Skip to main content
Erschienen in: Journal of Polymer Research 4/2010

01.07.2010 | Original Paper

A novel biodegradable amphiphilic diblock copolymers based on poly(lactic acid) and hyaluronic acid as biomaterials for drug delivery

verfasst von: Chia Chang Liu, Ken Yuan Chang, Yng Jiin Wang

Erschienen in: Journal of Polymer Research | Ausgabe 4/2010

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

An amphiphilic poly((lactic acid)-b-hyaluronic acid) diblock copolymer, poly(LA-b-HA), was synthesized from short-chain hyaluronic acid and poly(lactic acid). The synthesis was conducted by coupling the N, N′- dicyclohexylcarbodiimide activated poly(lactic acid) to a short-chain hyaluronic acid which was pre-aminated with 1, 2-ethylenediamine at the reducing end followed by NaCNBH3 reduction. The poly (LA-b-HA) copolymers synthesized were verified by the spectral analyses of FTIR and 1H NMR. The poly(LA-b-HA) molecules can self-assemble into micelles in aqueous solution. The average diameters of polymeric micelles were estimated to be 116 ± 17 and 98 ± 11 nm for the polymeric micelles derived from the poly(lactic acid)s of MW 3,200 and MW 16,900, respectively. The poly(LA-b-HA) copolymeric material is non-cytotoxic and can be used as micellar drug carriers. The drug encapsulation capabilities of these poly(LA-b-HA) micelles were demonstrated by using ellagic acid and lidocaine chloride as model compounds. These new biodegradable micelles have a great potential to be used as drug delivery carrier for biomedical applications.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literatur
1.
Zurück zum Zitat Jones M-C, Leroux J-C (1999) Polymeric micelles—a new generation of colloidal drug carriers. Eur J Pharm Biopharm 48:101–111CrossRef Jones M-C, Leroux J-C (1999) Polymeric micelles—a new generation of colloidal drug carriers. Eur J Pharm Biopharm 48:101–111CrossRef
2.
Zurück zum Zitat Kumar N, Ravikumar MNV, Domb AJ (2001) Biodegradable block copolymers. Adv Drug Deliv Rev 53:23–44CrossRef Kumar N, Ravikumar MNV, Domb AJ (2001) Biodegradable block copolymers. Adv Drug Deliv Rev 53:23–44CrossRef
3.
Zurück zum Zitat Nishiyama N, Okazaki S, Cabral H, Miyamoto M, Kato Y, Sugiyama Y, Nishio K, Matsumura Y, Kataoka K (2003) Novel cisplatin-incorporated polymeric micelles can eradicate solid tumors in mice. Cancer Res 63:8977–8983 Nishiyama N, Okazaki S, Cabral H, Miyamoto M, Kato Y, Sugiyama Y, Nishio K, Matsumura Y, Kataoka K (2003) Novel cisplatin-incorporated polymeric micelles can eradicate solid tumors in mice. Cancer Res 63:8977–8983
4.
Zurück zum Zitat Allen C, Han J, Yu Y, Maysinger D, Eisenberg A (2000) Polycaprolactone-b-poly(ethylene oxide) copolymer micelles as a delivery vehicle for dihydrotestosteron. J Contr Release 63:275–286CrossRef Allen C, Han J, Yu Y, Maysinger D, Eisenberg A (2000) Polycaprolactone-b-poly(ethylene oxide) copolymer micelles as a delivery vehicle for dihydrotestosteron. J Contr Release 63:275–286CrossRef
5.
Zurück zum Zitat Lin W-J, Juang L-W, Lin C-C (2003) Stability and release performance of a series of pegylated copolymeric micelles. Pharmaceut Res 20(4):668–673CrossRef Lin W-J, Juang L-W, Lin C-C (2003) Stability and release performance of a series of pegylated copolymeric micelles. Pharmaceut Res 20(4):668–673CrossRef
6.
Zurück zum Zitat Kataoka K, Harada A, Nagasaki Y (2001) Block copolymer micelles for drug delivery: design, characterization and biological significance. Adv Drug Deliv Rev 47:113–131CrossRef Kataoka K, Harada A, Nagasaki Y (2001) Block copolymer micelles for drug delivery: design, characterization and biological significance. Adv Drug Deliv Rev 47:113–131CrossRef
7.
Zurück zum Zitat Shin LL, Kim SY, Lee YM, Cho CS, Sung YK (1998) Methoxy poly(ethylene glycol) /e-caprolactone amphiphilic block copolymeric micelle containing indomethacin. I. Preparation and characterization. J Contr Release 51:1–11CrossRef Shin LL, Kim SY, Lee YM, Cho CS, Sung YK (1998) Methoxy poly(ethylene glycol) /e-caprolactone amphiphilic block copolymeric micelle containing indomethacin. I. Preparation and characterization. J Contr Release 51:1–11CrossRef
8.
Zurück zum Zitat Yokoyama M, Okano T, Sakurai Y, Suwa S (1996) Introduction of cisplatin into polymeric micelles. J Contr Release 39:351–356CrossRef Yokoyama M, Okano T, Sakurai Y, Suwa S (1996) Introduction of cisplatin into polymeric micelles. J Contr Release 39:351–356CrossRef
9.
Zurück zum Zitat Yokoyama M, Okano T, Sakurai Y, Fukushima S, Okamoto K, Kataoka K (1999) Selectivity delivery of adriamycin to loading level. A solid tumor using a polymeric micelle carrier system. J Drug Target 7:171–186CrossRef Yokoyama M, Okano T, Sakurai Y, Fukushima S, Okamoto K, Kataoka K (1999) Selectivity delivery of adriamycin to loading level. A solid tumor using a polymeric micelle carrier system. J Drug Target 7:171–186CrossRef
10.
Zurück zum Zitat Yeh MK, Jenkins PG, Davis SS, Coombes AGA (1995) Improving the delivery capacity of microparticle systems using blends of poly(DL-lactide-co-glycolide) and poly-(ethylene glycol). J Contr Release 37:1–9CrossRef Yeh MK, Jenkins PG, Davis SS, Coombes AGA (1995) Improving the delivery capacity of microparticle systems using blends of poly(DL-lactide-co-glycolide) and poly-(ethylene glycol). J Contr Release 37:1–9CrossRef
11.
Zurück zum Zitat Abuchowski A, Van Es T, Palczuk NC, Davis FF (1977) Alteration of immunological properties of bovine serum albuminby covalent attachment of polyethylene glycol. J Biol Chem 252:3578–3581 Abuchowski A, Van Es T, Palczuk NC, Davis FF (1977) Alteration of immunological properties of bovine serum albuminby covalent attachment of polyethylene glycol. J Biol Chem 252:3578–3581
12.
Zurück zum Zitat Abuchowski A, McCoy JR, Palczuk NC, Van Es T, Davis FF (1977) Effect of covalent attachment of polyethylene glycol on immunogenicity and circulating life of bovine liver lacticcatalase. J Biol Chem 252:3582–3586 Abuchowski A, McCoy JR, Palczuk NC, Van Es T, Davis FF (1977) Effect of covalent attachment of polyethylene glycol on immunogenicity and circulating life of bovine liver lacticcatalase. J Biol Chem 252:3582–3586
13.
Zurück zum Zitat Davis S, Abuchowski A, Park YK, Davis FF (1981) Alteration of the circulating life and antigenic properties of bovine adenosine deaminase in mice by attachment of polyethylene glycol. Clin Exp Immunol 46:649–652 Davis S, Abuchowski A, Park YK, Davis FF (1981) Alteration of the circulating life and antigenic properties of bovine adenosine deaminase in mice by attachment of polyethylene glycol. Clin Exp Immunol 46:649–652
14.
15.
Zurück zum Zitat Miyauchi S, Horie K, Morita M, Nagahara M, Shimizu K (1996) Protective efficacy of sodium hyaluronate on the corneal endothelium against the damage induced by sonication. J Ocul Pharmacol Ther 12:27–34CrossRef Miyauchi S, Horie K, Morita M, Nagahara M, Shimizu K (1996) Protective efficacy of sodium hyaluronate on the corneal endothelium against the damage induced by sonication. J Ocul Pharmacol Ther 12:27–34CrossRef
16.
Zurück zum Zitat Miyauchi S, Iwata S (1986) Evaluations on the usefulness of viscous agents in anterior segment surgery. I. The ability to maintain the deepness of the anterior chamber. J Ocul Pharmacol 2:267–274CrossRef Miyauchi S, Iwata S (1986) Evaluations on the usefulness of viscous agents in anterior segment surgery. I. The ability to maintain the deepness of the anterior chamber. J Ocul Pharmacol 2:267–274CrossRef
17.
Zurück zum Zitat Liesegang TJ (1990) Viscoelastic substances in ophthalmology. Surv Ophthalmol 34:268–293CrossRef Liesegang TJ (1990) Viscoelastic substances in ophthalmology. Surv Ophthalmol 34:268–293CrossRef
18.
Zurück zum Zitat Palumbo FS, Pitarresi G (2006) New graft copolymers of hyaluronic acid and polylactic acid: synthesis and characterization. Carbohydr Polymer 66:379–385CrossRef Palumbo FS, Pitarresi G (2006) New graft copolymers of hyaluronic acid and polylactic acid: synthesis and characterization. Carbohydr Polymer 66:379–385CrossRef
19.
Zurück zum Zitat Miyoshi R, Hashimoto N, Koyanagi K, Sumihiro Y, Sakai T (1996) Int Polym Process XI:320 Miyoshi R, Hashimoto N, Koyanagi K, Sumihiro Y, Sakai T (1996) Int Polym Process XI:320
20.
Zurück zum Zitat Chen G-X, Kim H-S, Kim E-S, Yoon J-S (2006) Synthesis of high-molecular-weight poly(L-lactic acid) through the direct condensation polymerization of L-lactic acid in bulk state. Eur Polymer J 42:468–472CrossRef Chen G-X, Kim H-S, Kim E-S, Yoon J-S (2006) Synthesis of high-molecular-weight poly(L-lactic acid) through the direct condensation polymerization of L-lactic acid in bulk state. Eur Polymer J 42:468–472CrossRef
21.
Zurück zum Zitat Raja RH, Leboeuf RD, Stone GW, Weigel PH (1984) Preparation of alkylamine and 125I-Radiolabeled derivatives of hyaluronic acid uniquely modified at the reducing end. Anal Biochem 139:168–l77CrossRef Raja RH, Leboeuf RD, Stone GW, Weigel PH (1984) Preparation of alkylamine and 125I-Radiolabeled derivatives of hyaluronic acid uniquely modified at the reducing end. Anal Biochem 139:168–l77CrossRef
22.
Zurück zum Zitat Roy R, Katzenellenbogen E, Jennings HJ (1984) Improved procedures for the conjugation of oligosaccharides to protein by reductive amination. Can J Biochem Cell Biol 62(5):270–251CrossRef Roy R, Katzenellenbogen E, Jennings HJ (1984) Improved procedures for the conjugation of oligosaccharides to protein by reductive amination. Can J Biochem Cell Biol 62(5):270–251CrossRef
23.
Zurück zum Zitat Yoshida T, Lee YC (1994) Glycamine formation via reductive amination of oligosaccharides with benzylamine: efficient coupling of oligosaccharides to protein; corresponding author. Carbohydr Res 251(3):175–186CrossRef Yoshida T, Lee YC (1994) Glycamine formation via reductive amination of oligosaccharides with benzylamine: efficient coupling of oligosaccharides to protein; corresponding author. Carbohydr Res 251(3):175–186CrossRef
24.
Zurück zum Zitat Stoll MS, Hounsell EF (1988) Selective purification of reduced oligosaccharides using a phenylboronic acid bond elut column: potential application in HPLC, mass spectrometry, reductive amination procedures and antigenic/serum analysis. Biomed Chrom 2(6):249–253CrossRef Stoll MS, Hounsell EF (1988) Selective purification of reduced oligosaccharides using a phenylboronic acid bond elut column: potential application in HPLC, mass spectrometry, reductive amination procedures and antigenic/serum analysis. Biomed Chrom 2(6):249–253CrossRef
25.
Zurück zum Zitat Evangelista RA, Fu-Tai AC, Guttman A (1996) Reductive amination of N-linked oligosaccharides using organic acid catalysts. J Chromatogr A 745(1):273–280CrossRef Evangelista RA, Fu-Tai AC, Guttman A (1996) Reductive amination of N-linked oligosaccharides using organic acid catalysts. J Chromatogr A 745(1):273–280CrossRef
26.
Zurück zum Zitat Bala V, Bhardwaj S, Hariharan SV, Kharade N, Kumar MNVR (2006) Sustained release nanoparticulate formulation containing antioxidant ellagic acid as potential prophylaxis system for oral administration. J Drug Target 14:27–34CrossRef Bala V, Bhardwaj S, Hariharan SV, Kharade N, Kumar MNVR (2006) Sustained release nanoparticulate formulation containing antioxidant ellagic acid as potential prophylaxis system for oral administration. J Drug Target 14:27–34CrossRef
27.
Zurück zum Zitat Bala V, Bhardwaj S, Hariharan SV, Kumar MNVR (2006) Analytical methods for assay of ellagic acid and its solubility studies. J Pharm Biomed Anal 40:206–210CrossRef Bala V, Bhardwaj S, Hariharan SV, Kumar MNVR (2006) Analytical methods for assay of ellagic acid and its solubility studies. J Pharm Biomed Anal 40:206–210CrossRef
28.
Zurück zum Zitat Klink D, Qian-Chun Yu, Glick MC, Scanlin T (2003) Lactosylated Poly-L-Lysine targets a potential lactose receptor in cystic fibrosis and non-cystic fibrosis airway epithelial cells. Mol Ther 7(1):73–80CrossRef Klink D, Qian-Chun Yu, Glick MC, Scanlin T (2003) Lactosylated Poly-L-Lysine targets a potential lactose receptor in cystic fibrosis and non-cystic fibrosis airway epithelial cells. Mol Ther 7(1):73–80CrossRef
29.
Zurück zum Zitat Harkach JS, Peracchia MT, Domb A, Lotan N, Langer R (1997) Nanotechnology for biomaterials engineering: structural characterization of amphiphilic polymeric nanoparticles by 1H NMR spectroscopy. Biomaterials 18:27–30CrossRef Harkach JS, Peracchia MT, Domb A, Lotan N, Langer R (1997) Nanotechnology for biomaterials engineering: structural characterization of amphiphilic polymeric nanoparticles by 1H NMR spectroscopy. Biomaterials 18:27–30CrossRef
30.
Zurück zum Zitat Kim SY, Shin IG, Lee YM, Cho CS, Sung YK (1998) Methoxy poly(ethylene glycol) and ɛ -caprolactone amphiphilic block copolymeric micelle containing indomethacin II. Micelle formation and drug release behaviours. J Contr Release 51:13–22CrossRef Kim SY, Shin IG, Lee YM, Cho CS, Sung YK (1998) Methoxy poly(ethylene glycol) and ɛ -caprolactone amphiphilic block copolymeric micelle containing indomethacin II. Micelle formation and drug release behaviours. J Contr Release 51:13–22CrossRef
31.
Zurück zum Zitat Lin W-J, Juang L-W, Lin C-C (2003) Stability and release performance of a series of pegylated copolymeric micelles. Pharm Res 20:668–673CrossRef Lin W-J, Juang L-W, Lin C-C (2003) Stability and release performance of a series of pegylated copolymeric micelles. Pharm Res 20:668–673CrossRef
32.
Zurück zum Zitat Lee J, Cho EC, Cho K (2004) Incorporation and release behavior of hydrophobic drug in functionalized poly(D, L-lactide)-block–poly(ethylene oxide) micelles. J Contr Release 94:323–335CrossRef Lee J, Cho EC, Cho K (2004) Incorporation and release behavior of hydrophobic drug in functionalized poly(D, L-lactide)-block–poly(ethylene oxide) micelles. J Contr Release 94:323–335CrossRef
33.
Zurück zum Zitat Kamentsky LA, Melamed MR (1965) Spectrophotometer: new instrument ultrarapid cell analysis. Science 150:630–631CrossRef Kamentsky LA, Melamed MR (1965) Spectrophotometer: new instrument ultrarapid cell analysis. Science 150:630–631CrossRef
34.
Zurück zum Zitat Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55–63CrossRef Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55–63CrossRef
35.
Zurück zum Zitat Walum E, Peterson A (1982) Tritiated 2-deoxy-D-glucose as a probe for cell membrane permeability studies. Anal Biochem 120:8–11CrossRef Walum E, Peterson A (1982) Tritiated 2-deoxy-D-glucose as a probe for cell membrane permeability studies. Anal Biochem 120:8–11CrossRef
36.
Zurück zum Zitat Toyotama A, Kugimiya S, Yamanaka J, Yonese M (2001) Preparation of a novel aggregate like sugar-ball micelle composed of poly(methylglutamate) and poly(ethyleneglycol) modified by lactose and its molecular recognition by lectin. Chem Pharm Bull 49:169–172CrossRef Toyotama A, Kugimiya S, Yamanaka J, Yonese M (2001) Preparation of a novel aggregate like sugar-ball micelle composed of poly(methylglutamate) and poly(ethyleneglycol) modified by lactose and its molecular recognition by lectin. Chem Pharm Bull 49:169–172CrossRef
Metadaten
Titel
A novel biodegradable amphiphilic diblock copolymers based on poly(lactic acid) and hyaluronic acid as biomaterials for drug delivery
verfasst von
Chia Chang Liu
Ken Yuan Chang
Yng Jiin Wang
Publikationsdatum
01.07.2010
Verlag
Springer Netherlands
Erschienen in
Journal of Polymer Research / Ausgabe 4/2010
Print ISSN: 1022-9760
Elektronische ISSN: 1572-8935
DOI
https://doi.org/10.1007/s10965-009-9332-5

Weitere Artikel der Ausgabe 4/2010

Journal of Polymer Research 4/2010 Zur Ausgabe

    Marktübersichten

    Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.