Skip to main content
SpringerLink
Log in

Thermoresponsive sustainable release of anticancer drugs using cyto-compatible pyrenylated hydrogel as vehicle

  • REGULAR ARTICLE
  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

Pyrene-based fluorogenic amphiphilic probe (1) has been synthesized, which can form a thixotropic (injectable) hydrogel in the aqueous medium. The biocompatible hydrogel, so formed, is involved in the thermoresponsive, sustainable delivery of two anticancer drugs, Doxorubicin (DOX) and Mitoxantrone (MT). A substantial difference in the extent of drug release is noticed at 25 and 37 °C, even at physiological pH. The cumulative releases of ~80% and ~70% for DOX and MT, respectively, from the drug-loaded hydrogel samples, are observed for 72 h. In both cases, drug molecule release follows zero-order kinetics and non-Fickian diffusion pathways. The excellent stability of 1 against proteinase enzyme suggests that the present system can be used for sustainable, targeted release of drug molecules under in-vivo conditions. As expected, DOX-loaded hydrogels kill cancer cells more efficiently than the free drug (i.e., DOX).

Graphical abstract

A pyrene-based amphiphilic probe has been synthesized, which can form a thixotropic hydrogel in the aqueous medium. The biocompatible hydrogel was involved in the thermoresponsive, sustainable delivery of two anticancer drugs, Doxorubicin (DOX) and Mitoxantrone (MT). Moreover, the DOX-loaded hydrogel could kill cancer cells more efficiently than the free drug.

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

Figure 1
Figure 2
Figure 3
Figure 4
Figure 5

Similar content being viewed by others

References

  1. Díaz D D, Kühbecka D and Koopmans R J 2011 Stimuli-responsive gels as reaction vessels and reusable catalysts Chem. Soc. Rev. 40 427

    Article  Google Scholar 

  2. Shi Q, Liu H, Tang D, Li Y, Li X J and Xu F 2019 Bioactuators based on stimulus-responsive hydrogels and their emerging biomedical applications NPG Asia Mater. 11 64

    Article  CAS  Google Scholar 

  3. Biswakarma D, Dey N and Bhattacharya S 2022 A biocompatible hydrogel as a template for oxidative decomposition reactions: a chemodosimetric analysis and in vitro imaging of hypochlorite Chem. Sci. 13 2286

    Article  CAS  Google Scholar 

  4. Pourjavadi A, Heydarpour R and Tehrani Z M 2021 Multi-stimuli-responsive hydrogels and their medical applications New J. Chem. 45 15705

    Article  CAS  Google Scholar 

  5. Sood N, Bhardwaj A, Mehta S and Mehta A 2016 Stimuli-responsive hydrogels in drug delivery and tissue engineering Drug Deliv. 23 748

    Article  CAS  Google Scholar 

  6. Andrade F, Roca-Melendres M M, Durán-Lara E F, Rafael D and Jr. S S 2021 Stimuli-Responsive Hydrogels for Cancer Treatment: The Role of pH, Light, Ionic Strength and Magnetic Field Cancers 13 1164

  7. Li Z, Zhou Y, Li T, Zhang J and Tian H 2022 Stimuli-responsive hydrogels: Fabrication and biomedical applications View 3 20200112

    Article  CAS  Google Scholar 

  8. Narayanaswamy R and Torchilin V P 2019 Hydrogels and Their Applications in Targeted Drug Deliv. Mol. 24 603

    Google Scholar 

  9. Shen Z, Guo Z, Tan T, Hu J and Zhang Y 2020 Reactive Oxygen Species Scavenging and Biodegradable Peptide Hydrogel as 3D Culture Scaffold for Cardiomyocytes ACS Biomater. Sci. Eng. 6 3957

    Article  CAS  Google Scholar 

  10. Biswakarma D, Dey N and Bhattacharya S 2020 A two-component charge transfer hydrogel with excellent sensitivity towards the microenvironment: a responsive platform for biogenic thiols Soft Matter. 16 9882

    Article  CAS  Google Scholar 

  11. Panda J J, Mishra A, Basu A and Chauhan V S 2008 Stimuli Responsive Self-Assembled Hydrogel of a Low Molecular Weight Free Dipeptide with Potential for Tunable Drug Delivery Biomacromolecules 9 2244

    Article  CAS  Google Scholar 

  12. Zhu Y-J and Chen F 2015 pH-Responsive Drug-Delivery Systems Chem. Asian J. 10 284

    Article  CAS  Google Scholar 

  13. (a) Huang Y, Qiu Z, Xu Y, Shi J, Lina H and Zhang Y 2011 Supramolecular hydrogels based on short peptides linked with conformational switch Org. Biomol. Chem. 9 2149; (b) Srivastava A, Ghorai S, Bhattacharjya A and Bhattacharya S 2005 A tetrameric sugar-based azobenzene that gels water at various pH values and in the presence of salts J. Org. Chem. 70 6574

  14. Ji W, Liu G F, Xu M X and Feng C L 2015 A Redox-Responsive Supramolecular Hydrogel for Controllable Dye Release Macromol. Chem. Phys. 216 1945

    Article  CAS  Google Scholar 

  15. Biswakarma D, Dey N and Bhattacharya S 2020 A thermo-responsive supramolecular hydrogel that senses cholera toxin via color-changing response Chem. Commun. 56 7789

    Article  CAS  Google Scholar 

  16. Pramanik B, Singha N and Das D 2019 Sol-, Gel-, and Paper-Based Detection of Picric Acid at Femtogram Level by a Short Peptide Gelator ACS Appl. Polym. Mater. 1 833

    Article  CAS  Google Scholar 

  17. Dutta S and Bhattacharya S 2015 Multifarious facets of sugar-derived molecular gels: molecular features, mechanisms of self-assembly and emerging applications Chem. Soc. Rev. 44 5596

    Article  Google Scholar 

  18. Biswakarma D, Dey N and Bhattacharya S 2022 Molecular design of amphiphiles for Microenvironment-Sensitive kinetically controlled gelation and their utility in probing alcohol contents J. Colloid Interface Sci. 615 335

    Article  CAS  Google Scholar 

  19. Pertici V, Pin-Barre C, Rivera C, Pellegrino C, Laurin J, Gigmes D and Trimaille T 2019 Degradable and Injectable Hydrogel for Drug Delivery in Soft Tissues Biomacromolecules 20 149

    Article  CAS  Google Scholar 

  20. Xiong L, Luo Q, Wang Y, Li X, Shena Z and Zhu W 2015 An injectable drug-loaded hydrogel based on a supramolecular polymeric prodrug Chem. Commun. 51 14644

    Article  CAS  Google Scholar 

  21. Moon H J, Ko D Y, Park M H, Joo M K and Jeong B M 2012 Temperature-responsive compounds as in situ gelling biomedical materials Chem. Soc. Rev. 41 4860

    Article  CAS  Google Scholar 

  22. Hoche J, Schmitt H C, Humeniuk A, Fischer I, Mitric R and Rohr M I S 2017 The mechanism of excimer formation: an experimental and theoretical study on the pyrene dimer Phys. Chem. Chem. Phys. 219 25002

    Article  Google Scholar 

  23. Yan N, Xu Z, Diehn K K, Raghavan S R, Fang Y and Weiss R G 2013 How Do Liquid Mixtures Solubize Insoluble Gelators? Self-Assembly Properties of Pyrenyl-Linker-Glucono Gelators in Tetrahydrofuran-Water Mixtures J. Am. Chem. Soc. 135 8989

    Article  CAS  Google Scholar 

  24. Basu K, Baral A, Basak S, Dehsorkhi A, Nanda J, Bhunia D, et al. 2016 Peptide based hydrogels for cancer drug release: modulation of stiffness, drug release and proteolytic stability of hydrogels by incorporating d-amino acid residue(s) Chem. Commun. 52 5045

    Article  CAS  Google Scholar 

  25. Moitra P, Kumar K, Kondaiah P and Bhattacharya S 2014 Efficacious Anticancer Drug Delivery Mediated by a pH-Sensitive Self-Assembly of a Conserved Tripeptide Derived from Tyrosine Kinase NGF Receptor Angew. Chem. Int. Ed. 53 1113

    Article  CAS  Google Scholar 

  26. Sanson C, Schatz C, Le Meins J-F, Soum A, Thévenot J, Garanger E and Lecommandoux S 2010 A simple method to achieve high doxorubicin loading in biodegradable polymersomes J. Control. Release 147 428

    Article  CAS  Google Scholar 

  27. Dey N, Ali A, Mohini K and Bhattacharya S 2019 Simultaneous sensing of ferritin and apoferritin proteins using an iron-responsive dye and evaluation of physiological parameters associated with serum iron estimation J. Mater. Chem. B 7 986

    Article  CAS  Google Scholar 

  28. Singh M, Kundu S, Reddy M A, Sreekanth V, Motiani R K, Sengupta S, et al. 2014 Injectable small molecule hydrogel as a potential nanocarrier for localized and sustained in vivo delivery of doxorubicin Nanoscale 6 12849

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Prof. S. Bhattacharya thanks the Department of Science and Technology for the J. C. Bose Fellowship. D. Biswakarma thanks DSKPDF for funding.

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560012, India

    Dipen Biswakarma & Santanu Bhattacharya

  2. Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, 560012, India

    Dipen Biswakarma

  3. Department of Chemistry, Birla Institute of Technology and Science Pilani, Hyderabad, 500078, India

    Nilanjan Dey

Authors
  1. Dipen Biswakarma
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nilanjan Dey
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Santanu Bhattacharya
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

SB designed the project; DB and ND did experimental findings and data collection. DB prepared the original manuscript draft, and DB, ND, and SB did review and editing.

Corresponding author

Correspondence to Santanu Bhattacharya.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 477 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Biswakarma, D., Dey, N. & Bhattacharya, S. Thermoresponsive sustainable release of anticancer drugs using cyto-compatible pyrenylated hydrogel as vehicle. J Chem Sci 135, 7 (2023). https://doi.org/10.1007/s12039-022-02124-3

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s12039-022-02124-3

Keywords

Search

Navigation