Advertisement

AAPS PharmSciTech

, Volume 19, Issue 8, pp 3895–3906 | Cite as

Green Synthesis of Carbon Nanotubes-Reinforced Molecularly Imprinted Polymer Composites for Drug Delivery of Fenbufen

  • Xin-Lu Liu
  • Hong-Fei Yao
  • Mei-Hong Chai
  • Wei He
  • Yan-Ping Huang
  • Zhao-Sheng Liu
Research Article
  • 55 Downloads

Abstract

The facile fabrication of single-walled carbon nanotubes (SWCNTs)-doping molecularly imprinted polymer (MIP) nanocomposite-based binary green porogen system, room-temperature ionic liquids (RTILs), and deep eutectic solvents (DESs) was developed for drug delivery system. With fenbufen (FB) as template molecule, 4-vinylpyridine (4-VP) was used as functional monomer, ethylene glycol dimethacrylate as cross-linking monomer, and 1-butyl-3-methylimidazoliumtetrafluoroborate and choline chloride/ethylene glycol as binary green solvent, in the presence of SWCNTs. The imprinting effect of the SWCNT–MIP composites was optimized by regulation of the amount of SWCNTs, ratio of RTILs and DES, and the composition of DES. Blue shifts of UV bands strongly suggested that interaction between 4-VP and FB can be enhanced due to SWCNT doping in the process of self-assembly. The reinforced imprinted effect of CNT-doping MIP can provide superior controlled release characteristics. Compared with the control MIP prepared without SWCNTs, the imprinting factor of the SWCNT–MIP composites exhibited a twofold increase. In the analysis for the FB release kinetics from all samples, the SWCNT-reinforced MIP produced the lowest value of drug diffusivity. The relative bioavailability of the SWCNT–MIP composites (F %) displayed the highest value of 143.3% compared with the commercial FB tablet, whereas the control MIP and SWCNT–non-MIP composites was only 48.3% and 44.4%, respectively. The results indicated that the SWCNT–MIP nanocomposites developed here have potentials as the controlled-release device.

KEY WORDS

polymer nanocomposites molecularly imprinted polymer deep eutectic solvents drug delivery carbon nanotubes fenbufen 

Abbreviations

[BMIM]BF4

1-butyl-3-methylimidazoliumtetrafluoroborate

CNT

carbon nanotube

ChCl

choline chloride

DES

deep eutectic solvent

EG

ethylene glycol

FB

fenbufen

FLU

flurbiprofen

IBU

ibuprofen

IF

imprinting factor

MIP

molecularly imprinted polymer

NAP

naproxen

NIP

non-molecularly imprinted polymer

RTIL

room-temperature ionic liquid

SWCNT

single-walled carbon nanotube

4-VP

4-vinylpyridine

Notes

Acknowledgments

Financial support from the National Natural Science Foundation of China (grant no. 21775109) and Innovation and Entrepreneurship Training Program for College Students in Jiangsu (201810316049x) is greatly acknowledged.

Author Contributions

The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript.

Compliance with Ethical Standards

Conflict of Interest

The authors declare no competing financial interest.

Supplementary material

12249_2018_1192_MOESM1_ESM.doc (3 mb)
ESM 1 (DOC 3072 kb)

References

  1. 1.
    Genix AC, Oberdisse J. Nanoparticle self-assembly: from interactions in suspension to polymer nanocomposites. Soft Matter. 2018;14:5161–79.CrossRefPubMedGoogle Scholar
  2. 2.
    Ha CS. Polymer based hybrid nanocomposites: a progress toward enhancing interfacial interaction and tailoring advanced applications. Chem Rec. 2018;18:759–75.CrossRefPubMedGoogle Scholar
  3. 3.
    Prusty RK, Rathore DK, Ray BC. CNT/polymer interface in polymeric composites and its sensitivity study at different environments. Adv Colloid Interf Sci. 2017;240:77–106.CrossRefGoogle Scholar
  4. 4.
    Heinz H, Ramezani-Dakhel H. Simulations of inorganic–bioorganic interfaces to discover new materials: insights, comparisons to experiment, challenges, and opportunities. Chem Soc Rev. 2015;45:412–48.CrossRefGoogle Scholar
  5. 5.
    Lee JW, Yoo YT, Lee JY. Ionic polymer–metal composite actuators based on triple-layered polyelectrolytes composed of individually functionalized layers. ACS Appl Mater Interfaces. 2014;6:1266–71.CrossRefPubMedGoogle Scholar
  6. 6.
    Atar N, Grossman E, Gouzman I, Bolker A, Murray VJ, Marshall BC, et al. Atomic-oxygen-durable and electrically-conductive CNT-POSS polyimide flexible films for space applications. ACS Appl Mater Interfaces. 2015;7:12047–56.CrossRefPubMedGoogle Scholar
  7. 7.
    Saito N, Aoki K, Usui Y, Shimizu M, Hara K, Narita N, et al. Application of carbon fibers to biomaterials: a new era of nano-level control of carbon fibers after 30-years of development. Chem Soc Rev. 2011;40:3824–34.CrossRefPubMedGoogle Scholar
  8. 8.
    Sun XM, Sun H, Li HP, Peng HS. Developing polymer composite materials: carbon nanotubes or graphene. Adv Mater. 2013;25:5153–76.CrossRefPubMedGoogle Scholar
  9. 9.
    Ajayan PM, Stephan O, Colliex C, Trauth D. Aligned carbon nanotube arrays formed by cutting a polymer resin–nanotube composite. Science. 1994;265:1212–4.CrossRefPubMedGoogle Scholar
  10. 10.
    Spitalsky Z, Tasisb D, Papagelis K, Galiotis C. Carbon nanotube–polymer composites: chemistry, processing, mechanical and electrical properties. Prog Polym Sci. 2010;35:357–401.CrossRefGoogle Scholar
  11. 11.
    Coleman JN, Khan U, Blau WJ, Gun’ko YK. Small but strong: a review of the mechanical properties of carbon nanotube–polymer composites. Carbon. 2006;44:1624–52.CrossRefGoogle Scholar
  12. 12.
    Tserpes KI, Chanteli A. Parametric numerical evaluation of the effective elastic properties of carbon nanotube-reinforced polymers. Compos Struct. 2013;99:366–74.CrossRefGoogle Scholar
  13. 13.
    Chen L, Wang X, Lu W, Wu X, Li J. Molecular imprinting: perspectives and applications. Chem Soc Rev. 2016;45:2137–211.CrossRefPubMedGoogle Scholar
  14. 14.
    Yoshikawa M, Tharpa K, Dima ŞO. Molecularly imprinted membranes: past, present, and future. Chem Rev. 2016;116:11500–28.CrossRefPubMedGoogle Scholar
  15. 15.
    Haupt K, Linares AV, Bompart M, Bui BT. Molecularly imprinted polymers. Top Curr Chem. 2012;325:1–28.PubMedGoogle Scholar
  16. 16.
    Li XX, Hao LF, Huang YP, Duan HQ, Liu ZS. Release evaluation of molecularly imprinted polymers prepared under molecular crowding conditions. Polym Eng Sci. 2012;52: 1440-9.  CrossRefGoogle Scholar
  17. 17.
    Tang L, Zhao C-Y, Wang X-H, Li R-S, Yang J-R, Huang Y-P, et al. Macromolecular crowding of molecular imprinting: a facile pathway to produce drug delivery devices for zero-order sustained release. Int J Pharm. 2015;496:822–33.CrossRefPubMedGoogle Scholar
  18. 18.
    Ban L, Zhao L, Deng B-L, Huang Y-P, Liu Z-S. Preparation and characterization of imprinted monolith by atom transfer radical polymerization assisted with crowding agents. Anal Bioanal Chem. 2013;405(7):2245–53.CrossRefPubMedGoogle Scholar
  19. 19.
    Zhang Z, Liu J. Molecularly imprinted polymers with DNA aptamer fragments as macromonomers. ACS Appl Mater Interfaces. 2016;8:6371–8.CrossRefPubMedGoogle Scholar
  20. 20.
    Hamdan S, Moore JL, Lejeune J, Hasan F, Carlisle TK, Bara JE, et al. Ionic liquid crosslinkers for chiral imprinted nanoGUMBOS. J Colloid Interface Sci. 2016;463:29–36.CrossRefPubMedGoogle Scholar
  21. 21.
    Booker K, Bowyer MC, Holdsworth CI, McCluskey A. Efficient preparation and improved sensitivity of molecularly imprinted polymers using room temperature ionic liquids. Chem Commun. 2006;(16):1730–2.Google Scholar
  22. 22.
    Ausman KD, Piner R, Lourie O, Ruoff RS, Korobov M. Organic solvent dispersions of single-walled carbon nanotubes: toward solutions of pristine nanotubes. J Phys Chem B. 2000;104:8911–5.CrossRefGoogle Scholar
  23. 23.
    Hwang JY, Nish A, Doig J, Douven S, Chen CW, Chen LC, et al. Polymer structure and solvent effects on the selective dispersion of single-walled carbon nanotubes. J Am Chem Soc. 2008;130:3543–53.CrossRefPubMedGoogle Scholar
  24. 24.
    Fukushima T, Kosaka A, Ishimura Y, Yamamoto T, Takigawa T, Ishii N, et al. Molecular ordering of organic molten salts triggered by single-walled carbon nanotubes. Science. 2003;300:2072–4.CrossRefPubMedGoogle Scholar
  25. 25.
    Zhang L-S, Gao S-P, Huang Y-P, Liu Z-S. Green synthesis of polymer monoliths incorporated with carbon nanotubes in room temperature ionic liquid and deep eutectic solvents. Talanta. 2016;154:335–40.CrossRefPubMedGoogle Scholar
  26. 26.
    Carriazo D, Arco MD, Fernandez A, Martin C, Rives V. Inclusion and release of fenbufen in mesoporous silica. J Pharm Sci. 2010;99:3372–80.CrossRefPubMedGoogle Scholar
  27. 27.
    Meng ZX, Xu XX, Zheng W, Zhou HM, Li L, Zheng YF, et al. Preparation and characterization of electrospun PLGA/gelatin nanofibers as a potential drug delivery system. Colloids Surf B Biointerfaces. 2011;84:97–102.CrossRefPubMedGoogle Scholar
  28. 28.
    Li B, He J, Evans DG, Duan X. Enteric-coated layered double hydroxides as a controlled release drug delivery system. Int J Pharm. 2004;287:89–95.CrossRefPubMedGoogle Scholar
  29. 29.
    Umpleby RJ II, Baxter SC, Chen Y, Shah RN, Shimizu KD. Characterization of molecularly imprinted polymers with the Langmuir−Freundlich isotherm. Anal Chem. 2001;73:4584–91.CrossRefPubMedGoogle Scholar
  30. 30.
    Siepmann J, Siepmann F. Modeling of diffusion controlled drug delivery. J Control Release. 2012;161:351–62.CrossRefPubMedGoogle Scholar
  31. 31.
    Gandhi M, Srikar R, Yarin AL, Megaridis CM, Gemeinhart RA. Mechanistic examination of protein release from polymer nanofibers. Mol Pharm. 2009;6:641–7.CrossRefPubMedPubMedCentralGoogle Scholar
  32. 32.
    Fujigaya T, Nakashima N. Methodology for homogeneous dispersion of single-walled carbon nanotubes by physical modification. Polym J. 2008;40:577–89.CrossRefGoogle Scholar
  33. 33.
    Qin S, Qin D, Ford WT, Herrera JE, Resasco DE. Grafting of poly(4-vinylpyridine) to single-walled carbon nanotubes and assembly of multilayer films. Macromolecules. 2004;37:9963–7.CrossRefGoogle Scholar
  34. 34.
    Li G, Wang W, Wang Q, Zhu T. Deep eutectic solvents modified molecular imprinted polymers for optimized purification of chlorogenic acid from honeysuckle. J Chromatogr Sci. 2016;54:271–9.PubMedGoogle Scholar
  35. 35.
    Sing KSW. Reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity. Pure Appl Chem. 1982;54:2201–18.CrossRefGoogle Scholar
  36. 36.
    Yang S, Guo W, Lin Y, Deng X, Wang H, Sun H, et al. Biodistribution of pristine single-walled carbon nanotubes in vivo. J Phys Chem C. 2007;11:17761–4.CrossRefGoogle Scholar
  37. 37.
    Liu Z, Davis C, Cai W, He L, Chen X, Dai H. Circulation and long-term fate of functionalized, biocompatible single-walled carbon nanotubes in mice probed by Raman spectroscopy. PNAS. 2008;105:1410–5.CrossRefPubMedGoogle Scholar
  38. 38.
    Xiao D, Dramou P, Xiong N, He H, Li H, Yuan D, et al. Development of novel molecularly imprinted magnetic solid-phase extraction materials based on magnetic carbon nanotubes and their application for the determination of gatifloxacin in serum samples coupled with high performance liquid chromatography. J Chromatogr A. 2013;1274:44–53.CrossRefPubMedGoogle Scholar
  39. 39.
    Madrakian T, Ahmadi M, Afkhami A, Soleimani M. Selective solid-phase extraction of naproxen drug from human urine samples using molecularly imprinted polymer-coated magnetic multi-walled carbon nanotubes prior to its spectrofluorometric determination. Analyst. 2013;138:4542–9.CrossRefPubMedGoogle Scholar
  40. 40.
    Yang W, Jiao F, Zhou L, Chen X, Jiang X. Molecularly imprinted polymers coated on multi-walled carbon nanotubes through a simple indirect method for the determination of 2,4-dichlorophenoxyacetic acid in environmental water. Appl Sur Sci. 2013;284:692–9.CrossRefGoogle Scholar

Copyright information

© American Association of Pharmaceutical Scientists 2018

Authors and Affiliations

  1. 1.State Key Laboratory of Natural Medicines, Department of Pharmaceutics, School of PharmacyChina Pharmaceutical UniversityNanjingPeople’s Republic of China
  2. 2.Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics (Theranostics), School of PharmacyTianjin Medical UniversityTianjinPeople’s Republic of China

Personalised recommendations