journal article·2017-11

Synthesis and characterization of three novel amphiphilic dextran self-assembled micelles as potential drug delivery system

Shubin Li, Juanjuan Yi, Wei Li, Lu Wang, Zhenyu Wang

Journal of Materials Science· Volume 52· Issue 21
Publisher page

Abstract

Three types of amphiphilic dextran derivatives were synthesized via the connection of different diamine compounds between the carboxyl group of stearic acid (SA) and aldehyde group of oxidized dextran. These three amphiphilic dextran derivatives self-assemble to form polymer micelles in aqueous medium. The critical micelle concentration depended on the graft ratio of SA, which ranged from 0.0700 to 0.158 mg mL−1. These three amphiphilic dextran micelles can form typical core–shell structures of various sizes. Curcumin (Cur) was used as a model drug, and all amphiphilic micelle dextran derivatives had excellent drug loading capacity and drug encapsulation efficiency. The in vitro drug release from amphiphilic dextran derivatives/Cur micelles could be prolonged by adjusting the type of diamine compounds and composition of Cur content. These results show the superior properties of polymer micelles and suggest that these micelles are promising carriers for drug delivery systems.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Nanoparticle-Based Drug Delivery · Advanced Polymer Synthesis and Characterization · Dendrimers and Hyperbranched Polymers

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

References (51)

Show source-provided references
1. Kamaly N, Yameen B, Wu J, Farokhzad OC (2016) Degradable controlled-release polymers and polymeric nanoparticles: mechanisms of controlling drug release. Chem Rev 116:2602–266310.1021/acs.chemrev.5b00346 ↗
2. Kemp JA, Shim MS, Heo CY, Kwon YJ (2016) “Combo” nanomedicine: co-delivery of multi-modal therapeutics for efficient, targeted, and safe cancer therapy. Adv Drug Deliv Rev 98:3–1810.1016/j.addr.2015.10.019 ↗
3. Wang Y, Wang J, Han H, Liu J, Zhao H, Shen M, Xu Y, Xu J, Li L, Guo X (2016) Self-assembled micelles of N-phthaloylchitosan-g-poly (N-vinylcaprolactam) for temperature-triggered non-steroidal anti-inflammatory drug delivery. J Mater Sci 51:1591–1599. doi: 10.1007/s10853-015-9482-210.1007/s10853-015-9482-2 ↗
4. Peer D, Karp JM, Hong S, FaroKhzad OC, Margalit R, Langer R (2007) Nanocarriers as an emerging platform for cancer therapy. Nature Nanotechnol 2:751–76010.1038/nnano.2007.387 ↗
5. Du JZ, Sun TM, Song WJ, Wu J, Wang J (2010) A Tumor-acidity-activated charge-conversional nanogel as an intelligent vehicle for promoted tumoral-cell uptake and drug delivery. Angew Chem Int Ed 49:3621–362610.1002/anie.200907210 ↗
6. Gao W, Chan JM, Farokhzad OC (2010) pH-Responsive nanoparticles for drug delivery. Mol Pharm 7:1913–192010.1021/mp100253e ↗
7. Petros RA, DeSimone JM (2010) Strategies in the design of nanoparticles for therapeutic applications. Nat Rev Drug Discov 9:615–62710.1038/nrd2591 ↗
8. Stuart MAC, Huck WTS, Genzer J, Mueller M, Ober C, Stamm M, Sukhorukov GB, Szleifer I, Tsukruk VV, Urban M, Winnik F, Zauscher S, Luzinov I, Minko S (2010) Emerging applications of stimuli-responsive polymer materials. Nat Mater 9:101–11310.1038/nmat2614 ↗
9. Ke X, Coady DJ, Yang C, Engler AC, Hedrick JL, Yang YY (2014) pH-sensitive polycarbonate micelles for enhanced intracellular release of anticancer drugs: a strategy to circumvent multidrug resistance. Polym Chem 5:2621–262810.1039/c3py01784b ↗
10. Kumari A, Yadav SK, Yadav SC (2010) Biodegradable polymeric nanoparticles based drug delivery systems. Colloids Surf B Biointerfaces 75:1–1810.1016/j.colsurfb.2009.09.001 ↗
11. Mura S, Nicolas J, Couvreur P (2013) Stimuli-responsive nanocarriers for drug delivery. Nat Mater 12:991–100310.1038/nmat3776 ↗
12. Wicki A, Witzigmann D, Balasubramanian V, Huwyler J (2015) Nanomedicine in cancer therapy: challenges, opportunities, and clinical applications. J Control Release 200:138–15710.1016/j.jconrel.2014.12.030 ↗
13. Dash M, Chiellini F, Ottenbrite RM, Chiellini E (2011) Chitosan-A versatile semi-synthetic polymer in biomedical applications. Prog Polym Sci 36:981–101410.1016/j.progpolymsci.2011.02.001 ↗
14. Kamaly N, Xiao Z, Valencia PM, Radovic-Moreno AF, Farokhzad OC (2012) Targeted polymeric therapeutic nanoparticles: design, development and clinical translation. Chem Soc Rev 41:2971–301010.1039/c2cs15344k ↗
15. Luo Y-L, Huang R-J, Xu F, Chen Y-S (2014) pH-Sensitive biodegradable PMAA(2)-b-PLA-b-PMAA(2) H-type multiblock copolymer micelles: synthesis, characterization, and drug release applications. J Mater Sci 49:7730–7741. doi: 10.1007/s10853-014-8483-x10.1007/s10853-014-8483-x ↗
16. Filip D, Macocinschi D (2014) Aggregation behaviour of some beta-cyclodextrin-based side-chain azo amphiphilic polyurethanes. J Mater Sci 49:3451–3460. doi: 10.1007/s10853-014-8057-y10.1007/s10853-014-8057-y ↗
17. Elsabahy M, Wooley KL (2012) Design of polymeric nanoparticles for biomedical delivery applications. Chem Soc Rev 41:2545–256110.1039/c2cs15327k ↗
18. Biju V (2014) Chemical modifications and bioconjugate reactions of nanomaterials for sensing, imaging, drug delivery and therapy. Chem Soc Rev 43:744–76410.1039/C3CS60273G ↗
19. Torchilin VP (2014) Multifunctional, stimuli-sensitive nanoparticulate systems for drug delivery. Nat Rev Drug Discov 13:813–82710.1038/nrd4333 ↗
20. Muthu MS, Leong DT, Mei L, Feng S-S (2014) Nanotheranostics-Application and Further Development of Nanomedicine Strategies for Advanced Theranostics. Theranostics 4:660–67710.7150/thno.8698 ↗
21. Naksuriya O, Okonogi S, Schiffelers RM, Hennink WE (2014) Curcumin nanoformulations: a review of pharmaceutical properties and preclinical studies and clinical data related to cancer treatment. Biomaterials 35:3365–338310.1016/j.biomaterials.2013.12.090 ↗
22. Suk JS, Xu Q, Kim N, Hanes J, Ensign LM (2016) PEGylation as a strategy for improving nanoparticle-based drug and gene delivery. Adv Drug Deliv Rev 99:28–5110.1016/j.addr.2015.09.012 ↗
23. Semyonov D, Ramon O, Shoham Y, Shimoni E (2014) Enzymatically synthesized dextran nanoparticles and their use as carriers for nutraceuticals. Food Funct 5:2463–247410.1039/C4FO00103F ↗
24. Horev B, Klein MI, Hwang G, Li Y, Kim D, Koo H, Benoit DSW (2015) pH-Activated Nanoparticles for Controlled Topical Delivery of Farnesol To Disrupt Oral Biofilm Virulence. ACS Nano 9:2390–240410.1021/nn507170s ↗
25. Li M, Tang Z, Zhang D, Sun H, Liu H, Zhang Y, Zhang Y, Chen X (2015) Doxorubicin-loaded polysaccharide nanoparticles suppress the growth of murine colorectal carcinoma and inhibit the metastasis of murine mammary carcinoma in rodent models. Biomaterials 51:161–17210.1016/j.biomaterials.2015.02.002 ↗
26. Zhang H, Fei J, Yan X, Wang A, Li J (2015) Enzyme-responsive release of doxorubicin from monodisperse dipeptide-based nanocarriers for highly efficient cancer treatment in vitro. Adv Funct Mater 25:1193–120410.1002/adfm.201403119 ↗
27. Hu F-Q, Liu L-N, Du Y-Z, Yuan H (2009) Synthesis and antitumor activity of doxorubicin conjugated stearic acid-g-chitosan oligosaccharide polymeric micelles. Biomaterials 30:6955–696310.1016/j.biomaterials.2009.09.008 ↗
28. Zhang JS, Liu F, Huang L (2005) Implications of pharmacokinetic behavior of lipoplex for its inflammatory toxicity. Adv Drug Deliv Rev 57:689–69810.1016/j.addr.2004.12.004 ↗
29. Allen TM, Cullis PR (2013) Liposomal drug delivery systems: from concept to clinical applications. Adv Drug Deliv Rev 65:36–4810.1016/j.addr.2012.09.037 ↗
30. Gibis M, Vogt E, Weiss J (2012) Encapsulation of polyphenolic grape seed extract in polymer-coated liposomes. Food Funct 3:246–25410.1039/C1FO10181A ↗
31. Tan C, Xue J, Lou X, Abbas S, Guan Y, Feng B, Zhang X, Xia S (2014) Liposomes as delivery systems for carotenoids: comparative studies of loading ability, storage stability and in vitro release. Food Funct 5:1232–124010.1039/c3fo60498e ↗
32. Susa M, Iyer AK, Ryu K, Hornicek FJ, Mankin H, Amiji MM, Duan Z (2009) Doxorubicin loaded Polymeric Nanoparticulate Delivery System to overcome drug resistance in osteosarcoma. BMC Cancer 9:399. doi: 10.1186/1471-2407-9-39910.1186/1471-2407-9-399 ↗
33. Susa M, Iyer AK, Ryu K, Choy E, Hornicek FJ, Mankin H, Milane L, Amiji MM, Duan Z (2010) Inhibition of ABCB1 (MDR1) Expression by an siRNA Nanoparticulate Delivery System to Overcome Drug Resistance in Osteosarcoma. PLoS ONE 5:e10764. doi: 10.1371/journal.pone.001076410.1371/journal.pone.0010764 ↗
34. Zhang QN, Yie GQ, Li Y, Yang QS, Nagai YT (2000) Studies on the cyclosporin a loaded stearic acid nanoparticles. Int J Pharm 200:153–15910.1016/S0378-5173(00)00361-6 ↗
35. Massia SP, Stark J, Letbetter DS (2000) Surface-immobilized dextran limits cell adhesion and spreading. Biomaterials 21:2253–226110.1016/S0142-9612(00)00151-4 ↗
36. Maia J, Ferreira L, Carvalho R, Ramos MA, Gil MH (2005) Synthesis and characterization of new injectable and degradable dextran-based hydrogels. Polymer 46:9604–961410.1016/j.polymer.2005.07.089 ↗
37. Jeong YI, Kim DH, Chung CW, Yoo JJ, Choi KH, Kim CH, Ha SH, Kang DH (2011) Doxorubicin-incorporated polymeric micelles composed of dextran-b-poly(DL-lactide-co-glycolide) copolymer. Int J Nanomed 6:1415–142710.2147/IJN.S19491 ↗
38. Kim DH, Kim MD, Choi CW, Chung CW, Ha SH, Kim CH, Shim YH, Jeong YI, Kang DH (2012) Antitumor activity of sorafenib-incorporated nanoparticles of dextran/poly(dl-lactide-co-glycolide) block copolymer. Nanoscale Res Lett 7:91. doi: 10.1186/1556-276X-7-9110.1186/1556-276X-7-91 ↗
39. Slaughter JN, Schmidt KM, Byram JL, Mecozzi S (2007) Synthesis and self-assembly properties of a novel poly(ethylene glycol) -fluorocarbon-phospholipid triblock copolymer. Tetrahedron Lett 48:3879–388210.1016/j.tetlet.2007.03.148 ↗
40. Liu S, Yang H (2014) Stearic acid hybridizing coal-series kaolin composite phase change material for thermal energy storage. Appl Clay Sci 101:277–28110.1016/j.clay.2014.09.002 ↗
41. Du YZ, Weng Q, Yuan H, Hu FQ (2010) Synthesis and antitumor activity of stearate-g-dextran micelles for intracellular doxorubicin delivery. ACS Nano 4:6894–690210.1021/nn100927t ↗
42. Bhaisare ML, Pandey S, Khan MS, Talib A, Wu HF (2015) Fluorophotometric determination of critical micelle concentration (CMC) of ionic and non-ionic surfactants with carbon dots via Stokes shift. Talanta 132:572–57810.1016/j.talanta.2014.09.011 ↗
43. Urbani CN, Bell CA, Lonsdale D, Whittaker MR, Monteiro MJ (2008) Self-assembly of amphiphilic polymeric dendrimers synthesized with selective degradable linkages. Macromolecules 41:76–8610.1021/ma701993w ↗
44. Kale TS, Klaikherd A, Popere B, Thayumanavan S (2009) Supramolecular assemblies of amphiphilic homopolymers. Langmuir 25:9660–967010.1021/la900734d ↗
45. Lu Y, Park K (2013) Polymeric micelles and alternative nanonized delivery vehicles for poorly soluble drugs. Int J Pharm 453:198–21410.1016/j.ijpharm.2012.08.042 ↗
46. Su HY, Liu YH, Wang D, Wu CQ, Xia CC, Gong QY, Song B, Ai H (2013) Amphiphilic starlike dextran wrapped superparamagnetic iron oxide nanoparticle clsuters as effective magnetic resonance imaging probes. Biomaterials 34:1193–120310.1016/j.biomaterials.2012.10.056 ↗
47. Fielding LA, Lane JA, Derry MJ, Mykhaylyk OO, Armes SP (2014) Thermo-responsive diblock copolymer worm gels in non-polar solvents. J Am Chem Soc 136:5790–579810.1021/ja501756h ↗
48. Aggarwal BB, Kumar A, Bharti AC (2003) Anticancer potential of curcumin: preclinical and clinical studies. Anticancer Res 23:363–398
49. Kant V, Gopal A, Kumar D, Pathak NN, Ram M, Jangir BL, Tandan SK, Kumar D (2015) Curcumin-induced angiogenesis hastens wound healing in diabetic rats. J Surg Res 193:978–98810.1016/j.jss.2014.10.019 ↗
50. Shi Y, van Steenbergen MJ, Teunissen EA, Novo L, Gradmann S, Baldus M, van Nostrum CF, Hennink WE (2013) Pi-Pi stacking increases the stability and loading capacity of thermosensitive polymeric micelles for chemotherapeutic drugs. Biomacromolecules 14:1826–183710.1021/bm400234c ↗
51. Jeong YI, Chung KD, Kim DH, Kim YH, Lee YS, Choi KC (2013) All-trans retinoic acid-incorporated nanoparticles of deoxycholic acid-conjugated dextran for treatment of CT26 colorectal carcinoma cells. Int J Nanomed 8:485–493