journal article·2011-09

Nanoparticle carriers based on copolymers of poly(l-aspartic acid co-l-lactide)-1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine for drug delivery

Siyuan Han, Huan Wang, Xingjie Liang, Liming Hu, Min Li, Yan Wu

Journal of Nanoparticle Research· Volume 13· Issue 9
Publisher page

Abstract

A novel poly(l-aspartic) derivative (PAL-DPPE) containing polylactide and 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (DPPE) segments has been successfully synthesized. The chemical structures of the copolymers were confirmed by Fourier-transform infrared spectroscopy (FTIR), NMR (1H NMR, 13C NMR, 31P NMR), and thermogravimetric analysis (TGA). Fluorescence spectroscopy, dynamic light scattering (DLS), and transmission electron microscopy (TEM) confirmed the formation of micelles of the PAL-DPPE copolymers. In order to estimate the feasibility as novel drug carriers, an anti-tumor model drug doxorubicin (DOX) was incorporated into polymeric micelles by double emulsion and nanoprecipitation method. The DOX-loaded micelle size, size distribution, and encapsulation efficiency (EE) were influenced by the feed weight ratio of the copolymer to DOX. In addition, in vitro release experiments of the DOX-loaded PAL-DPPE micelles exhibited that faster release in pH 5.0 than their release in pH 7.4 buffer. The poly(l-aspartic) derivative copolymer was proved to be an available carrier for the preparation of micelles for anti-tumor drug delivery.
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Research context

OpenAlex topics: Nanoparticle-Based Drug Delivery · biodegradable polymer synthesis and properties · Graphene and Nanomaterials Applications

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (40)

Show source-provided references
1. Arimura H, Ohya Y, Ouchi T (2005) Formation of core-shell type biodegradable polymeric micelles from amphiphilic poly(aspartic acid)-block-polylactide diblock copolymer. Biomacromolecules 6:720–72510.1021/bm0494491 ↗
2. Axén R, Ernback S (1971) Chemical fixation of enzymes to cyanogen halide activated polysaccharide carriers. Eur J Biochem 18:351–36010.1111/j.1432-1033.1971.tb01250.x ↗
3. Bae Y, Fukushima S, Harada A, Kataoka K (2003) Design of environment-sensitive supramolecular assemblies for intracellular drug delivery: polymeric micelles that are responsive to intracellular pH change. Angew Chem Int Ed 42:4640–464310.1002/anie.200250653 ↗
4. Baras B, Benoit MA, Gillard J (2000) Parameters influencing the antigen release from spray-dried poly(DL-lactide) microparticles. Int J Pharm 200:133–14510.1016/S0378-5173(00)00363-X ↗
5. Gao Z, Lukyanov AN, Singhal A, Torchilin VP (2002) Diacyllipid-polymer micelles as nanocarriers for poorly soluble anticancer drugs. Nano Lett. 2:979–98710.1021/nl025604a ↗
6. Gao L, Zhang DR, Chen MH (2008) Drug nanocrystals for the formulation of poorly soluble drugs and its application as a potential drug delivery system. J Nanopart Res 10:845–86210.1007/s11051-008-9357-4 ↗
7. Govender T, Stolnik S, Garnett MC, Illum L, Davis SS (1999) PLGA nanoparticles prepared by nanoprecipitation: drug loading and release studies of a water soluble drug. J Control Rel 57:171–18510.1016/S0168-3659(98)00116-3 ↗
8. Hosei S, Yukik A, Akio S, Kimiko T (2003) Synthesis and characterization of amphiphilic biodegradable copolymer, poly(aspartic acid-co-lactic acid). Macromol Biosci 3:34–4310.1002/mabi.200390007 ↗
9. Ida P, Maja G, Ema Z, Majda Z (2008) Molar mass and structural characteristics poly[(lactide-co-(aspartic acid)] block copolymers. Macromol Symp 272:75–8010.1002/masy.200851210 ↗
10. Laakso T, Stjärnkvist P, Sjöholm I (1987) Biodegradable microspheres VI: lysosomal release of covalently bound antiparasitic drugs from starch microparticles. J Pharm Sci 76:134–14010.1002/jps.2600760210 ↗
11. Lamprecht A, Ubrich N, Hombreiro Perez M, Lehr CM, Hoffman M, Maincent P (1999) Biodegradable monodispersed nanoparticles prepared by pressure homogenization-emulsification. Int. J. Pharm. 184:97–10510.1016/S0378-5173(99)00107-6 ↗
12. Lebouc F, Dez I, Madec P (2005) NMR study of the phosphonomethylation reaction on chitosan. Polymer 46:319–32510.1016/j.polymer.2004.11.017 ↗
13. Lukyanov AN, Gao Z, Mazzola L, Torchilin VP (2002) Polyethylene glycol-diacyllipid micelles demonstrate increased accumulation in subcutaneous tumors in mice. Pharm Res 19:1424–142910.1023/A:1020488012264 ↗
14. Maeda H, Wu J, Sawa T, Matsumura Y, Hori K (2000) Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review. J Control Rel 65:271–28410.1016/S0168-3659(99)00248-5 ↗
15. Marre AD, Schacht E (1992) Preparation of 4-nitrophenyl carbonate esters of poly[N-(2-hydroxyethyl)-l-glutamine] and coupling bioactive agents. Makromol Chem 193:3023–303010.1002/macp.1992.021931208 ↗
16. Mazumder B, Dey S, Bhattacharya S, Sarkar S, Mohanta B (2009) Studies of formulation and characterization of cellulose-based microspheres of chlorpheniramine maleate. Arch Pharm Sci Res 1:66–74
17. Nouvel C, Raynaud J, Marie E, Dellacherie E, Six JL, Durand A (2009) Biodegradable nanoparticles made from polylactide-grafted dextran copolymers. J Colloid Interface Sci 330:337–34310.1016/j.jcis.2008.10.069 ↗
18. Nozaki T, Maeda Y, Ito K, Kitano H (1995) Cyclodextrins modified with polymer chains which are responsive to external stimuli. Macromolecules 28:522–52410.1021/ma00106a016 ↗
19. Onozuka S, Kojima M, Hattori K, Toda F (1980) Novel core (polyester)-shell(polysaccharide) nanoparticles: protein loading and surface modification with lectins. Bull Chem Soc Jpn 53:3221–322410.1246/bcsj.53.3221 ↗
20. Ooya T, Yui N (1999) Synthesis of theophylline–polyrotaxane conjugates and their drug release via supramolecular dissociation. J Control Rel 58:251–26910.1016/S0168-3659(98)00163-1 ↗
21. Percot A, Briane D, Coudert R, Reynier P, Bouchemal N, Lièvre N, Hantz E, Salzmann JL, Cao A (2004) Hydroxyethylated cholesterol-based cationic lipid for DNA delivery: effect of conditioning. Int J Pharm 278:143–16310.1016/j.ijpharm.2004.03.003 ↗
22. Perez C, Sanchez A, Putnam D et al (2001) Poly(lactic acid)-poly(ethylene glycol) nanoparticles as new carriers for the delivery of plasmid DNA. J Control Rel 75:211–22410.1016/S0168-3659(01)00397-2 ↗
23. Prompruk K, Govender T, Zhang S, Xiong CD, Stolnik S (2005) Synthesis of a novel PEG-block-poly(aspartic acid-stat-phenylalanine) copolymer shows potential for formation of a micellar drug carrier. Int J Pharm 297:242–25310.1016/j.ijpharm.2005.02.025 ↗
24. Rodrigues JS, Santos-Magalhaes NS, Coelho LCBB, Couvreur P, Ponchel G, Gref R (2003) Novel core (polyester)-shell(polysaccharide) nanoparticles: protein loading and surface modification with lectins. J Control Rel 92:103–11210.1016/S0168-3659(03)00296-7 ↗
25. Sabesan S, Neria S (1992) Synthesis glycosyl phosphates and azides. Carbohydr Res 223:169–18510.1016/0008-6215(92)80015-S ↗
26. Slager J, Domb AJ (2002) Stereocomplexes based on poly(lactic acid)and insulin:formulation and release studies. Biomaterials 23:4389–439610.1016/S0142-9612(02)00179-5 ↗
27. Suh H, Hwang YS, Lee JE, Han CD, Park JC (2001) Behavior of osteoblasts on a type I atelocollagen grafted ozone oxidized poly l-lactic acid membrane. Biomaterials 22:219–23010.1016/S0142-9612(00)00177-0 ↗
28. Tabata K, Abe H, Doi Y (2000) Microbial degradation of poly(aspartic acid) by two isolated strains of Pedobacter sp. and Sphingomonas sp. Biomacromolecules 1:157–16110.1021/bm9900038 ↗
29. Tarvainen T, Karjalainen T, Minna M, Pohjolainen S, Tuominen J, Seppala J, Jarvinen K (2002) Degradation of and drug release from a novel 2, 2-bis(2-oxazoline)linked poly(lactic acid)polymer. J Control Rel 81:251–26110.1016/S0168-3659(02)00081-0 ↗
30. Trubetskoy VS, Torchilin VP (1995) Use of polyoxyethylene-lipid conjugates as long-circulating carriers for delivery of therapeutic and diagnostic agents. Adv Drug Deliv Rev 16:311–32010.1016/0169-409X(95)00032-3 ↗
31. Vandoorne F, Bruneel D, Schacht E (1990) Effect of chemical modification of dextran on the degradation by dextranase. Bioact Compat Polym 5:4–1510.1177/088391159000500102 ↗
32. Wang Z, Chui WK, Ho PC (2009) Design of a multifunctional PLGA nanoparticulate drug delivery system: evaluation of its physicochemical properties and anticancer activity to malignant cancer cells. Pharm Res 26:1162–117110.1007/s11095-009-9837-y ↗
33. Wen J, Mao HQ, Li WP, Lin KY, Leong KW (2004) Biodegradable polyphosphoester micelles for gene delivery. J Pharm Sci 93:2142–215710.1002/jps.20121 ↗
34. Yoo HS, Park TG (2001) Biodegradable polymeric micelles composed of doxorubicin conjugated PLGA–PEG block copolymer. J Control Rel 70:63–7010.1016/S0168-3659(00)00340-0 ↗
35. Yoo HS, Park TG (2004) Folate receptor targeted biodegradable polymeric doxorubicin micelles. J Control Rel 96:273–28310.1016/j.jconrel.2004.02.003 ↗
36. Yoo HS, Lee EA, Park TG (2002) Doxorubicin conjugated biodegradable polymeric micelles having acid-cleavable linkages. J Control Rel 82:17–2710.1016/S0168-3659(02)00088-3 ↗
37. Yuan F, Leunig M, Huang SK, Berk DA, Papahadjopoulos D, Jai RK (1994) Microvascular permeability and interstitial penetration of sterically stabilized(stealth) liposomes in a human tumor xenograft. Cancer Res 54:3352–3356
38. Zhang LM (2001) New water-soluble ampholytic polysaccharides for oilfield drilling treatment: a preliminary study. Carbohydr Polym 45:1–1010.1016/S0144-8617(00)00276-9 ↗
39. Zhang WF, Chen XG, Li PW, He QZ, Zhou HY (2008) Preparation and characterization of theophylline loaded chitosan/β-cyclodextrin microspheres. J Mater Sci Mater Med 19:305–31010.1007/s10856-006-0021-1 ↗
40. Zhou SB, Liao XY, Li XH et al (2003) Poly-d, l-lactide-co-poly(ethylene glycol)microspheres as potential vaccine delivery systems. J Control Rel 86:195–20510.1016/S0168-3659(02)00423-6 ↗