Journal of Materials Science

, Volume 53, Issue 7, pp 5125–5139 | Cite as

Ab initio design of drug carriers for zoledronate guest molecule using phosphonated and sulfonated calix[4]arene and calix[4]resorcinarene host molecules

  • Yong-Man Jang
  • Chol-Jun Yu
  • Jin-Song Kim
  • Song-Un Kim


Monomolecular drug carriers based on calix[n]arenes and calix[n]resorcinarenes containing the interior cavity can enhance the affinity and specificity of the osteoporosis inhibitor drug zoledronate (ZOD). In this work, we investigated the suitability of nine different calix[4]arenes- and calix[4]resorcinarenes-based macrocycles as hosts for the ZOD guest molecule by conducting ab initio density functional theory calculations for structures and energetics of eighteen different host-guest complexes. For the optimized molecular structures of the free, phosphonated, sulfonated calix[4]arenes and calix[4]resorcinarenes, the geometric sizes of their interior cavities were measured and compared with those of the host-guest complexes in order to check the appropriateness for host-guest complex formation. Our calculations of binding energies indicated that in gaseous states some of the complexes might be unstable but in aqueous states almost all of the complexes can be formed spontaneously. Of the two different docking ways, the insertion of ZOD with the P–O–P branch into the cavity of host was easier than that with the nitrogen-containing heterocycle of ZOD. The work will open a way for developing effective drug delivering systems for the ZOD drug and promote experimentalists to synthesize them.



This work is supported by the State Committee of Science and Technology, Democratic People’s Republic of Korea. Computation was done on the HP Blade System C7000 (HP BL460c) that is owned by Faculty of Materials Science, Kim Il Sung University.

Compliance with ethical standards

Conflicts of interest

The authors declare that they have no competing interest


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© Springer Science+Business Media, LLC, part of Springer Nature 2017

Authors and Affiliations

  1. 1.Department of Organic Chemistry, Faculty of ChemistryKim Il Sung UniversityPyongyangDemocratic People’s Republic of Korea
  2. 2.Natural Science CentreKim Il Sung UniversityPyongyangDemocratic People’s Republic of Korea
  3. 3.Department of Computational Materials Design (CMD), Faculty of Materials ScienceKim Il Sung UniversityPyongyangDemocratic People’s Republic of Korea

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