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

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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.

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References

  1. Hoskins C, Thoo-Lin PK, Cheng WP (2012) A review on comb-shaped amphiphilic polymers for hydrophobic drug solubilization. Ther Deliv 3:59–79

    Article  Google Scholar 

  2. Jańczewski D, Tomczak N, Han MY, Vancso GJ (2011) Synthesis of functionalized amphiphilic polymers for coating quantum dots. Nat Protoc 6:1546–1553

    Article  Google Scholar 

  3. Lin CJ, Sperling RA, Li JK, Yang TY (2008) Design of an amphiphilic polymer for nanoparticle coating and functionalization. Small 4:334–341

    Article  Google Scholar 

  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 308:25–32

    Article  Google Scholar 

  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 47:6072–6080

    Article  Google Scholar 

  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 4:1445–1458

    Article  Google Scholar 

  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 68:981–989

    Article  Google Scholar 

  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 279:68–77

    Article  Google Scholar 

  9. Dang JM, Leong KW (2006) Natural polymers for gene delivery and tissue engineering. Adv Drug Deliv Rev 58:487–499

    Article  Google Scholar 

  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/s10853-012-6804-5

    Article  Google Scholar 

  11. Virkutyte J, Varma RS (2011) Green synthesis of metal nanoparticles: biodegradable polymers and enzymes in stabilization and surface functionalization. Chem Sci 2:837–846

    Article  Google Scholar 

  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 25:1392–1399

    Article  Google Scholar 

  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/s10853-014-8301-5

    Article  Google Scholar 

  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/s10853-011-5599-0

    Article  Google Scholar 

  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 12:179–186

    Article  Google Scholar 

  16. Huang HZ, Yang XR (2004) Synthesis of Chitosan-stabilized gold nanoparticles in the absence/presence of tripolyphosphate. Biomacromolecules 5:2340–2346

    Article  Google Scholar 

  17. Boufi S, Vilar MR, Ferraria AM, Rego AMB (2013) In situ photochemical generation of silver and gold nanoparticles on chitosan. Colloids Surf A 439:151–158

    Article  Google Scholar 

  18. Mourya VK, Inamdar NN (2008) Chitosan-modifications and applications: opportunities galore. React Funct Polym 68:1013–1051

    Article  Google Scholar 

  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 346:2445–2450

    Article  Google Scholar 

  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 6:2562–2571

    Article  Google Scholar 

  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 112:5432–5438

    Article  Google Scholar 

  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/s10853-011-6075-6

    Article  Google Scholar 

  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-x

    Article  Google Scholar 

  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. 77:231–236

    Article  Google Scholar 

  25. Prabaharan M, Gong S (2008) Novel thiolated carboxymethyl chitosan-g-β-cyclodextrin as mucoadhesive hydrophobic drug delivery carriers. Carbonhydr. Polym. 73:117–125

    Article  Google Scholar 

  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-z

    Article  Google Scholar 

  27. Zhu XX, Nichifor M (2002) Polymeric materials containing bile acids. Acc Chem Res 35:539–546

    Article  Google Scholar 

  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 142:27–34

    Article  Google Scholar 

  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 31:378–383

    Article  Google Scholar 

  30. Lee KY, Kwon IC, Kim YH, Jo WH, Jeong SY (1998) Preparation of chitosan selfaggregates as a gene delivery system. J Control Release 51:213–220

    Article  Google Scholar 

  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 278:1216–1219

    Article  Google Scholar 

  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 109:330–344

    Article  Google Scholar 

  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 6:1154–1158

    Article  Google Scholar 

  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 11:3480–3486

    Article  Google Scholar 

  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 84:1192–1200

    Article  Google Scholar 

  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/s10856-013-5113-0

    Google Scholar 

  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 117:1261–1268

    Article  Google Scholar 

  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 16:1575–1593

    Article  Google Scholar 

  39. Park K, Kim K, Byun Y (2004) Preparation and characterization of self-assembled nanoparticles of heparin-deoxycholic acid conjugates. Langmuir 20:11726–11731

    Article  Google Scholar 

  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 256:29–33

    Article  Google Scholar 

  41. Prabha S, Zhou WZ, Panyam J, Labhasetwar V (2002) Size-dependency of nanoparticle-mediated gene transfection, studies with fractionated nanoparticles. Int J Pharm 244:105–115

    Article  Google Scholar 

  42. Sui WP, Wang S, Chen GH, Xu GY (2004) Surface and aggregate properties of an amphiphilic derivative of carboxymethylchitosan. Carbohydr Res 339:1113–1118

    Article  Google Scholar 

  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 48:13–16

    Article  Google Scholar 

  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

    Google Scholar 

  45. Khalil MMH, Ismail EH, El-Magdoub F (2012) Biosynthesis of Au nanoparticles using olive leaves extract. Arab J Chem 5:431–437

    Article  Google Scholar 

  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 22:577–583

    Article  Google Scholar 

Download references

Acknowledgements

This study was supported by the International Science Cooperation Project of Shandong Province, China (2012GHZ20205), the National Natural Science Foundation of China (Nos. 51102114), and the Doctor Foundation (No. XBS1204) and Science Research Foundation (XKY1214) from University of Jinan.

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Correspondence to Guobao Li or Weiping Sui.

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Li, G., Song, P., Wang, K. et al. An amphiphilic chitosan derivative modified by deoxycholic acid: preparation, physicochemical characterization, and application. J Mater Sci 50, 2634–2642 (2015). https://doi.org/10.1007/s10853-015-8852-0

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  • DOI: https://doi.org/10.1007/s10853-015-8852-0

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