Skip to main content
SpringerLink
Log in

Controlled drug release study of a quinolone antibiotic coupled to layered zinc hydroxide nanohybrids and its chitosan nanocarriers

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

1-Ethyl-7-methyl-4-oxo-[1,8]naphthyridine-3-carboxylic acid (nalidixic acid) is one of the most important and highly-consumed quinolone antibiotic drugs. In the present study, we prepared and characterized the nalidixic acid (NA)-layered zinc hydroxide (LZH) nanohybrid composites. The two subsequent ratios of the nanocomposites showed a basal spacing of 10.56 and 11.18 Å. These prepared nanocomposites were analyzed by PXRD, FTIR, TGA/DTA, BET, EDS, and FESEM, all representing the successful intercalation of NA into LZH nanohybrid gallery spaces. Accordingly, by the PXRD analysis, the average particle size and micro-strain values of the LZH and the two ratios of the nanocomposites were calculated and compared. The biopolymer NA-chitosan and NA-LZH-chitosan nanocomposites were prepared. Furthermore, drug release studies from LZH and chitosan substrates were measured at pH = 4.8 and 7.4 and acetate-buffered and phosphate-buffered saline solutions, respectively.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. Nabipour, H., Hossaini Sadr, M., Soltani, B.: Synthesis, identification and in vitro drug release of layered zinc hydroxide-gemifloxacin nanohybrids. J. Incl. Phenom. Macrocycl. Chem. 85(3), 261–269 (2016)

    Article  CAS  Google Scholar 

  2. Cursino, A.C.T., Rives, V., Carlos, L.D., Rocha, J., Wypych, F.: Layered zinc hydroxide salts intercalated with anionic surfactants and adsolubilized with UV absorbing organic molecules. J. Braz. Chem. Soc. 26(9), 1769–1780 (2015)

    CAS  Google Scholar 

  3. Feipeng, J., Hailei, S., Weijie, Y., Xinyu, J., Xiaoqing, C., Jingang, Y.: Enantioselective separation of tryptophan by Mg–Al layered double hydroxides intercalated with tartaric acid derivative. Appl. Clay Sci. 75–76, 92–99 (2013)

    Google Scholar 

  4. Senapati, S., Thakur, R., Verma, S.P., Duggal, S., Mishra, D.P., Das, P., Shripathi, T., Kumar, M., Rana, D., Maiti, P.: Layered double hydroxides as effective carrier for anticancer drugs and tailoring of release rate through interlayer anions. J. Control Release. 28(224), 186–198 (2016)

    Article  Google Scholar 

  5. Ogawa, M., Kuroda, K.: Photofunctions of intercalation compounds. Chem. Rev. 95, 399–438 (1995)

    Article  CAS  Google Scholar 

  6. Laurence, P., Noureddine, J., Fernand, F.: Layered hydroxide metal acetates (metal = zinc, cobalt, and nickel): elaboration via hydrolysis in polyol medium and comparative study. Chem. Mater. 12, 3123–3132 (2000)

    Article  Google Scholar 

  7. William, G.R., O’Hare, D.: Towards understanding, control and application of layered double hydroxide chemistry. J. Mater. Chem. 16, 3065–3074 (2006)

    Article  Google Scholar 

  8. Mohd Zobir Bin, H., Siti Halimah, S., Asmah Hj., Y., Zulkarnain, Z.: Synthesis of 4-chlorophenoxyacetate-zinc-aluminium-layered double hydroxide nanocomposite: physico-chemical and controlled release properties. J. Nanosci. Nanotechnol. 7, 2852–2862 (2007)

    Article  Google Scholar 

  9. Kandare, E., Hossenlopp, J.M.: Hydroxy double salt anion exchange kinetics: effects of precursor structure and anion size. J. Phys. Chem. B 109, 8469–8475 (2005)

    Article  CAS  Google Scholar 

  10. Tammaro, L., Costantino, U., Bolognese, A., Sammartino, G., Marenzi, G., Calignano, A., Tete´, S., Mastrangelo, F., Califano, L., Vittoria, V.: Nanohybrids for controlled antibiotic release in topical applications. Int. J. Antimicrob. Ag. 29, 417–423 (2007)

    Article  CAS  Google Scholar 

  11. Berber, M.R., Minagawa, K., Katoh, M., Mori, T., Tanaka, M.: Nanocomposites of 2-arylpropionic acid drugs based on Mg–Al layered double hydroxide for dissolution enhancement. Eur. J. Pharm. Sci. 35(4), 354–360 (2008)

    Article  CAS  Google Scholar 

  12. Zeng, Q.H., Yu, A.B., Lu, G.Q., Paul, D.R.: Clay-based polymer nanocomposites: research and commercial development. J. Nanosci. Nanotechnol. 5, 1574–1592 (2005)

    Article  CAS  Google Scholar 

  13. Marangoni, R., Ramos, L.P., Wypych, F.: New multifunctional materials obtained by the intercalation of anionic dyes into layered zinc hydroxide nitrate followed by dispersion into poly(vinyl alcohol) (PVA). J. Colloid Interface Sci. 330(2), 303–309 (2009)

    Article  CAS  Google Scholar 

  14. Barahuie, F., Hussein, M.Z., Fakurazi, S., Zainal, Z.: Development of drug delivery systems based on layered hydroxides for nanomedicine. Int. J. Mol. Sci. 15, 7750–7786 (2014)

    Article  Google Scholar 

  15. Louer, M., Louer, D., Grandjean, D.: Etude structurale des hydroxynitrates de nickel et de zinc. I. Classification structurale. Acta. Crystallogr. B 29(8), 1696–1703 (1973)

    Article  CAS  Google Scholar 

  16. Stahlin, W., Oswald, H.R.: The crystal structure of zinc hydroxide nitrate, Zn5(OH)8(NO3)2·2H2O. Acta. Crystallogr. B 26(6), 860–863 (1970)

    Article  Google Scholar 

  17. Hussein, M.Z., Ali, S.H., Zainal, Z., Haki, M.N.: Development of antiproliferative nanohybrid compound with controlled release property using ellagic acid as the active agent. Int. J. Nanomed. 6, 1373–1383 (2011)

    Article  CAS  Google Scholar 

  18. Barahuie, F., Hussein, M.Z., Gani, S.A., Fakurazi, S., Zainal, Z.: Synthesis of protocatechuic acid–zinc/aluminium-layered double hydroxide nanocomposite as an anticancer nanodelivery system. J. Solid State Chem. 221, 21–31 (2015)

    Article  CAS  Google Scholar 

  19. Barahuie, F., Hussein, M.Z., Gani, S.A., Fakurazi, S., Zainal, Z.: Anticancer nanodelivery system with controlled release property based on protocatechuate–zinc layered hydroxide nanohybrid. Int. J. Nanomed. 9, 3137–3149 (2014)

    Article  Google Scholar 

  20. Arizaga, G.G.C., Mangrich, A.S., Wypych, F.: Cu2+ ions as a paramagnetic probe to study the surface chemical modification process of layered double hydroxides and hydroxide salts with nitrate and carboxylate anions. J. Colloid Interface Sci. 320(1), 238–244 (2008)

    Article  CAS  Google Scholar 

  21. Emmerson, A.M., Jones, A.M.: The quinolones: decades of development and use. J. Antimicrob. Chemother. 51, 13–20 (2003)

    Article  CAS  Google Scholar 

  22. Pommier, Y., Leo, E., Zhang, H., Marchand, C.: DNA topoisomerases and their poisoning by anticancer and antibacterial drugs. Chem. Biol. 17, 421–433 (2010)

    Article  CAS  Google Scholar 

  23. Trikeriotis, M., Ghanotakis, D.F.: Intercalation of hydrophilic and hydrophobic antibiotics in layered double hydroxides. Int. J. Pharmaceutics. 332, 176–184 (2007)

    Article  CAS  Google Scholar 

  24. Nabipour, H., Hossaini Sadr, M., Thomas, N.: Synthesis, controlled release and antibacterial studies of nalidixic acid–zinc hydroxide nitrate nanocomposites, New J. Chem. 40, 238–244 (2016)

    Article  CAS  Google Scholar 

  25. Zinc, J.K.: An essential trace element for parenteral nutrition. Gastroenterology. 137(5), S7–S12 (2009)

    Article  Google Scholar 

  26. Xia, S.J., Ni, Z.M., Xu, Q., Hu, B.X., Hu, J.: Layered double hydroxides as supports for intercalation and sustained release of antihypertensive drugs. J. Solid State Chem. 181(10), 2610–2619 (2008)

    Article  CAS  Google Scholar 

  27. Faiz, U., Butt, T., Satti, L., Hussain, W., Hanif, F.: Efficacy of zinc as an antibacterial agent against enteric bacterial pathogens. J Ayub Med Coll Abbottabad. 23(2), 18–21 (2011)

    Google Scholar 

  28. Abouzarzadeh, A., Forouzani, M., Jahanshahi, M., Bahramifar, N.: Synthesis and evaluation of uniformly sized nalidixic acid-imprinted nanospheres based on precipitation polymerization method for analytical and biomedical applications. J. Mol. Recognit. 25(7), 404–413 (2012)

    Article  CAS  Google Scholar 

  29. Lee, J.S., Jung, Y.J., Doh, M.J., Kim, Y.M.: Synthesis and properties of dextran-nalidixic acid ester as a colon-specific prodrug of nalidixic acid. Drug Dev. Ind. Pharm. 27(4), 331–336 (2001)

    Article  CAS  Google Scholar 

  30. Georgeta, M., Elie, A.J., Didier, L., Luc, P., Adrian, C., Guy, M.: Synthesis of Chitosan microspheres containing pendant cyclodextrin moieties and their interaction with biological active molecules. Curr. Drug. Deliv. 1(3), 227–233 (2004)

    Article  CAS  Google Scholar 

  31. Krivovichev, S.V., Yakovenchuk, V.N., Zhitova, E.S., Zolotarev, A.A., Pakhomovsky, Y.A., Ivanyuk, G.Y.: Crystal chemistry of natural layered double hydroxides. 1. Quintinite-2H-3c from the Kovdor alkaline massif, Kola peninsula, Russia. Mineral. Mag. 74(5), 821–832 (2010)

    Article  CAS  Google Scholar 

  32. JCPDS PDF-2 database, International centre for diffraction data, Newtown Square, PA, USA. Release 54, (2004)

  33. Djebbi, M.A., Braiek, M., Namoura, P., Amara, A.B.H., Jaffrezic-Renault, N.: Layered double hydroxide materials coated carbon electrode: new challenge to future electrochemical power devices. Appl. Surf. Sci. 386, 352–363 (2016)

    Article  CAS  Google Scholar 

  34. Gangavaram, S., Raghavender, S., Sanphui, P., Pal, S., Manjunatha, S.G., Nambiar, S., Nangia, A., Polymorphs and cocrystals of nalidixic acid. Cryst. Growth Des. 12, 4963–4971 (2012)

    Article  CAS  Google Scholar 

  35. Zhurko, G.A., Zhurko, D.A.: Chemcraft Version 1.7 (build 132). HTML: http://www.chemcraftprog.com (2014)

  36. Gunawan, P., Xu, R.: Direct control of drug release behavior from layered double hydroxides through particle interactions. J. Pharm. Sci. 97, 4367 (2008)

    Article  CAS  Google Scholar 

  37. Meyn, M., Beneke, K., Lagaly, G.: Anion-exchange reactions of layered double hydroxides. Inorg. Chem. 29(26), 5201–5207 (1990)

    Article  CAS  Google Scholar 

  38. Debnath, A., Mogha, N.K., Masram, D.T.: Metal complex of the first-generation quinolone antimicrobial drug nalidixic acid: structure and its biological evaluation. Appl. Biochem. Biotechnol. 175(5), 2659–2667 (2015)

    Article  CAS  Google Scholar 

  39. Nabipour, H., Hossaini Sadr, M.: Layered zinc hydroxide–ibuprofen nanohybrids: synthesis and characterization. Bull. Mater. Sci. 38(6), 1561–1567 (2015)

    Article  CAS  Google Scholar 

  40. Wang, Z., Wang, E., Gao, L., Xu, L.: Synthesis and properties of Mg2Al layered double hydroxides containing 5-fluorouracil. J. Solid State Chem. 178(3), 736–741 (2005)

    Article  CAS  Google Scholar 

  41. Ghamami, S., Golzani, M., Lashgari, A.: New inorganic-based nanohybrids of layered zinc hydroxide/Parkinson’s disease drug and its chitosan biopolymer nanocarriers with controlled release rate. J. Incl. Phenom. Macrocycl. Chem. 86(1), 67–78 (2016)

    Article  CAS  Google Scholar 

  42. Ali, H.A., Al-Qubaisi, M., Hussein, M.Z., Ismail, M., Hakim, M.N.: Controlled-release formulation of antihistamine based on cetirizine zinc-layered hydroxide nanocomposites and its effect on histamine release from basophilic leukemia (RBL-2H3) cells. Int. J. Nanomed. 7, 3351–3363 (2012)

    Article  Google Scholar 

  43. Miao, J., Xue, M., Itoh, H., Feng, Q.: Hydrothermal synthesis of layered hydroxide zinc benzoate compounds and their exfoliation reactions. J. Mater. Chem. 16(5), 474–480 (2005)

    Article  Google Scholar 

  44. Sing, K.S.W., Everett, D.H., Haul, R.A.W., Moscou, L., Pierotti, R.A., Rouquerol, J., Siemieniewska, T.: Reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity. Pure Appl. Chem. 57(4), 603–619 (1985)

    Article  CAS  Google Scholar 

  45. Malak-Polaczyk, A., Vix-Guterl, C., Frackowiak, E.: Carbon/layered double hydroxide (LDH) composites for supercapacitor application. Energy Fuels. 24(6), 3346–3351 (2010)

    Article  CAS  Google Scholar 

  46. Farahnaz, B., Mohd Zobir, H., Palanisamy, A., Sharida, F., Zulkarnain, Z.: Controlled in vitro release of the anticancer drug chlorogenic acid using magnesium/aluminium-layered double hydroxide as a nanomatrix. Sci. Adv. Mater. 8(3), 501–513 (2016)

    Article  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge support from the research council of Imam Khomeini International University.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Imam Khomeini International University, Qazvin, 34148-96818, Iran

    Shahriar Ghamami, Amir Lashgari & Mojdeh Golzani

Authors
  1. Shahriar Ghamami
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Amir Lashgari
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mojdeh Golzani
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Shahriar Ghamami.

Ethics declarations

Conflict of interest

The authors declare that there is no conflict of interest regarding the publication of this paper.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ghamami, S., Lashgari, A. & Golzani, M. Controlled drug release study of a quinolone antibiotic coupled to layered zinc hydroxide nanohybrids and its chitosan nanocarriers. J Incl Phenom Macrocycl Chem 88, 1–14 (2017). https://doi.org/10.1007/s10847-017-0703-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-017-0703-y

Keywords

Search

Navigation