Inclusion complexes of isoflavones with two commercially available dendrimers: Solubility, stability, structures, release behaviors, cytotoxicity, and anti-oxidant activities

International Journal of Pharmaceutics

Volumn 421, Issue 2, 2011, Pages 301-309

  Zhao, Chen ^a   Wang, Yitong ^a   Su, Yunzhang ^a   Zhang, Hongfeng ^a   Ding, Lingxiao ^a   Yan, Xiaofeng ^a   Zhao, Di ^a   Shao, Naimin ^a   Ye, Xiyun ^a   Cheng, Yiyun ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

Daidzein; Dendrimer; Isoflavones; PAMAM; PPI

Indexed keywords

DAIDZEIN; DENDRIMER; IMINE; POLY(PROPYLENE IMINE); POLYAMIDOAMINE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; COMPLEX FORMATION; CYTOTOXICITY; DRUG RELEASE; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; ENCAPSULATION; HYDROPHOBICITY; NUCLEAR MAGNETIC RESONANCE; OXIDATIVE STRESS; PRIORITY JOURNAL;

ANTIOXIDANTS; CELL LINE, TUMOR; CELL SURVIVAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DENDRIMERS; DRUG STABILITY; HUMANS; HYDROGEN PEROXIDE; ISOFLAVONES; MAGNETIC RESONANCE SPECTROSCOPY; POLYPROPYLENES; SOLUBILITY;

EID: 81755173466     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2011.09.044     Document Type: Article

References (46)

1. A. Agarwal, A. Asthana, U. Gupta, and N.K. Jain Tumour and dendrimers: a review on drug delivery aspects J. Pharm. Pharmacol. 60 2008 671 688
2. A. Agarwal, U. Gupta, A. Asthana, and N.K. Jain Dextran conjugated dendritic nanoconstructs as potential vectors for anti-cancer agent Biomaterials 30 2009 3588 3596
3. A.C. Barbosa, F.M. Lajolo, and M.I. Genovese Effect of free or protein-associated soy isoflavones on the antioxidant status in rats J. Sci. Food Agric. 91 2011 721 731
4. G.S. Borghetti, A.P. Pinto, I.S. Lula, R.D. Sinisterra, H.F. Teixeira, and V.L. Bassani Daidzein/cyclodextrin/hydrophilic polymer ternary systems Drug Dev. Ind. Pharm. 37 2011 886 893
5. J.S. Byun, and S.S. Lee Effect of soybeans and sword beans on bone metabolism in a rat model of osteoporosis Ann. Nutr. Metab. 56 2010 106 112
6. A.M. Caminade, R. Laurent, and J.P. Majoral Characterization of dendrimers Adv. Drug Deliv. Rev. 57 2005 2130 2146
7. C. Cannava, V. Crupi, P. Ficarra, M. Guardo, D. Majolino, A. Mazzaglia, R. Stancanelli, and V. Venuti Physico-chemical characterization of an amphiphilic cyclodextrin/genistein complex J. Pharm. Biomed. Anal. 51 2010 1064 1068
8. Y.Y. Cheng, Y.W. Li, Q.L. Wu, J.H. Zhang, and T.W. Xu Generation-dependent encapsulation/electrostatic attachment of phenobarbital molecules by poly(amidoamine) dendrimers: evidence from 2D-NOESY investigations Eur. J. Med. Chem. 44 2009 2219 2223
9. Y.Y. Cheng, Q.L. Wu, Y.W. Li, and T.W. Xu External electrostatic interaction versus internal encapsulation between cationic dendrimers and negatively charged drugs: which contributes more to solubility enhancement of the drugs? J. Phys. Chem. B 112 2008 8884 8890
10. Y.Y. Cheng, L.B. Zhao, Y.W. Li, and T.W. Xu Design of biocompatible dendrimers for cancer diagnosis and therapy: current status and future perspectives Chem. Soc. Rev. 40 2011 2673 2703
11. A. D'Emanuele, and D. Attwood Dendrimer-drug interactions Adv. Drug Deliv. Rev. 57 2005 2147 2162
12. R. Duncan, and L. Izzo Dendrimer biocompatibility and toxicity Adv. Drug Deliv. Rev. 57 2005 2215 2237
13. Y. Gao, W. Gu, L. Chen, Z. Xu, and Y.P. Li The role of daidzein-loaded sterically stabilized solid lipid nanoparticles in therapy for cardio-cerebrovascular diseases Biomaterials 29 2008 4129 4136
14. Y.B. Ge, D.W. Chen, L.P. Xie, and R.Q. Zhang Optimized preparation of daidzein-loaded chitosan microspheres and in vivo evaluation after intramuscular injection in rats Int. J. Pharm. 338 2007 142 151
15. U. Gupta, H.B. Agashe, A. Asthana, and N.K. Jain Dendrimers: novel polymeric nanoarchitectures for solubility enhancement Biomacromolecules 7 2006 649 658
16. H.J. Heo, M.J. Kim, Y.M. Suh, S.J. Choi, N.S. Mun, H.K. Kim, E.K. Kim, and D.H. Shin Protective effects of daidzein on oxidative stress-induced neurotoxicity and scopolamine-mediated cognitive defect J. Food Sci. 70 2005 S91 S94
17. J.J. Hu, Y.Y. Cheng, Y.R. Ma, Q.L. Wu, and T.W. Xu Host-guest chemistry and physico-chemical properties of dendrimer-mycophenolic acid complexes J. Phys. Chem. B 113 2009 64 74
18. K. Jain, P. Kesharwani, U. Gupta, and N.K. Jain Dendrimer toxicity: let's meet the challenge Int. J. Pharm. 394 2010 122 142
19. N.K. Jain, and U. Gupta Application of dendrimer-drug complexation in the enhancement of drug solubility and bioavailability Expert Opin. Drug Metab. Toxicol. 4 2008 1035 1052
20. Q. Jiang, F. Payton-Stewart, S. Elliott, J. Driver, L.V. Rhodes, Q. Zhang, S. Zheng, D. Bhatnagar, S.M. Boue, B.M. Collins-Burow, J. Sridhar, C. Stevens, J.A. McLachlan, T.E. Wiese, M.E. Burow, and G. Wang Effects of 7-O substitutions on estrogenic and anti-estrogenic activities of daidzein analogues in MCF-7 breast cancer cells J. Med. Chem. 53 2010 6153 6163
21. D. Kannaiyan, and T. Imae pH-dependent encapsulation of pyrene in PPI-core: PAMAM-shell dendrimers Langmuir 25 2009 5282 5285
22. S.Y. Kim, S.J. Kim, J.Y. Lee, W.G. Kim, W.S. Park, Y.C. Sim, and S.J. Lee Protective effects of dietary soy isoflavones against UV-induced skin-aging in hairless mouse model J. Am. Coll. Nutr. 23 2004 157 162
23. S.H. Lee, Y.H. Kim, H.J. Yu, N.S. Cho, T.H. Kim, D.C. Kim, C.B. Chung, Y.I. Hwang, and K.H. Kim Enhanced bioavailability of soy isoflavones by complexation with beta-cyclodextrin in rats Biosci. Biotechnol. Biochem. 71 2007 2927 2933
24. Y.J. Lei, M. Yu, and K. Zhao Preparation and characterization of inclusion complex of daidzein with beta-cyclodextrin Food Sci. 26 2005 134 137
25. V. Mishra, U. Gupta, and N.K. Jain Surface-engineered dendrimers: a solution for toxicity issues J. Biomater. Sci. Polym. Ed. 20 2009 141 166
26. V. Mishra, U. Gupta, and N.K. Jain Influence of different generations of poly(propylene imine) dendrimers on human erythrocytes Pharmazie 65 2010 891 895
27. E. Reiter, E. Reiter, V. Beck, S. Medjakovic, and A. Jungbauer Isoflavones are safe compounds for therapeutical applications - evaluation of in vitro data Gynecol. Endocrinol. 25 2009 554 580
28. D.L. Richter-Egger, A. Tesfai, and S.A. Tucker Spectroscopic investigations of poly(propyleneimine) dendrimers using the solvatochromic probe phenol blue and comparisons to poly(amidoamine) dendrimers Anal. Chem. 73 2001 5743 5751
29. Q. Shen, X. Li, D. Yuan, and W. Jia Enhanced oral bioavailability of daidzein by self-microemulsifying drug delivery system Chem. Pharm. Bull. 58 2010 639 643
30. X.Y. Shi, I.H. Lee, X.S. Chen, M.W. Shen, S.L. Xiao, M.F. Zhu, J.R. Baker Jr., and S.H. Wang Influence of dendrimer surface charge on the bioactivity of 2-methoxyetradiol complexed with dendrimers Soft Matter 6 2010 2539 2545
31. P.E.S. Smith, J.R. Brender, H. Ulrich, N. Durr, J.D. Xu, D.G. Mullen, Banaszak, M.M. Holl, and A. Ramamoorthy Solid-state NMR reveals the hydrophobic-core location of poly(amidoamine) dendrimers in biomembranes J. Am. Chem. Soc. 132 2010 8087 8097
32. P. Sojitra, A. Raval, D. Kothwala, H. Kotadia, and Adeshara Covalently conjugation of genistein with biodegradable poly l-lactide Trends Biomater. Artif. Organs 23 2010 144 148
33. R. Stancanelli, A. Mazzaglia, S. Tomamasini, M.L. Calabro, and V. Villari The enhancement of isoflavones water solubility by complexation with modified cyclodextrins: a spectroscopic investigation with implications in the pharmaceutical analysis J. Pharm. Biomed. Anal. 44 2007 980 984
34. D.A. Tomalia Birth of a new macromolecular architecture: dendrimers as quantized building blocks for nanoscale synthetic polymer chemistry Prog. Polym. Sci. 30 2005 294 324
35. A.E. Valsecchi, S. Franchi, A.E. Panerai, A. Rossi, P. Sacerdote, and M. Colleoni The soy isoflavone genistein reverses oxidative and inflammatory state, neuropathic pain, neurotrophic and vasculature deficits in diabetes mouse model Eur. J. Pharmacol. 650 2011 694 702
36. Y. Wang, R. Guo, X. Cao, M. Shen, and X.Y. Shi Encapsulation of 2-methoxyestradiol within multifunctional poly(amidoamine) dendrimers for targeted cancer therapy Biomaterials 32 2011 3322 3329
37. H.A. Ward, and G.G. Kuhnle Phytoestrogen consumption and association with breast, prostate and colorectal cancer in EPIC Norfolk Arch. Biochem. Biophys. 501 2010 170 175
38. A. Warri, N.M. Saarinen, S. Makela, and L. Hilakivi-Clarke The role of early life genistein exposures in modifying breast cancer risk Br. J. Cancer 98 2008 1485 1493
39. W.L. Whaley, J.D. Rummel, and N. Kastrapeli Interaction of genistein and related isoflavones with lipid micelles Langmuir 22 2006 7175 7184
40. Q.L. Wu, Y.Y. Cheng, J.J. Hu, L.B. Zhao, and T.W. Xu Insights into the interactions between dendrimers and bioactive surfactants: 3. Size-dependent and hydrophobic property-dependent encapsulation of bile salts J. Phys. Chem. B 113 2009 12934 12943
41. C.R. Xavier, A.P.C. Silva, L.C. Schwingel, G.S. Borghetti, B.L. Koester, P. Mayorga, H.F. Teixeira, and V.L. Bassani Improvement of genistein content in solid genistein/beta-cylcodextrin complexes Quim. Nova 33 2010 587 590
42. W.J. Yang, Y.Y. Cheng, T.W. Xu, X.Y. Wang, and L.P. Wen Targeting cancer cells with biotin-dendrimer conjugates Eur. J. Med. Chem. 44 2008 862 868
43. Z.W. Zhang, Y. Huang, F. Gao, H.H. Bu, W.W. Gu, and Y.P. Li Daidzein-phospholipid complex loaded lipid nanocarriers improved oral absorption: in vitro characteristics and in vivo behavior in rats Nanoscale 3 2011 1780 1787
44. L.B. Zhao, Y.Y. Cheng, J.J. Hu, Q.L. Wu, and T.W. Xu Host-guest chemistry of dendrimer-drug complexes. 3. Competitive binding of multiple drugs by a single dendrimer for combination therapy J. Phys. Chem. B 113 2009 14172 14179
45. L.B. Zhao, Q.L. Wu, Y.Y. Cheng, J.H. Zhang, J.H. Wu, and T.W. Xu High-throughput screening of dendrimer-binding drugs J. Am. Chem. Soc. 132 2010 13182 13184
46. J.H. Zou, W.F. Shi, J. Wang, and J. Bo Encapsulation and controlled release of a hydrophobic drug using a novel nanoparticle-forming hyperbranched polyester Macromol. Biosci. 5 2005 662 668