Silibinin solubilization: combined effect of co-solvency and inclusion complex formation

References

• Panapisal V, Charoensri S, Tantituvanont A. Formulation of microemulsion systems for dermal delivery of silymarin. AAPS PharmSciTech. 2012;13(2):389–399. doi: 10.1208/s12249-012-9762-y.
   PubMed Web of Science ®Google Scholar
• Kren V, Walterová D. Silybin and silymarin- new effects and applications. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2005;149(1):29–41. doi: 10.5507/bp.2005.002.
   PubMedGoogle Scholar
• Singh RP, Raina K, Sharma G, et al. Silibinin inhibits established prostate tumor growth, progression, invasion, and ­metastasis and suppresses tumor angiogenesis and epithelial-mesenchymal transition in transgenic adenocarcinoma of the mouse prostate model mice. Clin Cancer Res. 2008;14(23):7773–7780. doi: 10.1158/1078-0432.CCR-08-1309.
   PubMed Web of Science ®Google Scholar
• Tan W, Lu J, Huang M, et al. Anti-cancer natural products isolated from chinese medicinal herbs. Chin Med. 2011;6(1):27. doi: 10.1186/1749-8546-6-27.
   PubMed Web of Science ®Google Scholar
• Singh RP, Raina K, Deep G, et al. Silibinin suppresses growth of human prostate carcinoma PC-3 orthotopic xenograft via activation of extracellular signal-regulated kinase 1/2 and inhibition of signal transducers and activators of transcription signaling. Clin Cancer Res. 2009;15(2):613–621. doi: 10.1158/1078-0432.CCR-08-1846.
   PubMed Web of Science ®Google Scholar
• Tiwari P, Kumar A, Balakrishnan S, et al. Silibinin-induced apoptosis in MCF7 and T47D human breast carcinoma cells involves caspase-8 activation and mitochondrial pathway. Cancer Invest. 2011;29(1):12–20. doi: 10.3109/07357907.2010.535053.
   PubMed Web of Science ®Google Scholar
• Zohreh J, Nasrin M, Beate R, et al. Silibinin to improve cancer therapeutics, as an apoptotic inducer, autophagy modulator, cell cycle inhibitor, and microRNAs regulator. Life Sci. 2018;213:236–247.
   PubMed Web of Science ®Google Scholar
• Silibinin Clinical Trials. 2023. https//www.clinicaltrials.gov/search?term=Silibinin&aggFilters=phase4%203%202%201%200
   Google Scholar
• Sahibzada MUK, Sadiq A, Khan S, et al. Fabrication, characterization and in vitro evaluation of silibinin nanoparticles: an attempt to enhance its oral bioavailability.Drug Des Devel Ther. 2017;11:1453–1464. doi: 10.2147/DDDT.S133806.
   PubMed Web of Science ®Google Scholar
• Li A, Yalkowsky SH. Solubility of organic solutes in ethanol/water mixtures. J Pharm Sci. 1994;83(12):1735–1740. doi: 10.1002/jps.2600831217.
   PubMed Web of Science ®Google Scholar
• Kim JIY, Kim S, Papp M, et al. Hydrotropic solubilization of poorly water-soluble drugs. J Pharm Sci. 2010;99(9):3953–3965. doi: 10.1002/jps.22241.
   PubMed Web of Science ®Google Scholar
• Charumanee S, Okonogi S, Sirithunyalug J, et al. Effect of cyclodextrin types and co-solvent on solubility of a poorly water soluble drug. Sci Pharm. 2016;84(4):694–704. doi: 10.3390/scipharm84040694.
   PubMed Web of Science ®Google Scholar
• Li S, Madan P, Lin S. Effect of ionization of drug on drug ­solubilization in SMEDDS prepared using capmul MCM and caprylic acid. Asian J Pharm Sci. 2017;12(1):73–82. doi: 10.1016/j.ajps.2016.10.001.
   PubMed Web of Science ®Google Scholar
• Farías T, de Ménorval LC, Zajac J, et al. Solubilization of drugs by cationic surfactants micelles: conductivity and 1H NMR experiments. Colloids Surfaces A Physicochem Eng Asp. 2009;345(1–3):51–57. doi: 10.1016/j.colsurfa.2009.04.022.
   Web of Science ®Google Scholar
• Abolghasem J. HandBook of solubility data for pharmaceuticals. New York: CRC Press; 2010.
   Google Scholar
• Gharbia S, Balta C, Herman H, et al. Enhancement of silymarin anti-fibrotic effects by complexation with hydroxypropyl (HPBCD) and randomly methylated (RAMEB) β -Cyclodextrins in a mouse model of liver fibrosis. Front Pharmacol. 2018;9:883. doi: 10.3389/fphar.2018.00883.
   PubMed Web of Science ®Google Scholar
• Hasson KJ. Complexation of diclofenac sodium with hydroxy propyl beta- cyclodextrin improves its solubility and stability in ampoule solution which is determined by HPLC. J Pharm Res Rev. 2018;2:1–9.
   Google Scholar
• Rawat S, Jain SK. Solubility enhancement of celecoxib using b -cyclodextrin inclusion complexes. Eur J Pharm Biopharm. 2004;57(2):263–267. doi: 10.1016/j.ejpb.2003.10.020.
   PubMed Web of Science ®Google Scholar
• Challa R, Ahuja A, Ali J, et al. Cyclodextrins in drug delivery: an updated review. AAPS PharmSciTech. 2005;6(2):E329–57. doi: 10.1208/pt060243.
   PubMed Web of Science ®Google Scholar
• Wahyuni W, Fristiohady A, Malaka MH, et al. Effects of indonesian marine sponges ethanol extracts on the lipid profile of hyperlipidemic rats. J Appl Pharm Sci. 2019;9:1–8.
   Google Scholar
• Li P, Zhao L, Yalkowsky SH. Combined effect of cosolvent and cyclodextrin on solubilization of nonpolar drugs. J Pharm Sci. 1999;88(11):1107–1111. doi: 10.1021/js990159d.
   PubMed Web of Science ®Google Scholar
• Ansari M. Investigations of polyethylene glycol mediated ternary molecular inclusion complexes of silymarin with beta cyclodextrins. J Appl Pharm Sci. 2015;5:26–31.
   Google Scholar
• Shakeel F, Anwer K. Dissolution thermodynamics and solubility of silymarin in PEG 400-water mixtures at different temperatures. DRUG Dev Ind Pharm. 2015;9045:1–5.
   Google Scholar
• Shakeel F, Anwer K, Shazly GA, et al. Measurement and correlation of solubility of bioactive compound silymarin in five different green solvents at 298.15 K to 333.15 K. J Mol Liq. 2014;195:255–258. doi: 10.1016/j.molliq.2014.02.039.
   Web of Science ®Google Scholar
• Javed S, Kohli K, Ali M. Reassessing bioavailability of silymarin. Altern Med Rev. 2011;16(3):239–249.
   PubMed Web of Science ®Google Scholar
• Lambora A, Gupta K, Chopra K. Genetic algorithm – a literature review. 2019 International Conference on Machine Learning, Big Data, Cloud and Parallel Computing. 2019. p. 380–384.
   Google Scholar
• Yalkowsky SH, Roseman TJ. Solubilization of drugs by Co-solvents. In: Yalkowsky SH, editor. Tech solubilization drugs chapter 3. New York: Dekker; 1981. p. 91–134.
   Google Scholar
• He Y, Li P, Yalkowsky SH. Solubilization of fluasterone in ­cosolvent/cyclodextrin combinations. Int J Pharm. 2003;264(1–2):25–34. doi: 10.1016/s0378-5173(03)00389-2.
   PubMedGoogle Scholar
• Bai TC, Yan GB, Hu J, et al. Solubility of silybin in aqueous poly(ethylene glycol) solution. Int J Pharm. 2006;308(1–2):100–106. doi: 10.1016/j.ijpharm.2005.10.032.
   PubMedGoogle Scholar
• Orellano MS, Porporatto C, Silber JJ, et al. AOT reverse micelles as versatile reaction media for chitosan nanoparticles synthesis. Carbohydr Polym. 2017;171:85–93. doi: 10.1016/j.carbpol.2017.04.074.
   PubMed Web of Science ®Google Scholar
• Giron D, Goldbronn C, Mutz M, et al. Solid state characterizations of pharmaceutical hydrates. J Therm Anal Calorim. 2002;68(2):453–465. doi: 10.1023/A:1016031517430.
   Web of Science ®Google Scholar
• Yao WW, Bai TC, Sun JP, et al. Thermodynamic properties for the system of silybin and poly(ethylene glycol) 6000. Thermochim Acta. 2005;437(1-2):17–20. doi: 10.1016/j.tca.2005.06.012.
   Web of Science ®Google Scholar
• ICH harmonized Tripartite Guideline. 20056. Validation of analytical procedures: text and methodology Q2(R1). International conference on harmonization of technical requirements for registration of pharmaceuticals for human use.
   Google Scholar
• Heller J, Park M, Baker RW. Theory and practice of controlled drug delivery from bioerodible polymers [internet]. In: Baker RW, editor. Controlled release of bioactive materials. New York: Academic Press, Inc.; 1980.
   Google Scholar
• Bhattacharjee S. Understanding the burst release phenomenon: toward designing effective nanoparticulate drug-delivery systems. Ther Deliv. 2021;12(1):21–36. doi: 10.4155/tde-2020-0099.
   PubMed Web of Science ®Google Scholar
• Nguyen MH, Yu H, Dong B, et al. A supersaturating delivery system of silibinin exhibiting high payload achieved by amorphous nano-complexation with chitosan. Eur J Pharm Sci. 2016;89:163–171. doi: 10.1016/j.ejps.2016.04.036.
   PubMed Web of Science ®Google Scholar
• Biedermann D, Vavříková E, Cvak L, et al. Chemistry of silybin. Nat Prod Rep. 2014;31(9):1138–1157. doi: 10.1039/c3np70122k.
   PubMed Web of Science ®Google Scholar
• Ghosh A, Biswas S, Ghosh T. Preparation and evaluation of silymarin β-cyclodextrin molecular inclusion complexes. J Young Pharm. 2011;3(3):205–210. doi: 10.4103/0975-1483.83759.
   PubMedGoogle Scholar
• Boonyarattanakalin KS, Wolschann P, Lawtrakul L. Molecular dynamics of β-CD in water/co-solvent mixtures. J Incl Phenom Macrocycl Chem. 2011;70(3-4):279–290. doi: 10.1007/s10847-010-9913-2.
   Web of Science ®Google Scholar
• Loftsson T, Ólafsdóttir BJ, Friðriksdóttir H, et al. Cyclodextrin complexation of NSAIDSs: physicochemical characteristics. Eur J Pharm Sci. 1993;1(2):95–101. doi: 10.1016/0928-0987(93)90023-4.
   Web of Science ®Google Scholar
• Faucci MT, Mura P. Effect of water-soluble polymers on naproxen complexation with natural and chemically modified β-cyclodextrins. Drug Dev Ind Pharm. 2001;27(9):909–917. doi: 10.1080/03639045.2020.12098150.
   PubMed Web of Science ®Google Scholar
• Babos G, Rydz J, Kawalec M, et al. Poly(3-hydroxybutyrate)-based nanoparticles for sorafenib and doxorubicin anticancer drug delivery. Int J Mol Sci. 2020;21:1–17.
   Web of Science ®Google Scholar
• Shahnaz G, Edagwa BJ, McMillan J, HEG., et al. Development of mannose-anchored thiolated amphotericin B nanocarriers for treatment of visceral leishmaniasis. Nanomedicine (Lond). 2016;12(2):99–115. doi: 10.2217/nnm-2016-0325.
   PubMed Web of Science ®Google Scholar
• Mombeini M, Saki G, Khorsandi L, et al. Effects of silymarin-loaded nanoparticles on HT-29 human Colon cancer cells. Med. 2018;54:1–9.
   Google Scholar