Enhanced oral bioavailability of koumine by complexation with hydroxypropyl-β-cyclodextrin: preparation, optimization, ex vivo and in vivo characterization

References

• Al-Heibshy FNS, Basaran E, Ozturk N, et al. (2020). Preparation and in vitro characterization of rosuvastatin calcium incorporated methyl beta cyclodextrin and Captisol® inclusion complexes. Drug Dev Ind Pharm 46:1495–506.
   PubMed Web of Science ®Google Scholar
• Arya P, Raghav N. (2021). In-vitro studies of Curcumin-β-cyclodextrin inclusion complex as sustained release system. J Mol Struct 1228:129774.
   Web of Science ®Google Scholar
• Braga SS, El-Saleh F, Lysenko K, et al. (2021). Inclusion compound of efavirenz and gamma-cyclodextrin: solid state studies and effect on solubility. Molecules 26:519.
   PubMed Web of Science ®Google Scholar
• Chen JZ, Li Y, Xiao JP, et al. (2013). Development of a sensitive and rapid UPLC-MS/MS method for the determination of koumine in rat plasma: application to a pharmacokinetic study. Biomed Chromatogr 27:736–40.
   PubMed Web of Science ®Google Scholar
• Chen S, Zhang J, Wu L, et al. (2018). Paeonol nanoemulsion for enhanced oral bioavailability: optimization and mechanism. Nanomedicine 13:269–82.
   PubMed Web of Science ®Google Scholar
• Garcia-Otero X, Diaz-Tome V, Varela-Fernandez R, et al. (2021). Development and characterization of a tacrolimus/hydroxypropyl-beta-cyclodextrin eye drop. Pharmaceutics 13:149.
   PubMed Web of Science ®Google Scholar
• Giri BR, Lee J, Lim DY, et al. (2021). Docetaxel/dimethyl-β-cyclodextrin inclusion complexes: preparation, in vitro evaluation and physicochemical characterization. Drug Dev Ind Pharm 47:319–28.
   PubMed Web of Science ®Google Scholar
• Ho GT, Moodie FM, Satsangi J. (2003). Multidrug resistance 1 gene (P-glycoprotein 170): an important determinant in gastrointestinal disease? Gut 52:759–66.
   PubMed Web of Science ®Google Scholar
• Hu SC, Lai YC, Lin CL, et al. (2019). Inclusion complex of saikosaponin-d with hydroxypropyl-β-cyclodextrin: Improved physicochemical properties and anti-skin cancer activity. Phytomedicine 57:174–82.
   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
• Jin GL, Su YP, Liu M, et al. (2014). Medicinal plants of the genus Gelsemium (Gelsemiaceae, Gentianales)-a review of their phytochemistry, pharmacology, toxicology and traditional use. J Ethnopharmacol 152:33–52.
   PubMed Web of Science ®Google Scholar
• Khalid Q, Ahmad M, Minhas MU, et al. (2021). Novel β-cyclodextrin nanosponges by chain growth condensation for solubility enhancement of dexibuprofen: characterization and acute oral toxicity studies. J Drug Deliv Sci Technol 61:102089.
   Web of Science ®Google Scholar
• Khalid Q, Ahmad M, Usman Minhas M. (2018). Hydroxypropyl-β-cyclodextrin hybrid nanogels as nano-drug delivery carriers to enhance the solubility of dexibuprofen: characterization, in vitro release, and acute oral toxicity studies. Adv Polym Technol 37:2171–85.
   Web of Science ®Google Scholar
• Khushbu JR. (2021). RSM-CCD optimized microwave assisted synthesis of chitosan and sodium alginate based nanocomposite containing inclusion complexes of β-cyclodextrin and amlodipine besylate for sustained drug delivery systems. J Drug Deliv Sci Technol 61:102325.
   Web of Science ®Google Scholar
• Liu S, Ho PC. (2017). Formulation optimization of scutellarin-loaded HP-β-CD/chitosan nanoparticles using response surface methodology with Box-Behnken design. Asian J Pharm Sci 12:378–85.
   PubMed Web of Science ®Google Scholar
• Lo Y-l. (2003). Relationships between the hydrophilic–lipophilic balance values of pharmaceutical excipients and their multidrug resistance modulating effect in Caco-2 cells and rat intestines. J Controlled Release 90:37–48.
   PubMed Web of Science ®Google Scholar
• Loftsson T, Hreinsdottir D, Masson M. (2005). Evaluation of cyclodextrin solubilization of drugs. Int J Pharm 302:18–28.
   PubMed Web of Science ®Google Scholar
• Manta K, Papakyriakopoulou P, Chountoulesi M, et al. (2020). Preparation and biophysical characterization of quercetin inclusion complexes with β-cyclodextrin derivatives to be formulated as possible nose-to-brain quercetin delivery systems. Mol Pharm 17:4241–55.
   PubMed Web of Science ®Google Scholar
• McCartney F, Rosa M, Brayden DJ. (2019). Evaluation of sucrose laurate as an intestinal permeation enhancer for macromolecules: ex vivo and in vivo studies. Pharmaceutics 11:565.
   PubMed Web of Science ®Google Scholar
• Ming LIU, Jie SHEN, Hao LIU, et al. (2011). Gelsenicine from Gelsemium elegans attenuates neuropathic and inflammatory pain in mice. Biol Pharm Bull 34:1877–80.
   PubMed Web of Science ®Google Scholar
• Nagayasu M, Ozeki K, Sakurai Y, et al. (2019). Simplified method to determine the efflux ratio on P-glycoprotein substrates using three-compartment model analysis for Caco-2 cell assay data. Pharm Res 37:13.
   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
• Patel MH, Sawant KK. (2019). Self microemulsifying drug delivery system of lurasidone hydrochloride for enhanced oral bioavailability by lymphatic targeting: in vitro, Caco-2 cell line and in vivo evaluation. Eur J Pharm Sci 138:105027.
   PubMed Web of Science ®Google Scholar
• Pinto LMA, Adeoye O, Thomasi SS, et al. (2020). Preparation and characterization of a synthetic curcumin analog inclusion complex and preliminary evaluation of in vitro antileishmanial activity. Int J Pharm 589:1–8.
   Google Scholar
• Qiu HQ, Xu Y, Jin GL, et al. (2015). Koumine enhances spinal cord 3α-hydroxysteroid oxidoreductase expression and activity in a rat model of neuropathic pain . Mol Pain 11:46.
   PubMed Web of Science ®Google Scholar
• Raza A, Sun H, Bano S, et al. (2017). Preparation, characterization, and in vitro anti-inflammatory evaluation of novel water soluble kamebakaurin/hydroxypropyl-β-cyclodextrin inclusion complex. J Mol Struct 1130:319–26.
   Web of Science ®Google 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
• Rong Z, Xu Y, Zhang C, et al. (2013). Evaluation of intestinal absorption of amtolmetin guacyl in rats: breast cancer resistant protein as a primary barrier of oral bioavailability. Life Sci 92:245–51.
   PubMed Web of Science ®Google Scholar
• Shankar VK, 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
• Silva JAd, Sampaio PA, Dulcey LJL, et al. (2021). Preparation and characterization of [6]-gingerol/β-cyclodextrin inclusion complexes. J Drug Deliv Sci Technol 61:102103.
   Web of Science ®Google Scholar
• Su YP, Shen J, Xu Y, et al. (2011). Preparative separation of alkaloids from Gelsemium elegans Benth. Using pH-zone-refining counter-current chromatography. J Chromatogr A 1218:3695–8.
   PubMed Web of Science ®Google Scholar
• Higuchi T, Connors KA. (1965). Phase solubility techniques. Advanced Analytical Chemistry of Instrumentation 4:117–212.
   Google Scholar
• Tambe A, Mokashi P, Pandita N. (2019). Ex-vivo intestinal absorption study of boswellic acid, cyclodextrin complexes and poloxamer solid dispersions using everted gut sac technique. J Pharm Biomed Anal 167:66–73.
   PubMed Web of Science ®Google Scholar
• Wang S, Tan N, Ma C, et al. (2018). Inhibitory effects of benzaldehyde, vanillin, muscone and borneol on P-glycoprotein in Caco-2 cells and everted gut sac. Pharmacology 101:269–77.
   PubMed Web of Science ®Google Scholar
• Wang ZY, Zuo MT, Liu ZY. (2019). The metabolism and disposition of koumine, gelsemine and humantenmine from gelsemium. CDM 20:583–91.
   Google Scholar
• Vikas Y, Sandeep K, Braham D, et al. (2018). Cyclodextrin complexes: an approach to improve the physicochemical properties of drugs and applications of cyclodextrin complexes. AJPS 12:394–409.
   Google Scholar
• Yang J, Cai HD, Zeng YL, et al. (2016). Effects of koumine on adjuvant- and collagen-induced arthritis in rats. J Nat Prod 79:2635–43.
   PubMed Web of Science ®Google Scholar
• Yu CX, Xu Y, Yang J, et al. (2015). Use of koumine and its homologues in preparation of medicament for treatment of autoimmune diseases of involved bones and joints (US Patent No. 9078890B2).
   Google Scholar
• Yuan ZH, Liang ZE, Wu J, et al. (2016). A potential mechanism for the anti-apoptotic property of koumine involving mitochondrial pathway in LPS-Mediated RAW 264.7 macrophages. Molecules 21:1317.
   PubMed Web of Science ®Google Scholar
• Zhang JY, Wang YX. (2015). Gelsemium analgesia and the spinal glycine receptor/allopregnanolone pathway. Fitoterapia 100:35–43.
   PubMed Web of Science ®Google Scholar
• Zhang X, Wu D, Lai J, et al. (2009). Piroxicam/2-hydroxypropyl-beta-cyclodextrin inclusion complex prepared by a new fluid-bed coating technique. J Pharm Sci 98:665–75.
   PubMed Web of Science ®Google Scholar
• Zhao X, Qiu N, Ma Y, et al. (2021). Preparation, characterization and biological evaluation of β-cyclodextrin-biotin conjugate based podophyllotoxin complex. Eur J Pharm Sci 160:105745.
   PubMed Web of Science ®Google Scholar