Skip to main content
Log in

The synergistic cooperation between MCM-41 and azithromycin: a pH responsive system for drug adsorption and release

  • Published:
Journal of Porous Materials Aims and scope Submit manuscript

Abstract

The capability of MCM-41 silica for accepting and delivering poorly soluble azithromycin (AZT) in water is reported as robust drug delivery system. This property has been evidenced by using two MCM-41 samples with different pore sizes as hosts of AZT. The choice of this macrolide antibiotic is due not only to its low bioavailability but also to its molecular size which lies in the range of pore diameter of MCM-41s. The drug was loaded inside the pore voids of the mesoporous when MCM-41 was stirred at AZT solution, based on XRD, Nitrogen adsorption–desorption isotherms, TGA analysis data and FT-IR spectroscopy. The amount of AZT stored inside the pores of MCM-41 s was between 22 and 25 wt%. The loaded drug was released in different rates from the particles by changing the pH (1.7 and 7.4) to give a smart pH-responsive carrier system. The drug release kinetics was fitted to Korsmeyer–Peppas and Higuchi models which indicated that the rate of drug release was controlled by the diffusion of the drug. The result of the present study confirms that the controlled adsorption and liberation of AZT may improve the oral bioavailability of poor water soluble AZT. This study demonstrates the feasibility of designing reliable drug delivery systems by appropriate choice of the matrix and the organic molecule. In general, MCM-41 is a promising matrix for AZT adsorption with different application from drug delivery to wastewater filtration.

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

Access this article

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

Instant access to the full article PDF.

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

Similar content being viewed by others

References

  1. F. Davis, S. Higson, Macrocycles: Construction, Chemistry and Nanotechnology Applications (Wiley, Chennai, 2011)

    Book  Google Scholar 

  2. J. Brnjas-Kraljevi, G. Pifat-Mrzljak, Supramolecular Structure and Function, vol. 10. (Springer, Dordrecht, 2011)

    Book  Google Scholar 

  3. H. Dodziuk, Introduction to Supramolecular Chemistry (Kluwer Academic Publishers, Dordrecht, 2011)

    Google Scholar 

  4. J.W. Steed, J.L. Atwood Supramolecular Chemistry (Wiley, Chichester, 2006)

    Google Scholar 

  5. K. Ariga, T. Kunitake Supramolecular Chemistry, Fundamentals and Applications (Springer, Berlin, 2006)

    Google Scholar 

  6. F. Balas, J. Am. Chem. Soc. 128, 8116–8117 (2006)

    Article  CAS  PubMed  Google Scholar 

  7. R. Gandhi, O. Pillai, R. Thilagavathi, B. Gopalakrishnan, C. Lal Kaul, R. Panchagnula, Eur. J. Pharm. Sci. 16, 175 (2002)

    Article  CAS  PubMed  Google Scholar 

  8. P.M. Bartold, A.H. du Bois, S. Gannon, D.R. Haynes, R.S. Hirsch, Inflammopharmacology 21, 321 (2013)

    Article  CAS  PubMed  Google Scholar 

  9. T.S. Harrison, S.J. Keam (2007) Drugs, 67, 773

    Article  CAS  Google Scholar 

  10. S. Sheybani, T. Hosseinifar, M. Abdouss, S. Mazinani, RSC Adv. 5, 98880 (2015)

    Article  CAS  Google Scholar 

  11. S. Ullah, M.R. Shah, M. Shoaib, M. Imran, S.W. Shah, I. Ali, F. Ahmed, Drug Dev. Ind. Pharm. 43, 1011 (2017)

    Article  CAS  PubMed  Google Scholar 

  12. S. Wang, Micropor. Mesopor. Mater. 117, 1 (2009)

    Article  CAS  Google Scholar 

  13. W. Zeng, Q. Xue-Feng, Y. Jie, Z. Zi-Kang, Mater. Chem. Phys. 97, 437 (2006)

    Article  CAS  Google Scholar 

  14. K.C. Sousa, E.M. Souza, B. Sousa, Acta Biomater. 4, 671(2008)

    Article  CAS  PubMed  Google Scholar 

  15. Qu F, Zhu G, Huang S, Li S, Sun J, Zhang D, Qiu S, Micropor. Mesopor. Mater. 92, 1 (2006)

    Article  CAS  Google Scholar 

  16. N.K. Mal, M. Fujiwara, T. Yuko, T. Takahisa, M. Masahiko, Chem. Mater. 15, 3385 (2003)

    Article  CAS  Google Scholar 

  17. R. Aiello, G. Cavallaro, G. Giammona, L. Pasqua, Pierro, F. Testa, Stud. Surf. Sci. Catal. 142B, 1165 (2002)

    Article  CAS  Google Scholar 

  18. C. Gennara, Pierro, F. Salvatore, F. Testa, L. Pasqua, R. Aiello, Drug Deliv. 11, 41 (2004)

    Article  CAS  Google Scholar 

  19. M. Vallet-Regi’, F. Balas, D. Arcos, Angew. Chem. Int. Ed 46, 7548 (2007)

    Article  CAS  Google Scholar 

  20. W. Xu, Y. Xu, D. Wu, Y. Sun, Stud. Surf. Sci. Catal. 170, 861 (2007)

    Article  Google Scholar 

  21. M. Manzano, V. Aina, C.O. Are´an, F.A. Balas, V. Cauda, M. Colilla, M.R. Delgado, M. Vallet-Regi, Chem. Eng. J. 137, 30 (2008)

    Article  CAS  Google Scholar 

  22. I.S. Carino, L. Pasqua, F. Testa, F. Aiello, F. Iemma, N. Picci, Drug Deliv. 14, 491 (2007)

    Article  CAS  PubMed  Google Scholar 

  23. C.D. Nunes, P.D. Vaz, A.C. Fernandes, Ferreira, C.C. Romao, M.J. Calhorda, Eur. J. Pharm. Biopharm. 66, 357 (2007)

    Article  CAS  PubMed  Google Scholar 

  24. M. Vallet-Regí, A. Ramila, R.P. del Real, J. Peŕez-Pariente, Chem. Mater. 13, 308 (2001)

    Article  CAS  Google Scholar 

  25. M. Popova, A. Szegedi, V. Mavrodinova, N. NovakTušar, J. Mihály, S. Klébert, N. Benbassat, K. Yonchev, J. Solid State Chem. 219, 37 (2014)

    Article  CAS  Google Scholar 

  26. P. Horcajada, A. Rámila, J. Pérez-Pariente, M. Vallet-Regí, Micropor. Mesopor. Mater. 68, 105 (2004)

    Article  CAS  Google Scholar 

  27. S. Sung, M. Hyung, K. Dae Sung, P. Sang-Eon, J. Indust. Eng. Chem. 5, 191 (1999)

    Google Scholar 

  28. A. Ramila, B. Mun̄oz, J. Peŕez-Pariente, M. Vallet-Regí, J. Sol–Gel Sci. Technol. 26, 1199 (2003)

    Article  CAS  Google Scholar 

  29. S. Djokic, G. Kobrehel, N. Lopotar, B. Kamenar, A. Nagl, D. Mrvos, J. Chem. Res. 152, 1239 (1988)

    Google Scholar 

  30. H.R. Darabi, A. Darestani Farahani, M. Hashemi Karouei, K. Aghapoor, R. Firouzi, R. Herges, A.R. Mohebbi, C. Naether, Supramol. Chem. 24, 653 (2012)

    Article  CAS  Google Scholar 

  31. H.R. Darabi, M. Azimzadeh Arani, A. Motamedi, R. Firouzi, R. Herges, A.R. Mohebbi, S. Nasseri, C. Nather, Supramol. Chem. 21, 632 (2009)

    Article  CAS  Google Scholar 

  32. H.R. Darabi, K. Jadidi, A.R. Mohebbi, L. Faraji, K. Aghapoor, S. Shahbazian, M.A. Arani, S.M. Nasseri, Supramol. Chem. 20, 373 (2008)

    Article  CAS  Google Scholar 

  33. H.R. Darabi, M. Mirza-Aghayan, L. Ali-Saraie, M. Bolourtchian, B. Neumueller, M. Ghassemzadeh, Supramol. Chem. 15, 55 (2003)

    Article  CAS  Google Scholar 

  34. H.R. Darabi, A.R. Mohebbi, M. Bolourtchian, Supramol. Chem. 15, 465 (2003)

    Article  CAS  Google Scholar 

  35. T. Kawase, Y. Seirai, H.R. Darabi, M. Oda, Y. Sarakai, K. Tashiro, Angew. Chem. Int. Ed. Engl. 42, 1621 (2003)

    Article  CAS  PubMed  Google Scholar 

  36. T. Kawase, K. Tanaka, N. Fujiwara, H.R. Darabi, M. Oda, Angew. Chem. Int. Ed. Engl. 42, 1624 (2003)

    Article  CAS  PubMed  Google Scholar 

  37. H.R. Darabi, A.E. Saghafinia, A. Aghaiee, E. Khatamifar, Shifa Pharmed Industrial Group Co, Terramark Markencreation Gmbh, (2011). WO2011/015219- PCT/EP2009/005710

  38. H.R. Darabi, A. Roozkhosh, M.J. Tehrani, K. Aghapoor, H. Sayahi, Y. Balavar, F. Mohsenzadeh, Appl. Surf. Sci. 288, 122 (2014)

    Article  CAS  Google Scholar 

  39. K. Aghapoor, M.M. Amini, K. Jadidi, F. Mohsenzadeh, H.R. Darabi, H. Sayahi, M.R. Jalali, Solid State Sci. 49, 10 (2015)

    Article  CAS  Google Scholar 

  40. K. Aghapoor, M.M. Amini, K. Jadidi, F. Mohsenzadeh, H.R. Darabi, Z. Naturforsch. 70, 475 (2015)

    Article  CAS  Google Scholar 

  41. K. Aghapoor, M.M. Amini, K. Jadidi, H.R. Darabi, Acta Chim. Slov. 62, 95 (2015)

    Article  CAS  PubMed  Google Scholar 

  42. N. Sultana, M.S. Arayne, F. Hussain, A. Fatima, Pak. J. Pharm. Sci. 19, 98 (2006)

    CAS  PubMed  Google Scholar 

  43. A. Cardenas-Peña, J.G. Ibanez, R. Vasquez-Medrano, Int. J. Electrochem. Sci. 7, 6142 (2012)

    Google Scholar 

  44. S. Somani, S. Rajesh, J. Porous Mater. 12, 87 (2005)

    Article  CAS  Google Scholar 

  45. S. Sing, S.W. Kenneth, Pure Appl. Chem. 57, 603 (1985)

    Article  CAS  Google Scholar 

  46. T. Heikkilä, Drug Deliv. 14, 337 (2007)

    Article  CAS  PubMed  Google Scholar 

  47. T. Heikkilä, Int. J. Pharm. 331, 133 (2007)

    Article  CAS  PubMed  Google Scholar 

  48. Y. Hu, J. Colloid Interface Sci. 363, 410 (2011)

    Article  CAS  PubMed  Google Scholar 

  49. M. Hamzehloo, J. Karimi, N. Eghbali, M. Mirzakhani, K. Aghapoor, H.R. Darabi, Drying Technol. (2017). https://doi.org/10.1080/07373937.2016.1269807

    Article  Google Scholar 

  50. Z. Liu, Y. Wei, Y. Qi, S. Zhang, Y. Zhang, Z. Liu, Micropor. Mesopor. Mater. 93, 205 (2006)

    Article  CAS  Google Scholar 

  51. M. Zoran, Z. Weitner, M. Ilijaš, J. Pharm. Biomed. Anal. 33, 647 (2003)

    Article  CAS  Google Scholar 

  52. D. Vuković, Chem. Eng. J. 157, 238 (2010)

    Article  CAS  Google Scholar 

  53. I. Langmuir, J. Am. Chem. Soc. 38, 2221 (1916)

    Article  CAS  Google Scholar 

  54. H.M.F. Freundlich, Z. Phys. Chem. A 57, 385 (1906)

    CAS  Google Scholar 

  55. B. Stephen, Hugh Emmett, E. Teller, J. Am. Chem. Soc. 60, 309 (1938)

    Article  Google Scholar 

  56. W.J. Weber, Physicochemical Processes for Water Quality Control. (Wiley, New York, 1972)

    Google Scholar 

  57. L. Serra, D. Joseph, N.A. Peppas, Biomaterials 27, 5440 (2006)

    Article  CAS  PubMed  Google Scholar 

  58. J. Siepmann, N.A. Peppas, Adv. Drug Deliv. Rev. 64, 163 (2012)

    Article  Google Scholar 

  59. P. Horcajada, A. Ramila, J. Perez-Pariente, M. Vallet-Regi, Micropor. Mesopor. Mater. 68, 105 (2004)

    Article  CAS  Google Scholar 

  60. I. Izquierdo-Barba, A. Martinez, A.L. Doadrio, J. Perez-Pariente, M. Vallet-Regi, Eur. J. Pharm. Sci. 26, 365 (2005)

    Article  CAS  PubMed  Google Scholar 

  61. J.C. Doadrio, E.M.B. Sousa, I. Izquierdo-Barba, A.L. Doadrio, J. Perez-Pariente, M. Vallet-Regi, J. Mater. Chem. 16, 462 (2006)

    Article  CAS  Google Scholar 

  62. J. Siepmann, F. Siepmann, Int. J. Pharm. 364, 328 (2008)

    Article  CAS  PubMed  Google Scholar 

  63. S. Dash, P.N. Murthy, L. Nath, Chowdhur, Acta Pol. Pharm. 67, 217 (2010)

    CAS  PubMed  Google Scholar 

Download references

Acknowledgements

The Ministry of Science, Research and Technology of Iran is acknowledged for partial financial assistance of this work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hossein Reza Darabi.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 681 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hamzehloo, M., Karimi, J., Aghapoor, K. et al. The synergistic cooperation between MCM-41 and azithromycin: a pH responsive system for drug adsorption and release. J Porous Mater 25, 1275–1285 (2018). https://doi.org/10.1007/s10934-017-0538-3

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10934-017-0538-3

Keywords

Navigation