Complexation of fisetin with novel cyclosophoroase dimer to improve solubility and bioavailability

Carbohydrate Polymers

Volumn 97, Issue 1, 2013, Pages 196-202

  Jeong, Daham ^a   Choi, Jae Min ^a   Choi, Youngjin ^b   Jeong, Karpjoo ^a   Cho, Eunae ^a   Jung, Seunho ^a  

^a Konkuk University   (South Korea)

^b Hoseo University   (South Korea)

Author keywords

Cationic cyclosophoraose dimer; Cyclosophoraoses; Fisetin; Rhizobium leguminosarum; Solubility; Cyclodextrin

Indexed keywords

BIOCHEMISTRY; CYCLODEXTRINS; MASS SPECTROMETRY; MOLECULAR MODELING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUBILITY;

CYCLOSOPHORAOSES; FISETIN; FTIR SPECTROSCOPY; HARDLY SOLUBLE DRUG; MALDI-TOF MASS SPECTROMETRY; MOLECULAR DOCKING SIMULATIONS; RHIZOBIUM LEGUMINOSARUM; RHIZOBIUM SPECIES;

DIMERS;

RHIZOBIUM; RHIZOBIUM LEGUMINOSARUM;

BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; FISETIN; FLAVONOID; GLUCAN;

CELL SURVIVAL; CHEMISTRY; DIMERIZATION; DRUG EFFECTS; HELA CELL LINE; HUMAN; METABOLISM; RHIZOBIUM; SOLUBILITY; TOXICITY;

BETA-CYCLODEXTRINS; CELL SURVIVAL; DIMERIZATION; FLAVONOIDS; GLUCANS; HELA CELLS; HUMANS; RHIZOBIUM; SOLUBILITY;

EID: 84878161558     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2013.04.066     Document Type: Article

References (38)

1. Abe, M., Amemura, A., & Higashi, S. (1982). Studies on cyclic β-1,2-glucan obtained from periplasmic space of Rhizobium trifolii cells. Plant and Soil, 64(3), 315-324.
2. Amemura, A., Hisamatsu, M., Mitani, H., & Harada, T. (1983). Cyclic (1→2)- β-d-glucan and the octasaccharide repeating-units of extracellular acidic polysaccharides produced by Rhizobium. Carbohydrate Research, 114(2), 277-285.
3. Arai, Y., Watanabe, S., Kimira, M., Shimoi, K., Mochizuki, R., & Kinae, N. (2000). Dietary intakes of flavonols flavones and isoflavones by Japanese women and the inverse correlation between quercetin intake and plasma LDL cholesterol concentration. The Journal of Nutrition, 130(9), 2243-2250.
4. Chien, C.-S., Shen, K.-H., Huang, J.-S., Ko, S.-C., & Shih, Y.-W. (2010). Antimetastatic potential of fisetin involves inactivation of the PI3K/Akt and JNK signaling pathways with downregulation of MMP-2/9 expressions in prostate cancer PC-3 cells. Molecular and Cellular Biochemistry, 333(1-2), 169-180.
5. Choi, Y.-H, Yang, C.-H., Kim, H.-W., & Jung, S. (2000). Molecular dynamics simulations of cyclohenicosakis-[(1→2)-β-d-gluco- henicosapyranosyl], a cyclic (1→2)-β- d-glucan (a 'cyclosophoraose') of DP 21. Carbohydrate Research, 326(3), 227-234. (Pubitemid 30336345)
6. Del Valle, E. M. M. (2004). Cyclodextrins and their uses: A review. Process Biochemistry, 39(9), 1033-1046. (Pubitemid 38527174)
7. DuBois, M., Gilles, K. A., Hamilton, J. K., Rebers, P. A., & Smith, F. (1956). Colorimetric method for determination of sugars and related substances. Analytical Chemistry, 28(3), 350-356.
8. Dylan, T., Ielpi, L., Stanfield, S., Kashyap, L., Douglas, C., Yanofsky, M., et al. (1986). Rhizobium meliloti genes required for nodule development are related to chromosomal virulence genes in Agrobacterium tumefaciens. Proceedings of the National Academy of Sciences, 83(12), 4403-4407. (Pubitemid 16057056)
9. Friesner, R. A., Banks, J. L., Murphy, R. B., Halgren, T. A., Klicic, J. J., Mainz, D. T., et al. (2004). Glide: A new approach for rapid, accurate docking and scoring 1. Method and assessment of docking accuracy. Journal of Medicinal Chemistry, 47(7), 1739-1749. (Pubitemid 38380917)
10. Geremia, R. A., Cavaignac, S., Zorreguieta, A., Toro, N., Olivares, J., & Ugalde, R. A. (1987). A Rhizobium meliloti mutant that forms ineffective pseudonodules in alfalfa produces exopolysaccharide but fails to form beta-(1-2) glucan. Journal of Bacteriology, 169(2), 880-884. (Pubitemid 17010909)
11. Giordano, F., Novak, C., & Moyano, J. R. (2001). Thermal analysis of cyclodextrins and their inclusion compounds. Thermochimica Acta, 380(2), 123-151. (Pubitemid 33100003)
12. Guzzo, M. R., Uemi, M., Donate, P. M., Nikolaou, S., Machado, A. E. H., & Okano, L. T. (2006). Study of the complexation of fisetin with cyclodextrins. Journal of Physical Chemistry A, 110(36), 10545-10551. (Pubitemid 44547241)
13. Harada, A., Furue, M., & Nozakura, S.-i. (1980). Cooperative binding by cyclodextrin dimers. Polymer Journal, 12(1), 29-33.
14. Higuchi, T., & Connors, K. A. (1965). Phase-solubility techniques. Advances in Analytical Chemistry and Instrumentation, 4, 117-212.
15. Hilmi, F., Gertsch, J., Bremner, P., Valovic, S., Heinrich, M., Sticher, O., et al. (2003). Cytotoxic versus anti-inflammatory effects in HeLa Jurkat Tand human peripheral blood cells caused by guaianolide-type sesquiterpene lactones. Bioorganic and Medicinal Chemistry, 11(17), 3659-3663. (Pubitemid 36952264)
16. Jeon, Y., Kwon, C., Cho, E., & Jung, S. (2010). Carboxymethylated cyclosophoraose as a novel chiral additive for the stereoisomeric separation of some flavonoids by capillary electrophoresis. Carbohydrate Research, 345(16), 2408-2412.
17. Jeong, D., Piao, J., Kwon, C., & Jung, S. (2012). Synthesis of oligomeric microbial cyclosophoraoses as novel complexation agents. Bulletin of the Korean Chemical Society, 33(6), 2095-2098.
18. Job, P. (1928). Job's method of continuous variation. Annali di Chimica, 10, 113-203.
19. Kimira, M., Arai, Y., Shimoi, K., & Watanabe, S. (1998). Japanese intake of flavonoids and isoflavonoids from foods. Journal of Epidemiology, 8(3), 168-175. (Pubitemid 128788426)
20. Koizumi, K., Okada, Y., Horiyama, S., Utamura, T., Higashiura, T., & Ikeda, M. (1984). Preparation of cyclosophoraose-A and its complex-forming ability. Journal of Inclusion Phenomena, 2(3-4), 891-899.
21. Kwon, C., & Jung, S. (2011). pH-Dependent Inclusion Complexation of Highly Succinylated Cyclosophoraoses with 4'-Hydroxyflavanone. Bulletin of the Korean Chemical Society, 32(8), 2791-2794.
22. Kwon, C., Choi, Y., Jeong, D., Kim, J., Choi, J., Chun, S., et al. (2012). Inclusion complexation of naproxen with cyclosophoraoses and succinylated cyclosophoraoses in different pH environments. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 74(1-4), 325-333.
23. Lee, S., Park, H., Seo, D., Choi, Y., & Jung, S. (2004). Synthesis and characterization of carboxymethylated cyclosophoraose, and its inclusion complexation behavior. Carbohydrate Research, 339(3), 519-527. (Pubitemid 38167651)
24. Li, J., Xiao, H., Li, J., & Zhong, Y. (2004). Drug carrier systems based on water-soluble cationic β-cyclodextrin polymers. International Journal of Pharmaceutics, 278(2), 329-342. (Pubitemid 38759506)
25. Lipinski, C. A. (2000). Drug-like properties and the causes of poor solubility and poor permeability. Journal of Pharmacological and Toxicological Methods, 44(1), 235-249. (Pubitemid 32239479)
26. Misiuk, W., & Zalewska, M. (2009). Investigation of inclusion complex of trazodone hydrochloride with hydroxypropyl-β-cyclodextrin. Carbohydrate Polymers, 77(3), 482-488.
27. Okada, Y., Horiyama, S., & Koizumi, K. (1986). Studies on inclusion complexes of nonsteroidal anti-inflammatory agents with cyclosophoraose-A. Yakugaku Zasshi, 106(3), 240-247. (Pubitemid 16143593)
28. Park, H., Lee, S., Kang, S., Jung, Y., & Jung, S. (2004). Enantioseparation using sulfated cyclosophoraoses as a novel chiral additive in capillary electrophoresis. Electrophoresis, 25(16), 2671-2674. (Pubitemid 39236497)
29. Ragelle, H., Crauste-Manciet, S., Seguin, J., Brossard, D., Scherman, D., Arnaud, P., et al. (2012). Nanoemulsion formulation of fisetin improves bioavailability and antitumour activity in mice. International Journal of Pharmaceutics, 427(2), 452-459.
30. Samal, S. K., Dash, M., Van Vlierberghe, S., Kaplan, D. L., Chiellini, E., van Blitterswijk, C., et al. (2012). Cationic polymers and their therapeutic potential. Chemical Society Reviews, 41(21), 7147-7194.
31. Schneider, H.-J., Hacket, F., Rüdiger, V., & Ikeda, H. (1998). NMR studies of cyclodextrins and cyclodextrin complexes. Chemical Reviews, 98(5), 1755-1786.
32. Spaink, H. (1992). Rhizobial lipo-oligosaccharides: Answers and questions. Plant Molecular Biology, 20(5), 977-986.
33. Szente, L. (1996). Cyclodextrins. In J. Szejtli, & T. Osa (Eds.), Comprehensive supramolecular chemistry (pp. 253-278). Oxford, UK: Pergamon.
34. Vaara, M. (1992). Agents that increase the permeability of the outer membrane. Microbiological Reviews, 56(3), 395-411.
35. Wen, J., Liu, B., Yuan, E., Ma, Y., & Zhu, Y. (2010). Preparation and physicochemical properties of the complex of naringenin with hydroxypropyl-β-cyclodextrin. Molecules, 15(6), 4401-4407.
36. Xiao, H., & Cezar, N. (2005). Cationic-modified cyclodextrin nanosphere/anionic polymer as flocculation/sorption systems. Journal of Colloid and Interface Science, 283(2), 406-413. (Pubitemid 40254968)
37. Yang, L.-J., Chen, W., Ma, S.-X., Gao, Y.-T., Huang, R., Yan, S.-J., et al. (2011). Host-guest system of taxifolin and native cyclodextrin or its derivative: Preparation, characterization, inclusion mode, and solubilization. Carbohydrate Polymers, 85(3), 629-637.
38. Ying, T.-H., Yang, S.-F., Tsai, S.-J., Hsieh, S.-C., Huang, Y.-C., Bau, D.-T., et al. (2012). Fisetin induces apoptosis in human cervical cancer HeLa cells through ERK1/2- mediated activation of caspase-8-/caspase-3-dependent pathway. Archives of Toxicology, 86(2), 263-273.