Molecular model and in vitro antioxidant activity of a water-soluble and stable phloretin/hydroxypropyl-β-cyclodextrin inclusion complex

Journal of Molecular Liquids

Volumn 236, Issue , 2017, Pages 68-75

  Wei, Yongqin ^a   Zhang, Jin ^a   Memon, Amjad Hussain ^a   Liang, Hao ^a  

^a BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY   (China)

Author keywords

Hydroxypropyl cyclodextrin; Inclusion complex; Phloretin

Indexed keywords

ANTIOXIDANTS; BIOCHEMISTRY; CYCLODEXTRINS; FREE RADICALS;

ANTI-OXIDANT ACTIVITIES; BIOLOGICAL PROPERTIES; CLINICAL APPLICATION; CO-EVAPORATION METHOD; DPPH RADICAL SCAVENGING CAPACITIES; INCLUSION COMPLEX; PHASE-SOLUBILITY STUDIES; PHLORETIN;

SOLUBILITY;

EID: 85017100965     PISSN: 01677322     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molliq.2017.03.098     Document Type: Article

References (53)

1. [1] Crespy, V., Aprikian, O., Morand, C., Besson, C., Manach, C., Demigne, C., Remesy, C., Bioavailability of phloretin and phloridzin in rats. J. Nutr., 2001, 3227–3230.
2. [2] Lu, Y., Foo, L.Y., Identification and quantification of major polyphenols in apple pomace. Food Chem. 59 (1997), 187–194.
3. [3] Rezk, B.M., Haenen, G.R.M.M., van der Vijgh, W.J.F., Bast, A., The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids. Biochem. Biophys. Res. Commun. 295 (2002), 9–13.
4. [4] Zuo, A.-R., Yu, Y.-Y., Shu, Q.-L., Zheng, L.-X., Wang, X.-M., Peng, S.-H., Xie, Y.-F., Cao, S.-W., Hepatoprotective effects and antioxidant, antityrosinase activities of phloretin and phloretin isonicotinyl hydrazone. J. Chin. Med. Assoc. 77 (2014), 290–301.
5. [5] Wang, L., Li, Z.-W., Zhang, W., Xu, R., Gao, F., Liu, Y.-F., Li, Y.-J., Synthesis, crystal structure, and biological evaluation of a series of phloretin derivatives. Molecules, 2014, 16447–16457.
6. [6] Yang, K., Tsai, C., Wang, Y., Wei, P., Lee, C., Chen, J., Wu, C., Ho, Y., Apple polyphenol phloretin potentiates the anticancer actions of paclitaxel through induction of apoptosis in human hep G2 cells. Mol. Carcinog., 2009.
7. [7] Gao, S.S., Chen, X.Y., Zhu, R.Z., Choi, B.-M., Kim, S.J., Kim, B.-R., Dual effects of phloretin on aflatoxin B1 metabolism: activation and detoxification of aflatoxin B1. Biofactors 38 (2012), 34–43.
8. [8] Sampatha, C., Zhub, Y., Sangb, S., Ahmednaa, M., Bioactive compounds isolated from apple, tea, and ginger protect against dicarbonyl induced stress in cultured human retinal epithelial cells. Phytomedicine, 2016, 200–213.
9. [9] Murphy, W.A., Lumsden, R.D., Phloretin inhibition of glucose transport by the tapeworm Hymenolepis diminuta: a kinetic analysis, comparative biochemistry and physiology. Physiology, 1984, 749–754.
10. [10] Park, A., Jeong, H.-H., Lee, J., Lee, C.-S., The inhibitory effect of phloretin on the formation of Escherichia coli O157:H7 biofilm in a microfluidic system. BioChip J., 2012, 299–305.
11. [11] Auner, B.G., Valenta, C., Hadgraft, J., Influence of phloretin and 6-ketocholestanol on the skin permeation of sodium-fluorescein. J. Control. Release 89 (2003), 321–328.
12. [12] Blazsó, G., Gábor, M., Effects of prostaglandin antagonist phloretin derivatives on mouse ear edema induced with different skin irritants. Prostaglandins 50 (1995), 161–168.
13. [13] Nithiya, T., Udayakumar, R., In vitro antioxidant properties of Phloretin-an important Phytocompound. J. Biosci. Med. 04 (2016), 85–94.
14. [14] Oresajo, C., Stephens, T., Hino, P.D., Law, R.M., Yatskayer, M., Foltis, P., Pillai, S., Pinnell, S.R., Protective effects of a topical antioxidant mixture containing vitamin C, ferulic acid, and phloretin against ultraviolet-induced photodamage in human skin. J. Cosmet. Dermatol., 2009, 290–297.
15. [15] Bala, S., Kombrabail, M.H., Prabhananda, B.S., Effect of phloretin on ionophore mediated electroneutral transmembrane translocations of H +, K + and Na + in phospholipid vesicles. Biochim. Biophys. Acta Biomembr., 2001, 258–269.
16. [16] Zuo, A., Yanying, Y., Li, J., Binbin, X., Xiongying, Y., Yan, Q., Shuwen, C., Study on the relation of structure and antioxidant activity of isorhamnetin, quercetin, phloretin, silybin and phloretin isonicotinyl hydrazone. Free Radicals Antioxid. 1 (2011), 39–47.
17. [17] Alguel, Y., Meng, C., Terán, W., Krell, T., Ramos, J.L., Gallegos, M.-T., Zhang, X., Crystal structures of multidrug binding protein TtgR in complex with antibiotics and plant antimicrobials. J. Mol. Biol. 369 (2007), 829–840.
18. [18] Bungaruang, L., Gutmann, A., Nidetzky, B., β-Cyclodextrin Improves Solubility and Enzymatic C-Glucosylation of the Flavonoid Phloretin. Adv. Synth. Catal., 2016, 486–493.
19. [19] Davis, M.E., Brewster, M.E., Cyclodextrin-based pharmaceutics: past, present and future. Nat. Rev. Drug Discov. 3 (2004), 1023–1035.
20. [20] Loftsson, T., Brewester, M.E., Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J. Pharm. Sci. 85 (1996), 1017–1025.
21. [21] Rekharsky, M.V., Inoue, Y., Complexation thermodynamics of cyclodextrins. Chem. Rev. 98 (1998), 1875–1917.
22. [22] Loftsson, T., Hreinsdóttir, D., Másson, M., Evaluation of cyclodextrin solubilization of drugs. Int. J. Pharm. 302 (2005), 18–28.
23. [23] Misiuk, W., Investigation of inclusion complex of HP-γ-cyclodextrin with ceftazidime. J. Mol. Liq. 224 (2016), 387–392 Part A.
24. [24] Li, W., Lu, B., Sheng, A., Yang, F., Wang, Z., Spectroscopic and theoretical study on inclusion complexation of beta-cyclodextrin with permethrin. J. Mol. Struct. 981 (2010), 194–203.
25. [25] de Melo, P.N., Barbosa, E.G., de Caland, L.B., Carpegianni, H., Garnero, C., Longhi, M., de Freitas Fernades-Pedrosa, M., da Silva-Júnior, A.A., Host–guest interactions between benznidazole and beta-cyclodextrin in multicomponent complex systems involving hydrophilic polymers and triethanolamine in aqueous solution. J. Mol. Liq. 186 (2013), 147–156.
26. [26] Fernandes, C.M., Teresa Vieira, M., Veiga, F.J.B., Physicochemical characterization and in vitro dissolution behavior of nicardipine–cyclodextrins inclusion compounds. Eur. J. Pharm. Sci. 15 (2002), 79–88.
27. [27] Misiuk, W., Jozefowicz, M., Study on a host–guest interaction of hydroxypropyl-β-cyclodextrin. J. Mol. Liq. 202 (2015), 101–106.
28. [28] Yuan, C., Jin, Z., Xu, X., Zhuang, H., Shen, W., Preparation and stability of the inclusion complex of astaxanthin with hydroxypropyl-β-cyclodextrin. Food Chem. 109 (2008), 264–268.
29. [29] Wu, H., Liang, H., Yuan, Q., Wang, T., Yan, X., Preparation and stability investigation of the inclusion complex of sulforaphane with hydroxypropyl-β-cyclodextrin. Carbohydr. Polym. 82 (2010), 613–617.
30. [30] Raza, A., Sun, H., Bano, S., Zhao, Y., Xu, X., Tang, J., Preparation, characterization, and in vitro anti-inflammatory evaluation of novel water soluble kamebakaurin/hydroxypropyl-β-cyclodextrin inclusion complex. J. Mol. Struct. 1130 (2017), 319–326.
31. [31] Yang, Y., Gao, J., Ma, X., Huang, G., Inclusion complex of tamibarotene with hydroxypropyl-β-cyclodextrin: preparation, characterization, in-vitro and in-vivo evaluation. Asian J. Pharm. Sci. 12 (2017), 187–192.
32. [32] Stepniak, A., Belica-Pacha, S., Rozalska, S., Dlugonski, J., Urbaniak, P., Palecz, B., Study on a host–guest interaction of β-cyclodextrin with tebuconazole in water. J. Mol. Liq. 211 (2015), 288–293.
33. [33] Szejtli, J., Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98 (1998), 1743–1753.
34. [34] Qiu, N., Cheng, X., Wang, G., Wang, W., Wen, J., Zhang, Y., Song, H., Ma, L., Wei, Y., Peng, A., Chen, L., Inclusion complex of barbigerone with hydroxypropyl-β-cyclodextrin: preparation and in vitro evaluation. Carbohydr. Polym. 101 (2014), 623–630.
35. [35] Yanga, L.-J., Xiaa, S., Maa, S.-X., Zhoua, S.-Y., Zhaoa, X.-Q., Wanga, S.-H., Lic, M.-Y., Yangb, X.-D., Host-guest system of hesperetin and β-cyclodextrin or its derivatives: preparation, characterization, inclusion mode, solubilization and stability. Mater. Sci. Eng. C Mater. Biol. Appl., 2016, 1016–1024.
36. [36] Stegemann, S., Leveiller, F., Franchi, D., de Jong, H., Lindén, H., When poor solubility becomes an issue: from early stage to proof of concept. Eur. J. Pharm. Sci. 31 (2007), 249–261.
37. [37] Moraes, C.M., Abrami, P., de Paula, E., Braga, A.F.A., Fraceto, L.F., Study of the interaction between S(−) bupivacaine and 2-hydroxypropyl-β-cyclodextrin. Int. J. Pharm. 331 (2007), 99–106.
38. [38] Del Valle, E.M.M., Cyclodextrins and their uses: a review. Process Biochem. 39 (2004), 1033–1046.
39. [39] Peeters, J., Neeskens, P., Tollenaere, J.P., Remoortere, P.V., Brewster, M.E., Characterization of the interaction of 2-hydroxypropyl-beta-cyclodextrin with itraconazole at pH 2, 4, and 7. J. Pharm. Sci., 2002, 1414–1422.
40. [40] Al-Marzouqi, A.H., Shehatta, I., Jobe, B., Dowaidar, A., Phase solubility and inclusion complex of itraconazole with beta-cyclodextrin using supercritical carbon dioxide. J. Pharm. Sci., 2006, 292–304.
41. [41] Michalska, P., Wojnicz, A., Ruiz-Nuño, A., Abril, S., Buendia, I., León, R., Inclusion complex of ITH12674 with 2-hydroxypropyl-β-cyclodextrin: preparation, physical characterization and pharmacological effect. Carbohydr. Polym. 157 (2017), 94–104.
42. [42] Higuchi, T., Connors, K.A., Phase solubility technique. Adv. Anal. Chem. Instrum. 4 (1965), 117–212.
43. [43] Jun, S.W., Kim, M.-S., Kim, J.-S., Park, H.J., Lee, S., Woo, J.-S., Hwang, S.-J., Preparation and characterization of simvastatin/hydroxypropyl-β-cyclodextrin inclusion complex using supercritical antisolvent (SAS) process. Eur. J. Pharm. Biopharm. 66 (2007), 413–421.
44. [44] Gannimani, R., Perumal, A., Ramesh, M., Pillay, K., Soliman, M.E., Govender, P., Antipyrine–gamma cyclodextrin inclusion complex: molecular modeling, preparation, characterization and cytotoxicity studies. J. Mol. Struct. 1089 (2015), 38–47.
45. [45] Yuan, C., Jin, Z., Xu, X., Inclusion complex of astaxanthin with hydroxypropyl-beta-cyclodextrin: UV, FTIR, 1H NMR and molecular modeling studies. Carbohydr. Polym. 89 (2012), 492–496.
46. [46] Bothner-By, A.A., Stephens, R.L., Lee, J., Warren, C.D., Jeanloz, R.W., Structure determination of a tetrasaccharide: transient nuclear Overhauser effects in the rotating frame. J. Am. Chem. Soc. 106 (1984), 811–813.
47. [47] Yang, L.-J., Xia, S., Ma, S.-X., Zhou, S.-Y., Zhao, X.-Q., Wang, S.-H., Li, M.-Y., Yang, X.-D., Host–guest system of hesperetin and β-cyclodextrin or its derivatives: preparation, characterization, inclusion mode, solubilization and stability. Mater. Sci. Eng. C 59 (2016), 1016–1024.
48. [48] Yang, L.-J., Ma, S.-X., Zhou, S.-Y., Chen, W., Yuan, M.-W., Yin, Y.-Q., Yang, X.-D., Preparation and characterization of inclusion complexes of naringenin with beta-cyclodextrin or its derivative. Carbohydr. Polym. 98 (2013), 861–869.
49. [49] Jabbari, M., Jabbari, A., Antioxidant potential and DPPH radical scavenging kinetics of water-insoluble flavonoid naringenin in aqueous solution of micelles. Colloids Surf. A Physicochem. Eng. Asp. 489 (2016), 392–399.
50. [50] Lee, C.-C., Chen, Y.-T., Chiu, C.-C., Liao, W.-T., Liu, Y.-C., David Wang, H.-M., Polygonum cuspidatum extracts as bioactive antioxidaion, anti-tyrosinase, immune stimulation and anticancer agents. J. Biosci. Bioeng. 119 (2015), 464–469.
51. [51] Wang, B., Li, B., Zeng, Q., Liu, H., Antioxidant and free radical scavenging activities of pigments extracted from molasses alcohol wastewater. Food Chem. 107 (2008), 1198–1204.
52. [52] Zhang, Z., Kong, F., Ni, H., Mo, Z., Wan, J.-B., Hua, D., Yan, C., Structural characterization, α-glucosidase inhibitory and DPPH• scavenging activities of polysaccharides from guava. Carbohydr. Polym. 144 (2016), 106–114.
53. [53] Mercader-Ros, M.T., Lucas-Abellán, C., Fortea, M.I., Gabaldón, J.A., Núez-Delicado, E., Effect of HP-β-cyclodextrins complexation on the antioxidant activity of flavonols. Food Chem., 2010, 769–773.