Rational formulation engineering of fraxinellone utilizing 6-O-α-D-maltosyl-β-cyclodextrin for enhanced oral bioavailability and hepatic fibrosis therapy

References

• Aihara R, Messerschmid R, Mizoguchi M, et al. (2021). In vitro-in vivo correlation in the effect of cyclodextrin on oral absorption of poorly soluble drugs. Int J Pharm 600:120494.
   PubMed Web of Science ®Google Scholar
• Aytac Z, Kusku S, Durgun E, Uyar T. (2016). Quercetin/β-cyclodextrin inclusion complex embedded nanofibres: slow release and high solubility. Food Chem 197:864–71.
   PubMed Web of Science ®Google Scholar
• Bergström C, Charman W, Porter C. (2016). Computational prediction of formulation strategies for beyond-rule-of-5 compounds. Adv Drug Deliv Rev 101:6–21.
   PubMed Web of Science ®Google Scholar
• Chen R, Huang L, Hu K. (2020). Natural products remodel cancer-associated fibroblasts in desmoplastic tumors. Acta Pharm Sin B 10:2140–55.
   PubMed Web of Science ®Google Scholar
• Chi L, Liu R, Guo T, et al. (2015). Dramatic improvement of the solubility of pseudolaric acid B by cyclodextrin complexation: preparation, characterization and validation. Int J Pharm 479:349–56.
   PubMed Web of Science ®Google Scholar
• Chuang EY, Lin KJ, Huang TY, et al. (2018). An intestinal “transformers”-like nanocarrier system for enhancing the oral bioavailability of poorly water-soluble drugs. ACS Nano 12:6389–97.
   PubMed Web of Science ®Google Scholar
• Cui H, Siva S, Lin L. (2019). Ultrasound processed cuminaldehyde/2-hydroxypropyl-β-cyclodextrin inclusion complex: preparation, characterization and antibacterial activity. Ultrason Sonochem 56:84–93.
   PubMed Web of Science ®Google Scholar
• Devasari N, Dora CP, Singh C, et al. (2015). Inclusion complex of erlotinib with sulfobutyl ether-β-cyclodextrin: preparation, characterization, in silico, in vitro and in vivo evaluation. Carbohydr Polym 134:547–56.
   PubMed Web of Science ®Google Scholar
• dos Santos Silva Araújo L, Lazzara G, Chiappisi L. (2021). Cyclodextrin/surfactant inclusion complexes: an integrated view of their thermodynamic and structural properties. Adv Colloid Interface Sci 289:102375.
   PubMed Web of Science ®Google Scholar
• Gratieri T, Pinho L, Oliveira M, et al. (2020). Hydroxypropyl-β-cyclodextrin-complexed naringenin by solvent change precipitation for improving anti-inflammatory effect in vivo. Carbohydr Polym 231:115769.
   PubMed Web of Science ®Google Scholar
• Jambhekar S, Breen P. (2013). Drug dissolution: significance of physicochemical properties and physiological conditions. Drug Discov Today 18:1173–84.
   PubMed Web of Science ®Google Scholar
• Jambhekar S, Breen P. (2016). Cyclodextrins in pharmaceutical formulations I: structure and physicochemical properties, formation of complexes, and types of complex. Drug Discov Today 21:356–62.
   PubMed Web of Science ®Google Scholar
• Jansook P, Ogawa N, Loftsson T. (2018). Cyclodextrins: structure, physicochemical properties and pharmaceutical applications. Int J Pharm 535:272–84.
   PubMed Web of Science ®Google Scholar
• Kfoury M, Landy D, Ruellan S, et al. (2017). Nootkatone encapsulation by cyclodextrins: effect on water solubility and photostability. Food Chem 236:41–8.
   PubMed Web of Science ®Google Scholar
• Koziolek M, Grimm M, Schneider F, et al. (2016). Navigating the human gastrointestinal tract for oral drug delivery: uncharted waters and new frontiers. Adv Drug Deliv Rev 101:75–88.
   PubMed Web of Science ®Google Scholar
• Li B, Liu B, Li J, et al. (2015). Experimental and theoretical investigations on the supermolecular structure of isoliquiritigenin and 6-O-α-D-maltosyl-β-cyclodextrin inclusion complex. Int J Mol Sci 16:17999–8017.
   PubMed Web of Science ®Google Scholar
• Li J, Yang Y, Ning E, et al. (2019). Mechanisms of poor oral bioavailability of flavonoid Morin in rats: from physicochemical to biopharmaceutical evaluations. Eur J Pharm Sci 128:290–8.
   PubMed Web of Science ®Google Scholar
• Lima B, Campos C, da Silva Santos A, et al. (2019). Development of morin/hydroxypropyl-β-cyclodextrin inclusion complex: enhancement of bioavailability, antihyperalgesic and anti-inflammatory effects. Food Chem Toxicol 126:15–24.
   PubMed Web of Science ®Google Scholar
• Lodagekar A, Borkar R, Thatikonda S, et al. (2019). Formulation and evaluation of cyclodextrin complexes for improved anticancer activity of repurposed drug: niclosamide. Carbohydr Polym 212:252–9.
   PubMed Web of Science ®Google Scholar
• Loftsson T, Hreinsdóttir D, Másson M. (2005). Evaluation of cyclodextrin solubilization of drugs. Int J Pharm 302:18–28.
   PubMed Web of Science ®Google Scholar
• Lucas-Abellán C, Gabaldón-Hernández J, Penalva J, et al. (2008). Preparation and characterization of the inclusion complex of chlorpyrifos in cyclodextrins to improve insecticide formulations. J Agric Food Chem 56:8081–5.
   PubMed Web of Science ®Google Scholar
• Matencio A, Caldera F, Rubin Pedrazzo A, et al. (2021). A physicochemical, thermodynamical, structural and computational evaluation of kynurenic acid/cyclodextrin complexes. Food Chem 356:129639.
   PubMed Web of Science ®Google Scholar
• Miller J, Dahan A. (2012). Predicting the solubility-permeability interplay when using cyclodextrins in solubility-enabling formulations: model validation. Int J Pharm 430:388–91.
   PubMed Web of Science ®Google Scholar
• Mohandoss S, Atchudan R, Immanuel Edison TNJ, et al. (2019). Enhanced solubility of guanosine by inclusion complexes with cyclodextrin derivatives: preparation, characterization, and evaluation. Carbohydr Polym 224:115166.
   PubMed Web of Science ®Google Scholar
• Mohtar N, Taylor KMG, Sheikh K, Somavarapu S. (2017). Design and development of dry powder sulfobutylether-β-cyclodextrin complex for pulmonary delivery of fisetin. Eur J Pharm Biopharm 113:1–10.
   PubMed Web of Science ®Google Scholar
• Nair AB, Attimarad M, Al-Dhubiab BE, et al. (2014). Enhanced oral bioavailability of acyclovir by inclusion complex using hydroxypropyl-β-cyclodextrin. Drug Deliv 21:540–7.
   PubMed Web of Science ®Google Scholar
• Pei Y, Chen L, Huang Y, et al. (2019). Sequential targeting TGF-β signaling and KRAS mutation increases therapeutic efficacy in pancreatic cancer. Small 15:e1900631.
   PubMed Web of Science ®Google Scholar
• Pinho E, Grootveld M, Soares G, Henriques M. (2014). Cyclodextrins as encapsulation agents for plant bioactive compounds. Carbohydr Polym 101:121–35.
   PubMed Web of Science ®Google Scholar
• Ran Q, Ruan L, Zhu D, Yu B. (2007). Improving the solubility of fraxinellone to increase its oral bioavailability and hepatoprotective action against acute liver injury in mice. Yao Xue Bao 42:675–80.
   PubMedGoogle Scholar
• Ren L, Wang J, Chen G. (2019). Preparation, optimization of the inclusion complex of glaucocalyxin A with sulfobutylether-β-cyclodextrin and antitumor study. Drug Deliv 26:309–17.
   PubMed Web of Science ®Google Scholar
• Rescifina A, Surdo E, Cardile V, et al. (2019). Gemcitabine anticancer activity enhancement by water soluble celecoxib/sulfobutyl ether-β-cyclodextrin inclusion complex. Carbohydr Polym 206:792–800.
   PubMed Web of Science ®Google Scholar
• Ruan LP, Chen S, Yu BY, et al. (2006). Prediction of human absorption of natural compounds by the non-everted rat intestinal sac model. Eur J Med Chem 41:605–10.
   PubMed Web of Science ®Google Scholar
• Shankar V, Police A, Pandey P, et al. (2021). Optimization of sulfobutyl-ether-β-cyclodextrin levels in oral formulations to enhance progesterone bioavailability. Int J Pharm 596:120212.
   PubMed Web of Science ®Google Scholar
• Sun H, Liu K, Liu W, et al. (2012). Development and characterization of a novel nanoemulsion drug-delivery system for potential application in oral delivery of protein drugs. Int J Nanomedicine 7:5529–43.
   PubMed Web of Science ®Google Scholar
• Tang P, Li S, Wang L, et al. (2015). Inclusion complexes of chlorzoxazone with β- and hydroxypropyl-β-cyclodextrin: characterization, dissolution, and cytotoxicity. Carbohydr Polym 131:297–305.
   PubMed Web of Science ®Google Scholar
• Tsopelas F, Giaginis C, Tsantili-Kakoulidou A. (2017). Lipophilicity and biomimetic properties to support drug discovery. Expert Opin Drug Discov 12:885–96.
   PubMed Web of Science ®Google Scholar
• Tye C, Wang Z, Dockens R, et al. (2016). Pre-absorption physicochemical compatibility assessment of 8-drug metabolic cocktail. Int J Pharm 514:364–73.
   PubMed Web of Science ®Google Scholar
• Ünal S, Aktaş Y, Benito J, Bilensoy E. (2020). Cyclodextrin nanoparticle bound oral camptothecin for colorectal cancer: formulation development and optimization. Int J Pharm 584:119468.
   PubMed Web of Science ®Google Scholar
• Wang Z, Landy D, Sizun C, et al. (2020). Cyclodextrin complexation studies as the first step for repurposing of chlorpromazine. Int J Pharm 584:119391.
   PubMed Web of Science ®Google Scholar
• Wu X, Wu X, Ma Y, et al. (2016). CUG-binding protein 1 regulates HSC activation and liver fibrogenesis. Nat Commun 7:13498.
   PubMed Web of Science ®Google Scholar
• Xing Y, Mi C, Wang Z, et al. (2018). Fraxinellone has anticancer activity in vivo by inhibiting programmed cell death-ligand 1 expression by reducing hypoxia-inducible factor-1α and STAT3. Pharmacol Res 135:166–80.
   PubMed Web of Science ®Google Scholar
• Yan J, Tang B, Wu D, et al. (2016). Synthesis and characterization of β-cyclodextrin/fraxinellone inclusion complex and its influence on interaction with human serum albumin. Spectrosc Lett 49:542–50.
   Web of Science ®Google Scholar
• Yan J, Tung H, Li S, et al. (2019). Aryl hydrocarbon receptor signaling prevents activation of hepatic stellate cells and liver fibrogenesis in mice. Gastroenterology 157:793–806.e14.
   PubMed Web of Science ®Google Scholar
• Yang L, Yang B, Chen W, et al. (2010). Host-guest system of nimbin and beta-cyclodextrin or its derivatives: preparation, characterization, inclusion mode, and solubilization. J Agric Food Chem 58:8545–52.
   PubMed Web of Science ®Google Scholar
• Yasmin N, Ishitsuka Y, Fukaura M, et al. (2019). In vitro and in vivo evaluation of 6-O-α-Maltosyl-β-cyclodextrin as a potential therapeutic agent against Niemann-Pick disease type C. Int J Mol Sci 20:1152.
   PubMed Web of Science ®Google Scholar
• Yildiz Z, Celebioglu A, Uyar T. (2017). Polymer-free electrospun nanofibers from sulfobutyl ether-beta-cyclodextrin (SBE-β-CD) inclusion complex with sulfisoxazole: fast-dissolving and enhanced water-solubility of sulfisoxazole. Int J Pharm 531:550–8.
   PubMed Web of Science ®Google Scholar
• Zhang J, Li J, Ju Y, et al. (2015). Mechanism of enhanced oral absorption of morin by phospholipid complex based self-nanoemulsifying drug delivery system. Mol Pharm 12:504–13.
   PubMed Web of Science ®Google Scholar
• Zheng B, Yuan M, Wang S, et al. (2021). Fraxinellone alleviates kidney fibrosis by inhibiting CUG-binding protein 1-mediated fibroblast activation. Toxicol Appl Pharmacol 420:115530.
   PubMed Web of Science ®Google Scholar