Inclusion complexation between baicalein and β-cyclodextrin and the influence of β-cyclodextrin on the binding of baicalein with DNA: a spectroscopic approach

References

• Ali, A. E., Reza, H., & Sara, E. (2009). Study on the interaction between morin-bi (III) complex and DNA with the use of methylene blue dye as a fluorophor probe. Journal of the Brazilian Chemical Society, 20, 266–276.
   Web of Science ®Google Scholar
• Allen, T. M., & Cullis, P. R. (2004). Drug delivery systems: Entering the mainstream. Science, 303, 1818–1822. 10.1126/science.1095833
   PubMed Web of Science ®Google Scholar
• Astray, G., Gonzalez-Barreiro, C., Mejuto, J. C., Rial-Otero, R., & Simal-Gándara, J. (2009). A review on the use of cyclodextrins in foods. Food Hydrocolloids, 23, 1631–1640. 10.1016/j.foodhyd.2009.01.001
   Web of Science ®Google Scholar
• Bernstein, H. J. (2011). RasMol 2.7.5.2. Molecular graphics visualisation tool. Based on RasMol 2.6 by Roger Saylebiomolecular structures group. Stevenage: Glaxo Wellcome Research and Development.
   Google Scholar
• Bushroa, A. R., Rahbari, R. G., Masjuki, H. H., & Muhamad, M. R. (2012). Approximation of crystallite size and microstrain via XRD line broadening analysis in TiSiN thin films. Vacuum, 86, 1107–1112. 10.1016/j.vacuum.2011.10.011
   Web of Science ®Google Scholar
• Butković, V., Klasinc, L., & Bors, W. (2004). Kinetic study of flavonoid reactions with stable radicals. Journal of Agricultural and Food Chemistry, 52, 2816–2820. 10.1021/jf049880h
   PubMed Web of Science ®Google Scholar
• Cave, G. W. V., Antesberger, J., Barbour, L. J., McKinlay, R. M., & Atwood, J. L. (2004). Inner core structure responds to communication between nanocapsule walls. Angewandte Chemie International Edition, 43, 5263–5266. 10.1002/(ISSN)1521-3773
   PubMed Web of Science ®Google Scholar
• Chao, J., Su, J., Li, J., Zhao, W., Huang, S., & Du, R. (2011). Investigation on the inclusion behaviour of baicalein with β-cyclodextrin and derivatives and their antioxidant ability study. Supramolecular Chemistry, 23, 641–649. 10.1080/10610278.2011.593630
   Web of Science ®Google Scholar
• Choi, J. H., Choi, A. Y., Yoon, H., Choe, W., Yoon, K. S., Ha, J., … Kang, I. (2010). Baicalein protects HT22 murine hippocampal neuronal cells against endoplasmic reticulum stress-induced apoptosis through inhibition of reactive oxygen species production and CHOP induction. Experimental and Molecular Medicine, 42, 811–822. 10.3858/emm.2010.42.12.084
   PubMed Web of Science ®Google Scholar
• Chou, D.-S., Lee, J.-J., Hsiao, G., Hsieh, C.-Y., Tsai, Y.-J., Chen, T.-F., & Sheu, J.-R. (2007). Baicalein induction of hydroxyl radical formation via 12-lipoxygenase in human platelets: An ESR study. Journal of Agricultural and Food Chemistry, 55, 649–655. 10.1021/jf062584f
   PubMed Web of Science ®Google Scholar
• Ding, D., Zhang, B., Meng, T., Ma, Y., Wang, X., Peng, H., & Shen, J. (2011). Novel synthetic baicalein derivatives caused apoptosis and activated AMP-activated protein kinase in human tumor cells. Organic and Biomolecular Chemistry, 9, 7287–7291. 10.1039/c1ob06094e
   PubMed Web of Science ®Google Scholar
• Enoch, I. V. M. V., & Swaminathan, M. (2005). Dual fluorescence and photoprototropic characteristics of 2-aminodiphenylsulphone-β-cyclodextrin inclusion complex. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 53, 149–154. 10.1007/s10847-005-2633-3
   Web of Science ®Google Scholar
• Enoch, I. V. M. V., & Yousuf, S. (2013). β-cyclodextrin inclusion complexes of 2-hydroxyfluorene and 2-hydroxy-9-fluorenone: Differences in stoichiometry and excited state prototropic equilibrium. Journal of Solution Chemistry, 42, 470–484. 10.1007/s10953-013-9965-1
   Web of Science ®Google Scholar
• Fultz, B., & Howe, J. M. (2013). Transmission electron microscopy and diffractometry of materials (pp. 59–115). Berlin Heidelberg: Springer-Verlag. 10.1007/978-3-642-29761-8
   Google Scholar
• Goldenber, G., & Tannock, I. (1998). The basic science of oncology (pp. 392–419). New York, NY: McGraw–Hill.
   Google Scholar
• Havermann, S., Rohrig, R., Chovolou, Y., Humpf, H. U., & Wätjen, W. (2013). Molecular effects of baicalein in Hct116 cells and Caenorhabditis elegans: Activation of the Nrf2 signaling pathway and prolongation of lifespan. Journal of Agricultural and Food Chemistry, 61, 2158–2164. 10.1021/jf304553g
   PubMed Web of Science ®Google Scholar
• Heo, H. J., Kim, D. O., Choi, S. J., Shin, D. H., & Lee, C. Y. (2004). Potent inhibitory effect of flavonoids in Scutellaria baicalensis on amyloid β protein-induced neurotoxicity. Journal of Agricultural and Food Chemistry, 52, 4128–4132. 10.1021/jf049953x
   PubMed Web of Science ®Google Scholar
• Hingerty, B., Klar, B., Hardgrove, G. L., Betzel, Ch., & Saenger, W. (1984). Neutron diffraction of alpha, beta and gamma cyclodextrins: Hydrogen bonding patterns. Journal of Biomolecular Structure and Dynamics, 2, 249–260. 10.1080/07391102.1984.10507561
   PubMed Web of Science ®Google Scholar
• Ibrahim, M. S., Shehatta, I. S., & Al-Nayeli, A. A. (2002). Voltammetric studies of the interaction of lumazine with cyclodextrins and DNA. Journal of Pharmaceutical and Biomedical Analysis, 28, 217–225. 10.1016/S0731-7085(01)00624-0
   PubMed Web of Science ®Google Scholar
• Kuntz, I. D., Jr., Gasparro, F. P., Johnston, M. D., Jr., & Taylor, R. P. (1968). Molecular interactions and the Benesi-Hildebrand equation. Journal of the American Chemical Society, 90, 4778–4781. 10.1021/ja01020a004
   Web of Science ®Google Scholar
• Lakowicz, J. R. (1999). Principles of fluorescence spectroscopy. New York, NY: Plenum Press. 10.1007/978-1-4757-3061-6
   Google Scholar
• Lee, Y., Yeo, H., Liu, S. H., Jiang, Z., Savizky, R. M., Austin, D. J., & Cheng, Y. C. (2004). Increased anti-P-glycoprotein activity of baicalein by alkylation on the A ring. Journal of Medicinal Chemistry, 47, 5555–5566. 10.1021/jm049949c
   PubMed Web of Science ®Google Scholar
• Li, J., Han, L., & Chao, J. (2012). Preparation and characterization of the inclusion complex of baicalein with γ-cyclodextrin: An antioxidant ability study. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 73, 247–254. 10.1007/s10847-011-0048-x
   Web of Science ®Google Scholar
• Li, S., & Purdy, W. C. (1992). Cyclodextrins and their applications in analytical chemistry. Chemical Reviews, 92, 1457–1470.
   Web of Science ®Google Scholar
• Lippard, S. J., & Berg, J. M. (1994). Principles of bio-inorganic chemistry. California: University Science Books.
   Google Scholar
• Lu, Y., Wang, G. K., Lv, J., Zhang, G. S., & Liu, Q. F. (2011). Study on the interaction of an anthracycline disaccharide with DNA by spectroscopic techniques and molecular modeling. Journal of Fluorescence, 21, 409–414. 10.1007/s10895-010-0729-7
   PubMed Web of Science ®Google Scholar
• Marcolino, V. A., Zanin, G. M., Durrant, L. R., Benassi, M. D. T., & Matioli, G. (2011). Interaction of curcumin and bixin with β-cyclodextrin: Complexation methods, stability, and applications in food. Journal of Agricultural and Food Chemistry, 59, 3348–3357. 10.1021/jf104223k
   PubMed Web of Science ®Google Scholar
• Qiuna, Z., Xiaohui, W., Wei, D., Guixin, C., & Zhengtao, W. (2013). Preparation and characterization of inclusion complexes formed between baicalein and cyclodextrins. Carbohydrate Polymers, 95, 733–739.
   PubMed Web of Science ®Google Scholar
• Raman, N., Jeyamurugan, R., Sudharsan, S., Karuppasamy, K., & Mitu, L. (2013). Metal based pharmacologically active agents: Synthesis, structural elucidation, DNA interaction, in vitro antimicrobial and in vitro cytotoxic screening of copper(II) and zinc(II) complexes derived from amino acid based pyrazolone derivatives. Arabian Journal of Chemistry, 6, 235–247. 10.1016/j.arabjc.2012.04.010
   Web of Science ®Google Scholar
• Sameena, Y., & Enoch, I. V. M. V. (2013). The influence of β-cyclodextrin on the interaction of hesperetin and its bismuth (III) complex with calf thymus DNA. Journal of Luminescence, 138, 105–116. 10.1016/j.jlumin.2012.12.003
   Web of Science ®Google Scholar
• Sameena, Y., Radhika, D., Enoch, I. V. M. V., & Murugesh, E. (2012). The influence of β-cyclodextrin encapsulation on the binding of 2’-hydroxyflavanone with calf thymus DNA. Spectrochimica Acta A., 98, 405–412.
   PubMed Web of Science ®Google Scholar
• Sandip, P., & Chabita, S. (2014). A review on structure–affinity relationship of dietary flavonoids with serum albumins. Journal of Biomolecular Structure and Dynamics, 32, 1132–1147.
   PubMed Web of Science ®Google Scholar
• Westheimer, F. H. (1997). Louis Plack Hammett (1894–1987) – A biographical memoir by Westheimer, F. H, National academy of sciences (pp. 137–149). Washington, DC: National Academies Press.
   Google Scholar
• Wu, J. Y., Chung, K. T., Liu, Y. W., Lu, F. J., Tsai, R. S., & Chen, C. H. J. (2008). Synthesis and biological evaluation of novel C(6) modified baicalein derivatives as antioxidative agents. Journal of Agricultural and Food Chemistry, 56, 2838–2845. 10.1021/jf073224a
   PubMed Web of Science ®Google Scholar
• Yousuf, S., Sudha, N., Murugesan, G., & Enoch, I. V. M. V. (2013). Isolation of Prunin from the fruit shell of Bixa orellana and the effect of β-cyclodextrin on its binding with calf thymus DNA. Carbohydrate Research., 365, 46–51.10.1016/j.carres.2012.10.003
   PubMed Web of Science ®Google Scholar
• Yu, D. N., Mikheikin, A. L., Streltsov, S. A., Zasedatelev, A. S., & Nabiev, I. R. (2001). Mixed mode of ligand-DNA binding results in S-shaped binding curves. Journal of Biomolecular Structure and Dynamics, 18, 703–708.
   PubMed Web of Science ®Google Scholar
• Zapata-Torres, G., Opazo, F., Salgado, C., Muñoz, J. P., Krautwurst, H., Mascayano, C., … Cassels, B. K. (2004). Effects of natural flavones and flavonols on the kinase activity of Cdk5. Journal of Natural Products, 67, 416–420. 10.1021/np034011s
   PubMed Web of Science ®Google Scholar
• Zhang, Z., Cui, W., Li, G., Yuan, S., Xu, D., Hoi, M. P. M., … Lee, S. M. Y. (2012). Baicalein protects against 6-OHDA-induced neurotoxicity through activation of Keap1/Nrf2/HO-1 and involving PKCα and PI3K/AKT signaling pathways. Journal of Agricultural and Food Chemistry, 60, 8171–8182. 10.1021/jf301511m
   PubMed Web of Science ®Google Scholar
• Zhou, Y., Hirotani, M., Yoshikawa, T., & Furuya, T. (1997). Flavonoids and phenylethanoids from hairy root cultures of Scutellaria baicalensis. Phytochemistry, 44, 83–87. 10.1016/S0031-9422(96)00443-8
   Web of Science ®Google Scholar