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pH-responsive nanoparticles based on sodium dodecylbenzene sulfonate and polyamine-modified cyclodextrins for controlled release of metformin hydrochloride

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Abstract

Metformin hydrochloride (Metf) is a first-line oral drug for the treatment of type 2 diabetes and it is primarily absorbed in the small intestine. However, it degrades easily before reaching the intestine, so its use is limited. In order to solve this problem, the supramolecular nanoparticles were successfully constructed based on electrostatic interaction of cationic β-CD derivative (DPN-β-CD and anionic surfactant sodium dodecylbenzene sulfonate (SDBS). The nanoparticles were characterized by UV–visible absorption, X-ray diffraction, dynamic light scattering, transmission electron microscopy and zeta potential techniques. The average diameter of the obtained nanoparticles is 254 nm, the main structure is spherical, and they are uniformly distributed in solution with a zeta potential of − 9.04 mV. Subsequently, it was found that the obtained nanoparticles can be disassembled by increasing the pH and reassembled by reducing to the initial pH value. The SDBS/DPN-β-CD supramolecular nanoparticles can efficiently encapsulate model diabetes drug such as Metf. More importantly, the in vitro release at different physiological pH values of 2.0, 6.3 and 8.0 showed a controlled release of Metf from the system and the release rate of Metf is lower in a simulated gastric environment (pH 2.0), while the release is higher in a simulated intestinal environment (pH 8.0). This system helps to reduce the stimulation of Metf to the stomach and improve its absorption rate in the small intestine. Therefore, the anti-diabetic small intestine specific drug delivery system is of potential importance in the treatment of diabetes.

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Data availability statement

The data that support the findings of this study are available from the corresponding author upon reasonable request.

References

  1. Artasensi A, Pedretti A, Vistoli G (2020) Type 2 diabetes mellitus: a review of multi-target drugs. Molecules 25:1987

    Article  CAS  Google Scholar 

  2. Packer M (2018) Is metformin beneficial for heart failure in patients with type 2 diabetes? Diabetes Res Clin Pract 136:168–170

    Article  CAS  Google Scholar 

  3. Smith JD, Mills Eand Carlisle SE (2016) Treatment of pediatric type 2 diabetes. Ann Pharmacother 50:768–777

    Article  CAS  Google Scholar 

  4. Migdadi EM, Courtenay AJ, Tekko IA (2018) Hydrogel-forming microneedles enhance transdermal delivery of metformin hydrochloride. J Control Release 285:142–151

    Article  CAS  Google Scholar 

  5. Zaghloul AA, Lila A, Abd-Allah F (2017) Preparation and in vitro/in vivo evaluation of metformin hydrochloride rectal dosage forms for treatment of patients with type II diabetes. J Drug Target 25:463–470

    Article  CAS  Google Scholar 

  6. Zhang J, Zhou ZH, Li L (2020) Dual stimuli-responsive supramolecular self-assemblies based on the host-guest interaction between beta-cyclodextrin and azobenzene for cellular drug release. Mol Pharm 17:1100–1113

    Article  CAS  Google Scholar 

  7. Farjadian F, Ghasemi S, Andami Z (2020) Thermo-responsive nanocarrier based on poly(N-isopropylacrylamide) serving as a smart doxorubicin delivery system. Iran Polym J 29:197–207

    Article  CAS  Google Scholar 

  8. Liu YN, Qu R, Li X (2021) Integration of catalytic capability and pH-responsive wettability in a VxOy-based dual-mesh system: towards solving the trade-off between the separation flow rate and degradation efficiency. J Mater Chem A 9:5454–5467

    Article  CAS  Google Scholar 

  9. Zou YQ, Hu B, Chen L (2020) Novel pH- and thermoresponsive supramolecular dendronized copolymer. Iran Polym J 30:47–56

    Article  Google Scholar 

  10. Spinelli E, Requena T, Caruso M (2020) Fate of methicillin-resistant staphylococcus aureus (MRSA) under simulated acidic conditions of the human stomach. Food Sci Nutr 8:4739–4745

    Article  CAS  Google Scholar 

  11. Saini M, GhoshS KV (2020) Selective release of doxorubicin from cucurbit[8]uril stabilized gold supra-pyramid host at pH of small intestine. Chem Eur J 26:15150–15158

    Article  CAS  Google Scholar 

  12. Zhu J, Huo Q, Liu Y (2018) Bortezomib-catechol conjugated prodrug micelles: combining bone targeting and aryl boronate-based pH-responsive drug release for cancer bone-metastasis therapy. Nanoscale 10:18387–18397

    Article  CAS  Google Scholar 

  13. Proksch E (2018) pH in nature, humans and skin. J Dermatol 45:1044–1052

    Article  CAS  Google Scholar 

  14. Zhu H, Shangguan L, Huang F (2018) Recent progress in macrocyclic amphiphiles and macrocyclic host-based supra-amphiphiles. Mater Chem Front 2:2152–2174

    Article  CAS  Google Scholar 

  15. Nakamura H, Iwamori H, Hirahara Y (2019) Geochemical mapping of slab-derived fluid and source mantle along Japan arcs. Gondwana Res 70:36–49

    Article  CAS  Google Scholar 

  16. Chakraborty G, Singh PK, Pal H (2021) A cationic cyclodextrin assisted aggregation of an anionic pyrene derivative and its stimuli responsive behavior. J MolLiq 321:114499

    CAS  Google Scholar 

  17. Gannimani R, Walvekar P, Govender T (2020) Acetal containing polymers as pH-responsive nano-drug delivery systems. J Control Release 328:736–761

    Article  CAS  Google Scholar 

  18. Zhang YH, Zhang YM, Liu Y (2019) Boronate-crosslinked polysaccharide conjugates for pH-responsive and targeted drug delivery. Chem Commun 55:1164–1167

    Article  CAS  Google Scholar 

  19. Yan Y, Ding H (2020) pH-responsive nanoparticles for cancer immunotherapy: a brief review. Nanomaterials 10:1613

    Article  CAS  Google Scholar 

  20. Zhao J, Zheng D, Lei J (2020) Self-assembled pH-responsive polymeric nanoparticles based on lignin-histidine conjugate with small particle size for efficient delivery of anti-tumor drugs. Biochem Eng J 156:107526

    Article  CAS  Google Scholar 

  21. Yue L, Li J, Zhao Y (2020) Host-guest interaction between 20(S)-protopanaxatriol and three polyamine-modified β-cyclodextrins: preparation, characterization, inclusion modes, and solubilization. J Inclus Phenom Macrocyclic Chem 97:29–42

    Article  CAS  Google Scholar 

  22. Shi RJ, Chen Y, Liu Y (2016) Effect of head/tail groups on molecular induced aggregation of polycationic cyclodextrin towards anionic surfactants. Rsc Adv 6:15175–15179

    Article  CAS  Google Scholar 

  23. Li JJ, Zhang HY, Liu Y (2019) Roomtemperature phosphorescence and reversible white light switch based on a cyclodextrin polypseudorotaxane xerogel. Adv Opt Mater 7:1900589

    Article  CAS  Google Scholar 

  24. Liu J, Liu X, Wang L (2018) Supramolecular modular approach toward conveniently constructing and multifunctioning a pH/redox dual-responsive drug delivery nanoplatform for improved cancer chemotherapy. ACS Appl Mater Interfaces 10:26473–26484

    Article  CAS  Google Scholar 

  25. Rençber S, Gündoğdu E, Başpınar Y (2021) Preparation and characterization of mucoadhesive gels containing pentoxifylline loaded nanoparticles for vaginal delivery of genital ulcer. Iran Polym J 30:569–582

    Article  Google Scholar 

  26. Yew HC, Misran M (2016) Preparation and characterization of pH dependent κ-carrageenan-chitosan nanoparticle as potential slow release delivery carrier. Iran Polym J 25:1037–1046

    Article  CAS  Google Scholar 

  27. Yue L, Jin W, Zhao Y (2020) pH-responsive chitosan/sulfobutyl ether-β-cyclodextrin supramolecular nanoparticles for controlled release of sodium ferulate. Polym Eng Sci 60:2403–2413

    Article  CAS  Google Scholar 

  28. Duan Z, Gao YJ, Wang H (2015) pH-sensitive polymer assisted self-aggregation of bis(pyrene) in living cells in situ with turn-on fluorescence. Nanotechnology 26:355703

    Article  Google Scholar 

  29. Chen SL, Li ZW, Zhao Y (2020) Preparation, characterization and solubilization evaluation of two novel host-guest complexes based on two different functional groups of modified β-cyclodextrins and 20(S)-protopanaxatriol. J Mol Struct 1204:127494

    Article  CAS  Google Scholar 

  30. Chen XY, Yang HW, Zhao Y (2021) Solubility and biological activity enhancement of docetaxel via formation of inclusion complexes with three alkylenediamine-modified β-cyclodextrins. RSC Adv 11:6292–6303

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundations (Nos. 21961046, 21362046, and 21062030), which are gratefully acknowledged.

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming, 650500, People’s Republic of China

    Jinkui Teng, Siling Chen, Jin Zhang, Jianmei Yang, Ran Pang, Xiangye Zhi, Tong Yang & Yan Zhao

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  1. Jinkui Teng
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  2. Siling Chen
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  3. Jin Zhang
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  4. Jianmei Yang
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  5. Ran Pang
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  6. Xiangye Zhi
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  7. Tong Yang
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  8. Yan Zhao
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Correspondence to Yan Zhao.

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Teng, J., Chen, S., Zhang, J. et al. pH-responsive nanoparticles based on sodium dodecylbenzene sulfonate and polyamine-modified cyclodextrins for controlled release of metformin hydrochloride. Iran Polym J 31, 1069–1078 (2022). https://doi.org/10.1007/s13726-022-01060-w

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  • DOI: https://doi.org/10.1007/s13726-022-01060-w

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