Abstract
Dynamic covalent hydrogels are considered smart materials with a stimuli-sensitive nature and possessing great importance in biomedical applications. In the current work, a new hydrogel based on polylysine (PLL), cellulose nanowhisker dialdehyde (DACNW), and chitosan (Cs) containing pH-sensitive dynamic covalent imine bonds was synthesized and along with its synthesis its potential application in curcumin (CUR) delivery was studied. Also, the antibacterial activities of hydrogel and drug-loaded hydrogels were evaluated. The prepared hydrogel also was characterized using techniques such as XRD, UV–VIS, FE-SEM, TGA, FT-IR and 1H-NMR spectroscopy. The resulting hydrogel showed excellent pH dependent curcumin delivery. Moreover, curcumin-loaded hydrogel showed good antibacterial activity against both Gram-negative and Gram-positive bacteria. The resulting hydrogel due to its pH-sensitive imine bonds could be considered as smart anticancer drug carrier system with high antibacterial properties.
Similar content being viewed by others
References
Xu Z, Yang D, Long T, Yuan L, Qiu S, Li D, Ge L (2022) pH-Sensitive nanoparticles based on amphiphilic imidazole/cholesterol modified hydroxyethyl starch for tumor chemotherapy. Carbohydr polym 277:118827. https://doi.org/10.1016/j.carbpol.2021.118827
Tehrani AD, Parsamanesh M (2017) Preparation, characterization and drug delivery study of a novel nanobiopolymeric multidrug delivery system. Mater Sci Eng C 73:516–524. https://doi.org/10.1016/j.msec.2016.12.103
Young SA, Muthami J, Pitcher M, Antovski P, Wamea P, Murphy RD, Sheikhi A (2022) Engineering hairy cellulose nanocrystals for chemotherapy drug capture. Mater Today Chem 23:100711. https://doi.org/10.1016/j.mtchem.2021.100711
Ye Y, Bremner DH, Zhang H, Chen X, Lou J, Zhu LM (2022) Functionalized layered double hydroxide nanoparticles as an intelligent nanoplatform for synergistic photothermal therapy and chemotherapy of tumors. Colloids Surf B Biointerfaces 210:112261. https://doi.org/10.1016/j.colsurfb.2021.112261
Anirudhan TS, Mohan M, Rajeev MR (2022) Modified chitosan-hyaluronic acid based hydrogel for the pH-responsive Co-delivery of cisplatin and doxorubicin. Int J Biol Macromol 201:378–388. https://doi.org/10.1016/j.ijbiomac.2022.01.022
Shahriari MH, Hadjizadeh A, Abdouss M (2022) Advances in self-healing hydrogels to repair tissue defects. Polym Bull. https://doi.org/10.1007/s00289-022-04133-1
Zhang W, Wang Y, Guo J, Huang C, Hu Y (2021) Polysaccharide supramolecular hydrogel microparticles based on carboxymethyl β-cyclodextrin/chitosan complex and edta-chitosan for controlled release of protein drugs. Polym Bull. https://doi.org/10.1007/s00289-021-03807-6
Dissanayake S, Denny WA, Gamage S, Sarojini V (2017) Recent developments in anticancer drug delivery using cell penetrating and tumor targeting peptides. J Control Release 250:62–76. https://doi.org/10.1016/j.jconrel.2017.02.006
Thakur S, Sharma B, Thakur A, Gupta VK, Alsanie WF, Makatsoris C, Thakur VK (2022) Synthesis and characterisation of zinc oxide modified biorenewable polysaccharides based sustainable hydrogel nanocomposite for Hg2+ ion removal: towards a circular bioeconomy. Bioresour Technol 348:126708. https://doi.org/10.1016/j.biortech.2022.126708
Dash TK, Konkimalla VB (2012) Polymeric modification and its implication in drug delivery: poly-ε-caprolactone (PCL) as a model polymer. Mol Pharm 9(9):2365–2379. https://doi.org/10.1021/mp3001952
Dheer D, Arora D, Jaglan S, Rawal RK, Shankar R (2017) Polysaccharides based nanomaterials for targeted anti-cancer drug delivery. J Drug Target 25(1):1–16. https://doi.org/10.3109/1061186X.2016.1172589
Shojaeiarani J, Shirzadifar A, Bajwa DS (2021) Robust and porous 3D-printed multifunctional hydrogels for efficient removal of cationic and anionic dyes from aqueous solution. Microporous Mesoporous Mater 327:111382. https://doi.org/10.1016/j.micromeso.2021.111382
Nascimento DM, Nunes YL, Figueirêdo MC, de Azeredo HM, Aouada FA, Feitosa JP, Dufresne A (2018) Nanocellulose nanocomposite hydrogels: technological and environmental issues. Green Chem 20(11):2428–2448. https://doi.org/10.1039/c8gc00205c
Croisier F, Jérôme C (2013) Chitosan-based biomaterials for tissue engineering. Eur Polym J 49(4):780–792. https://doi.org/10.1016/j.eurpolymj.2012.12.009
Rodríguez-Félix DE, Pérez-Caballero D, del Castillo-Castro T, Castillo-Ortega MM, Garmendía-Diago Y, Alvarado-Ibarra J, Burruel-Ibarra SE (2022) Chitosan hydrogels chemically crosslinked with L-glutamic acid and their potential use in drug delivery. Polym Bull. https://doi.org/10.1007/s00289-022-04152-y
Emam HE, Shaheen TI (2022) Design of a dual pH and temperature responsive hydrogel based on esterified cellulose nanocrystals for potential drug release. Carbohydr Polym 278:118925. https://doi.org/10.1016/j.carbpol.2021.118925
Heydari S, Eshagh Ahmadi S (2022) Fabrication and characterization of polymer based magnetic dialdehyde carboxymethyl cellulose/cysteine nanocomposites for methylene blue removal. Polym Bull. https://doi.org/10.1007/s00289-022-04210-5
Laçin NT (2014) Development of biodegradable antibacterial cellulose based hydrogel membranes for wound healing. Int J Biol Macromol 67:22–27. https://doi.org/10.1016/j.ijbiomac.2014.03.003
Zou P, Yao J, Cui YN, Zhao T, Che J, Yang M, Gao C (2022) Advances in cellulose-based hydrogels for biomedical engineering: a review summary. Gels 8(6):364. https://doi.org/10.3390/gels8060364
Larsson PA, Pettersson T, Wågberg L (2014) Improved barrier films of cross-linked cellulose nanofibrils: a microscopy study. Green Mater 2(4):163–168. https://doi.org/10.1680/gmat.14.00018
Kim UJ, Wada M, Kuga S (2004) Solubilization of dialdehyde cellulose by hot water. Carbohydr Polym 56(1):7–10. https://doi.org/10.1016/j.carbpol.2003.10.013
Hou Q, Liu W, Liu Z, Duan B, Bai L (2008) Characteristics of antimicrobial fibers prepared with wood periodate oxycellulose. Carbohydr Polym 74(2):235–240. https://doi.org/10.1016/j.carbpol.2008.02.010
Scholl M, Nguyen TQ, Bruchmann B, Klok HA (2007) The thermal polymerization of amino acids revisited; synthesis and structural characterization of hyperbranched polymers from l-lysine. J Polym Sci Part A Polym Chem 45(23):5494–5508. https://doi.org/10.1002/pola.22295
Lindh J, Carlsson DO, Strømme M, Mihranyan A (2014) Convenient one-pot formation of 2, 3-dialdehyde cellulose beads via periodate oxidation of cellulose in water. Biomacromol 15(5):1928–1932. https://doi.org/10.1021/bm5002944
Soleimani K, Tehrani AD, Adeli M (2018) Bioconjugated graphene oxide hydrogel as an effective adsorbent for cationic dyes removal. Ecotoxicol Enviro Saf 147:34–42. https://doi.org/10.1016/j.ecoenv.2017.08.021
Mu C, Guo J, Li X, Lin W, Li D (2012) Preparation and properties of dialdehyde carboxymethyl cellulose crosslinked gelatin edible films. Food Hydrocolloids 27(1):22–29. https://doi.org/10.1016/j.foodhyd.2011.09.005
LI, Y. (2015) Synthesis and biological activity of new spherical polylysine oligosaccharide dendrimers. Sen’i Gakkaishi. https://doi.org/10.2115/fiber.71.10
Nejati K, Keypour H, Nezhad PDK, Rezvani Z, Asadpour-Zeynali K (2015) Preparation and characterization of cetirizine intercalated layered double hydroxide and chitosan nanocomposites. J Taiwan Inst Chem Eng 53:168–175. https://doi.org/10.1016/j.jtice.2015.02.035
Udeni Gunathilake TMS, Ching YC, Chuah CH (2017) Enhancement of curcumin bioavailability using nanocellulose reinforced chitosan hydrogel. Polymers 9(2):64. https://doi.org/10.3390/polym9020064
Kim UJ, Kim HJ, Choi JW, Kimura S, Wada M (2017) Cellulose-chitosan beads crosslinked by dialdehyde cellulose. Cellulose 24(12):5517–5528. https://doi.org/10.1007/s10570-017-1528-y
Kushwaha DRS, Mathur KB, Balasubramanian D (1980) Poly(ε-L-lysine): synthesis and conformation. Biopolymers 19(2):219–229. https://doi.org/10.1002/bip.1980.360190202
Kumari S, Rath P, Kumar ASH, Tiwari TN (2015) Extraction and characterization of chitin and chitosan from fishery waste by chemical method. Environ Technol Innov 3:77–85. https://doi.org/10.1016/j.eti.2015.01.002
Xuan Yang, Jiang Guancheng, Li Yingying, Yang Lili, Zhang Xianmin (2015) Biodegradable oligo (poly-L-lysine) as a high-performance hydration inhibitor for shale. RSC Adv 5(103):84947–84958. https://doi.org/10.1039/C5RA16003K
Lim BY, Poh CS, Voon CH, Salmah H (2015) Rheological and thermal study of chitosan filled thermoplastic elastomer composites. Appl Mech Mater 754:34–38. https://doi.org/10.4028/www.scientific.net/AMM.754-755.34
Lu FF, Yu HY, Zhou Y, Yao JM (2016) Spherical and rod-like dialdehyde cellulose nanocrystals by sodium periodate oxidation: optimization with double response surface model and templates for silver nanoparticles. Express Polym Lett. https://doi.org/10.3144/expresspolymlett.2016.90
Acknowledgements
We gratefully acknowledge the financial support of the Lorestan University.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
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.
About this article
Cite this article
Razani, S., Dadkhah Tehrani, A. Preparation of new eco-friendly covalent dynamic network based on polylysine, cellulose nanowhisker dialdehyde, and chitosan for curcumin delivery. Polym. Bull. 81, 4893–4909 (2024). https://doi.org/10.1007/s00289-023-04938-8
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-023-04938-8