Synthesis and antitumor activity of doxorubicin conjugated stearic acid-g-chitosan oligosaccharide polymeric micelles

Biomaterials

Volumn 30, Issue 36, 2009, Pages 6955-6963

  Hu, Fu Qiang ^a   Liu, Li Na ^a   Du, Yong Zhong ^a   Yuan, Hong ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Antitumor activity; Chitosan oligosaccharide; Cis aconityl linkage; Doxorubicin; Drug resistance; Polymeric micelles

Indexed keywords

ANTITUMOR ACTIVITY; CHITOSAN OLIGOSACCHARIDE; CIS-ACONITYL LINKAGE; DOXORUBICIN; DRUG RESISTANCE; POLYMERIC MICELLES;

ACIDS; CELL MEMBRANES; CHITIN; CHITOSAN; COMBINED SEWERS; CRITICAL MICELLE CONCENTRATION; OLIGOSACCHARIDES; ORGANIC POLYMERS; POLYMERS; SIMULATED ANNEALING; STEARIC ACID; SYNTHESIS (CHEMICAL); TUMORS; ZETA POTENTIAL;

MICELLES;

CHITOSAN DERIVATIVE; DOXORUBICIN; STEARIC ACID;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; CRITICAL MICELLE CONCENTRATION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; LIVER CELL CARCINOMA; MICELLIZATION; MOUSE; MULTIDRUG RESISTANCE; NONHUMAN; PH MEASUREMENT; PRIORITY JOURNAL; ZETA POTENTIAL;

ANIMALS; ANTINEOPLASTIC AGENTS; BIOCOMPATIBLE MATERIALS; CELL LINE, TUMOR; CHITOSAN; DOXORUBICIN; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; HUMANS; MATERIALS TESTING; MICE; MICE, INBRED BALB C; MICE, NUDE; MICELLES; MICROSCOPY, ATOMIC FORCE; MOLECULAR STRUCTURE; NEOPLASM TRANSPLANTATION; OLIGOSACCHARIDES; PARTICLE SIZE; POLYMERS; STEARIC ACIDS;

ANIMALIA;

EID: 70350211845     PISSN: 01429612     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2009.09.008     Document Type: Article

References (29)

1. Pasut G., and Veronese F.M. Polymer-drug conjugation, recent achievements and general strategies. Prog Polym Sci 32 (2007) 933-961
2. Li S.D., and Huang L. Pharmacokinetics and biodistribution of nanoparticles. Mol Pharmacol 5 (2008) 496-504
3. Gaucher G., Dufresne M.H., Sant V.P., Kang N., Maysinger D., and Leroux J.C. Block copolymer micelles: preparation, characterization and application in drug delivery. J Control Release 109 (2005) 169-188
4. Omelyaneko V., Kopeckova P., Gentry C., and Kopecek J. Targetable HPMA copolymer adriamycin conjugates. Recognition, internalization, and subcellular fate. J Control Release 53 (1998) 25-37
5. Park J.H., Kwon S., Lee M., Chung H., Kim J.H., Kim Y.S., et al. Self-assembled nanoparticles based on glycol chitosan bearing hydrophobic moieties as carriers for doxorubicin: in vivo biodistribution and anti-tumor activity. Biomaterials 27 (2006) 119-126
6. Chytil P., Etrych T., Konak C., Sirova M., Mrkvan T., and Rihova B. Properties of HPMA copolymer-doxorubicin conjugates with pH-controlled activation: effect of polymer chain modification. J Control Release 115 (2006) 26-36
7. Teodori E., Dei S., Scapecchi S., and Gualtieri F. The medicinal chemistry of multidrug resistance (MDR) reversing drugs. IL Farmaco 57 (2002) 385-415
8. 6 does not induce P-glycoprotein-mediated multidrug resistance. Biomaterials 21 (2000) 2203-2210
9. Gottesman M.M., Fojo T., and Bates S.E. Multidrug resistance in cancer: role of ATP-dependent transporters. Nat Rev Cancer 2 (2002) 48-58
10. Kabanov A.V., Batrakova E.V., and Alakhov V.Y. Pluronic block copolymers for overcoming drug resistance in cancer. Adv Drug Deliv Rev 54 (2002) 759-779
11. Stastny M., Strohalm J., Plocova D., Ulbrich K., and Rihova B. A possibility to overcome P-glycoprotein (PGP)-mediated multidrug resistance by antibody-targeted drugs Conjugated to N-(2-hydroxypropyl) methacrylamide (HPMA) copolymer carrier. Eur J Cancer 35 (1999) 459-466
12. Fornari F.A., Randolph J.K., Yalowich J.C., Ritke M.K., and Gewirtz D.A. Interference by doxorubicin with DNA unwinding in MCF-7 breast tumor cells. Mol Pharmacol 45 (1994) 649-656
13. Barry E., Alvarez J.A., Scully R.E., Miller T.L., and Lipshultz S.E. Anthracycline-induced cardiotoxicity: course, pathophysiology, prevention and management. Expert Opin Pharmacother 8 (2007) 1039-1058
14. Mechetner E., Kyshtoobayeva A., Zonis S., Kim H., Stroup R., Garcia R., et al. Levels of multi-drug resistance (MDR1) P-glycoprotein expression by human breast cancer correlate with in vitro resistance to taxol and doxorubicin. Clin Cancer Res 4 (1998) 389-398
15. Hu F.Q., Ren G.F., Yuan H., Du Y.Z., and Zeng S. shell cross-linked stearic acid grafted chitosan oligosaccharide self-aggregated micelles for controlled release of paclitaxel. Colloids Surf B Biointerfaces 50 (2006) 97-103
16. You J., Hu F.Q., Du Y.Z., and Yuan H. Polymeric micelles with glycolipid-like structure and multiple hydrophobic domains for mediating-target delivery of paclitaxel. Biomacromolecules 8 (2007) 2450-2456
17. Hu F.Q., Wu X.L., Du Y.Z., You J., and Yuan H. Cellular uptake and cytotoxicity of shell crosslinked stearic acid grafted chitosan oligosaccharide micelles encapsulating doxorubicin. Eur J Pharm Biopharm 69 (2008) 117-125
18. Hu F.Q., Meng P., Dai Y.Q., Du Y.Z., You J., Wei X.H., et al. PEGylated chitosan based polymer micelle as an intracellular delivery carrier for anti-tumor targeting therapy. Eur J Pharm Biopharm 70 (2008) 749-757
19. Shen W.C., and Ryser H.J. Cis-aconityl spacer between daunomycin and macromolecular carriers: a model of pH-sensitive linkage releasing drug from a lysosomotropic conjugate. Biochem Biophys Res Commun 102 (1981) 1048-1054
20. Kohori F., Yokoyama M., Sakai K., and Okanob T. Process design for efficient and controlled drug incorporation into polymeric micelle carrier systems. J Control Release 78 (2002) 155-163
21. Slaughter J.N., Schmidt K.M., Byram J.L., and Mecozzi S. Synthesis and self-assembly properties of a novel [poly(ethylene glycol)]-fluorocarbon-phospholipids triblock copolymer. Tetrahedron Lett 48 (2007) 3879-3882
22. Nogusa H., Yano T., Okuno S., Hamana H., and Inoue K. Synthesis of carboxymethylpullulan- peptide- doxorubicin conjugates and their properties. Chem Pharm Bull (Tokyo) 43 (1995) 1931-1936
23. Grabarek Z., and Gergely J. Zero-length crosslinking procedure with the use of active esters. Anal Biochem 185 (1990) 131-135
24. You J., Hu F.Q., Du Y.Z., and Yuan H. Improved cytotoxicity of doxorubicin by enhancing its nuclear delivery mediated via nanosized micelles. Nanotechnology 19 (2008) 255103
25. Cunningham D., Littleford R.E., Smith W.E., Lundahl P.J., Khan I., McComb D.W., et al. Practical control of SERRS enhancement. Faraday Discuss 132 (2006) 135-145
26. ® H40, poly(l-lactide) and poly(ethylene glycol) for tumor-targeted drug delivery. Biomaterials 30 (2009) 3009-3019
27. Lee E.S., Na K., and Bae Y.H. Doxorubicin loaded pH-sensitive polymeric micelles for reversal of resistant MCF-7 tumor. J Control Release 103 (2005) 405-418
28. Moreira J.N., Gaspar R., and Allen T.M. Targeting stealth liposomes in a murine model of human small cell lung cancer. Biochim Biophys Acta 1515 (2001) 167-176
29. Liu D., Mori A., and Huang L. Role of liposome size and RES blockade in controlling biodistribution and tumor uptake of GM1-containing liposomes. Biochim Biophys Acta 1104 (1992) 95-101