Abstract
This work includes the synthesis of a new ionic liquid (IL) derived from benzisothiazolinon (Bit) by the reaction of benzisothiazolinon with HCl at room temperature. This ionic liquid (BitIL) was characterized using FTIR, 1HNMR, 13C-NMR, and elemental analysis. Furthermore, eggshell membrane protein polymer (ESMP) was used as a natural polymer to prepare its nanocomposite with titanium oxide nanoparticles (TiO2 NPs) (ESMP-TiO2). At the end of the synthesis route, the as-prepared benzisothiazolinon ionic liquid (BitIL) was grafted on the surface of the nanocomposite to synthesis benzisothiazolinon ionic liquid@ eggshell membrane protein polymer–titanium oxide (BitIL@ESMP-TiO2) nanocomposite by the one-pot method. The BitIL@ESMP-TiO2 nanocomposite was characterized using FTIR, XRD, and TEM. Moreover, the kinetics of in vitro release of BitIL from BitIL@ESMP-TiO2 was studied using Korsmeyer and Peppas equation at two different temperatures and pHs. From the results, it was found that the BitIL released from ESMP-TiO2 was about 85%, at 37 °C. Furthermore, the pH = 1.2 (stomach acidity) produced n values of 0.645 and 0.761, indicating the prevalence of anomalous type, whereas the pH = 7.2 (blood acidity) produced quasi-Fickian type diffusion.
Similar content being viewed by others
References
A. Srivastava, T. Yadav, S. Sharma, A. Nayak, A.A. Kumari, N. Mishra, Polymers in drug delivery. J. Biosci. Med. 4(1), 69–84 (2015)
D. Schmaljohann, Thermo-and pH-responsive polymers in drug delivery. Adv. Drug. Deliv. Rev. 58(15), 1655–1670 (2006)
J. Sharma, L. Kaur, N. Kanuja, M. Nagpal, R. Bala, Natural polymers-promising potential in drug delivery. Int. J. Pharm. Tech. Res. 5(2), 684–699 (2013)
B. Bangar, N. Shinde, S. Deshmukh, B. Kale, Natural polymers in drug delivery development. Res. J. Pharm. Dosage Forms Technol. 6(1), 54–57 (2014)
J.J. Milligan, S. Saha, I.C. Jenkins, A. Chilkoti, Genetically encoded elastin-like polypeptide nanoparticles for drug delivery. Curr. Opin. Biotechnol. 74, 146–153 (2022)
M. Rahim Labbafzadeh, M.H. Vakili, Application of magnetic electrospun polyvinyl alcohol/collagen nanofibres for drug delivery systems. Mol. Simul. 48(1), 1–7 (2022)
C. Lei, X.R. Liu, Q.B. Chen, Y. Li, J.L. Zhou, L.Y. Zhou, T. Zou, Hyaluronic acid and albumin based nanoparticles for drug delivery. J. Control. Release 331, 416–433 (2021)
P. Severino, C.F. da Silva, L.N. Andrade, D. de Lima Oliveira, J. Campos, E.B. Souto, Alginate nanoparticles for drug delivery and targeting. Curr. Pharm. Des. 25(11), 1312–1334 (2019)
R. Parhi, Drug delivery applications of chitin and chitosan: a review. Environ. Chem. Lett. 18(3), 577–594 (2020)
R. Jayasree, K. Madhumathi, D. Rana, M. Ramalingam, R.P. Nankar, M. Doble, T.S. Kumar, Development of egg shell derived carbonated apatite nanocarrier system for drug delivery. J. Nanosci. Nanotechnol. 18(4), 2318–2324 (2018)
F. Yi, Z.X. Guo, L.X. Zhang, J. Yu, Q. Li, Soluble eggshell membrane protein: preparation, characterization and biocompatibility. Biomaterials 25(19), 4591–4599 (2004)
M.A. Alheety, A. Raoof, S.A. Al-Jibori, A. Karadağ, A.I. Khaleel, H. Akbaş, O. Uzun, Eco-friendly C60-SESMP-Fe3O4 inorganic magnetizable nanocomposite as high-performance adsorbent for magnetic removal of arsenic from crude oil and water samples. Mater. Chem. Phys. 231, 292–300 (2019)
E. Ohto-Fujita, T. Konno, M. Shimizu, K. Ishihara, T. Sugitate, J. Miyake, Y. Atomi, Hydrolyzed eggshell membrane immobilized on phosphorylcholine polymer supplies extracellular matrix environment for human dermal fibroblasts. Cell Tissue Res. 345(1), 177–190 (2011)
H. Razmi, S.J. Musevi, R. Mohammad-Rezaei, Solid phase extraction of mercury (II) using soluble eggshell membrane protein doped with reduced graphene oxide, and its quantitation by anodic stripping voltammetry. Microchim. Acta 183(2), 555–562 (2016)
Y. Zhang, W. Wang, L. Li, Y. Huang, J. Cao, Eggshell membrane-based solid-phase extraction combined with hydride generation atomic fluorescence spectrometry for trace arsenic (V) in environmental water samples. Talanta 80(5), 1907–1912 (2010)
A. Mittal, M. Teotia, R.K. Soni, J. Mittal, Applications of egg shell and egg shell membrane as adsorbents: a review. J. Mol. Liq. 223, 376–387 (2016)
F. Yi, J. Yu, Z.X. Guo, L.X. Zhang, Q. Li, Natural bioactive material: a preparation of soluble eggshell membrane protein. Macromol. Biosci. 3(5), 234–237 (2003)
S. Sarkar, S. Dutta, S. Chakrabarti, P. Bairi, T. Pal, Redox-switchable copper (I) metallogel: a metal–organic material for selective and naked-eye sensing of picric acid. ACS Appl. Mater. Int. 6(9), 6308–6316 (2014)
J.L. Segura, The chemistry of electroluminescent organic materials. Acta Polym. 49(7), 319–344 (1998)
J. Rivnay, R.M. Owens, G.G. Malliaras, The rise of organic bioelectronics. Chem. Mater. 26(1), 679–685 (2014)
, B. Iddon, Benzo [c] thiophenes, in Advances in Heterocyclic Chemistry, vol. 14 (Academic Press, 1972), pp. 331–381
T. Ishikawa, Benzo [c] phenanthridine bases and their antituberculosis activity. Med. Res. Rev. 21(1), 61–72 (2001)
N. Kaur, Cobalt-catalyzed C–N, C–O, C–S bond formation: synthesis of heterocycles. J. Iran. Chem. Soc. 16(12), 2525–2553 (2019)
M. Edrisi, N. Azizi, Sulfonic acid-functionalized graphitic carbon nitride composite: a novel and reusable catalyst for the one-pot synthesis of polysubstituted pyridine in water under sonication. J. Iran. Chem. Soc. 17(4), 901–910 (2020)
Zabiulla, F.H. Al-Ostoot, A.M. S, M. Al-Ghorbani, S.A. Khanum, Recent investigation on heterocycles with one nitrogen [piperidine, pyridine and quinoline], two nitrogen [1,3,4-thiadiazole and pyrazole] and three nitrogen [1,2,4-triazole]: a review. J. Iran. Chem. Soc. 19, 23–54 (2022). https://doi.org/10.1007/s13738-021-02293-x
F.H. Al-Ostoot, S. Salah, S.A. Khanum, Recent investigations into synthesis and pharmacological activities of phenoxy acetamide and its derivatives (chalcone, indole and quinoline) as possible therapeutic candidates. J. Iran. Chem. Soc. 18(8), 1839–1875 (2021)
Y. Volkova, S. Baranin, I. Zavarzin, A3 coupling reaction in the synthesis of heterocyclic compounds. Adv. Synth. Catal. 363(1), 40–61 (2021)
M. Malekshahi Byranvand, A. Nemati Kharat, L. Fatholahi, Z. Malekshahi Beiranvand, A review on synthesis of nano-TiO2 via different methods. J. nanostruct. 3(1), 1–9 (2013)
R.N. Esfahani, S. Khaghani, A. Azizi, F. Mortazaeinezhad, M. Gomarian, Facile and eco-friendly synthesis of TiO2 NPs using extracts of Verbascum thapsus plant: an efficient photocatalyst for reduction of Cr (VI) ions in the aqueous solution. J. Iran. Chem. Soc. 17(1), 205–213 (2020)
Y. Sun, S. Wang, J. Zheng, Biosynthesis of TiO2 nanoparticles and their application for treatment of brain injury-An in-vitro toxicity study towards central nervous system. J. Photochem. Photobiol. B 194, 1–5 (2019)
R.J. Kamble, P.V. Gaikwad, K.M. Garadkar, S.R. Sabale, V.R. Puri, S.S. Mahajan, Photocatalytic degradation of malachite green using hydrothermally synthesized cobalt-doped TiO2 nanoparticles. J. Iran. Chem. Soc. 19(1), 303–312 (2022)
S. Freiberg, X.X. Zhu, Polymer microspheres for controlled drug release. Int. J. Pharm. 282(1–2), 1–18 (2004)
S. Puttipipatkhachorn, J. Nunthanid, K. Yamamoto, G.E. Peck, Drug physical state and drug–polymer interaction on drug release from chitosan matrix films. J. Control. Release 75(1–2), 143–153 (2001)
I. Zaborniak, A. Macior, P. Chmielarz, Smart, naturally-derived macromolecules for controlled drug release. Molecules 26(7), 1918 (2021)
Y. Ali, A. Alqudah, S. Ahmad, S. Abd Hamid, U. Farooq, Macromolecules as targeted drugs delivery vehicles: an overview. Des. Monomers Polym. 22, 91 (2019)
M. Jahanshahi, Z. Babaei, Protein nanoparticle: a unique system as drug delivery vehicles. Afr. J. Biotechnol. 7(25), 4926–4934 (2008)
D. Ghosh, X. Peng, J. Leal, R.P. Mohanty, Peptides as drug delivery vehicles across biological barriers. J. Pharm. Investig. 48(1), 89–111 (2018)
T. Wang, H. Jiang, L. Wan, Q. Zhao, T. Jiang, B. Wang, S. Wang, Potential application of functional porous TiO2 nanoparticles in light-controlled drug release and targeted drug delivery. Acta Biomater. 13, 354–363 (2015)
M.A. Alheety, S.A. Al-Jibori, A.H. Ali, A.R. Mahmood, H. Akbaş, A. Karadağ, O. Uzun, M.H. Ahmed, Ag (I)-benzisothiazolinone complex: synthesis, characterization, H2 storage ability, nano transformation to different Ag nanostructures and Ag nanoflakes antimicrobial activity. Mater. Res. Exp. 6(12), 125071 (2019)
H. Azizi-Toupkanloo, M. Karimi-Nazarabad, G.R. Amini, A. Darroudi, Immobilization of AgCl@ TiO2 on the woven wire mesh: Sunlight-responsive environmental photocatalyst with high durability. Sol. Energy 196, 653–662 (2020)
M. Karimi-Nazarabad, E.K. Goharshadi, M. Aziznezhad, Solar mineralization of hard-degradable amphetamine using TiO2/RGO nanocomposite. Chem. Select 4(48), 14175–14183 (2019)
A.H. Majeed, D.H. Hussain, E.T.B. Al-Tikrity, M.A. Alheety, Poly (o-Phenylenediamine-GO-TiO2) nanocomposite: modulation, characterization and thermodynamic calculations on its H2 storage capacity. Chem. Data Collect. 28, 100450 (2020)
G.M. Khan, J.B. Zhu, Studies on drug release kinetics from ibuprofen–carbomer hydrophilic matrix tablets: influence of co-excipients on release rate of the drug. J. Control. Release 57(2), 197–203 (1999)
N.A. Peppas, P. Colombo, Analysis of drug release behavior from swellable polymer carriers using the dimensionality index. J. Control. Release 45(1), 35–40 (1997)
M.J. Durrani, A. Andrews, R. Whitaker, S.C. Benner, Studies on drug release kinetics from carbomer matrices. Drug. Dev. Ind. Pharm. 20(15), 2439–2447 (1994)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Alheety, M.A., Majeed, A.H., Ali, A.H. et al. Synthesis and characterization of eggshell membrane polymer-TiO2 nanocomposite for newly synthesized ionic liquid release. J IRAN CHEM SOC 19, 4005–4015 (2022). https://doi.org/10.1007/s13738-022-02584-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13738-022-02584-x