Investigation of the Potential of Adsorption and Drug Delivery Application of the Duloxetine Antipsychotic by using its Molecular Imprinted Polymer

Subject Areas : Polymer

Seyyedeh Fatemeh Hoseini chehreghani ¹ , Parviz Aberoomand Azar ² , Maryam Shekarchi ³ , Bahram Daraei ⁴

1 - Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran
2 - Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran
3 - Food and Drug Laboratory Research Center, Food and Drug Organization, MOH & ME, Tehran, Iran Pharmaceutical Science Research Center, Tehran University of Medical Science, Tehran, Iran
4 - Department of Toxicology and Pharmacology, School of pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran

Received: 2023-12-16 Accepted : 2023-12-16 Published : 2024-01-01

Keywords:

Abstract :

The synthesis and application of a molecular imprinted polymer (MIP) as a carrier for drug delivery of Duloxetine (DUL) antipsychotic was investigated. Mimicking the natural receptors of DUL drug by synthesizing its MIP would lead to formation of some special active sites, which make able the MIP to accept only this special medicinal compound. Therefore, this MIP, which has been templated by DUL, could selectively absorb the molecules of DUL from the mediums in certain conditions and could release those chemical species in another place with different conditions. This MIP with its artificial receptors could be applied as a carrier for drug delivery applications and sustained released tablets. In order to synthesize this MIP based carrier, the precipitation polymerization method was applied. Also, methacrylic acid (MAA; as the functional monomer), 2,2-azobisissobutyronitrile (AIBN; as the initiator), and ethylene glycol dimethacrylate (EGDMA;as the cross-linker), were applied to obtain this sorbent. Moreover, the release kinetics of the drug was investigated by HPLC system, which was shown to be fitted with the Higuchi expressionpattern at least at 5.8, and 6.8 pHs. Finally, the results revealed that the synthesized MIP is able to be used in formulation of the sustained released tablets.

References:

1. Poyurovsky M, Braverman L, Weizman A. Beneficial effect of quetiapine monotherapy in patients with bipolar depression and comorbid obsessive-compulsive disorder. International Clinical Psychopharmacology. 2021 Jan 1;36(1):50-3.


2. Garakani A, Buono FD, Marotta RF. Sublingual oxytocin with clozapine in a patient with persisting psychotic symptoms, suicidal thinking with self-harm. Journal of Clinical Psychopharmacology. 2020 Sep 1;40(5):507-9.


3. Jain M. Quetiapine associated Central Serous Chorioretinopathy: Implicit role of serotonin and dopamine pathways. Indian Journal of Ophthalmology. 2019 Feb;67(2):292.


4. Papazisis G, Siafis S. The added value of liquid antipsychotics: the case of quetiapine. Current Clinical Pharmacology. 2019 Aug 1;14(2):101-7.


5. Wang M, Wang M, Zhang Q, Zong S, Lv C. Pharmacokinetics and safety of levetiracetam extended-release tablets and relative bioavailability compared with immediate-release tablets in healthy Chinese subjects. European Journal of Drug Metabolism and Pharmacokinetics. 2018 Aug;43:405-13.


6. Eriksson A, Jeppesen S, Krebs L. Induction of labour in nulliparous women-quick or slow: a cohort study comparing slow-release vaginal insert with low-dose misoprostol oral tablets. BMC Pregnancy and Childbirth. 2020 Dec;20:1-8.


7. Shah KH, Makwana RP. A review of novel drug delivery controlled porosity osmotic pump tablets therapeutic approach and future trend. Journal of Drug Delivery and Therapeutics. 2021 Feb 4;11(1):201-4.


8. a) Motaharian A, Naseri K, Mehrpour O, Shoeibi S. Electrochemical determination of atypical antipsychotic drug quetiapine using nano-molecularly imprinted polymer modified carbon paste electrode. Analytica Chimica Acta. 2020 Feb 8;1097:214-21; b) He S, Zhang L, Bai S, Yang H, Cui Z, Zhang X, Li Y. Advances of molecularly imprinted polymers (MIP) and the application in drug delivery. European Polymer Journal. 2021 Jan 15;143:110179.


9. Bodratti AM, Alexandridis P. Formulation of poloxamers for drug delivery. J Funct Biomater 9 (1): 11.


10. Lee HY, Kim HE, Jeong SH. One-pot synthesis of silane-modified hyaluronic acid hydrogels for effective antibacterial drug delivery via sol–gel stabilization. Colloids and Surfaces B: Biointerfaces. 2019 Feb 1;174:308-15.


11. Zaidi SA. Molecular imprinting: A useful approach for drug delivery. Materials Science for Energy Technologies. 2020 Jan 1;3:72-7.


12. Marcelo G, Ferreira IC, Viveiros R, Casimiro T. Development of itaconic acid-based molecular imprinted polymers using supercritical fluid technology for pH-triggered drug delivery. International Journal of Pharmaceutics. 2018 May 5;542(1-2):125-31.


13. Ali F, Shah Z, Khan A, Saadia M, AlOthman ZA, Cheong WJ. Synthesis, column packing and liquid chromatography of molecularly imprinted polymers for the acid black 1, acid black 210, and acid Brown 703 dyes. RSC advances. 2022;12(30):19611-23.


14. a) Sadegh N, Asfaram A, Javadian H, Haddadi H, Sharifpour E. Ultrasound-assisted solid phase microextraction-HPLC method based on Fe3O4@ SiO2-NH2-molecularly imprinted polymer magnetic nano-sorbent for rapid and efficient extraction of harmaline from Peganum harmala extract. Journal of Chromatography B. 2021 May 1;1171:122640; b) Siadati SA, Alinezhad M. A theoretical study on the functionalisation process of C18NB fullerene through its open [5, 5] cycloaddition with 4-pyridine nitrile oxide. Progress in Reaction Kinetics and Mechanism. 2015 Apr;40(2):169-76.


15. Weber P, Riegger BR, Niedergall K, Tovar GE, Bach M, Gauglitz G. Nano-MIP based sensor for penicillin G: Sensitive layer and analytical validation. Sensors and Actuators B: Chemical. 2018 Aug 15;267:26-33.


16. Park R, Jeon S, Jeong J, Park SY, Han DW, Hong SW. Recent advances of point-of-care devices integrated with molecularly imprinted polymers-based biosensors: From biomolecule sensing design to intraoral fluid testing. Biosensors. 2022 Feb 22;12(3):136.


17. Nahhas AF, Webster TJ. The promising use of nano-molecular imprinted templates for improved SARS-CoV-2 detection, drug delivery and research. Journal of Nanobiotechnology. 2021 Dec;19(1):1-4.


18. a) Ghiasi R, Khanjari Z, Mohtat B. Computational Investigation of Chemisorption of Thiophosgene on Co@ B. Russian Journal of Physical Chemistry A. 2022 Feb;96(2):267-72; b) Aberoomand Azar P, Shekarchi M, Daraei B. Synthesis, evaluation of drug delivery potential, and the quantum chemical investigation on a molecular imprinted polymer for quetiapine antipsychotic; a joint experimental and density functional theory study. Frontiers in Chemistry. 2022 Oct 14;10:1001685.


19. a) Behnia N, Azar PA, Shekarchi M, Tehrani MS, Adib N. Synthesis of a new molecular imprinted polymer for oxycodone opioid and its formulation for transdermal controlled drug delivery application: A joint experimental and quantum chemical study. ChemistrySelect. 2022 Oct 13;7(38):e202202553; b) Siadati A. A theoretical study on the possibility of functionalization of C20 fullerene via its Diels-Alder reaction with 1, 3-butadiene. Letters in Organic Chemistry. 2016 Jan 1;13(1):2-6.


20. a) Dadras A, Rezvanfar MA, Beheshti A, Naeimi SS, Siadati SA. An urgent industrial scheme both for total synthesis, and for pharmaceutical analytical analysis of umifenovir as an anti-viral API for treatment of COVID-19. Combinatorial Chemistry & High Throughput Screening. 2022 Apr 1;25(5):838-46; b) Siadati SA, Davoudi S, Soheilizad M, Firoozpour L, Payab M, Bagherpour S, Kolivand S. The synthesis and the mechanism of a five-membered ring formation between an isothiocyanate and an amide leading to the yield of Enzalutamide anticancer API; a joint experimental and theoretical study. Journal of Molecular Structure. 2023 May 15;1280:135057.


21. a) Nezhadali A, Mojarrab M. Computational design and multivariate optimization of an electrochemical metoprolol sensor based on molecular imprinting in combination with carbon nanotubes. Analytica chimica acta. 2016 Jun 14;924:86-98.; b) Pakravan P, Siadati SA. The possibility of using C20 fullerene and graphene as semiconductor segments for detection, and destruction of cyanogen-chloride chemical agent. Journal of Molecular Graphics and Modelling. 2017 Aug 1;75:80-4.


22. a) Demeestere K, Petrović M, Gros M, Dewulf J, Van Langenhove H, Barceló D. Trace analysis of antidepressants in environmental waters by molecularly imprinted polymer-based solid-phase extraction followed by ultra-performance liquid chromatography coupled to triple quadrupole mass spectrometry. Analytical and bioanalytical chemistry. 2010 Jan;396:825-37; b) Siadati SA, Soheilizad M, Firoozpour L, Samadi M, Payab M, Bagherpour S, Mousavi SM. An Industrial Approach to Production of Tofacitinib Citrate (TFC) as an Anti-COVID-19 Agent: A Joint Experimental and Theoretical Study. Journal of Chemistry. 2022 Dec 9;2022.


23. a) Beheshti A, Kamalzadeha Z, Haj-Maleka M, Payaba M, Rezvanfar M, Siadati S. Development and validation of a reversed-phase HPLC method for determination of assay content of Teriflunomide by the aid of BOMD simulations. Current Chemistry Letters. 2021;10(3):281-94; b) Hudson AD, Solà R, Ueta JT, Battell W, Jamieson O, Dunbar T, Maciá B, Peeters M. Synthesis of optimized molecularly imprinted polymers for the isolation and detection of antidepressants via HPLC. Biomimetics. 2019 Feb 20;4(1):18.


24. Ng SF, Rouse J, Sanderson D, Eccleston G. A comparative study of transmembrane diffusion and permeation of ibuprofen across synthetic membranes using Franz diffusion cells. Pharmaceutics. 2010 May 18;2(2):209-23.


25. Seo JE, Kim S, Kim BH. In vitro skin absorption tests of three types of parabens using a Franz diffusion cell. Journal of exposure science & environmental epidemiology. 2017 May;27(3):320-5.


26. Jyoti, Żołek T, Maciejewska D, Gilant E, Gniazdowska E, Kutner A, Noworyta KR, Kutner W. Polytyramine Film-Coated Single-Walled Carbon Nanotube Electrochemical Chemosensor with Molecularly Imprinted Polymer Nanoparticles for Duloxetine-Selective Determination in Human Plasma. ACS sensors. 2022 May 12;7(7):1829-36.