Improving pharmacologically relevant properties of sulfasalazine loaded in γ-cyclodextrin-based metal organic framework

Mikhail Agafonov; Anna Garibyan; Irina Terekhova

Journal of Industrial and Engineering Chemistry, Vol.106, 189-197, February, 2022

DOI10.1016/j.jiec.2021.10.028 Export Citation

Improving pharmacologically relevant properties of sulfasalazine loaded in γ-cyclodextrin-based metal organic framework

Mikhail Agafonov, Anna Garibyan, and Irina Terekhova^†

G.A. Krestov Institute of Solution Chemistry of RAS, 1 Akademicheskaya Str., 153045 Ivanovo, Russian Federation

E-mail:

The aim of this work was to improve the dissolution properties of poorly soluble drug sulfasalazine (SSZ) by encapsulation in the metal organic framework based on γ-cyclodextrin (γCD-MOF). Loading of SSZ in the framework was successfully performed by impregnation and co-crystallization methods. The obtained composites γCD-MOF/SSZ were investigated by several methods, including PXRD, N2 physisorption, FTIR, solid 13C NMR, SEM, and DLS. The SSZ release from γCD-MOF was examined with in vitro dissolution studies using simulated gastric and intestinal fluids. Sulfasalazine loaded in γCD-MOF exhibited the improved release. Release profiles of SSZ were compared and analyzed using different kinetic models. Some efforts were made to reduce the burst release of SSZ from γCD-MOF in the phosphate buffer (pH 6.8). Influence of γ-cyclodextrin on the membrane permeability of SSZ was examined.

Keywords:Cyclodextrin;Metal organic framework;Sulfasalazine;Dissolution;Permeability

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[Referenced By]

[1] Malaekehpoor S, Derakhshandeh K, Haddadi R, Nourian A, Ghorbani- Vaghei R, Polym. Chem., 11, 2408 (2020)

[2] Enc H, Cakit B, Nacir B, Saracoglu M, Kacar M, Erdem H, Clin. Rheumatol., 26, 1104 (2007)

[3] MacMullan PA, Madigan AM, Paul N, Peace A, Alagha A, Nolan KB, McCarthy GM, Kenny D, Clin. Rheumatol., 35, 447 (2016)

[4] da Costa MAB, Villa ALV, de C da Barros SA, Ricci-J?nior E, Santos EP, Braz. J. Pharm. Sci., 51, 449 (2015)

[5] Sabha SM, Sarkar R, Int. J. Womens Dermatol., 6, 191 (2020)

[6] Clarysse S, Brouwers J, Tack J, Annaert P, Augustijns P, Eur. J. Pharm. Sci., 43(4), 260 (2011)

[7] Akash M, Rehman K, Chen S, Polym. Rev., 55(3), 371 (2015)

[8] Meng Q, Zhong S, He S, Gao Y, Cui X, J. Ind. Eng. Chem., 99, 98 (2021)

[9] Akash M, Rehman K, Chen S, Pharm. Dev. Technol., 21(3), 367 (2015)

[10] Deshmukh R, Harwansh RK, Paul SD, Shukla R, J. Drug Deliv. Sci. Technol., 55 (2020)

[11] Aghaei M, Erfani-Moghadam V, Daneshmandi L, Soltani A, Abdolahi N, Cordani M, Yahyazadeh A, Rad SM, Tavassoli S, Balakheyli H, J. Mol. Struct., 1230 (2021)

[12] Sawangrat K, Morishita M, Kusamori K, Katsumi H, Sakane T, Yamamoto A, J. Pharm. Sci., 107, 2946 (2018)

[13] Volkova T, Kumeev R, Kochkina N, Terekhova I, J. Mol. Liq., 289 (2019)

[14] He S, Wu L, Li X, Sun H, Xiong T, Liu J, Huang C, Xu H, Sun H, Chen W, Gref R, Zhang J, Acta Pharm. Sin. B, (2021).

[15] Tian B, Hua S, Liu J, Carbohydr. Polym., 232 (2020)

[16] Smaldone RA, Forgan RS, Furukawa HH, Gassensmith JJ, Slawin AM, Yaghi OM, Stoddart JF, Angew. Chem. Int. Ed., 49(46) (2010)

[17] Karel KJ, Ferris DP, Holcroft JM, Kandela I, Stern CL, Nassar MS, Botros YY, Stoddart JF, Mol. Pharm., 14, 1831 (2017)

[18] Zhou Y, Niu B, Wu B, Luo S, Fu J, Zhao Y, Quan G, Pan X, Wu C, Acta Pharm. Sin. B, 10(12), 2404 (2020)

[19] Zhou Y, Zhao Y, Niu B, Luo Q, Zhang Y, Quan G, Pan X, Wu C, Int. J. Pharm., 588 (2020)

[20] Zhou Y, Zhang M, Wang C, Ren X, Guo T, Cao Z, Zhang J, Sun L, Wu L, Int. J. Pharm., 606 (2021)

[21] Kritskiy I, Volkova T, Surov A, Terekhova I, Carbohydr. Polym, 216, 224 (2019)

[22] Lia X, Porcino M, Martineau-Corcos C, Guoe, Xion T, Zhu W, Patriarche G, P?choux C, Perronne B, Hassan A, K?mmerle R, Michelet A, Zehnacker- Rentien A, Zhang J, Gref R, Int. J. Pharm., 585 (2020)

[23] Chen X, Guo T, Zhang K, Chen J, Wang C, Ren X, Wang Q, Yang Y, Liu C, Tan W, Gui S, Wu L, Zhang J, Acta Pharm. Sin. B, (2021).

[24] di Cagno M, Bibi HA, Bauer-Brandl A, Eur. J. Pharm. Sci., 73, 29 (2015)

[25] de J. Vel?squez-Hern?ndez M, Linares-Moreau M, Astria E, Carraro F, Alyami MZ, Khashab NM, Sumby CJ, Doonan CJ, Falcaro P, Coord. Chem. Rev., 429 (2021)

[26] Naeimi S, Faghihian H, Water Environ. J, (2018).

[27] Fu J, Zhu J, Wang Z, Wang Y, Wang S, Yan R, Xu Q, J. Colloid Interface Sci., 542, 123 (2019)

[28] Vijayakumar G, Tamilarasan R, Dharmendirakumar M, J. Mater. Environ. Sci., 3(1), 157 (2012)

[29] Nguyen C, Do DD, Carbon, 39, 1327 (2001)

[30] Ho YS, McKay G, Process Biochem., 34(5), 451 (1999)

[31] Harrache Z, Abbas M, Aksil T, Trari M, Microchem. J., 144, 180 (2019)

[32] Refat MS, El-Korashy SA, El-Deen IM, El-Sayed SM, Drug Test. Anal., 3(2), 116 (2011)

[33] Mehmood Y, Riaz H, Barkat K, Yousaf H, Malik AR, Raza SA, J. Polym. Res., 26 (2019)

[34] Agafonov M, Volkova T, Kumeev R, Chibunova E, Terekhova I, J. Mol. Liq., 274, 770 (2019)

[35] Y��lmaz H, Ustun Z, Demiralay EC, J. Iran. Chem. Soc., 13, 103 (2016)

[36] Fagerberg JH, Zarmpi P, Jabbar H, Fotaki N, J. Pharm. Sci., 110, 186 (2021)

[37] Li L, Frey M, Browning KJ, J. Eng. Fibers Fabr., 5 (2010)

[38] Korsmeyer RW, Gurny R, Doelker E, Buri P, Peppas NA, Int. J. Pharm., 15(1), 25 (1983)

[39] Wang S, Liu R, Fu Y, Kao WJ, Expert Opin. Drug Deliv., 17(9), 1289 (2020)

[40] Yoo J, Won Y, ACS Biomater. Sci. Eng., 6(11), 6053 (2020)

[41] Rajabi-Siahboomi AR, Bowtell RW, Mansfield P, Davies MC, Melia CD, Pharm. Res., 13, 376 (1996)

[42] Efentakis M, Pagoni I, Vlachou M, Avgoustaki K, Int. J. Pharm., 339, 66 (2007)

[43] Zhou Y, Luo S, Niu B, Wu B, Fu J, Zhao Y, Singh V, Lu C, Quan G, Pan X, Zhang J, Wu C, ACS Biomater. Sci. Eng., 5(10), 5180 (2019)

[44] Kuranov D, Chibunova E, Volkova T, Terekhova I, Russ. J. Gen. Chem., 88, 1325 (2018)