Synthesis of curdlan-graft-poly(ethylene glycol) and formulation of doxorubicin-loaded core-shell nanoparticles

Journal of Bioactive and Compatible Polymers

Volumn 27, Issue 1, 2012, Pages 3-17

  Lehtovaara, Benjamin C ^a   Verma, Mohit S ^a   Gu, Frank X ^a,b  

^a UNIVERSITY OF WATERLOO   (Canada)

^b UNIVERSITY OF WATERLOO   (Canada)

Author keywords

1,3 glucan; controlled release; core shell; curdlan; curdlan g PEG copolymer; doxorubicin; helix; nanoparticle

Indexed keywords

CONTROLLED RELEASE; CORE-SHELL; CURDLAN; DOXORUBICIN; HELIX;

BIOCOMPATIBILITY; ETHYLENE; FOOD ADDITIVES; GLYCOLS; GRAFT COPOLYMERS; GRAFTING (CHEMICAL); NANOPARTICLES; POLYETHYLENE OXIDES;

POLYETHYLENE GLYCOLS;

AMPHOPHILE; COPOLYMER; CURDLAN; DICYCLOHEXYLCARBODIIMIDE; DOXORUBICIN; HYDROXYL GROUP; MACROGOL; NANOPARTICLE; SELF ASSEMBLED MONOLAYER;

ARTICLE; BIOCOMPATIBILITY; HEMOLYSIS; HYDROPHOBICITY;

EID: 84856050064     PISSN: 08839115     EISSN: 15308030     Source Type: Journal    
DOI: 10.1177/0883911511432511     Document Type: Article

References (44)

1. Zhang HB, Nishinari K, Williams MAK, Foster TJ, Norton IT. A molecular description of the gelation mechanism of curdlan. Int J Biol Macromol. 2002 ; 30 (1). 7-16 (Pubitemid 34226562)
2. Ohno N, Furukawa M, Miura NN, Adachi Y, Motoi M, Yadomae T. Antitumor beta-glucan from the cultured fruit body of Agaricus blazei. Biol Pharm Bull. 2001 ; 24 (7). 820-828 (Pubitemid 32633492)
3. Rice PJ, Adams EL, Ozment-Skelton T, Gonzalez AJ, Goldman MP, Lockhart BE, et al. Oral delivery and gastrointestinal absorption of soluble glucans stimulate increased resistance to infectious challenge. J Pharmacol Exp Ther. 2005 ; 314 (3). 1079-1086 (Pubitemid 41205971)
4. Wei D, Zhang LY, Williams DL, Browder W. Glucan stimulates human dermal fibroblast collagen biosynthesis through a nuclear factor-1 dependent mechanism. Wound Repair Regen. 2002 ; 10 (3). 161-168 (Pubitemid 34760894)
5. Pillemer L, Blum L, Lepow IH, Ross OA, Todd EW, Wardlaw AC. The properdin system and immunity. I. Demonstration and isolation of a new serum protein, properdin, and its role in immune phenomena. Science. 1954 ; 120 (3112). 279-285
6. Vetvicka V, Thornton BP, Ross GD. Soluble beta-glucan polysaccharide binding to the lectin site of neutrophil or natural killer cell complement receptor type 3 (CD11b/CD18) generates a primed state of the receptor capable of mediating cytotoxicity of iC3b-opsonized target cells. J Clin Invest. 1996 ; 98 (1). 50-61 (Pubitemid 26243820)
7. Ross GD, Vetvicka V, Yan J, Xia Y, Vetvickova J. Therapeutic intervention with complement and beta-glucan in cancer. Immunopharmacology. 1999 ; 42 (1-3). 61-74 (Pubitemid 29322289)
8. Kataoka K, Muta T, Yamazaki S, Takeshige K. Activation of macrophages by linear (1 → 3)-beta-D-glucans-implications for the recognition of fungi by innate immunity. J Biol Chem. 2002 ; 277 (39). 36825-36831
9. Lehtovaara BC, Gu FX. Pharmacological structural, and drug delivery properties and applications of 1,3-β-glucans. J Agric Food Chem. 2011 ; 59 (13). 6813-6828
10. Sonck E, Stuyven E, Goddeeris B, Cox E. The effect of beta-glucans on porcine leukocytes. Vet Immunol Immunopathol. 2010 ; 135 (3-4). 199-207
11. Dritz SS, Shi J, Kielian TL, Goodband RD, Nelssen JL, Tokach MD, et al. Influence of dietary beta-glucan on growth-performance, nonspecific immunity, and resistance to streptococcus-suis infection in weanling pigs. J Anim Sci. 1995 ; 73 (11). 3341-3350
12. Eicher SD, McKee CA, Carroll JA, Pajor EA. Supplemental, vitamin C and yeast cell wall beta-glucan as growth enhancers in newborn pigs and as immunomodulators after an endotoxin challenge after weaning. J Anim Sci. 2006 ; 84 (9). 2352-2360 (Pubitemid 44367859)
13. Evans SG, Morrison D, Kaneko Y, Havlik I. The effect of curdlan sulphate on development in vitro of Plasmodium falciparum. Trans R Soc Trop Med Hyg. 1998 ; 92 (1). 87-89 (Pubitemid 28073742)
14. Jagodzinski PP, Wiaderkiewicz R, Kurzawski G, Kloczewiak M, Nakashima H, Hyjek E, et al. Mechanism of the inhibitory effect of curdlan sulfate on HIV-1 infection in-vitro. Virology. 1994 ; 202 (2). 735-745 (Pubitemid 24254887)
15. Osawa Z, Morota T, Hatanaka K, Akaike T, Matsuzaki K, Nakashima H, et al. Synthesis of sulfated derivatives of curdlan and their anti-HIV activity. Carbohydr Polym. 1993 ; 21 (4). 283-288
16. Borjihan G, Zhong GY, Baigude H, Nakashima H, Uryu T. Synthesis and anti-HIV activity of 6-amino-6-deoxy-(1 → 3)-beta-D-curdlan sulfate. Polym Adv Technol. 2003 ; 14 (3-5). 326-329 (Pubitemid 36619363)
17. Ungurenasu C, Pinteala M. Syntheses and characterization of water-soluble C-60-curdlan sulfates for biological applications. J Polym Sci Pol Chem. 2007 ; 45 (14). 3124-3128 (Pubitemid 47169808)
18. Nakao Y, Konno A, Taguchi T, Tawada T, Kasai H, Toda J, et al. Curdlan-properties and application to foods. J Food Sci. 1991 ; 56 (3). 769-772
19. Funami T, Funami M, Tawada T, Nakao Y. Decreasing oil uptake of doughnuts during deep-fat frying using curdlan. J Food Sci. 1999 ; 64 (5). 883-888 (Pubitemid 29536862)
20. Ferreira DS, Faria AF, Grosso CRF, Mercadante AZ. Encapsulation of blackberry anthocyanins by thermal gelation of curdlan. J Braz Chem Soc. 2009 ; 20 (10). 1908-1915
21. Na K, Park KH, Kim SW, Bae YH. Self-assembled hydrogel nanoparticles from curdlan derivatives: characterization, anti-cancer drug release and interaction with a hepatoma cell line (HepG2). J Controlled Release. 2000 ; 69 (2). 225-236
22. Subedi RK, Kang KW, Choi H. Preparation and characterization of solid lipid nanoparticles loaded with doxorubicin. Eur J Pharm Sci. 2009 ; 37 (3-4). 508-513
23. Li L, Gao F, Tang H, Bai Y, Li R, Li X, et al. Self-assembled nanoparticles of cholesterol-conjugated carboxymethyl curdlan as a novel carrier of epirubicin. Nanotechnology. 2010 ; 21 (26). 265601
24. Riess G. Micellization of block copolymers. Progr Polymer Sci. 2003 ; 28 (7). 1107-1170
25. Maeda H, Wu J, Sawa T, Matsumura Y, Hori K. Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review. J Control Release. 2000 ; 65 (1-2). 271-284 (Pubitemid 30122932)
26. Karinaga R, Anada T, Minari J, Mizu M, Koumoto K, Fukuda J, et al. Galactose-PEG dual conjugation of beta-(1 → 3)-D-glucan schizophyllan for antisense oligonucleotides delivery to enhance the cellular uptake. Biomaterials. 2006 ; 27 (8). 1626-1635 (Pubitemid 41739588)
27. Karinaga R, Koumoto K, Mizu M, Anada T, Shinkai S, Sakurai K. PEG-appended beta-(1 → 3)-D-glucan schizophyllan to deliver antisense-oligonucleotides with avoiding lysosomal degradation. Biomaterials. 2005 ; 26 (23). 4866-4873 (Pubitemid 40343034)
28. Ohya Y, Kuroda H, Hirai K, Ouchi T. Synthesis and cytotoxic activity of conjugates of monomethoxy poly(ethylene-glycol) end-capped with doxorubicin via ester, amide, or Schiff-base bond. J Bioact Compat Polym. 1995 ; 10 (1). 51-66
29. Yoo HS, Park TG. Biodegradable polymeric micelles composed of doxorubicin conjugated PLGA-PEG block copolymer. J Control Release. 2001 ; 70 (1-2). 63-70 (Pubitemid 32144793)
30. Pechar M, Braunova A, Ulbrich K, Jelinkova M, Rihova B. Poly(ethylene glycol)-doxorubicin conjugates with pH-controlled activation. J Bioact Compat Polym. 2005 ; 20 (4). 319-341 (Pubitemid 41104878)
31. Saito H, Hoffman AS, Ogawa HI. Delivery of doxorubicin from biodegradable PEG hydrogels having Schiff base linkages. J Bioact Compat Polym. 2007 ; 22 (6). 589-601 (Pubitemid 350145480)
32. Zeman SM, Phillips DR, Crothers DM. Characterization of covalent adriamycin-DNA adducts. Proc Natl Acad Sci USA. 1998 ; 95 (20). 11561-11565 (Pubitemid 28460454)
33. Xiong XY, Tam KC, Gan LH. Release kinetics of hydrophobic and hydrophilic model drugs from pluronic F127/poly(lactic acid) nanoparticles. J Control Release. 2005 ; 103 (1). 73-82 (Pubitemid 40248562)
34. Choi YH, Liu F, Kim JS, Choi YK, Park JS, Kim SW. Polyethylene glycol-grafted poly-l-lysine as polymeric gene carrier. J Control Release. 1998 ; 54 (1). 39-48 (Pubitemid 28255236)
35. Kang GD, Cheon SH, Song SC. Controlled release of doxorubicin from thermosensitive poly(organophosphazene) hydrogels. Int J Pharm. 2006 ; 319 (1-2). 29-36 (Pubitemid 44051797)
36. Siepmann J, Peppas NA. Modeling of drug release from delivery systems based on hydroxypropyl methylcellulose (HPMC). Adv Drug Deliv Rev. 2001 ; 48 (2-3). 139-157 (Pubitemid 32434400)
37. Mocanu G, Mihai D, Legros M, Picton L, LeCerf D. New polysaccharide-based microparticles crosslinked with siloxane: interactions with biologically active substances. J Bioact Compat Polym. 2008 ; 23 (1). 82-94 (Pubitemid 350277337)
38. Leung TC, Wong CK, Xie Y. Green synthesis of silver nanoparticles using biopolymers, carboxymethylated-curdlan and fucoidan. Mater Chem Phys. 2010 ; 121 (3). 402-405
39. Khandwekar AP, Patil DP, Khandwekar V, Shouche YS, Sawant S, Doble M. TecoflexTM functionalization by curdlan and its effect on protein adsorption and bacterial and tissue cell adhesion. J Mater Sci Mater Med. 2009 ; 20 (5). 1115-1129
40. Jo S, Park K. Surface modification using silanated poly(ethylene glycol)s. Biomaterials. 2000 ; 21 (6). 605-616 (Pubitemid 30083924)
41. Kohler N, Sun C, Fichtenholtz A, Gunn J, Fang C, Zhang MQ. Methotrexate-immobilized poly(ethylene glycol) magnetic nanoparticles for MR imaging and drug delivery. Small. 2006 ; 2 (6). 785-792 (Pubitemid 43745151)
42. Zhang Y, Kohler N, Zhang MQ. Surface modification of superparamagnetic magnetite nanoparticles and their intracellular uptake. Biomaterials. 2002 ; 23 (7). 1553-1561 (Pubitemid 34158578)
43. Farokhzad OC, Cheng JJ, Teply BA, Sherifi I, Jon S, Kantoff PW, et al. Targeted nanoparticle-aptamer bioconjugates for cancer chemotherapy in vivo. Proc Natl Acad Sci USA. 2006 ; 103 (16). 6315-6320
44. Luu YK, Kim K, Hsiao BS, Chu B, Hadjiargyrou M. Development of a nanostructured DNA delivery scaffold via electrospinning of PLGA and PLA-PEG block copolymers. J Control Release. 2003 ; 89 (2). 341-353 (Pubitemid 36507026)