Synthesis and Characterization of Ibuprofen Delivery System Based on β-cyclodextrin/Itaconic Acid Copolymer
DOI:
https://doi.org/10.48048/tis.2022.5825Keywords:
β-cyclodextrin, Itaconic acid, Ibuprofen, Free radical copolymerization, In vitro drug releaseAbstract
This study aims at preparation and characterization of drug delivery system based on grafted beta-cyclodextrin (β-CD) with itaconic acid (IA) using free-radical copolymerization technique, in the presence of N, N'-methylene bisacrylamide (BIS) and ammonium persulphate (APS) as a crosslinker and an initiator, respectively. The obtained copolymer (CD-PIA) was characterized using Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), X-ray diffraction patterns (XRD), transmission and scanning electron microscopes (TEM and SEM). Ibuprofen (IBU), as an anti-inflammatory drug model, was loaded during the preparation. The kinetic of the copolymerization was investigated in terms of grafting yield (GY %), grafting efficiency (GE %) and monomer conversion (%). Moreover, in vitro IBU release and kinetic of released using the different mathematical models (0-order, first-order and Higushi) were carried out in simulated gastric and intestinal fluids (SGF and SIF at pH 1.2 and 7.4, respectively) at 37 °. The results proved the successful preparation of the target copolymer with irregular spherical-like shape and particle size around 14 - 27.7 nm. After IBU loading, the copolymer exhibited thermal stability with crystalline nature. Also, the study showed that the synthesized copolymer, especially which high IA content is controlled the release of IBU after 4 h. Besides, it could be used as a potential IBU delivery system with sustained-release followed the first-order kinetic over 24 h.
HIGHLIGHTS
- The nanogels drug carriers used for nonsteroidal anti-inflammatory drugs to overcome the unfavorable release in the stomach due to unforeseen pH alterations
- The polymeric grafted β-CD derivatives using IA represent a unique class of the host materials with tunable inclusion properties and high affinity for Ibuprofen release
- In vitro kinetic of IBU released showed the best fit with first-order model
GRAPHICAL ABSTRACT
Downloads
References
M Murata, Y Uchida, T Takami, T Ito, R Anzai, S Sonotaki and Y Murakami. Dual drug release from hydrogels covalently containing polymeric micelles that possess different drug release properties. Colloids Surf. B Biointerfaces 2017; 153, 19-26.
Y Yu, R Feng, S Yu, J Li, Y Wang, Y Song, X Yang, W Pan and S Li. Nanostructured lipid carrier-based pH and temperature dual-responsive hydrogel composed of carboxymethyl chitosan and poloxamer for drug delivery. Int. J. Biol. Macromol. 2018; 114, 462-9.
AJ Xie, HS Yin, HM Liu, CY Zhu and YJ Yang. Chinese quince seed gum and poly (N,N-diethylacryl amide-co-methacrylic acid) based pH-sensitive hydrogel for use in drug delivery. Carbohydr. Polym. 2018; 185, 96-104.
SJ Hossieni-Aghdam, B Foroughi-Nia, Z Zare-Akbari, S Mojarad-Jabali and H Farhadnejad. Facile fabrication and characterization of a novel oral pH-sensitive drug delivery system based on CMC hydrogel and HNT-AT nanohybrid. Int. J. Biol. Macromol. 2018; 107, 2436-49.
Y Hu, X Wu and X JinRui. Self-axssembled supramolecular hydrogels formed by biodegradable PLA/CS diblock copolymers and β-cyclodetrin for controlled dual drug delivery. Int. J. Biol. Macromol. 2018; 108, 18-23.
A Haroun, F Ayoob, EHA Nashy, O Mohamed and AG Rabie. Sol-gel preparation and in vitro kinetic release study of albendazole-immobilized MWCNTs. Egy. J. Chem. 2019; 62, 645-54.
M Hamidi, A Azadi and P Rafiei. Hydrogel nanoparticles in drug delivery. Adv. Drug Del. Rev. 2008; 60, 1638-49.
A Shakeri, MT Nakhjiri, H Salehi, F Ghorbani and N Khankeshipour. Preparation of polymer-carbon nanotubes composite hydrogel and its application as forward osmosis draw agent. J. Water Proc. Eng. 2018; 24, 42-8.
EA Kamoun, ERS Kenawy and X Chen. A review on polymeric hydrogel membranes for wound dressing applications: PVA-based hydrogel dressings. J. Adv. Res. 2017; 8, 217-33.
A Osman, AA Haroun, SA Ahmed and AHH Elghandour. Preparation and in vitro release study of ibuprofen-loaded modified montmorillonite using miniemulsion technique. J. Appl. Chem. Sci. Int. 2016; 6, 203-9.
LP Fonseca, RB Trinca and MI Felisberti. Amphiphilic polyurethane hydrogels as smart carriers for acidic hydrophobic drugs. Int. J. Pharm. 2018; 546, 106-14.
RD Manga and PK Jha. Mathematical models for controlled drug release through pH-responsive polymeric hydrogels. J. Pharm. Sci. 2017; 106, 629-38.
AA Haroun, AM El Nahrawy and P Maincent. Enoxaparin-immobilized poly(ε-caprolactone)- based nanogels for sustained drug delivery systems. Pure Appl. Chem. 2014; 86, 691-700.
Y Yin, Q Dang, C Liu, J Yan, D Cha, Z Yu, Y Cao, Y Wang and B Fan. Itaconic acid grafted carboxymethyl chitosan and its nanoparticles: Preparation, characterization and evaluation. Int. J. Biol. Macromol. 2017; 102, 10-8.
N Milašinović, Z Knežević-Jugović, N Milosavljević, J Filipović and MK Krušić. Controlled release of lipase from Candida rugosa loaded into hydrogels of N-isopropylacrylamide and itaconic acid. Int. J. Pharm. 2012; 436, 332-40.
MC Koetting and NA Peppas. pH-Responsive poly(itaconic acid-co-N-vinylpyrrolidone) hydrogels with reduced ionic strength loading solutions offer improved oral delivery potential for high isoelectric point-exhibiting therapeutic proteins. Int. J. Pharm. 2014; 471, 83-91.
M Sakthivel, D Franklin, S Sudarsan, G Chitra, T Sridharan and S Guhanathan. Investigation on pH/salt-responsive multifunctional itaconic acid based polymeric biocompatible, antimicrobial and biodegradable hydrogels. React. Funct. Polym. 2018; 122, 9-21.
N Wierckx, G Agrimi, PS Lübeck, MG Steiger, NP Mira and PJ Punt. Metabolic specialization in itaconic acid production: A tale of two fungi. Curr. Opin. Biotechnol. 2020; 62, 153-9.
L Karaffa and CP Kubicek. Citric acid and itaconic acid accumulation: Variations of the same story? Appl. Microbiol. Biotechnol. 2019; 103, 2889-902.
SH Choi, JW Chung, RD Priestley and SY Kwak. Functionalization of polysulfone hollow fiber membranes with amphiphilic β-cyclodextrin and their applications for the removal of endocrine disrupting plasticizer. J. Membr. Sci. 2012; 409-410, 75-81.
B Medronho, R Andrade, V Vivod, A Ostlund, MG Miguel, B Lindman, B Voncina and A Valente. Cyclodextrin-grafted cellulose: Physico-chemical characterization. Carbohydr. Polym. 2013; 93, 324-30.
S Liu, X Chen, Q Zhang, W Wu, J Xin and J Li. Multifunctional hydrogels based on β-cyclodextrin with both biomineralization and anti-inflammatory properties. Carbohydr. Polym. 2014; 102, 869-76.
JY Liu, X Zhang and T Bıngren. Selective modifications at the different positions of cyclodextrins: A review of strategies. Turkish J. Chem. 2020; 44, 261-78.
FM Bezerra, MJ Lis, HB Firmino, JGD da Silva, RCSC Valle, JAB Valle, FA Scacchetti and AL Tessaro. The role of β-Cyclodextrin in the textile industry review. Molecules 2020; 25, 3624.
K Kiran, R Tiwari, K Tungala, S Krishnamoorthi and K Kumar. pH tempted Micellization of β-Cyclodextrin based Diblock copolymer and its application in solid/liquid separation. J. Polym. Res. 2020; 27, 150.
MY Xu, HL Jiang, ZW Xie, ZT Li, D Xu and FA He. Highly efficient selective adsorption of anionic dyes by modified β-cyclodextrin polymers. J. Taiwan Inst. Chem. Eng. 2020; 108, 114-28.
BTM Ferreira, FR Espinoza-Quiñones, CE Borba, AN Módenes, WLF Santos and FM Bezerra. Use of the β-Cyclodextrin additive as a good alternative for the substitution of environmentally harmful additives in industrial dyeing processes. Fiber. Polym. 2020; 21, 1266-74.
N Hedayati, M Montazer, M Mahmoudirad and T Toliyat. Ketoconazole and Ketoconazole/β-cyclodextrin performance on cotton wound dressing as fungal skin treatment. Carbohydr. Polym. 2020; 240, 116267.
Y El-Ghoul. Biological and microbiological performance of new polymer-based chitosan and synthesized amino-cyclodextrin finished polypropylene abdominal wall prosthesis biomaterial. Textil. Res. J. 2020; 90, 2690-702.
V Kadam, IL Kyratzis, YB Truong, L Wang and R Padhye. Air filter media functionalized with β-Cyclodextrin for efficient adsorption of volatile organic compounds. J. Appl. Polym. Sci. 2020; 137, 49228.
HL Jiang, MY Xu, ZW Xie, W Hai, XL Xie and FA He. Selective adsorption of anionic dyes from aqueous solution by a novel β-cyclodextrin-based polymer. J. Mol. Struct. 2020; 1203, 127373.
S Gao, Y Liu, J Jiang, Q Ji, Y Fu, L Zhao, C Li and F Ye. Physicochemical properties and fungicidal activity of inclusion complexes of fungicide chlorothalonil with β-cyclodextrin and hydroxypropyl-β-cyclodextrin. J. Mol. Liq. 2019; 293, 111513.
X Hu, Y Hu, G Xu, M Li, Y Zhu, L Jiang, Y Tu, X Zhu, X Xie and A Li. Green synthesis of a magnetic β-cyclodextrin polymer for rapid removal of organic micro-pollutants and heavy metals from dyeing wastewater. Environ. Res. 2020; 180, 108796.
M Song, L Li, Y Zhang, K Chen, H Wang and R Gong. Carboxymethyl-β-cyclodextrin grafted chitosan nanoparticles as oral delivery carrier of protein drugs. React. Funct. Polym. 2017; 117, 10-5.
AA Haroun and NR El-Halawany. Encapsulation of bovine serum albumin within β-cyclodextrin/gelatin-based polymeric hydrogel for controlled protein drug release. Innovat. Res. Biomed. Eng. 2010; 31, 234-41.
AA Haroun, AH Osman, SA Ahmed and AH Elghandour. Beta-cyclodextrin grafted with poly (ε-caprolactone) for ibuprofen delivery system. Egypt. J. Chem. 2019; 62, 827-35.
B Gidwani and A Vyas. Synthesis, characterization and application of Epichlorohydrin-β-cyclodextrin polymer. Colloids Surf. B Biointerfaces 2014; 114, 130-7.
G Angelini, C Campestre, S Boncompagni and C Gasbarri. Liposomes entrapping β-cyclodextrin/ ibuprofen inclusion complex: Role of the host and the guest on the bilayer integrity and microviscosity. Chem. Phys. Lipids 2017; 209, 61-5.
SK Das, N Kahali, A Bose and J Khanam. Physicochemical characterization and in vitro dissolution performance of ibuprofen-Captisol® (sulfobutylether sodium salt of β-CD) inclusion complexes. J. Mol. Liq. 2018; 261, 239-49.
S Heydari and RM kakhki. Thermodynamic study of complex formation of β-cyclodextrin with ibuprofen by conductometric method and determination of ibuprofen in pharmaceutical drugs. Arabian J. Chem. 2017; 10, S1223-S1226.
AA Haroun, NR El-Halawany, C Loira-Pastoriza and P Maincent. Synthesis and in vitro release study of ibuprofen-loaded gelatin graft copolymer nanoparticles. Drug Dev. Ind. Pharm. 2014; 40, 61-5.
S Asman, S Mohamad and NM Sarih. Effects of RAFT agent on the selective approach of molecularly imprinted polymers. Polymers 2015; 7, 484-503.
HJ Zheng, JT Ma, W Feng and Q Jia. Specific enrichment of glycoproteins with polymer monolith functionalized with glycocluster grafted β-cyclodextrin. J. Chrom. 2017; 1512, 88-97.
Y Wang, N Yang, D Wang, Y He, L Chen and Y Zhao. Poly (MAH-β-cyclodextrin-co-NIPAAm) hydrogels with drug hosting and thermo/pH-sensitive for controlled drug release. Polym. Degrad. Stabil. 2018; 147, 123-31.
M Sakthivel, D Franklin, S Sudarsan, G Chitra and S Guhanathan. Investigation on Au-nano incorporated pH-sensitive (itaconic acid/acrylic acid/triethylene glycol) based polymeric biocompatible hydrogels. Mater. Sci. Eng. C 2017; 75, 517-23.
M Nazi, RMA Malek and R Kotek. Modification of β-cyclodextrin with itaconic acid and application of the new derivative to cotton fabrics. Carbohydr. Polym. 2012; 88, 950-8.
M Erdős, M Frangou, TJ Vlugt and OA Moultos. Diffusivity of α-, β-, γ-cyclodextrin and the inclusion complex of β-cyclodextrin: Ibuprofen in aqueous solutions; A molecular dynamics simulation study. Fluid Phase Equil. 2021; 528, 112842.
S Masoumi, S Amiri and SH Bahrami. PCL-based nanofibers containing ibuprofen/cyclodextrins nanocontainers: A potential candidate for drug delivery application. J. Ind. Textil. 2019; 48, 1420-38.
D Son and YJ Kim. Morphological structure and characteristics of hydroxyapatite/β-cyclodextrin composite nanoparticles synthesized at different conditions. Mater. Sci. Eng. C 2013; 33, 499-506.
P Lv, Y Bin, Y Li, R Chen, X Wang and B Zhao. Studies on graft copolymerization of chitosan with acrylonitrile by the redox system. Polymer 2009; 50, 5675-80.
B Taşdelen, N Kayaman-Apohan, O Güven and BM Baysal. Preparation of poly(N-isopropylacrylamide/itaconic acid) copolymeric hydrogels and their drug release behavior. Int. J. Pharm. 2004; 69, 303-10.
K gounder Subramanian and V Vijayakumar. Synthesis and evaluation of chitosan-graft-poly (2-hydroxyethyl methacrylate-co-itaconic acid) as a drug carrier for controlled release of tramadol hydrochloride. Saudi Pharmaceut. J. 2012; 20, 263-71.
SL Tomić, MM Mićić, JM Filipović and EH Suljovrujić. Swelling and drug release behavior of poly(2-hydroxyethyl methacrylate/itaconic acid) copolymeric hydrogels obtained by gamma irradiation. Radiat. Phys. Chem. 2007; 76, 801-10.
A Nayak and A Jain. In vitro and in vivo study of poly(ethylene glycol) conjugated ibuprofen to extend the duration of action. Sci. Pharm. 2011; 79, 359-74.
GG Flores-Rojas and E Bucio. Radiation-grafting of ethylene glycol dimethacrylate (EGDMA) and glycidyl methacrylate (GMA) onto silicone rubber. Radiat. Phys. Chem. 2016; 127, 21-6.
K Yang, S Wan, B Chen, W Gao, J Chen, M Liu, B He and H Wu. Dual pH and temperature responsive hydrogels based on β-cyclodextrin derivatives for atorvastatin delivery. Carbohydr. Polym. 2016; 136, 300-6.
U Siemoneit, C Schmitt, C Alvarez-Lorenzo, A Luzardo, F Otero-Espinar, A Concheiro and J Blanco-Méndez. Acrylic/cyclodextrin hydrogels with enhanced drug loading and sustained release capability. Int. J. Pharm. 2006; 312, 66-74.
Downloads
Published
Issue
Section
License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
