Skip to main content
Log in

Comparing water solubility of β-cyclodextrin derivatives with dendrimers modified with β-cyclodextrin units, how significant is the change in water solubility?

  • Original Paper
  • Published:
MRS Advances Aims and scope Submit manuscript

Abstract

Nowadays, β-cyclodextrin (βCD) is considered a molecule of great interest for the pharmaceutical industry since it is widely used as a component in different formulations. Its properties as a complexing agent allow increasing the aqueous solubility of poorly soluble drugs, thereby improving their stability and bioavailability. βCD molecules exhibit moderate solubility in water. This phenomenon is caused by the high symmetry of its 3D structure, which limits its interaction with water molecules. When this symmetry is disrupted by the addition of adequate substituents in its structure, βCD becomes a molecule with significantly increased aqueous solubility. In this work, we compared the water solubility values for βCD and their improved derivatives and performed measurements of the quantitative water solubility for novel PAMAM-βCD and EDTA-βCD dendrimers in order to demonstrate that significant improvement in water solubility is possible using this new class of platforms, which are at least 27 times more soluble than βCD.

Graphical abstract

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

Access this article

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

Data availability

Not applicable.

References

  1. H.C. Babaoglu, A. Bayrak, N. Ozdemir, N. Ozgun, J. Food Process. Preserv. 41(5), e13202 (2017). https://doi.org/10.1111/jfpp.13202

    Article  CAS  Google Scholar 

  2. J. Rakmai, B. Cheirsilp, J.C. Mejuto, J. Simal-Gándara, A. Torrado-Agrasar, Ind. Crops Prod. 111, 219 (2018). https://doi.org/10.1016/j.indcrop.2017.10.027

    Article  CAS  Google Scholar 

  3. J. Szejtli, Chem. Rev. 98(5), 1743 (1998). https://doi.org/10.1021/cr970022c

    Article  CAS  PubMed  Google Scholar 

  4. Y.A. Tayade, S.A. Padvi, Y.B. Wagh, D.S. Dalal, Tetrahedron Lett. 56(19), 2441 (2015). https://doi.org/10.1016/j.tetlet.2015.03.084

    Article  CAS  Google Scholar 

  5. C. Jadhav, L.D. Khillare, M.R. Bhosle, Synth. Commun. 48(3), 233 (2018). https://doi.org/10.1080/00397911.2017.1390685

    Article  CAS  Google Scholar 

  6. S. Gould, R.C. Scott, Food Chem. Toxicol. 43(10), 1451 (2005). https://doi.org/10.1016/j.fct.2005.03.007

    Article  CAS  PubMed  Google Scholar 

  7. Y. Liu, Y. Chen, X. Gao, J. Fu, L. Hu, Crit. Rev. Food Sci. Nutr. 62(10), 2627 (2022). https://doi.org/10.1080/10408398.2020.1856035

    Article  CAS  PubMed  Google Scholar 

  8. M.E. Davis, M.E. Brewster, Nat. Rev. Drug Discov. 3(12), 1023 (2004). https://doi.org/10.1038/nrd1576

    Article  CAS  PubMed  Google Scholar 

  9. C.S. Marques, S.G. Carvalho, L.D. Bertoli, J.C.O. Villanova, P.F. Pinheiro, D.C.M. Dos Santos, P.C. Bernardes, Food Res. Int. 119, 499 (2019). https://doi.org/10.1016/j.foodres.2019.01.016

    Article  CAS  PubMed  Google Scholar 

  10. D. Arockia Jency, M. Umadevi, G.V. Sathe, J. Raman Spectrosc. 46(4), 377 (2015). https://doi.org/10.1002/jrs.4654

    Article  CAS  Google Scholar 

  11. E. Sabadini, T. Cosgrove, F.D.C. Egídio, Carbohydr. Res. 341(2), 270 (2006). https://doi.org/10.1016/j.carres.2005.11.004

    Article  CAS  PubMed  Google Scholar 

  12. P. Saokham, C. Muankaew, P. Jansook, T. Loftsson, Molecules (2018). https://doi.org/10.3390/molecules23051161

    Article  PubMed  PubMed Central  Google Scholar 

  13. A.W. Coleman, I. Nicolis, N. Keller, J.P. Dalbiez, J. Incl. Phenom. Macrocycl. Chem. 13, 139 (1992). https://doi.org/10.1007/BF01053637

    Article  CAS  Google Scholar 

  14. M. Cirri, F. Maestrelli, G. Corti, S. Furlanetto, P. Mura, J. Pharm. Biomed. Anal. 42(1), 126 (2006). https://doi.org/10.1016/j.jpba.2005.11.029

    Article  CAS  PubMed  Google Scholar 

  15. G. Crini, M. Morcellet, J. Sep. Sci. 25(13), 789 (2002). https://doi.org/10.1002/1615-9314(20020901)25:13%3c789::AID-JSSC789%3e3.0.CO;2-J

    Article  CAS  Google Scholar 

  16. M.L. Hart, J. Dev. Drugs (2013). https://doi.org/10.4172/2329-6631.1000115

    Article  Google Scholar 

  17. B. Devarakonda, D.P. Otto, A. Judefeind, R.A. Hill, M.M. de Villiers, Int. J. Pharm. 345, 142 (2007). https://doi.org/10.1016/j.ijpharm.2007.05.039

    Article  CAS  PubMed  Google Scholar 

  18. N.K. Jain, U. Gupta, Expert Opin. Drug Metab. Toxicol. 4, 1035 (2008). https://doi.org/10.1517/17425255.4.8.1035

    Article  CAS  PubMed  Google Scholar 

  19. A. Kasprzak, B. Dabrowski, A. Zuchowska, RSC Adv. 10, 23440 (2020). https://doi.org/10.1039/D0RA03694C

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. I. González-Méndez, A. Hameau, R. Laurent, C. Bijani, V. Bourdon, A.-M. Caminade, E. Rivera, K.I. Moineau-Chane Ching, Eur. J. Org. Chem. 2020, 1114–16 (2020). https://doi.org/10.1002/ejoc.201901823

    Article  CAS  Google Scholar 

  21. I. González-Méndez, E. Loera-Loera, K. Sorroza-Martínez, M. Vonlanthen, F. Cuétara-Guadarrama, M.J. Bernad-Bernad, E. Rivera, J. Gracia-Mora, Pharmaceutics 14, 2363 (2022). https://doi.org/10.3390/pharmaceutics14112363

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. I. González-Méndez, K. Sorroza-Martínez, I. González-Sánchez, J. Gracia-Mora, M.J. Bernad-Bernad, M. Cerbón, E. Rivera, A.K. Yatsimirsky, Int. J. Mol. Sci. 24, 14422 (2023). https://doi.org/10.3390/ijms241914422

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. T. Loftsson, P. Jarho, M. Másson, T. Järvinen, Expert Opin. Drug Deliv. 2(2), 335 (2005). https://doi.org/10.1517/17425247.2.1.335

    Article  CAS  PubMed  Google Scholar 

  24. M.J. Jozwiakowski, K.A. Connors, Carbohydr. Res. 143, 51 (1985). https://doi.org/10.1016/S0008-6215(00)90694-3

    Article  CAS  Google Scholar 

  25. U. Gupta, H.B. Agashe, A. Asthana, N.K. Jain, Biomacromolecules 7(3), 649 (2006). https://doi.org/10.1021/bm050802s

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgments

E.R. and K.S.-M. are grateful to CONACYT (Project 279380) and PAPIIT-DGAPA (Project IN103322) of Mexico.

Funding

This research received no external funding.

Author information

Authors and Affiliations

Authors

Contributions

Conceptualization: IG-M and ER; methodology: KS-M and IG-M; investigation: VEG-F and TES; data curation: IG-M and ER; and writing—original draft preparation: IG-M, KS-M, VEG-F, and TES. All authors have read and agreed with the published version of the manuscript.

Corresponding author

Correspondence to Israel González-Méndez.

Ethics declarations

Conflict of interest

The authors declare no conflicts of interest regarding this article.

Additional information

Publisher's Note

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

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sorroza-Martínez, K., González-Flores, V.E., Soto, T.E. et al. Comparing water solubility of β-cyclodextrin derivatives with dendrimers modified with β-cyclodextrin units, how significant is the change in water solubility?. MRS Advances 9, 270–274 (2024). https://doi.org/10.1557/s43580-023-00742-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1557/s43580-023-00742-8

Navigation