Abstract
In this study, amphoteric hydroxyethyl starch/p([2(acryloyloxy)ethyl]trimethylammonium chloride-co-itaconic acid (HES/p(AETAC-co-IA) hydrogels containing both cationic and anionic groups in their structure were synthesized by the redox polymerization method. The synthesized hydrogels were modified with gold nanoparticles, and nanocomposite hydrogels were obtained. The characterizations of the nanocomposite HES/p(AETAC-co-IA)@Au hydrogels prepared for biomedical applications were carried out by SEM, TEM, FT-IR, TGA, and XRD techniques and swelling tests in simulated biological environments. Hydrogels designed as drug carrier cargo materials were loaded with sodium diclofenac (NaDcF) and ibuprofen drugs, and their release properties were studied. The release mechanisms and release kinetics of the two drugs were studied. The release kinetics determined for the drug NaDcF is consistent with the Higuchi model, while the release kinetics determined for ibuprofen is consistent with the first-order model. In addition, the antibacterial and antifungal properties of the hydrogels were tested. It was found that the HES/p(AETAC-co-IA)@Au hydrogel was effective against gram-positive Staphylococcus aureus, gram-negative Pseudomonas aeruginosa, and the fungal species Candida albicans.
Similar content being viewed by others
References
Durmus S, Ozay O (2022) Synthesis and characterization of methacrylic acid based amphoteric hydrogels: use as a dual drug delivery system. J Macromol Sci A 59:646–656. https://doi.org/10.1080/10601325.2022.2107933
Lee JS, Nah H, Moon HJ, Lee SJ, Heo DN, Kwon IK (2020) Controllable delivery system: a temperature and pH-responsive injectable hydrogel from succinylated chitosan. Appl Surf Sci 528:146812. https://doi.org/10.1016/j.apsusc.2020.146812
Wu LP, Ficker M, Christensen JB, Trohopoulos PN, Moghimi SM (2015) Dendrimers in medicine: therapeutic concepts and pharmaceutical challenges. Bioconjugate Chem 26:1198–1211. https://doi.org/10.1021/acs.bioconjchem.5b00031B
Tan RS, Naruchi K, Amano M, Hinou H, Nishimura SI (2015) Rapid endolysosomal escape and controlled intracellular trafficking of cell surface mimetic quantum-dots-anchored peptides and glycopeptides. ACS Chem Biol 10:2073–2086. https://doi.org/10.1021/acschembio.5b00434
Yilmaz B, Ozay O (2022) Synthesis of antibiotic-modified silica nanoparticles and their use as a controlled drug release system with antibacterial properties. Phosphorus Sulfur Silicon Relat Elem 197:964–972. https://doi.org/10.1080/10426507.2022.2049267
Mitchell MJ, Billingsley MM, Haley RM, Wechsler ME, Peppas NA, Langer R (2021) Engineering precision nanoparticles for drug delivery. Nat Rev 20:101–124. https://doi.org/10.1038/s41573-020-0090-8
Kim J (2015) Development of polyethylene glycol-sebacic acid diacrylate microgels as a drug delivery system. Polym Korea 39:677–682. https://doi.org/10.7317/pk.2015.39.4.677
Soares DCF, Domingues SC, Viana DB (2020) Polymer-hybrid nanoparticles: current advances in biomedical applications. Biomed Pharmacother 131:110695. https://doi.org/10.1016/j.biopha.2020.110695
Ahmed EM (2015) Hydrogel: Preparation, characterization, and applications: a review. J Adv Res 6:105–121. https://doi.org/10.1016/j.jare.2013.07.006
Wang HY, Heilshorn SC (2015) Adaptable hydrogel networks with reversible linkages for tissue engineering. Adv Mater 27:3717–3736. https://doi.org/10.1002/adma.201501558
Jiang G, Qiu W, DeLuca PP (2003) Preparation and in vitro/in vivo evaluation of insulin-loaded poly(acryloyl-hydroxyethyl starch)-PLGA composite microspheres. Pharm Res 20:452–459. https://doi.org/10.1023/A:1022668507748
Ilgin P, Ozay H, Ozay O (2020) The efficient removal of anionic and cationic dyes from aqueous media using hydroxyethyl starch-based hydrogels. Cellulose 27:4787–4802. https://doi.org/10.1007/s10570-020-03074-0
Onder A, Ilgin P, Ozay H, Ozay O (2020) Removal of dye from aqueous medium with pH-sensitive poly[2-(acryloyloxy)ethyl]trimethylammonium chloride-co-1-vinyl-2-pyrrolidone cationic hydrogel. J Environ Chem Eng 8:104436. https://doi.org/10.1016/j.jece.2020.104436
Hong SJ, Kwon YR, Lim SH, Kim JS, Choi J, Chang YW, Kim DH (2021) Improved absorption performance of itaconic acid based superabsorbent hydrogel using vinyl sulfonic acid. Polym-Plast Tech Mat 60:1166–1175. https://doi.org/10.1080/25740881.2021.1888982
Cao B, Tang C, Li L, Mutevazi J, Wu H, Liu L, Ceng C (2013) Switchable antimicrobial and antifouling hydrogels with enhanced mechanical properties. Adv Healthc Mater 2:1096–1102. https://doi.org/10.1002/adhm.201200359
Kundu R, Payal P (2020) Antimicrobial hydrogels: promising soft biomaterials. ChemistrySelect 5:14800–14810. https://doi.org/10.1002/slct.202003666
Kharlampieva E, Unal IE, Sukhishvili SA (2007) Amphoteric surface hydrogels derived from hydrogen-bonded multilayers: reversible loading of dyes and macromolecules. Langmuir 23:175–181. https://doi.org/10.1021/la061652p
Tan HL, Teow SY, Pushpamalar J (2019) Application of metal nanoparticle–hydrogel composites in tissue regeneration. Bioengineering 6:17. https://doi.org/10.3390/bioengineering6010017
Ahmedian Z, Geybi H, Adeli M (2022) Efficient wound healing by antibacterial property: advances and trends of hydrogels, hydrogel-metal NP composites and photothermal therapy platforms. J Drug Deliv Sci Technol 73:103458. https://doi.org/10.1016/j.jddst.2022.103458
Durmus S, Yilmaz B, Onder A, Ilgin P, Ozay H, Ozay O (2022) An innovative approach to use zeolite as crosslinker for synthesis of p(HEMA-co-NIPAM) hydrogel. Monatsh fur Chem 153:369–382. https://doi.org/10.1007/s00706-022-02908-w
Ozay O (2013) Synthesis and swelling behavior of novel pH responsive hydrogels for environmental applications. Polym Plast Technol Eng 53:130–140. https://doi.org/10.1080/03602559.2013.843697
Ganguly S, Das CN (2015) Synthesis of a novel pH responsive phyllosilicate loaded polymeric hydrogel based on poly(acrylic acid-co-N-vinylpyrrolidone) and polyethylene glycol for drug delivery: modelling and kinetics study for the sustained release of an antibiotic drug. Rsc Adv 5:18312–18327. https://doi.org/10.1039/C4RA16119J
Ozay H, Ozay O (2013) Rhodamine based reusable and colorimetric naked-eye hydrogel sensors for Fe3+ ion. Chem Eng J 232:364–371. https://doi.org/10.1016/j.cej.2013.07.111
Ozay O, Ilgin P, Ozay H, Gungor Z, Yilmaz B, Kivanc MR (2020) The preparation of various shapes and porosites of hydroxyethyl starch/p(HEMA-co-NVP) IPN hydrogels as programmable carrier for drug delivery. J Macromol Sci A 57:379–387. https://doi.org/10.1080/10601325.2019.1700803
Ozay O, Ozay H (2014) Synthesis and characterization of drug microspheres containing phosphazene for biomedical applications. Colloids Surf A Physicochem Eng Asp 450:99–105. https://doi.org/10.1016/j.colsurfa.2014.03.022
Ozay H, Sahin O, Koc OK, Ozay O (2016) The preparation and applications of novel phosphazene crosslinked thermo and pH responsive hydrogels. J Ind Eng Chem 43:28–35. https://doi.org/10.1016/j.jiec.2016.07.043
Ilgin P, Zorer OS, Ozay O, Boran G (2017) Synthesis and characterization of 2-hydroxyethylmethacrylate/2-(3-indol-yl)ethylmethacrylamide-based novel hydrogels as drug carrier with in vitro antibacterial properties. J Appl Polym Sci 134:45550. https://doi.org/10.1002/app.45550
Caló E, Khutoryanskiy VV (2015) Biomedical applications of hydrogels: a review of patents and commercial products. Eur Polym J 65:252–267. https://doi.org/10.1016/j.eurpolymj.2014.11.024
Fuchs S, Shariati K, Ma M (2019) Specialty tough hydrogels and their biomedical applications. Adv Healthc Mater 9:1901396. https://doi.org/10.1002/adhm.201901396
Durmuş S, Yilmaz B, Kıvanç MR, Onder A, Ilgin P, Ozay H, Ozay O (2021) Synthesis, characterization, and in vitro drug release properties of AuNPs/p(AETAC-co-VI)/Q nanocomposite hydrogels. Gold Bull 54:75–87. https://doi.org/10.1007/s13404-021-00295-4
Ilgin P, Ozay O, Ozay H (2019) A novel hydrogel containing thioether group as selective support material for preparation of gold nanoparticles: synthesis and catalytic applications. Appl Catal B 241:415–423. https://doi.org/10.1016/j.apcatb.2018.09.066
Chitra G, Franklin DS, Sudarsan S, Sakthivel M, Guhanathan S (2018) Noncytotoxic silver and gold nanocomposite hydrogels with enhanced antibacterial and wound healing applications. Polym Eng Sci 58:2133–2142. https://doi.org/10.1002/pen.24824
Onder A, Kivanc MR, Ilgin P, Ozay H, Ozay O (2023) Synthesis of p(HEMA-co-AETAC) nanocomposite hydrogel with vinyl-function montmorillonite nanoparticles and effective removal of methyl orange from aqueous solution. J Macromol Sci A 60:108–123. https://doi.org/10.1080/10601325.2023.2169155
Erbil C, Uyanik N (2001) Interactions between poly(acrylamide)-poly(itaconic acid) and cerium(IV)-nitrilotriacetic acid redox pair in the synthesis of acrylamide and itaconic acid homo- and copolymers. Polym Int 50:792–795. https://doi.org/10.1002/pi.697
Kim SJ, Lee CK, Lee YM, Kim IY, Kim SI (2003) Electrical/pH-sensitive swelling behavior of polyelectrolyte hydrogels prepared with hyaluronic acid-poly(vinyl alcohol) interpenetrating polymer networks. React Funct Polym 55:291–298. https://doi.org/10.1016/S1381-5148(03)00019-1
Singh J, Kumar S, Dhaliwal AS (2020) Controlled release of amoxicillin and antioxidant potential of gold nanoparticles-xanthan gum/poly (acrylic acid) biodegradable nanocomposite. J Drug Deliv Sci Tec 55:101384. https://doi.org/10.1016/j.jddst.2019.101384
Ozay H, Tarimeri N, Gungor Z, Demirbakan B, Ozcan B, Sezginturk MK, Ozay O (2020) A new approach to synthesis of highly dispersed gold nanoparticles via glucose oxidase-immobilized hydrogel and usage in the reduction of 4-nitrophenol. ChemistrySelect 5:9143–9152. https://doi.org/10.1002/slct.202002327
Shaghaleh H, Hamoud YA, Xu X, Liu H, Wang S, Sheteiwy M, Dong F, Qian Y, Li P, Zhang S (2021) Thermo-/pH-responsive preservative delivery based on TEMPO cellulose nanofiber/cationic copolymer hydrogel film in fruit packaging. Int J Biol Macromol 183:1911–1924. https://doi.org/10.1016/j.ijbiomac.2021.05.208
Ferrer C, Massuelle D, Doelker E (2010) Towards elucidation of the drug release mechanism from compressed hydrophilic matrices made of cellulose ethers. II. Evaluation of a possible swelling-controlled drug release mechanism using dimensionless analysis. J Control Release 141:223–233. https://doi.org/10.1016/j.jconrel.2009.09.011
England CG, Miller MC, Kuttan A, Trent JO, Frieboes HB (2015) Release kinetics of paclitaxel and cisplatin from two and three layered gold nanoparticles. Eur J Pharm Biopharm 92:120–129. https://doi.org/10.1016/j.ejpb.2015.02.017
Rizzello L, Pompa PP (2014) Nanosilver-based antibacterial drugs and devices: mechanisms, methodological drawbacks and guidelines. Chem Soc Rev 43:1501–1518. https://doi.org/10.1039/c3cs60218d
Yuan H, Yu B, Fan L, Wang M, Zhu Y, Ding X, Xu F (2016) Multiple types of hydroxyl-rich cationic derivatives of PGMA for broad-spectrum antibacterial and antifouling coatings. Polym Chem 7:5709–5718. https://doi.org/10.1039/C6PY01242F
Guo J, Qin J, Ren Y, Wang B, Cui H, Ding Y, Yan F (2018) Antibacterial Activity of cationic polymers: side-chain or main-chain type? Polym Chem 9:4611–4616. https://doi.org/10.1039/c8py00665b
Chen J, Wang F, Liu Q, Du J (2014) Antibacterial polymeric nanostructures for biomedical applications. Chem Commun 50:14482–14493. https://doi.org/10.1039/C4CC03001J
Grace AN, Pandian K (2007) Antibacterial efficacy of aminoglycosidic antibiotics protected gold nanoparticles-a brief study. Colloids Surf A Physicochem Eng Asp 297:63–70. https://doi.org/10.1016/j.colsurfa.2006.10.024
Acknowledgements
This study was produced from the master thesis of Merve İlkiner.
Funding
This research was funded by the Çanakkale Onsekiz Mart University (FYL-2021-3854).
Author information
Authors and Affiliations
Contributions
Merve İlkiner: experimental studies, data processing, and writing. Ozgur Ozay: experimental studies, data processing, writing, and project management. All authors reviewed the manuscript.
Corresponding author
Ethics declarations
Competing interests
The authors declare no competing interests.
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.
About this article
Cite this article
Ilkiner, M., Ozay, O. Drug release properties of amphoteric HES/p(AETAC-co-IA) hydrogels decorated with gold nanoparticles. Gold Bull 56, 83–96 (2023). https://doi.org/10.1007/s13404-023-00334-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13404-023-00334-2