. 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.
38. Burt, H.; Zhang, X.; Toleikis, P.; Embree, L.; Hunter, W. Development of copolymers of poly(D,L-lactide) and methoxypolyethylene glycol as micellar carriers of paclitaxel. Colloids Surf., B 1999, 16, 161-171.
39. Das, G.; Rao, G.; Wilson, R.; Chandy, T. Controlled delivery of taxol from poly(ethylene glycol)-coated poly(lactic acid) microspheres. J. Biomed. Mater. Res. 2001, 55, 96-103.
40. Kan, P.; Chen, Z.; Lee, C.; Chu, I. Development of nonionic surfactant/ phospholipid o/w emulsion as a paclitaxel delivery system. J. Controlled Release 1999, 58, 271-278.
41. Feng, S.; Huang, G. Effects of emulsifiers on the controlled release of paclitaxel (Taxol) from nanospheres of biodegradable polymers. J. Controlled Release 2001, 71, 53-69.
42. Alkan, O. H.; Ramakrishnan, S.; Chai, H. B.; Pezzuto, J. M. A mixed micellar formulation suitable for the parenteral administration of taxol. Pharm. Res. 1994, 11, 206-212.
43. Shrama, U. S.; Balasubramanian, S. V.; Staubinger, R. M. Pharmaceutical and physical properties of paclitaxel (Taxol) complexes with cyclodextrins. J. Pharm. Sci. 1995, 84, 1223-1230.
44. Ooya, T.; Lee, J.; Park, K. Hydrotropic dendrimers of generations 4 and 5: synthesis, characterization, and hydrotropic, solubilization of paclitaxel. Bioconjugate Chem. 2004, 15, 1221-1229.
45. Johansen, P. B.; Jensen, S. E.; Rasmussen, S. N.; Dalmark, M. Pharmacokinetics of doxorubicin and its metabolite doxorubicinol in rabbits with induced acid and alkaline urine. Cancer Chemother. Pharmacol. 1984, 13, 5-8.
46. Clague, M. J. Molecular aspects of the endocytic pathway. Biochem. J. 1998, 336, 271-282.
47. Mukherjee, S.; Ghosh, R. N.; Maxfield, F. R. Endocytosis. Physiol. Rev. 1997, 77, 759-803.
48. Duncan, R. Drug-polymer conjugates: potential for improved chemotherapy. Anti-Cancer Drugs 1992, 3, 175-210.