journal article·2015-03

An amphiphilic chitosan derivative modified by deoxycholic acid: preparation, physicochemical characterization, and application

Guobao Li, Peng Song, Kaili Wang, Qi Xue, Weiping Sui, Xiangzheng Kong

Journal of Materials Science· Volume 50· Issue 6
Publisher page

Abstract

A new type of amphiphilic chitosan derivative, deoxycholic acid-hydroxypropyl chitosan (DCA-HPCHS), has been synthesized through coupling reaction between 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride, N-hydroxysuccinimide, and deoxycholic acid which acts as hydrophobic group. Physicochemical properties of DCA-HPCHS in aqueous media were studied by surface tension and fluorescence measurement. It was also used to prepare gold nanoparticles at room temperature by green synthesis. Results showed that DCA-HPCHS can be concentrated on the surface to decrease the surface tension, and to associate with hydrophobic chains to form aggregates in the solution. With increased degree of substitution of the hydrophobic group, the surface tension decreased at the same concentration of the derivative, and the aggregates formed at lower concentration of the derivative. The form and size of the aggregates were analyzed by transmission electron microscopy and dynamic light scattering, which showed that the aggregates were spherical, and the size of them in solution increased with increasing concentration. In biosynthesis of gold nanoparticles, DCA-HPCHS acts as reducing and stabilizing agent, and the pH of DCA-HPCHS solution influenced the shape and size of the gold nanoparticles. And the results indicate that it is a potential material used in green synthesis of metal nanomaterials.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Nanoparticles: synthesis and applications · Gold and Silver Nanoparticles Synthesis and Applications · Nanocomposite Films for Food Packaging

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

References (46)

Show source-provided references
1. Hoskins C, Thoo-Lin PK, Cheng WP (2012) A review on comb-shaped amphiphilic polymers for hydrophobic drug solubilization. Ther Deliv 3:59–7910.4155/tde.11.130 ↗
2. Jańczewski D, Tomczak N, Han MY, Vancso GJ (2011) Synthesis of functionalized amphiphilic polymers for coating quantum dots. Nat Protoc 6:1546–155310.1038/nprot.2011.381 ↗
3. Lin CJ, Sperling RA, Li JK, Yang TY (2008) Design of an amphiphilic polymer for nanoparticle coating and functionalization. Small 4:334–34110.1002/smll.200700654 ↗
4. Marie E, Rotureau E, Dellacherie E, Durand A (2007) From polymeric surfactants to colloidal systems 4. Neutral and anionic amphiphilic polysaccharides for miniemulsion stabilization and polymerization. Colloid Surf A 308:25–3210.1016/j.colsurfa.2007.05.025 ↗
5. Peng D, Zhang X, Huang X (2006) Synthesis of amphiphilic graft copolymer with hydrophilic poly(acrylic acid) backbone and hydrophobic polystyrene side chains. Polymer 47:6072–608010.1016/j.polymer.2006.06.045 ↗
6. Stemmelen M, Travelet C, Lapinte V, Borsalib R, Robin JJ (2013) Synthesis and self-assembly of amphiphilic polymers based on polyoxazoline and vegetable oil derivatives. Polym Chem 4:1445–145810.1039/c2py20840g ↗
7. Wei Y, Cheng F, Hou G, Sun S (2008) Amphiphilic cellulose: surface activity and aqueous self-assembly into nano-sized polymeric micelles. React Funct Polym 68:981–98910.1016/j.reactfunctpolym.2008.02.004 ↗
8. Rotureau E, Leonard M, Dellacherie E, Durand A (2004) Amphiphilic derivatives of dextran: adsorption at air/water and oil/water interfaces. J Colloid Interface Sci 279:68–7710.1016/j.jcis.2004.06.040 ↗
9. Dang JM, Leong KW (2006) Natural polymers for gene delivery and tissue engineering. Adv Drug Deliv Rev 58:487–49910.1016/j.addr.2006.03.001 ↗
10. Solı´s Y, Davidenko N, Carrodeguas RG, Cruz J, Herna´ndez A, Toma´s M, Cameron RE, Peniche C (2013) Preparation, characterization, and in vitro evaluation of nanostructured chitosan/apatite and chitosan/Si-doped apatite composites. J Mater Sci 48:841–849. doi: 10.1007/s10853-012-6804-510.1007/s10853-012-6804-5 ↗
11. Virkutyte J, Varma RS (2011) Green synthesis of metal nanoparticles: biodegradable polymers and enzymes in stabilization and surface functionalization. Chem Sci 2:837–84610.1039/c0sc00338g ↗
12. DuChene JS, Niu WX, Abendroth JM, Sun Q, Zhao WB, Huo FW, Wei WD (2013) Halide anions as shape-directing agents for obtaining high-quality anisotropic gold nanostructures. Chem Mater 25:1392–139910.1021/cm3020397 ↗
13. Guibal E, Vincent T, Navarro R (2014) Metal ion biosorption on chitosan for the synthesis of advanced materials. J Mater Sci 49:5505–5518. doi: 10.1007/s10853-014-8301-510.1007/s10853-014-8301-5 ↗
14. Nguyen TTT, Tae B, Park JS (2011) Synthesis and characterization of nanofiber webs of chitosan/poly(vinyl alcohol) blends incorporated with silver nanoparticles. J Mater Sci 46:6528–6537. doi: 10.1007/s10853-011-5599-010.1007/s10853-011-5599-0 ↗
15. Hortiguela MJ, Aranaz I, Gutie´ rrez MC, Ferrer ML, Monte F (2011) Chitosan gelation induced by the in situ formation of gold nanoparticles and its processing into macroporous scaffolds. Biomacromolecules 12:179–18610.1021/bm1010883 ↗
16. Huang HZ, Yang XR (2004) Synthesis of Chitosan-stabilized gold nanoparticles in the absence/presence of tripolyphosphate. Biomacromolecules 5:2340–234610.1021/bm0497116 ↗
17. Boufi S, Vilar MR, Ferraria AM, Rego AMB (2013) In situ photochemical generation of silver and gold nanoparticles on chitosan. Colloids Surf A 439:151–15810.1016/j.colsurfa.2012.12.036 ↗
18. Mourya VK, Inamdar NN (2008) Chitosan-modifications and applications: opportunities galore. React Funct Polym 68:1013–105110.1016/j.reactfunctpolym.2008.03.002 ↗
19. Xua T, Xin M, Li M, Huang H, Zhou S, Liu J (2011) Synthesis, characterization, and antibacterial activity of N,O-quaternary ammonium chitosan. Carbonhydr Res 346:2445–245010.1016/j.carres.2011.08.002 ↗
20. Tang H, Zhang P, Kieft TL, Ryan SJ, Baker SM (2010) Antibacterial action of a novel functionalized chitosan-arginine against Gram-negative bacteria. Acta Biomater 6:2562–257110.1016/j.actbio.2010.01.002 ↗
21. Zhu A, Yuan L, Dai S (2008) Preparation of well-dispersed superparamagnetic iron oxide nanoparticles in aqueous solution with biocompatible N-succinyl-O-carboxymethylchitosan. J Phys Chem C 112:5432–543810.1021/jp711319a ↗
22. Chen C, Dong AJ, Yang J, Deng LD (2012) Preparation and properties of an injectable thermo-sensitive double crosslinking hydrogel based on thiolated chitosan/beta-glycerophosphate. J Mater Sci 47:2509–2517. doi: 10.1007/s10853-011-6075-610.1007/s10853-011-6075-6 ↗
23. Ghosh A, Ali MA (2012) Studies on physicochemical characteristics of chitosan derivatives with dicarboxylic acids. J Mater Sci 47:1196–1204. doi: 10.1007/s10853-011-5885-x10.1007/s10853-011-5885-x ↗
24. Zhang Y, Huo M, Zhou J, Yu D, Wu Y (2009) Potential of amphiphilically modified low molecular weight chitosan as a novel carrier for hydrophobic anticancer drug: synthesis, characterization, micellization and cytotoxicity evaluation. Carbonhydr. Polym. 77:231–23610.1016/j.carbpol.2008.12.034 ↗
25. Prabaharan M, Gong S (2008) Novel thiolated carboxymethyl chitosan-g-β-cyclodextrin as mucoadhesive hydrophobic drug delivery carriers. Carbonhydr. Polym. 73:117–12510.1016/j.carbpol.2007.11.005 ↗
26. Wang QQ, Kong M, An Y, Liu Y, Li JJ, Zhou X, Feng C, Li J, Jiang SY, Cheng XJ, Chen XG (2013) Hydroxybutyl chitosan thermo-sensitive hydrogel: a potential drug delivery system. J Mater Sci 48:5614–5623. doi: 10.1007/s10853-013-7356-z10.1007/s10853-013-7356-z ↗
27. Zhu XX, Nichifor M (2002) Polymeric materials containing bile acids. Acc Chem Res 35:539–54610.1021/ar0101180 ↗
28. Díaz AN, Sánchez FG, Pareja AG (1998) Cholic acid behavior in water and organic solvent: study of normal and inverted aggregates. Colloid Surf A 142:27–3410.1016/S0927-7757(98)00370-7 ↗
29. Lee KY, Jo WH, Kwon IC, Kim YH, Jeong SY (1998) Structural determination and interior polarity of self-aggregates prepared from deoxycholic acid-modified chitosan in water. Macromolecules 31:378–38310.1021/ma9711304 ↗
30. Lee KY, Kwon IC, Kim YH, Jo WH, Jeong SY (1998) Preparation of chitosan selfaggregates as a gene delivery system. J Control Release 51:213–22010.1016/S0168-3659(97)00173-9 ↗
31. Lee KY, Kim JH, Kwon IC, Jeong SY (2000) Self-aggregates of deoxycholic acid-modified chitosan as a novel carrier of adriamycin. Colloid Polym Sci 278:1216–121910.1007/s003960000389 ↗
32. Chae SY, Son S, Lee M, Jang MK, Nah JW (2005) Deoxycholic acid-conjugated chitosan oligosaccharide nanoparticles for efficient gene carrier. J Control Release 109:330–34410.1016/j.jconrel.2005.09.040 ↗
33. Kim K, Kwon S, Park JH, Chung H, Jeong SY, Kwon IC, Kim IS (2005) Physicochemical characterizations of self-assembled nanoparticles of glycol chitosan-deoxycholic acid conjugates. Biomacromolecules 6:1154–115810.1021/bm049305m ↗
34. Zhou H, Yu W, Guo X, Liu X, Li N, Zhang Y, Ma X (2010) Synthesis and characterization of amphiphilic glycidol-chitosan-deoxycholic acid nanoparticles as a drug carrier for doxorubicin. Biomacromolecules 11:3480–348610.1021/bm100989x ↗
35. Wang F, Zhang D, Duan C, Jia L, Feng F, Liu Y, Wang Y, Hao L, Zhang Q (2011) Preparation and characterizations of a novel deoxycholic acid-O-carboxymethylated chitosan-folic acid conjugates and self-aggregates. Carbohydr Polym 84:1192–120010.1016/j.carbpol.2011.01.017 ↗
36. Shi Z, Guo R, Li W, Zhang Y, Xue W, Tang YYu, Zhang Y (2014) Nanoparticles of deoxycholic acid, polyethylene glycol and folic acid-modified chitosan for targeted delivery of doxorubicin. J Mater Sci 25:723–731. doi: 10.1007/s10856-013-5113-010.1007/s10856-013-5113-0 ↗
37. Chen D, Song P, Jiang F, Meng X, Sui WP, Shu C, Wan L (2013) pH-Responsive mechanism of a deoxycholic acid and folate comodified chitosan micelle under cancerous environment. J Phys Chem B 117:1261–126810.1021/jp310677p ↗
38. Amaral IF, Granja PL, Barbosa MA (2005) Chemical modification of chitosan by phosphorylation: an XPS, FT-IR and SEM study. J Biomater Sci Polym Ed 16:1575–159310.1163/156856205774576736 ↗
39. Park K, Kim K, Byun Y (2004) Preparation and characterization of self-assembled nanoparticles of heparin-deoxycholic acid conjugates. Langmuir 20:11726–1173110.1021/la048646i ↗
40. Sui WP, Song G, Chen G, Xu GY (2005) Aggregate formation and surface activity property of an amphiphilic derivative of chitosan. Colloid Surf A 256:29–3310.1016/j.colsurfa.2004.09.019 ↗
41. Prabha S, Zhou WZ, Panyam J, Labhasetwar V (2002) Size-dependency of nanoparticle-mediated gene transfection, studies with fractionated nanoparticles. Int J Pharm 244:105–11510.1016/S0378-5173(02)00315-0 ↗
42. Sui WP, Wang S, Chen GH, Xu GY (2004) Surface and aggregate properties of an amphiphilic derivative of carboxymethylchitosan. Carbohydr Res 339:1113–111810.1016/j.carres.2004.02.002 ↗
43. Sui WP, Yin C, Chen Y, Zhang Z, Kong XZ (2006) Self-assembly of an amphiphilic derivative of chitosan and micellar solubilization of puerarin. Colloids Surf B 48:13–1610.1016/j.colsurfb.2006.01.005 ↗
44. Ismail EH, Khalil MMH, Al Seif FA, El-Magdoub F (2014) Biosynthesis of gold nanoparticles using extract of grape (vitis vinifera) leaves and seeds. Prog Nanotechnol Nanomater 3:1–12
45. Khalil MMH, Ismail EH, El-Magdoub F (2012) Biosynthesis of Au nanoparticles using olive leaves extract. Arab J Chem 5:431–43710.1016/j.arabjc.2010.11.011 ↗
46. Chandran SP, Chaudhary M, Pasricha R, Ahmad A, Sastry M (2006) Synthesis of gold nanotriangles and silver nanoparticles using Aloe vera plant extract. Biotechnol Prog 22:577–58310.1021/bp0501423 ↗