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ارائه مدل جامع ترمودینامیکی برای پیش بینی حلالیت داروها در آب با استفاده از حلال‌های یوتکتیک عمیق به عنوان کمک حلال | ||
| شیمى کاربردى روز | ||
| دوره 20، شماره 74، فروردین 1404، صفحه 235-264 اصل مقاله (1.54 M) | ||
| نوع مقاله: مقاله علمی پژوهشی | ||
| شناسه دیجیتال (DOI): 10.22075/chem.2025.36862.2344 | ||
| نویسندگان | ||
| مائده سادات خیام نکویی؛ عاطفه رجبی؛ رضا حق بخش* | ||
| گروه مهندسی شیمی، دانشکده فنی و مهندسی ، دانشگاه اصفهان، اصفهان، ایران | ||
| تاریخ دریافت: 22 بهمن 1403، تاریخ بازنگری: 21 اردیبهشت 1404، تاریخ پذیرش: 28 خرداد 1404 | ||
| چکیده | ||
| باتوجه‌به پایین بودن نسبی میزان حلالیت داروها در آب، نیاز به استفاده از روش‌هایی برای افزایش میزان حلالیت داروها در آب در صنایع دارویی محسوس می‌باشد. از جمله این روش‌ها استفاده از حلال‌های کمکی است. در میان ترکیبات مختلف به‌عنوان کمک حلال، حلال‌های یوتکتیک عمیق به دلیل سازگاری با محیط‌زیست، ارزان بودن و قابلیت مهندسی شدن خواص آن، پتانسیل گسترده‌ای در صنایع داروسازی یافته‌اند. باتوجه‌به تعداد و تنوع فراوان انواع داروها و حلال‌های یوتکتیک عمیق، امکان انجام مطالعات آزمایشگاهی برای تعیین میزان اثرگذاری کمک حلال‌ها بر روی حلالیت انواع داروها امکان‌پذیر نمی‌باشد؛ لذا محققان با استفاده از ارائه مدل‌های ترمودینامیکی می‌توانند میزان افزایش حلالیت داروها در آب را تخمین بزنند. در این پژوهش به بررسی عملکرد 5 مدل ترمودینامیکی پرداخته شده است. مدل‌های موجود، تجربی هستند و در نتیجه قابلیت پیش‌بینی ندارند؛ لذا برای حل این مشکل، مدل خیام- رجبی-حق بخش (KRH) برای اولین بار به‌عنوان اولین مدل پیش‌بینی‌کننده جامع و دقیق برای تخمین میزان حلالیت انواع داروها در آب به کمک حلال‌های یوتکتیک عمیق به‌عنوان کمک حلال ارائه گردید. برای توسعه این مدل از بانک داده وسیعی شامل 1489 داده آزمایشگاهی برای 13 داروی متنوع و 17 حلال یوتکتیک عمیق استفاده گردید. میزان درصد AARD% این مدل برابر 00/13 که نشان‌دهنده دقت بالای این مدل می‌باشد. مطالعات آماری بر روی مدل KRH نشان‌دهنده رفتار قابل‌قبول و بدون سوگیری در تمام داروها و حلال‌های یوتکتیک عمیق بررسی شده می‌باشد. این مدل به دلیل جامعیت، دقت و نیازنداشتن به داده‌های آزمایشگاهی برای تخمین، کاربرد گسترده‌ای برای استفاده توسط محققان را دارد. | ||
| کلیدواژه‌ها | ||
| حلالیت دارو؛ حلال‌های سبز؛ حلال‌های کمکی؛ حلال‌های یوتکتیک عمیق؛ مدل‌های ترمودینامیکی | ||
| عنوان مقاله [English] | ||
| Proposing a comprehensive thermodynamic model for the prediction of drugs solubilities in water using Deep Eutectic Solvents as co-solvents | ||
| نویسندگان [English] | ||
| Maedeh Sadat Khayam Nekouei؛ Atefe Rajabi؛ Reza Haghbakhsh | ||
| Department of Chemical Engineering, Faculty of Engineering, University of Isfahan, Isfahan, Iran. | ||
| چکیده [English] | ||
| Given the common challenge of low solubility of many drugs in water, it is vital to implement novel methods to improve it. One method that is widely used across various applications is the use of co-solvents. In particular, Deep Eutectic Solvents have been recognized for their potential in the pharmaceutical industries. This potential is due to their environmental compatibility, cost-effectiveness, and desirable properties. Due to the large number and variety of deep eutectic solvents, it is not possible to perform experimental studies to determine the effect of Deep Eutectic Solvents on the solubility of drugs in water. Thus, it is vital to have thermodynamic models, to help researchers to estimate how the co-solvents enhance the solubility of drugs. This research investigates the performance of five relevant thermodynamic models. The investigated models are all empirical and require regression on the experimental data of each system to be used, which makes them non-predictive. Therefore, to overcome this issue, for the first time, the Khayam-Rajabi-Haghbakhsh model (KRH) has been developed as the first comprehensive and accurate predictive model for estimating the solubility of various drugs in water considering Deep Eutectic Solvents as co-solvents. For the development of this model, a comprehensive data bank including 1489 experimental data points for 13 different drugs and 17 Deep Eutectic Solvents has been used. The AARD% of this model has been calculated to be 13.00, indicating a high level of accuracy. Statistical analysis demonstrates acceptable and unbiased performance across all Deep Eutectic Solvents and drugs investigated. This model is widely utilized for various drug systems, water, and Deep Eutectic Solvents as co-solvents due to its comprehensiveness, accuracy, and capability to estimate drug solubility without needing experimental data. | ||
| کلیدواژه‌ها [English] | ||
| Drug solubility, Green solvents, Co-solvents, Deep Eutectic Solvents, Thermodynamic models | ||
| مراجع | ||
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[1] Sharma, A., & Sriganesan, P. (2018). Formulation development and optimization of fast dissolving film containing carvedilol nanocrystals for improved bioavailability. Journal of Drug Delivery and Therapeutics, 8(6),74-81.
[2] Taylor, K.M.G., & Aulton, M.E. (2021) Aulton's Pharmaceutics, 6th Edition, Elsevier Ltd.
[3] Kumar Janakiraman, A., Sumathi, B., Mohamed Saleem, T., Ramkanth, S., Odaya Kumar, P., & Venkatachalam, G. (2017). Design and evaluation of Carvedilol nanocrystals sustained release tablets. Journal of Applied Pharmaceutical Science, 7 (04), 061-068.
[4] Blagden, N., de Matas, M., Gavan, P.T., & York, P. (2007). Crystal engineering of active pharmaceutical ingredients to improve solubility and dissolution rates. Advanced Drug Delivery Reviews, 59 (2007), 617-630.
[5] Yuvaraja, K., & Khanam, J. (2014). Enhancement of carvedilol solubility by solid dispersion technique using cyclodextrins, water soluble polymers and hydroxyl acid. Journal of Pharmaceutical and Biomedical Analysis, 96(2014), 10-20.
[6] Sharma, A., & Jain, C.P. (2010). Preparation and characterization of solid dispersions of carvedilol with PVP K30. Res Pharm Sci, 5(1), 49-56.
[7] Planinšek, O., Kovačič, B., Vrečer, F. (2011). Carvedilol dissolution improvement bypreparation of solid dispersions with porous silica. International Journal of Pharmaceutics, 406(2011), 41–48.
[8] Chakraborty, S., Shukla, D., Jain, A., Mishra, B., & Singh, S. (2009). Assessment of solubilization characteristics of different surfactants for carvedilol phosphate as a function of Ph. Journal of Colloid and Interface Science, 335(2009), 242-249.
[9] Jouyban, a. (2019). Review of the Cosolvency Models for Predicting Drug Solubility in Solvent Mixtures: An Update. Journal of Pharmacy & Pharmaceutical Sciences. 22(2019), 466-485.
[10] Mokhtarpor, M., Shekaari, H., & Zafarani moatar, M.T. (2020). Measurements of the naproxen solubility in some choline-based deep eutectic solvents as novel green solvents in the pharmaceutical industry and the performance of the UNIIFAC model in this systems. Applied Chemistry Today, 15(54), 289-298. (in persian )
[11] Paiva, A., Craveiro, R., Aroso, I., Martins, M., L. Reis, R., Duarte, A.R. (2014). Natural Deep Eutectic Solvents - Solvents for the 21st Century. ACS Sustainable Chemistry & Engineering, 2(5), 1063-1071.
[12] Zarei, A., Haghbakhsh, R., & Raeissi, S. (2023). Overview and thermodynamic modelling of deep eutectic solvents as co-solvents to enhance drug solubilities in water. European Journal of Pharmaceutics and Biopharmaceutics, 193(2023), 1–15.
[13] Shekaari, H., Zafarani-Moattar, M.T., & Mokhtarpour, M. (2018). Experimental determination and correlation of acetaminophen solubility in aqueous solutions of choline chloride based deep eutectic solvents at various temperatures. Fluid Phase Equilibria, 462(2018), 100-110.
[14] Cao, J., Cao, J., Wang, H., Chen, L., Cao, F., & Su, E. (2020). Solubility improvement of phytochemicals using (natural) deep eutectic solvents and their bioactivity evaluation. Journal of Molecular Liquids, 318(2020), 113997.
[15] Tang, N., Zhong, J., & Yan, W. (2016). Solubilities of Three Flavonoids in Different Natural Deep Eutectic Solvents at T = (288.15 to 328.15) K. Journal of Chemical & Engineering Data, 61(12), 4203-4208.
[16] Mokhtarpour, M., Shekaari, H., Zafarani-Moattar, M.T., & Golgoun, S. (2020). Solubility and solvation behavior of some drugs in choline based deep eutectic solvents at different temperatures. Journal of Molecular Liquds, 297, 111799.
[17] Shekaari, H., Mokhtarpour, M., Faraji, S., & Zafarani-Moattar, M.T. (2021). Enhancement of curcumin solubility by some choline chloride-based deep eutectic solvents at different temperatures. Fluid Phase Equilibria, 532, 1127917.
[18] Lu, C., Cao, J., Wang, N., & Su, E. (2016). Significantly improving the solubility of non-steroidal anti-inflammatory drugs in deep eutectic solvents for potential non-aqueous liquid administration. Medchemcomm, 7, 955-959.
[19] Zarghampour, A., Moradi, M., Martinez, F., Hemmati, S., Rahimpour, E., & Jouyban, A. (2021). Solubility study of mesalazine in the aqueous mixtures of a deep-eutectic solvent at different temperatures. Journal of Molecular Liquids, 336, 116300.
[20] Tajmir, F., & Roosta, A. (2020). Solubility of cefixime in aqueous mixtures of deep eutectic solvents from experimental study and modelling. Journal of Molecular Liquids, 303, 112636.
[21] Sepúlveda-Orellana, B., Gajardo-Parra, N.F., Do, H.T., Pérez Correa, J.R., Held, C., Sadowski, G., & Canales, I. R. (2021). Measurement and PC-SAFT modeling of the solubility of Gallic acid in aqueous mixtures of deep eutectic solvents. Journal of Chemical & Engineering Data, 66(2), 958-967.
[22] Jeliński, T., & Cysewski, P. (2018). Application of a computational model of natural deep eutectic solvents utilizing the COSMO-RS approach for screening of solvents with high solubility of rutin. Journal of Molecular Modeling, 24, 180.
[23] Jeliński, T., Przybyłek, M., & Cysewski, P. (2019). Solubility advantage of sulfanilamide and sulfacetamide in natural deep eutectic systems: experimental and theoretical investigations. Drug Development and Industrial Pharmacy, 45, 1120-1129.
[24] Cysewski, P., & Jeliński, T. (2019). Optimization, thermodynamic characteristics and solubility predictions of natural deep eutectic solvents used for sulfonamide dissolution. International Journal of Pharmaceutics, 570, 118682.
[25] Shekaari, H., Zafarani-Moattar, M.T., Mokhtarpour, M., & Faraji, S. (2022). Effect of some choline based deep eutectic solvents on volumetric and ultrasonic properties of gabapentin drug in water at T = (288.15 to 318.15) K. Journal of Molecular Liquids, 346, 117073.
[26] Hayyan, M., Looi, C.Y., Hayyan, A., Wong, W.F., & Hashim, M.A. (2015). In vitro and in vivo toxicity profiling of ammonium-based deep eutectic solvents. PLoS One, 10(2), e0117934.
[27] Bakirtzi, C., Triantafyllidou, K., & Makris, D.P. (2016). Novel lactic acid-based natural deep eutectic solvents: Efficiency in the ultrasound-assisted extraction of antioxidant polyphenols from common native Greek medicinal plants. Journal of Applied Research on Medicinal and Aromatic Plants, 3(3), 120-127.
[28] Hajebrahimi, & S., Roosta, A. (2020). Solubility of acetaminophen in aqueous solutions of three natural deep eutectic solvents (NADESs) and individual components of the NADESs. Journal of Molecular Liquids, 316, 113867.
[29] Moradi, M., & Jouyban, A. (2022). Study of naproxen dissolution in the mixtures of a cholinebased deep eutectic solvent + water at different temperatures. Journal of Molecular Liquids, 345, 117023.
[30] Mokhtarpour, M., Shekaari, H., Martinez, F., & Zafarani-Moattar, M.T. (2019). Effect of tetrabutylammonium bromide-based deep eutectic solvents on the aqueous solubility of indomethacin at various temperatures: measurement, modeling, and prediction with three-dimensional Hansen solubility parameters. AAPS PharmSciTech, 20, 204.
[31] Shayanfar, A., Fakhree, M.A.A., Acree, W.E., & Jouyban, A. (2009). Solubility of lamotrigine, diazepam, and clonazepam in ethanol + water mixtures at 298.15 K. Journal of Chemical & Engineering Data, 54(3), 1107-1109.
[32] Golgoun, S., Mokhtarpour, M., & Shekaari, H. (2021). Solubility enhancement of betamethasone, meloxicam and piroxicam by use of choline-based deep eutectic solvents. Journal of Pharmaceutical Sciences, 27(1), 86-101.
[33] Mokhtarpour, M., Samberan, P.A., Golmohammadi, B., Fattah, S.G., Khorsandi, M., Behboudi, M. R., Shekaari, H., & Zafarani-Moattar, M.T. (2021). Paracetamol in aqueous solutions of polymeric-based deep eutectic solvents; solubility, partitioning, volumetric and compressibility studies. J. Chem. Thermodynamics, 158, 106390.
[34] WILLIAMS, N.A., & AMIDON, G.L. (1982). Excess Free Energy Approach to the Estimation of Solubility in Mixed Solvent Systems 11: Ethanol-Water Mixtures. Journal of Pharmaceutical Sciences, 73(1),14-18.
[35] Machatha, S.G., Bustamante, P., & Yalkowsky, S.H. (2004). Deviation from linearity of drug solubility in ethanol/water mixtures. International Journal of Pharmaceutics, 283(1-2), 83-88.
[36] Jouyban, A., Khoubnasabjafari, M., & Acree, W.E. (2005). Mathematical representation of solute solubility in binary mixture of supercritical fluids by the Jouyban-Acree model. Pharmazie, 60(7) ,527-529.
[37] Jouyban, A., Chew N. Y. K., Chan H. K., Khoubnasabjafari M., Acree W.E. (2006), "Solubility prediction of salicylic acid in water-ethanol-propylene glycol mixtures using the Jouyban-Acree model ", Pharmazie 61,318-321.
[38] Wang H., & Zhang, X. (2019). Estimation of the solubility with cosolvent composition by combinated of the Williams–Amidon model with quasi virial coefficient. Journal of Chemical Engineering, 15(1), e2340.
[39] Khorsandi, M., Shekaari, H., & Mokhtarpour, M. (2020). Measurement and correlation of coumarin solubility in aqueous solution of acidic deep eutectic solvents based on choline chloride. Fluid Phase Equilibria, 524,112788.
[40] Kamal, A., & Haghtalab, A. (2020). Experimental and thermodynamic modeling of cefixime trihydrate solubility in an aqueous deep eutectic system. Journal of Molecular Liquids, 304, 112727.
[41] Sepúlveda-Orellana, B., Gajardo-Parra, N.F., Do, H.T., Pérez Correa, J.R., Held, C., Sadowski, G., & Canales, I. R. (2021). Measurement and PC-SAFT modeling of the solubility of Gallic acid in aqueous mixtures of deep eutectic solvents. Journal of Chemical & Engineering Data, 66(2), 958-967.
[42] Mokhtarpour, M., Shekaari, H., Martinez, F., & Zafarani-Moattar, M.T. (2019). Study of naproxen in some aqueous solutions of choline-based deep eutectic solvents: Solubility measurements, volumetric and compressibility properties. International Journal of Pharmaceutics, 564, 197-206.
[43] Mokhtarpour, M., Shekaari, H., Martínez, F., & Zafarani-Moattar, M.T. (2019). Performance of local composition models to correlate the aqueous solubility of naproxen in some choline based deep eutectic solvents at T = (298.15-313.15) K. Journal of Pharmaceutical Sciences, 25(3), 244-253.
[44] Jouyban-Gharamaleki, A., Valaee, L., Barzegar-Jalali, M., Clark, B.J., & Acree, W.E. (1999). Comparison of various cosolvency models for calculating solute solubility in water–cosolvent mixtures. International Journal of Pharmaceutics, 177(1), 93-101.
[45] Jouyban, A., & Acree, W.E. (2006). In silico prediction of drug solubility in water-ethanol mixtures using JouybanAcree model. Journal of Pharmacy & Pharmaceutical Sciences, 9(2), 2662-269.
[46] Mohammadian, E., Jouyban, A., Barzegar-Jalali, M., Acree, W.E., & Rahimpour, E. (2019). Solubilization of naproxen: Experimental data and computational tools. Journal of Molecular Liquids, 288, 110985.
[47] Hildebrand, J. H., & Scott, R.I. (1950). TheSolutilitgd Nonelectrolytes. American Chemical Society Zfmgraph 3rd Edition.
[48] Chertkoff, M. J., A. N. Martin (1960) "The Solubility of Benzoic Acid in Mixed Solvents", Journal of Chemical & Engineering Data 49, 444-447, https://doi.org/10.1021/je060408x ????
[49] Adjei, A., Newburger, J., & Martin, A. (1980). Extended hildebrand approach: Solubility of caffeine in dioxane–water mixtures. Journal of Pharmaceutical Sciences, 69(6) , 659-661.
[50] Haghbakhsh, R., Raeissi, S., & C. Duarte, A.R. (2021). Group contribution and atomic contribution models for the prediction of various physical properties of deep eutectic solvents. Journal of nature, 11, 6684.
[51] Joback, K.G. (1982). A unified approach to physical property estimation using multivariate statistical techniques. Massachusetts Institute of Technology. | ||
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آمار تعداد مشاهده مقاله: 57 تعداد دریافت فایل اصل مقاله: 31 |
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