256
Views
15
CrossRef citations to date
0
Altmetric
ORIGINAL ARTICLES

Cyclodextrin encapsulation of daidzein and genistein by grinding: implication on the glycosaminoglycan accumulation in mucopolysaccharidosis type II and III fibroblasts

, , , &
Pages 1-12 | Received 16 May 2017, Accepted 17 Nov 2017, Published online: 04 Dec 2017

References

  • Archer LD, Langford-Smith KJ, Bigger BW, Fildes JE. Mucopolysaccharide diseases: A complex interplay between neuroinflammation, microglial activation and adaptive immunity. J Inherit Metab Dis, 2014;37(1):1–12.
  • Arfi A, Richard M, Gandolphe C, Scherman D. Storage correction in cells of patients suffering from mucopolysaccharidoses types IIIA and VII after treatment with genistein and other isoflavones. J Inherit Metab Dis, 2010;33(1):61–7.
  • Borghetti GS, Pinto AP, Lula IS, Sinisterra RD, Teixeira HF, Bassani VL. Daidzein/cyclodextrin/hydrophilic polymer ternary systems. Drug Dev Ind Pharm, 2011;37(8):886–93.
  • Cannavà C, Crupi V, Ficarra P, Guardo M, Majolino D, Mazzaglia A, Stancanelli R, Venuti V. Physico-chemical characterization of an amphiphilic cyclodextrin/genistein complex. J Pharm Biomed Anal, 2010;51(5):1064–8.
  • Chen F, Peng J, Lei D, Liu J, Zhao G. Optimization of genistein solubilization by κ-carrageenan hydrogel using response surface methodology. Food Sci Human Wellness, 2013;2(3-4):124–31.
  • Cimaz R, La Torre F. Mucopolysaccharidoses. Curr Rheumatol Rep, 2014;16:389–97.
  • Cinčić D, Brekalo I, Kaitner B. Solvent-free polymorphism control in a covalent mechanochemical reaction. Cryst Growth Des, 2012;12(1):44–8.
  • Colombo I, Grassi G, Grassi M. Drug mechanochemical activation. J Pharm Sci, 2009;98(11):3961–86.
  • Crupi V, Ficarra R, Guardo M, Majolino D, Stancanelli R, Venuti V. UV–-Vis and FTIR-ATR spectroscopic techniques to study the inclusion complexes of genistein with β-cyclodextrins. J Pharm Biomed Anal, 2007;44(1):110–7.
  • Cugovčan M, Jablan J, Lovrić J, Cinčić D, Galić N, Jug M. Biopharmaceutical characterization of praziquantel cocrystals and cyclodextrin complexes prepared by grinding. J Pharm Biomed Anal, 2017;137:42–53.
  • Danciu C, Soica C, Oltean M, Avram S, Borcan F, Csanyi E, Ambrus R, Zupko I, Muntean D, Dehelean CA, et al. Genistein in 1:1 inclusion complexes with ramified cyclodextrins: Theoretical, physicochemical and biological evaluation. IJMS, 2014;15:1962–82.
  • Daruházi ÁE, Kiss T, Vecsernyés M, Szente L, Szőke É, Lemberkovics É. Investigation of transport of genistein, daidzein and their inclusion complexes prepared with different cyclodextrins on Caco-2 cell line. J Pharm Biomed, 2013;84:112–6.
  • Daruházi ÁE, Szente L, Balogh B, Mátyus P, Béni S, Takács M, Gergely A, Horváth P, Szoke É, Lemberkovics É. Utility of cyclodextrins in the formulation of genistein. Part 1. Preparation and physicochemical properties of genistein complexes with native cyclodextrins. J Pharm Biomed Anal, 2008;48:636–40.
  • De Ruijter J, Valstar MJ, Narajczyk M, Wegrzyn G, Kulik W, Ijlst L, Wagemans T, Van Der Wal WM, Wijburg FA. Genistein in sanfilippo disease: A randomized controlled crossover trial. Ann Neurol, 2012;71(1):110–20.
  • Delgadillo V, Del Mar O’Callaghan M, Artuch R, Montero R, Pineda M. Genistein supplementation in patients affected by Sanfilippo disease. J Inherit Metab Dis, 2011;34(4):1039–44.
  • Deng Y, Pang Y, Guo Y, Ren Y, Wang F, Liao X, Yang B. Host-guest inclusion systems of daidzein with 2-hydroxypropyl-sz-cyclodextrin (HP-sz-CD) and sulfobutyl ether-sz-cyclodextrin (SBE-sz-CD): Preparation, binding behaviors and water solubility. J Mol Struct, 2016;1118:307–15.
  • Éhen Z, Giordano F, Sztatisz J, Jicsinszky L, Novők C. Thermal characterization of natural and modified cyclodextrins using TG-MS combined technique. J Therm Anal Calorim, 2005;80(2):419–24.
  • Farndale RW, Buttle DJ, Barrett AJ. Improved quantitation and discrimination of sulphated glycosaminoglycans by use of dimethylmethylene blue. Biochim Biophys Acta, 1986;883(2):173–7.
  • Friščić T. Supramolecular concepts and new techniques in mechanochemistry: Cocrystals, cages, rotaxanes, open metal-organic frameworks. Chem Soc Rev, 2012;41:3493–510.
  • Fumić B, Končić MZ, Jug M. Therapeutic potential of Hydroxypropyl-sz-Cyclodextrin-based extract of medicago sativa in the treatment of Mucopolysaccharidoses. Planta Med, 2017;83:40–50.
  • Gabig-Cimińska M, Jakóbkiewicz-Banecka J, Malinowska M, Kloska A, Piotrowska E, Chmielarz I, Moskot M, Węgrzyn A, Węgrzyn G. Combined therapies for lysosomal storage diseases. Curr Mol Med, 2015;15:746–71.
  • Gotoh K, Kariya R, Alam MM, Matsuda K, Hattori S, Maeda Y, Motoyama K, Kojima A, Arima H, Okada S. The antitumor effects of methyl-β-cyclodextrin against primary effusion lymphoma via the depletion of cholesterol from lipid rafts. Biochem Biophys Res Commun, 2014;455(3-4):285–9.
  • Hasa D, Schneider Rauber G, Voinovich D, Jones W. Cocrystal formation through mechanochemistry: From neat and liquid-assisted grinding to polymer-assisted grinding. Angew Chem Internat Ed, 2015;54(25):7371–5.
  • Jablan J, Bačić I, Kujundžić N, Jug M. Zaleplon co-ground complexes with natural and polymeric β-cyclodextrin. J Incl Phenom Macrocycl Chem, 2013;76(3-4):353–62.
  • Jambhekar SS, Breen P. Cyclodextrins in pharmaceutical formulations I: Structure and physicochemical properties, formation of complexes, and types of complex. Drug Discov Today, 2016;21(2):356–62.
  • James SL, Adams CJ, Bolm C, Braga D, Collier P, Friščić T, Grepioni F, Harri KDM, Hyett G, Jones W, et al. Mechanochemistry: Opportunities for new and cleaner synthesis. Chem Soc Rev, 2012;41(1):413–47.
  • Kamiński K, Kujdowicz M, Kajta M, Nowakowska M, Szczubiałka K. Enhanced delivery of daidzein into fibroblasts and neuronal cells with cationic derivatives of gamma-cyclodextrin for the control of cellular glycosaminoglycans. Eur J Pharm Biopharm, 2015;91:111–9.
  • Kim YJ, Sah RLY, Doong JYH, Grodzinsky AJ. Fluorometric assay of DNA in cartilage explants using Hoechst 33258. Anal Biochem, 1988;174(1):168–76.
  • Kiss T, Fenyvesi F, Bácskay I, Váradi J, Fenyvesi É, Iványi R, Szente L, Tósaki Á, Vecsernyés M. Evaluation of the cytotoxicity of beta-cyclodextrin derivatives: Evidence for the role of cholesterol extraction. Eur J Pharm Sci, 2010;40(4):376–80.
  • Kładna A, Berczyński P, Kruk I, Piechowska T, Aboul-Enein HY. Studies on the antioxidant properties of some phytoestrogens. Luminescence, 2016;31(6):1201–6.
  • Kloska A, Jakóbkiewicz-Banecka J, Narajczyk M, Banecka-Majkutewicz Z, Węgrzyn G. Effects of flavonoids on 1glycosaminoglycan synthesis: Implications for substrate reduction therapy in Sanfilippo disease and other mucopolysaccharidoses. Metab Brain Dis, 2011;26(1):1–8.
  • Kondo Y, Tokumaru H, Ishitsuka Y, Matsumoto T, Taguchi M, Motoyama K, Higashi T, Arima H, Matsuo M, Higaki K, et al. In vitro evaluation of 2-hydroxyalkylated sz-cyclodextrins as potential therapeutic agents for Niemann-Pick Type C disease. Mol Genet Metab, 2016;118(3):214–9.
  • Kurkov SV, Loftsson T. Cyclodextrins. Int J Pharm, 2013;453(1):167–80.
  • Lee CH, Yang L, Xu JZ, Yeung SYV, Huang Y, Chen Z. Relative antioxidant activity of soybean isoflavones and their glycosides. Food Chem, 2005;90(4):735–41.
  • Lin HL, Lin SY, Lin CC, Hsu CH, Wu TK, Huang YT. Mechanical grinding effect on thermodynamics and inclusion efficiency of loratadine-cyclodextrin inclusion complex formation. Carbohydr Polym, 2012;87(1):512–7.
  • Loftsson T, Brewster ME. Pharmaceutical applications of cyclodextrins: Basic science and product development. J Pharm Pharmacol, 2010;62(11):1607–21.
  • Martin LM, Castilho MC, Silveira MI, Abreu JM. Liquid chromatographic validation of a quantitation method for Phytoestrogens, Biochanin‐A, Coumestrol, Daidzein, Formononetin and Genistein in Lucerne. J Liq Chromatogr Relat Technol, 2006;29(19):2875–84.
  • Moskot M, Gabig-Cimińska M, Jakóbkiewicz-Banecka J, Węsierska M, Bocheńska K, Węgrzyn G. Cell cycle is disturbed in mucopolysaccharidosis type II fibroblasts, and can be improved by genistein. Gene, 2016;585(1):100–3.
  • Moskot M, Jakóbkiewicz-Banecka J, Kloska A, Smolińska E, Mozolewski P, Malinowska M, Rychłowski M, Banecki B, Węgrzyn G, Gabig-Cimińska M. Modulation of expression of genes involved in glycosaminoglycan metabolism and lysosome biogenesis by flavonoids. Sci Rep, 2015;5(1):9378.
  • Mura P. Analytical techniques for characterization of cyclodextrin complexes in the solid state: A review. J Pharm Biomed Anal, 2015;113:226–38.
  • Noh H, Lee JI. Current and potential therapeutic strategies for mucopolysaccharidoses. J Clin Pharm Ther, 2014;39(3):215–24.
  • Pinho E, Grootveld M, Soares G, Henrique M. Cyclodextrins as encapsulation agents for plant bioactive compounds. Carbohydr Polym, 2014;101:121–35.
  • Ren Y, Liu Y, Yang Z, Niu R, Gao K, Yang B, Liao X, Zhang J. Solid inclusion complexes of oleanolic acid with amino-appended β-cyclodextrins (ACDs): Preparation, characterization, water solubility and anticancer activity. Mater Sci Eng, 2016;69:68–76.
  • Rüfer CE, Kulling SE. Antioxidant activity of isoflavones and their major metabolites using different in vitro assays. J Agric Food Chem, 2006;54(8):2926–31.
  • Scherliess R. The MTT assay as tool to evaluate and compare excipient toxicity in vitro on respiratory epithelial cells. Int J Pharm, 2011;411(1-2):98–105.
  • Stancanelli R, Venuti V, Arigò A, Calabrò ML, Cannavà C, Crupi V, Majolino D, Tommasini S, Ventura CA. Isoflavone aglycons-sulfobutyl ether-β-cyclodextrin inclusion complexes: In solution and solid state studies. J Incl Phenom Macrocycl Chem, 2015;83(1-2):27–36.
  • Szente L, Fenyvesi É. Cyclodextrin-lipid complexes: Cavity size matters. Struct Chem, 2017;28(2):479–92.
  • Zhao C, Wang Y, Su Y, Zhang H, Ding L, Yan X, Zhao D, Shao N, Ye X, Cheng Y. Inclusion complexes of isoflavones with two commercially available dendrimers: Solubility, stability, structures, release behaviors, cytotoxicity, and anti-oxidant activities. Int J Pharm, 2011;421(2):301–9.
  • Zimmer S, Grebe A, Bakke SS, Bode N, Halvorsen B, Ulas T, Skjelland M, De Nardo D, Labzin LI, Kerksiek A, et al. Cyclodextrin promotes atherosclerosis regression via macrophage reprogramming. Sci Transl Med, 2016;8(333):1–11.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.