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Encapsulation of Risperidone by Methylated Β-Cyclodextrins: Physicochemical and Molecular Modeling Studies

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Encapsulation of Risperidone by Methylated Β-Cyclodextrins: Physicochemical and Molecular Modeling Studies molecules Article Encapsulation of Risperidone by Methylated β-Cyclodextrins: Physicochemical and Molecular Modeling Studies 1,2 3 1,2, 1,2 Laura Sbârcea , Ionut, -Mihai Tănase , Adriana Ledet, i * , Denisa Cîrcioban , Gabriela Vlase 4, Paul Barvinschi 5, Marinela Miclău 6, Renata-Maria Văru¸t 7, 8 1,2,3 Cristina Trandafirescu and Ionut, Ledet, i 1 Department of Pharmacy I, Faculty of Pharmacy, “Victor Babe¸s”University of Medicine and Pharmacy, 2 Eftimie Murgu Square, 300041 Timisoara, Romania; sbarcea.laura@umft.ro (L.S.); circioban.denisa@umft.ro (D.C.); ionut.ledeti@umft.ro (I.L.) 2 Advanced Instrumental Screening Center, Faculty of Pharmacy, “Victor Babes” University of Medicine and Pharmacy, 2 Eftimie Murgu Square, 300041 Timisoara, Romania 3 Faculty of Industrial Chemistry and Environmental Engineering, Politehnica University of Timisoara, 6 Vasile Parvan Blvd, 300223 Timisoara, Romania; ionut.tanase@student.upt.ro 4 Research Centre for Thermal Analysis in Environmental Problems, West University of Timisoara, 16 Pestalozzi Street, 300115 Timisoara, Romania; gabriela.vlase@e-uvt.ro 5 Faculty of Physics, West University of Timisoara, 4 Vasile Parvan Blvd, 300223 Timisoara, Romania; pc_barvi@yahoo.fr 6 National Institute for Research and Development in Electrochemistry and Condensed Matter, 144 Dr. A. Păunescu-Podeanu Street, 300587 Timisoara, Romania; marinela.miclau@gmail.com 7 Faculty of Pharmacy, University of Medicine and Pharmacy Craiova, 2–4 Petru Rares Street, 200349 Craiova, Romania; rennata_maria@yahoo.com 8 Department of Pharmacy II, Faculty of Pharmacy, “Victor Babe¸s”University of Medicine and Pharmacy, 2 Eftimie Murgu Square, 300041 Timisoara, Romania; trandafirescu.cristina@umft.ro * Correspondence: afulias@umft.ro Academic Editors: Tivadar Feczkó and László Biczók Received: 9 November 2020; Accepted: 1 December 2020; Published: 3 December 2020 Abstract: Risperidone (RSP) is an atypical antipsychotic drug which acts as a potent antagonist of serotonin-2 (5TH2) and dopamine-2 (D2) receptors in the brain; it is used to treat schizophrenia, behavioral and psychological symptoms of dementia and irritability associated with autism. It is a poorly water soluble benzoxazole derivative with high lipophilicity. Supramolecular adducts between drug substance and two methylated β-cyclodextrins, namely heptakis(2,6-di-O-methyl)-β- cyclodextrin (DM-β-CD) and heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TM-β-CD) were obtained in order to enhance RSP solubility and improve its biopharmaceutical profile. The inclusion complexes were evaluated by means of thermoanalytical methods (TG—thermogravimetry/DTG—derivative thermogravimetry/HF—heat flow), powder X-ray diffractometry (PXRD), universal-attenuated total reflectance Fourier transform infrared (UATR-FTIR), UV spectroscopy and saturation solubility studies. Job’s method was employed for the determination of the stoichiometry of the inclusion complexes, which was found to be 2:1 for both guest–host systems. Molecular modeling studies were carried out for an in-depth characterization of the interaction between drug substance and cyclodextrins (CDs). The physicochemical properties of the supramolecular systems differ from those of RSP, demonstrating the inclusion complex formation between drug and CDs. The RSP solubility was enhanced as a result of drug encapsulation in the CDs cavity, the higher increase being obtained with DM-β-CD as host; the guest–host system RSP/DM-β-CD can thus be a starting point for further research in developing new formulations containing RSP, with enhanced bioavailability. Molecules 2020, 25, 5694; doi:10.3390/molecules25235694 www.mdpi.com/journal/molecules Molecules 2020, 25, x FOR PEER REVIEW 2 of 15 Molecules 2020, 25, 5694 2 of 15 Keywords: risperidone; cyclodextrins; molecular encapsulation; inclusion complex; solubility Keywords: risperidone; cyclodextrins; molecular encapsulation; inclusion complex; solubility 1. Introduction 1. Introduction Cyclodextrins (CDs) are macrocyclic molecules that have been extensively used in the last decadeCyclodextrins in the pharmaceutical (CDs) are macrocyclic field, cosmetics, molecules food, that have textile, been separation extensively science used in theand last chemical decade industries.in the pharmaceutical They contain field, six, cosmetics, seven or eight food, D-glucopyranose textile, separation units science (α, and β and chemical γ-cyclodextrin) industries. linked They incontain α (1–4) six, to seven form or a eight hollow, D-glucopyranose truncated-cone-shape units (α, structureβ and γ-cyclodextrin) with hydrophilic linked outer in α (1–4)surface to formand hydrophobica hollow, truncated-cone-shape internal cavity. This structure particular with structure hydrophilic is responsible outer surface for CDs and property hydrophobic of establishing internal specificcavity. Thisinteraction particular with structure a variety isof responsibledrug molecules; for CDs guest–host property inclusion of establishing complexes specific are thus interaction formed bywith trapping a variety the of drug drug into molecules; CD cavity guest–host [1–5]. Mole inclusioncular encapsulation complexes are of thusbioactive formed compounds by trapping in the CDsdrug has into achieved CD cavity pharmaceutical [1–5]. Molecular relevance encapsulation since ofthe bioactive physical, compounds chemical inand the biopharmaceutical CDs has achieved characteristicspharmaceutical of relevance guest molecules since the are physical, remarkably chemical improved. and biopharmaceutical CD inclusion complexes characteristics can increase of guest the solubilitymolecules of are insoluble remarkably drug improved. molecules CD and inclusion the antioxidant complexes properties, can increase can the improve solubility the of insolublechemical stability,drug molecules the biological and the activity antioxidant and the properties, bioavailab canility improveof guest substances, the chemical may stability, reduce/eliminate the biological the unpleasantactivity and smell the bioavailability and taste, may of guest prevent substances, drug–excipient may reduce or /eliminatedrug–drug the interactions unpleasant [6–15]. smell and β- cyclodextrintaste, may prevent (β-CD) drug–excipient is the most frequently or drug–drug used in interactions the pharmaceutical [6–15]. β field-cyclodextrin due to its (β availability,-CD) is the appropriatemost frequently internal used cavity in the pharmaceuticalsize for an important field due number to its availability, of drug appropriatesubstances and internal economic cavity advantages.size for an important β-CD is also number non-toxic, of drug biodegradable, substances and but economic it has a limited advantages. aqueousβ-CD solubility is also [2,4,16]. non-toxic, In orderbiodegradable, to enhance but its itsolubility, has a limited CD derivatives aqueous solubility have been [2 ,developed,4,16]. In order among to enhance them methylated its solubility, β-CDs CD [17,18].derivatives have been developed, among them methylated β-CDs [17,18]. Risperidone (abbreviated(abbreviated RSP RSP in thisin paper),this paper),3-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]- 3-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1- yl]ethyl]-2-methyl-6,7,8,9-tetrahydropyrido2-methyl-6,7,8,9-tetrahydropyrido [1,2-a]pyrimidin-4-one [1,2-a]pyrimidin-4-one(Figure (Figure1) is an 1) atypical is an atypical antipsychotic antipsychotic drug, drug,belonging belonging to the class to the of pyridopyrimidinesclass of pyridopyrimidines used in treating used schizophrenia,in treating schizophrenia, behavioral and behavioral psychological and psychologicalsymptoms of dementiasymptoms and of dementia irritability and associated irritability with associated autism [with19,20 autism]. It is [19,20]. a potent It inhibitoris a potent of inhibitorserotonin-2 of serotonin-2 (5TH2) and (5 dopamine-2TH2) and dopamine-2 (D2) receptors (D2) receptors in the brain. in the brain. RSP belongs RSP belongs to class to class II in II the in theBiopharmaceutics Biopharmaceutics Classification Classification System System (BCS); (BCS); it is it practically is practically insoluble insoluble in water in water and exhibitsand exhibits high highlipophilicity lipophilicity (log (logP of P 3.49) of 3.49) [19 ,[19,21,22].21,22]. RSP RSP presents presents the the ability ability to to form form polymorphs polymorphs [[19],19], thatthat can possess different different solubility, dissolution rates, affecting affecting thus the biopharmaceutical profile profile of drug substance [23]. [23]. O N O F N N N Figure 1. StructuralStructural formula of risperidone (RSP). Among the the different different strategies strategies aiming aiming at atimprov improvinging the the solubility solubility of drug of drug substances substances withwith low solubilitylow solubility and andhigh high permeability, permeability, inclusion inclusion complexation complexation with with CDs CDs is isa avaluable valuable approach approach [23]. [23]. Encapsulation of of RSP RSP in in CDs CDs has has been been mentioned mentioned in the in theseveral several papers; papers; inclusion inclusion complexes complexes of drug of withdrug β with-CD βand-CD hydroxypropyl- and hydroxypropyl-β-CD β(HP--CDβ (HP--CD)β -CD)have havebeen beeninvestigated investigated and andformulated formulated for parenteralfor parenteral administration administration and nasal and nasalapplication application [24,25], [24 solid,25], dispersion solid dispersion of risperidone of risperidone with methyl- with βmethyl--cyclodextrinβ-cyclodextrin
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