Inclusion complexes of 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin with 2-hydroxypropyl-(-cyclodextrin
solubility and antimicrobial activity
DOI:
https://doi.org/10.1590/s2175-97902022e20013Palavras-chave:
3-(3-(2-Chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin, 2-Hydroxypropyl-β-cyclodextrin, Inclusion complexes, Phase solubility, Antimicrobial activityResumo
The aim of the present study is to improve the solubility and antimicrobial activity of 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin by formulating its inclusion complexes with 2-hydroxypropyl-β-cyclodextrin in solution and in solid state. The phase solubility study was used to investigate the interactions between 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin and 2-hydroxypropyl-β-cyclodextrin and to estimate the molar ratio between them. The structural characterization of binary systems (prepared by physical mixing, kneading and solvent evaporation methods) was analysed using the FTIR-ATM spectroscopy. The antimicrobial activity of 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin and inclusion complexes prepared by solvent evaporation method was tested by the diffusion and dilution methods on various strains of microorganisms. The results of phase solubility studies showed that 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin formed the inclusion complexes with 2-hydroxypropyl-β-cyclodextrin of AP type. The solubility of 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin was increased 64.05-fold with 50% w/w of 2-hydroxypropyl-β-cyclodextrin at 37 oC. The inclusion complexes in solid state, prepared by the solvent evaporation method, showed higher solubility in purified water and in phosphate buffer solutions in comparison with 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin alone. The inclusion complexes prepared by solvent evaporation method showed higher activity on Bacillus subtilis and Staphylococcus aureus compared to uncomplexed 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin due to improved aqueous solubility, thus increasing the amount of available 3-(3-(2-chlorophenyl)prop-2-enoyl)-4-hydroxycoumarin that crosses the bacterial membrane.
Downloads
Referências
Abdel-Mottaleb MSA, Hamed E, Saif M, Hafez HS. Binding, and thermodynamics of β-cyclodextrin inclusion complexes with some coumarin laser dyes and coumarin-based enzyme substrates: a simulation study. J Incl Phenom Macrocycl Chem. 2018;92(3-4):319-27.
Abdul MM. UV-visible spectrophotometric method and validation of organic compounds. Eur J Eng Res Sci. 2018;3(3):8-11.
Agarwal R, Gupta V. Cyclodextrins - a review on pharmaceutical application for drug delivery. Int J Pharm Front Res. 2012;2(1):96-113.
Ammar H, Forgues-Fery S, El Gharbi R. UV/VIS absorption and fluorescence spectroscopic study of novel symmetrical biscoumarin dyes. Dyes Pigments. 2003;357(3):259-65.
Balouiri M, Sadiki M, Ibnsouda SK. Methods for in vitro evaluating antimicrobial activity: A review. J Pharm Anal. 2016;6(2):71-9.
Carneiro SB, Costa Duarte FÍ, Heimfarth L, Siqueira Quintans JS, Quintans-Júnior LJ, Veiga Júnior VFD, et al. Cyclodextrin-drug inclusion complexes: in vivo and in vitro approaches. Int J Mol Sci. 2019;20(3):1-23.
Cheirsilp B, Rakmai J. Inclusion complex formation of cyclodextrin with its guest and their applications. Biol Eng Med. 2016;2(1):1-6.
Committee for Medicinal Products for Human use. CHMP. Guideline on the Investigation of Bioequivalence. London: European Medicines Agency. 2010. 25 p.
Conceicao J, Adeoye O, Cabral-Marques HM, Lobo JMS. Cyclodextrins as drug carriers in pharmaceutical technology: The state of the art. Curr Pharm Des. 2018;24(13):1405-33.
Côté JF, Brouillette D, Desnoyers EJ, Rouleau JF, St-Arnaud JM, Perron G. Dielectric constants of acetonitrile, γ-butyrolactone, prolylene carbonate, and 1,2-dimethoxyethane as a function of pressure and temperature. J Solution Chem. 1996;25(12):1163-73.
Das KS, Rayabalaja R, David S, Gani N, Khanam J, Nanda A. Cyclodextrins - the molecular container. Res J Pharm Biol Chem Sci. 2013;4(2):1694-1720.
European Pharmacopoeia. Ph.Eur. 8. ed. European Directorate for the Quality of Medicine (EDQM) Council of Europe 2014;Strasbourg: 5 p.
European Pharmacopoeia. Ph.Eur. 8. ed. European Directorate for the Quality of Medicine (EDQM) Council of Europe. 2014;Strasbourg:229-31p.
Feigenbrugel V, Loew C, Calve SL, Mirabel P. Near-UV molar absorptivities of acetone, alachlor, metolachlor, diazinon and dichlorvos in aqueous solution. J Photochem Photobiol A. 2005;174(1):76-81.
Florence AT, Attwood D. Physicochemical principles of pharmacy. 4th ed. London: Pharmaceutical Press; 2006. 81 p.
Guidance for Industry: Waiver of In Vivo Bioavailability and Bioequivalence Studies for Immediate-Release Solid Oral Dosage Forms Based on a Biopharmaceutics Classification System 2017. Washington: U.S. Department of Health and Human Services, Food and Drug Administration Center for Drug Evaluation and Research. 2017. 1-19 p.
Gupta PK. Solutions and phase equilibria. In: Felton L, editor. Remington: essentials of pharmaceutics. 1st ed. London: Pharmaceutical Press ; 2013. p. 219-39.
Higuchi T, Connors AK. Phase solubility techniques. In: Reilly CN, editor. Advances in Analytical Chemistry and Instrumentation. New York: Wiley-Interscience; 1965. p. 117-212.
International Council for Harmonisation of technical requirements for pharmaceuticals for human use. ICH. ICH harmonised guideline. Impurities: guideline for residual solvents Q3C(R6) 2016. ICH expert working group. 2016. 1-40 p.
Iacovino R, Rapuano F, Caso JV, Russo A, Lavorgna M, Russo C, et al. β-Cyclodextrin inclusion complex to improve physicochemical properties of pipemidic acid: characterization and bioactivity evaluation. Int J Mol Sci . 2013;14(7):13022-41.
Issa MG, Ferraz HG. Intrinsic dissolution as a tool for evaluating drug solubility in accordance with the biopharmaceutics classification system. Dissolution Technol. 2011;18(3):6-13.
Jambhekar SS, Breen P. Cyclodextrins in pharmaceutical formulations II: solubilization, binding constant, and complexation efficiency. Drug Discovery Today. 2016:21(2):363-8.
Jayashree BS, Nigam S, Pai A, Chowdary PVR. Overview on the recently developed coumarinyl heterocycles as useful therapeutic agents. Arab J Chem. 2014;7(6):885-99.
Khalafi L, Rafiee M. Cyclodextrin based spectral changes. In: Radis-Baptista G, editor. An integrated view of the molecular recognition and toxinology - from analytical procedures to biomedical applications. London: InTech. 2013. p. 471-93.
Kulkarni MV, Patil VD. Studies on coumarins. J Arch Pharm (Weinheim). 1981;314(8):708-11.
Leclercq L. Interactions between cyclodextrins and cellular components: towards greener medical applications? Beilstein J Org Chem. 2016;12:2644-62.
Loftsson T, Brewster ME. Pharmaceutical applications of cyclodextrins: effects on drug permeation through biological membranes. J Pharm Pharmacol. 2011;63(9):1119-35.
Loftsson T, Brewster ME, Masson M. Role of cyclodextrins in improving oral drug delivery. Am J Drug Deliv. 2004;2(4):261-75.
Loftsson T, Hreinsdóttir D, Másson M. The complexation efficiency. J Inclusion Phenom Macrocyclic Chem. 2007;57(1-4):545-52.
Muankaew C, Loftsson T. Cyclodextrin-based formulations: a non-invasive platform for targeted drug delivery. Basic Clin Pharmacol Toxicol. 2018;122(1):46-55.
Ol’khovich MV, Sharapova AV, Lavrenov SN, Blokhina SV, Perlovich GL. Inclusion complexes of hydroxypropyl-βcyclodextrin with novel cytotoxic compounds: Solubility and thermodynamic properties. Fluid Phase Equilib. 2014;384:68-72.
Pralhad T, Rajendrakumar K. Study of freeze-dried quercetin-cyclodextrin binary systems by DSC, FT-IR, X-ray diffraction and SEM analysis. J Pharm Biomed Anal. 2004;34(2):333-9.
Sambasevam KP, Mohamad S, Sarih NM, Ismail NA. Synthesis and characterization of the inclusion complex of β-cyclodextrin and azomethine. Int J Mol Sci . 2013;14(2):3671-82.
Saokham P, Muankaew C, Jansook P, Loftsson T. Solubility of cyclodextrins and drug/cyclodextrin complexes. Molecules. 2018;23(5):1161-76.
Savić IM, Jočić E, Nikolić VD, Popsavin MM, Rakić SJ, Savić-Gajić IM. The effect of complexation with cyclodextrins on the antioxidant and antimicrobial activity of ellagic acid. Pharm Dev Technol. 2019;24(4):410-18.
Stuart BH. Infrared spectroscopy: fundamentals and applications. London: John Wiley and Sons. 2004. 71-93 p.
Špirtović-Halilović S, Salihović M, Džudžević-Čančar H, Trifunović S, Roca S, Softić Dž, et al. DFT study and microbiology of some coumarin-based compounds containing a chalcone moiety. J Serb Chem Soc. 2014;79(4):435-43.
Taniguchi M, Lindsey JS. Database of absorption and fluorescence spectra of (300 common compounds for use in photochemCAD. Photochem Photobiol. 2018;94(2):290-327.
Tran P, Pyo YC, Kim DH, Lee SE, Kim JK, Park JS. Overview of the manufacturing methods of solid dispersion technology for improving the solubility of poorly water-soluble drugs and application to anticancer drugs. Pharmaceutics. 2019;11(132):1-26.
Završnik D, Špirtović-Halilović S, Softić Dž. Synthesis, structure and antibacterial activity of 3-substituted derivatives of 4-hydroxycoumarin. Period Biol. 2011;113(1):93-7.
Downloads
Publicado
Edição
Seção
Licença
Copyright (c) 2022 Brazilian Journal of Pharmaceutical Sciences
Este trabalho está licenciado sob uma licença Creative Commons Attribution 4.0 International License.
All content of the journal, except where identified, is licensed under a Creative Commons attribution-type BY.
The on line journal has open and free access.
