Skip to main content
SpringerLink
Log in

Fatty Acid Based Polyamide for Application in Drug Delivery System: Synthesis, Characterization, Drug Loading and In Vitro Drug Release Study

  • Published:
Journal of Inorganic and Organometallic Polymers and Materials Aims and scope Submit manuscript

Abstract

Application of degradable polymers for pharmaceutical formulations is an appropriate strategy to increase the efficacy and reduce the side effects of drugs. Methylprednisolone is a glucocorticoid used in the treatment of a wide range of inflammatory and immune disorders. Due to high rate of clearance of methylprednisolone from body, frequent administration is required which can increase its undesired effects. Therefore, the aim of this study was to prepare methylprednisolone loaded polymeric nanoparticles incorporating fatty acid based polyamide, to improve its efficacy and reduce the side effects. In this study, a new fatty acid based polyamide with ideal characteristics for application in pharmaceutical dosage forms was synthesized. Palmitic acid, a saturated fatty acid, a derivative of palm oil, was the main constituent of the polymer, which improved its degradability, flexibility, and hydrophobicity. Palmitic acid was functionalized by tris(2-aminoethyl)amine, and then polymerized by application of sebacoyl chloride as a cross linker. The structure of the polymer was confirmed by FTIR and 1HNMR spectroscopy. Cytotoxicity of the polymer was tested on WRL68cell line using cell proliferation (MTT) assay, which showed low toxicity profile of the polymer. To study the type of erosion, polymeric devices were prepared by melt casting method by using aluminium mold. The polymer had about 55% and 40% wet and dry weight loss respectively within 7 days. The scanning electron micrographs showed surface erosion of the polymer. Drug loaded polymeric nanoparticles (PNP) were prepared by using thin film hydration method. Drug loaded PNPs with a particles size of 60–300 nm and entrapment efficiency of 76% were achieved.

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
Fig. 11
Fig. 12

Similar content being viewed by others

References

  1. M.G. Fehlings, J.R. Wilson, J.S. Harrop, B.K. Kwon, L.A. Tetreault, P.M. Arnold, J.M. Singh, G. Hawryluk, J.R. Dettori, Global Spine J. 7, 116 (2017)

    Google Scholar 

  2. G.U. Meduri, R.A.C. Siemieniuk, R.A. Ness, S.J. Seyler, J. Intensive Care 6, 53 (2018)

    PubMed  PubMed Central  Google Scholar 

  3. I.N. van Schaik, F. Eftimov, P.A. van Doorn, E. Brusse, L.H. van den Berg, W.L. van der Pol, C.G. Faber, J.C. van Oostrom, O.J. Vogels, R.D. Hadden, Lancet Neurol. 9, 245 (2010)

    PubMed  Google Scholar 

  4. J. Hwang, K. Rodgers, J.C. Oliver, T. Schluep, Int. J. Nanomed. 3, 359 (2008)

    CAS  Google Scholar 

  5. Y.-T. Kim, J.-M. Caldwell, R.V. Bellamkonda, Biomaterials 30, 2582 (2009)

    CAS  PubMed  PubMed Central  Google Scholar 

  6. S.L. Pal, U. Jana, P. Manna, G. Mohanta, R. Manavalan, J. Appl. Pharm. Sci. 1(6), 228–234 (2011)

    Google Scholar 

  7. W. Chen, S. Zhou, L. Ge, W. Wu, X. Jiang, Biomacromol 19, 1732 (2018)

    CAS  Google Scholar 

  8. L.S. Nair, C.T. Laurencin, Prog. Polym. Sci. 32, 762 (2007)

    CAS  Google Scholar 

  9. M. Sokolsky-Papkov, A. Shikanov, N. Kumar, B. Vaisman, A.J. Domb, Bull. Israel Chem. Soc. 1139, 2572–2587 (2008)

    Google Scholar 

  10. I. Vroman, L. Tighzert, Materials 2, 307 (2009)

    CAS  PubMed Central  Google Scholar 

  11. A. Srivastava, T. Yadav, S. Sharma, A. Nayak, A.A. Kumari, N. Mishra, J. Biosci. Med. 4, 16 (2016)

    Google Scholar 

  12. S.G. Kumbar, S. Bhattacharyya, S.P. Nukavarapu, Y.M. Khan, L.S. Nair, C.T. Laurencin, J. Inorg. Organomet. Polym. Mater. 16, 365 (2006)

    CAS  Google Scholar 

  13. S.J. Wu, P.-L. Liu, L.-T. Ng, Mol. Nutr. Food Res 52, 921 (2008)

    CAS  PubMed  Google Scholar 

  14. C. Elson, A. Qureshi, Prostaglandins Leukot. Essent. Fatty Acids 52, 205 (1995)

    CAS  PubMed  Google Scholar 

  15. P. Keng, M. Basri, M. Zakaria, M.A. Rahman, A. Ariff, R.A. Rahman, A. Salleh, Ind. Crops Prod. 29, 37 (2009)

    CAS  Google Scholar 

  16. B. EkoPrasetyo, N. Azmi, A. Shamsuddin, Malays. J. Health Sci. 16, 5–8 (2018)

    Google Scholar 

  17. J.L. Zaro, J. Am. Assoc. Pharm. Sci. 17, 83 (2014)

    Google Scholar 

  18. N.P. Bharathi, N.U. Khan, M. Alam, S. Shreaz, A.A. Hashmi, J. Inorg. Organomet. Polym. Mater. 20, 839 (2010)

    CAS  Google Scholar 

  19. J.P. Jain, M. Sokolsky, N. Kumar, A. Domb, Polym. Rev. 48, 156 (2008)

    CAS  Google Scholar 

  20. C. Vilela, R. Rua, A.J. Silvestre, A. Gandini, Ind. Crops Prod. 32, 97 (2010)

    CAS  Google Scholar 

  21. C. Montoya, B. Cochard, A. Flori, D. Cros, R. Lopes, T. Cuellar, S. Espeout, I. Syaputra, P. Villeneuve, M. Pina, E. Ritter, T. Leroy, N. Billotte, PLoS ONE 9, 95412 (2014)

    Google Scholar 

  22. V. Incani, E. Tunis, B.A. Clements, C. Olson, C. Kucharski, A. Lavasanifar, H. Uludag, J. Biomed. Mater. Res. Part A 81, 493 (2007)

    Google Scholar 

  23. S.M. Sarett, K.V. Kilchrist, M. Miteva, C.L. Duvall, J. Biomed. Mater. Res. A. 103, 3107 (2014)

    Google Scholar 

  24. N. Kolb, M.A.R. Meier, Green Chem. 14, 2429 (2012)

    CAS  Google Scholar 

  25. M.Y. Krasko, A. Shikanov, A. Ezra, A.J. Domb, J. Polym Sci A 41, 1059 (2003)

    CAS  Google Scholar 

  26. J.P. Jain, S. Modi, N. Kumar, J. Biomedic. Mater. Res. A 84, 740 (2008)

    Google Scholar 

  27. D. Sgouras, R. Duncan, J. Mater. Sci. 1, 61 (1990)

    CAS  Google Scholar 

  28. T. Mosmann, J. Immunol. Methods 65, 55 (1983)

    CAS  PubMed  Google Scholar 

  29. P. Dehghan Kelishady, E. Saadat, F. Ravar, H. Akbari, F. Dorkoosh, Pharm. Dev. Technol. 20, 1009 (2015)

    CAS  PubMed  Google Scholar 

  30. Z. Wei, J. Hao, S. Yuan, Y. Li, W. Juan, X. Sha, X. Fang, Int. j. Pharm. 376, 176 (2009)

    CAS  PubMed  Google Scholar 

  31. S. D’souza, Adv. Pharm. (2014). https://doi.org/10.1557/adv.2018.320

    Article  Google Scholar 

  32. S. Azadi, H. Ashrafi, A. Azadi, J. Appl. Pharm. Sci 7, 125 (2017)

    CAS  Google Scholar 

  33. A. Kadivar, B. Kamalidehghan, H.A. Javar, E.T. Davoudi, N.D. Zaharuddin, B. Sabeti, L.Y. Chung, M.I. Noordin, PLoS ONE 10, 126874 (2015)

    Google Scholar 

  34. K. Ramteke, P. Dighe, A. Kharat, S. Patil, Sch. Acad. J. Pharm 3, 388 (2014)

    Google Scholar 

  35. I. Olivares, L. Bucio, V. Souza, A. Carabez, M. Gutiérrez-Ruiza, Toxicology 120, 133 (1997)

    CAS  PubMed  Google Scholar 

  36. P. Ramirez, L. Del Razo, M. Gutierrez-Ruiz, M. Gonsebatt, Carcinogenesis 21, 701 (2000)

    CAS  PubMed  Google Scholar 

  37. J.P. Jain, S. Modi, N. Kumar, J. Biomed. Mater. Res. A 84, 740 (2008)

    PubMed  Google Scholar 

  38. H.-B. Xu, Z.-B. Zhou, K.-X. Huang, T. Lei, T. Zhang, Z.-L. Liu, Polym. Bul. 46, 435 (2001)

    CAS  Google Scholar 

  39. D. Ghosh, A. Pramanik, N. Sikdar, S. Ghosh, P. Pramanik, Int. J. Pharm. Sci. Drug. Res. 2, 247 (2010)

    CAS  Google Scholar 

  40. J. Palacio, V.H. Orozco, B.L. López, J. Braz. Chem. Soc. 22, 2304 (2011)

    CAS  Google Scholar 

  41. A. Göpferich, Biomaterials 17, 103 (1996)

    PubMed  Google Scholar 

  42. F. Haghiralsadata, G. Amoabedinyb, S. Naderinezhadc, M.N. Helderd, E.A. Kharanaghie, B. Zandieh-Doulabid, Int. J. Polym. Mater. Polym. Biomater. 383, 982–994 (2017)

    Google Scholar 

  43. J. Hwang, K. Rodgers, J.C. Oliver, T. Schluep, Int. J. Nanomedicine 3, 359 (2008)

    CAS  PubMed  PubMed Central  Google Scholar 

  44. F. Alexis, E. Pridgen, L.K. Molnar, O.C. Farokhzad, Mol. Pharm. 5, 505 (2008)

    CAS  PubMed  PubMed Central  Google Scholar 

  45. J.M. Morachis, E.A. Mahmoud, J. Sankaranarayanan, A. Almutairi, J. Drug Deliv. (2012). https://doi.org/10.1155/2012/291219

    Article  PubMed  PubMed Central  Google Scholar 

  46. A. Azadi, M. Hamidi, M.-R. Rouini, Int. J. Biol. Macromol 62, 523 (2013)

    CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Pharmacy, Faculty of Medicine, University of Malaya, Kuala Lumpur, Malaysia

    Reyhaneh Akbari Javar & Mohammed Ibrahim Bin Noordin

  2. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran

    Mehdi Khoobi

  3. Department of Chemistry, Payame Noor University, Tehran, Iran

    Asiyeh Ghaedi

Authors
  1. Reyhaneh Akbari Javar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mohammed Ibrahim Bin Noordin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mehdi Khoobi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Asiyeh Ghaedi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Reyhaneh Akbari Javar.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Akbari Javar, R., Bin Noordin, M.I., Khoobi, M. et al. Fatty Acid Based Polyamide for Application in Drug Delivery System: Synthesis, Characterization, Drug Loading and In Vitro Drug Release Study. J Inorg Organomet Polym 30, 2520–2532 (2020). https://doi.org/10.1007/s10904-020-01512-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10904-020-01512-x

Keywords

Search

Navigation