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

International Journal of Pharmaceutics - Tập 421 - Trang 301-309 - 2011
Chen Zhao1, Yitong Wang1, Yunzhang Su1, Hongfeng Zhang1, Lingxiao Ding1, Xiaofeng Yan1, Di Zhao1, Naimin Shao1, Xiyun Ye1, Yiyun Cheng1
1School of Life Sciences, East China Normal University, Shanghai 200241, PR China

Tài liệu tham khảo

Agarwal, 2008, Tumour and dendrimers: a review on drug delivery aspects, J. Pharm. Pharmacol., 60, 671, 10.1211/jpp.60.6.0001 Agarwal, 2009, Dextran conjugated dendritic nanoconstructs as potential vectors for anti-cancer agent, Biomaterials, 30, 3588, 10.1016/j.biomaterials.2009.03.016 Barbosa, 2011, Effect of free or protein-associated soy isoflavones on the antioxidant status in rats, J. Sci. Food Agric., 91, 721, 10.1002/jsfa.4242 Borghetti, 2011, Daidzein/cyclodextrin/hydrophilic polymer ternary systems, Drug Dev. Ind. Pharm., 37, 886, 10.3109/03639045.2010.548066 Byun, 2010, Effect of soybeans and sword beans on bone metabolism in a rat model of osteoporosis, Ann. Nutr. Metab., 56, 106, 10.1159/000277663 Caminade, 2005, Characterization of dendrimers, Adv. Drug Deliv. Rev., 57, 2130, 10.1016/j.addr.2005.09.011 Cannava, 2010, Physico-chemical characterization of an amphiphilic cyclodextrin/genistein complex, J. Pharm. Biomed. Anal., 51, 1064, 10.1016/j.jpba.2009.11.025 Cheng, 2009, Generation-dependent encapsulation/electrostatic attachment of phenobarbital molecules by poly(amidoamine) dendrimers: evidence from 2D-NOESY investigations, Eur. J. Med. Chem., 44, 2219, 10.1016/j.ejmech.2008.05.031 Cheng, 2008, 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, 8884, 10.1021/jp801742t Cheng, 2011, Design of biocompatible dendrimers for cancer diagnosis and therapy: current status and future perspectives, Chem. Soc. Rev., 40, 2673, 10.1039/c0cs00097c D’Emanuele, 2005, Dendrimer–drug interactions, Adv. Drug Deliv. Rev., 57, 2147, 10.1016/j.addr.2005.09.012 Duncan, 2005, Dendrimer biocompatibility and toxicity, Adv. Drug Deliv. Rev., 57, 2215, 10.1016/j.addr.2005.09.019 Gao, 2008, The role of daidzein-loaded sterically stabilized solid lipid nanoparticles in therapy for cardio-cerebrovascular diseases, Biomaterials, 29, 4129, 10.1016/j.biomaterials.2008.07.008 Ge, 2007, Optimized preparation of daidzein-loaded chitosan microspheres and in vivo evaluation after intramuscular injection in rats, Int. J. Pharm., 338, 142, 10.1016/j.ijpharm.2007.01.046 Gupta, 2006, Dendrimers: novel polymeric nanoarchitectures for solubility enhancement, Biomacromolecules, 7, 649, 10.1021/bm050802s Heo, 2005, Protective effects of daidzein on oxidative stress-induced neurotoxicity and scopolamine-mediated cognitive defect, J. Food Sci., 70, S91, 10.1111/j.1365-2621.2005.tb07122.x Hu, 2009, Host–guest chemistry and physico-chemical properties of dendrimer–mycophenolic acid complexes, J. Phys. Chem. B, 113, 64, 10.1021/jp8078919 Jain, 2010, Dendrimer toxicity: let's meet the challenge, Int. J. Pharm., 394, 122, 10.1016/j.ijpharm.2010.04.027 Jain, 2008, Application of dendrimer–drug complexation in the enhancement of drug solubility and bioavailability, Expert Opin. Drug Metab. Toxicol., 4, 1035, 10.1517/17425255.4.8.1035 Jiang, 2010, Effects of 7-O substitutions on estrogenic and anti-estrogenic activities of daidzein analogues in MCF-7 breast cancer cells, J. Med. Chem., 53, 6153, 10.1021/jm100610w Kannaiyan, 2009, pH-dependent encapsulation of pyrene in PPI-core: PAMAM-shell dendrimers, Langmuir, 25, 5282, 10.1021/la8039847 Kim, 2004, Protective effects of dietary soy isoflavones against UV-induced skin-aging in hairless mouse model, J. Am. Coll. Nutr., 23, 157, 10.1080/07315724.2004.10719356 Lee, 2007, Enhanced bioavailability of soy isoflavones by complexation with beta-cyclodextrin in rats, Biosci. Biotechnol. Biochem., 71, 2927, 10.1271/bbb.70296 Lei, 2005, Preparation and characterization of inclusion complex of daidzein with beta-cyclodextrin, Food Sci., 26, 134 Mishra, 2009, Surface-engineered dendrimers: a solution for toxicity issues, J. Biomater. Sci. Polym. Ed., 20, 141, 10.1163/156856208X386246 Mishra, 2010, Influence of different generations of poly(propylene imine) dendrimers on human erythrocytes, Pharmazie, 65, 891 Reiter, 2009, Isoflavones are safe compounds for therapeutical applications—evaluation of in vitro data, Gynecol. Endocrinol., 25, 554, 10.1080/09513590802596461 Richter-Egger, 2001, Spectroscopic investigations of poly(propyleneimine) dendrimers using the solvatochromic probe phenol blue and comparisons to poly(amidoamine) dendrimers, Anal. Chem., 73, 5743, 10.1021/ac0155355 Shen, 2010, Enhanced oral bioavailability of daidzein by self-microemulsifying drug delivery system, Chem. Pharm. Bull., 58, 639, 10.1248/cpb.58.639 Shi, 2010, Influence of dendrimer surface charge on the bioactivity of 2-methoxyetradiol complexed with dendrimers, Soft Matter, 6, 2539, 10.1039/b925274f Smith, 2010, Solid-state NMR reveals the hydrophobic-core location of poly(amidoamine) dendrimers in biomembranes, J. Am. Chem. Soc., 132, 8087, 10.1021/ja101524z Sojitra, 2010, Covalently conjugation of genistein with biodegradable poly l-lactide, Trends Biomater. Artif. Organs, 23, 144 Stancanelli, 2007, 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, 980, 10.1016/j.jpba.2007.03.025 Tomalia, 2005, Birth of a new macromolecular architecture: dendrimers as quantized building blocks for nanoscale synthetic polymer chemistry, Prog. Polym. Sci., 30, 294, 10.1016/j.progpolymsci.2005.01.007 Valsecchi, 2011, The soy isoflavone genistein reverses oxidative and inflammatory state, neuropathic pain, neurotrophic and vasculature deficits in diabetes mouse model, Eur. J. Pharmacol., 650, 694, 10.1016/j.ejphar.2010.10.060 Wang, 2011, Encapsulation of 2-methoxyestradiol within multifunctional poly(amidoamine) dendrimers for targeted cancer therapy, Biomaterials, 32, 3322, 10.1016/j.biomaterials.2010.12.060 Ward, 2010, Phytoestrogen consumption and association with breast, prostate and colorectal cancer in EPIC Norfolk, Arch. Biochem. Biophys., 501, 170, 10.1016/j.abb.2010.05.018 Warri, 2008, The role of early life genistein exposures in modifying breast cancer risk, Br. J. Cancer, 98, 1485, 10.1038/sj.bjc.6604321 Whaley, 2006, Interaction of genistein and related isoflavones with lipid micelles, Langmuir, 22, 7175, 10.1021/la0606502 Wu, 2009, 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, 12934, 10.1021/jp906661z Xavier, 2010, Improvement of genistein content in solid genistein/beta-cylcodextrin complexes, Quim. Nova, 33, 587, 10.1590/S0100-40422010000300019 Yang, 2008, Targeting cancer cells with biotin–dendrimer conjugates, Eur. J. Med. Chem., 44, 862, 10.1016/j.ejmech.2008.04.021 Zhang, 2011, Daidzein–phospholipid complex loaded lipid nanocarriers improved oral absorption: in vitro characteristics and in vivo behavior in rats, Nanoscale, 3, 1780, 10.1039/c0nr00879f Zhao, 2009, 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, 14172, 10.1021/jp907437e Zhao, 2010, High-throughput screening of dendrimer-binding drugs, J. Am. Chem. Soc., 132, 13182, 10.1021/ja106128u Zou, 2005, Encapsulation and controlled release of a hydrophobic drug using a novel nanoparticle-forming hyperbranched polyester, Macromol. Biosci., 5, 662, 10.1002/mabi.200500015