Design of acid-responsive polymeric nanoparticles for 7, 3′, 4′-trihydroxyisoflavone topical administration

International Journal of Nanomedicine

Volumn 11, Issue , 2016, Pages 1615-1627

  Huang, Pao Hsien ^a   Hu, Stephen Chu Sung ^b,c   Lee, Chiang Wen ^d   Yeh, An Chi ^e   Tseng, Chih Hua ^a   Yen, Feng Lin ^a,f  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^c KAOHSIUNG MEDICAL UNIVERSITY HOSPITAL   (Taiwan)

^d CHANG GUNG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Taiwan)

^e CHENG SHIU UNIVERSITY   (Taiwan)

^f NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

Author keywords

7, 3 , 4 trihydroxyisoflavone; Nanoparticles; Skin penetration; Topical delivery; Water solubility

Indexed keywords

7,3',4' TRIHYDROXYISOFLAVONE; ACID RESPONSIVE POLYMERIC NANOPARTICLE; ANTIOXIDANT; EUDRAGIT; NANOPARTICLE; POLYVINYL ALCOHOL; UNCLASSIFIED DRUG; 1,1-DIPHENYL-2-PICRYLHYDRAZYL; 3',4',7-TRIHYDROXYISOFLAVONE; ACRYLIC ACID DERIVATIVE; BIPHENYL DERIVATIVE; ISOFLAVONE DERIVATIVE; PICRIC ACID; POLYMER; WATER;

AMORPHOUS TRANSFORMATION; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; CELL VIABILITY; CHEMICAL PARAMETERS; CONTROLLED STUDY; DIFFERENTIAL SCANNING CALORIMETRY; DPPH RADICAL SCAVENGING ASSAY; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG DOSAGE FORM COMPARISON; DRUG ENCAPSULATION EFFICIENCY; DRUG FORMULATION; DRUG LOADING EFFICIENCY; DRUG SOLUBILITY; DRUG STRUCTURE; ELECTRON MICROSCOPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDROGEN BOND; IN VITRO STUDY; INFRARED SPECTROSCOPY; KERATINOCYTE; MTT ASSAY; NANOPRECIPITATION; NANOTECHNOLOGY; NONHUMAN; PARTICLE SIZE; PHARMACOLOGICAL PARAMETERS; PHYSICAL CHEMISTRY; PIG; PROTON NUCLEAR MAGNETIC RESONANCE; SKIN PENETRATION; SOLUBILITY; WATER SOLUBILITY; X RAY DIFFRACTION; ANIMAL; CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; FREEZE DRYING; METABOLISM; SKIN; SKIN ABSORPTION; TOPICAL DRUG ADMINISTRATION;

ACRYLATES; ADMINISTRATION, TOPICAL; ANIMALS; ANTIOXIDANTS; BIPHENYL COMPOUNDS; CALORIMETRY, DIFFERENTIAL SCANNING; CELL SURVIVAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FREEZE DRYING; HUMANS; ISOFLAVONES; NANOPARTICLES; PARTICLE SIZE; PICRATES; POLYMERS; POLYVINYL ALCOHOL; PROTON MAGNETIC RESONANCE SPECTROSCOPY; SKIN; SKIN ABSORPTION; SOLUBILITY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SUS SCROFA; WATER; X-RAY DIFFRACTION;

EID: 84964497475     PISSN: 11769114     EISSN: 11782013     Source Type: Journal    
DOI: 10.2147/IJN.S100418     Document Type: Article

References (43)

1. Moghaddam AS, Entezari MH, Iraj B, Askari GR, Maracy MR. The effects of consumption of bread fortified with soy bean flour on metabolic profile in type 2 diabetic women: a cross-over randomized controlled clinical trial. Int J Prev Med. 2014;5:1529–1536.
2. Acharjee S, Zhou JR, Elajami TK, Welty FK. Effect of soy nuts and equol status on blood pressure, lipids and inflammation in postmenopausal women stratified by metabolic syndrome status. Metabolism. 2015;64:236–243.
3. Morimoto Y, Maskarinec G, Park SY, et al. Dietary isoflavone intake is not statistically significantly associated with breast cancer risk in the Multiethnic Cohort. Br J Nutr. 2014;112:976–983.
4. Talaei M, Koh WP, van Dam RM, Yuan JM, Pan A. Dietary soy intake is not associated with risk of cardiovascular disease mortality in Singapore Chinese adults. J Nutr. 2014;144:921–928.
5. Zhou J, Tzanetakis IE. Epidemiology of soybean vein necrosis-associated virus. Phytopathology. 2013;103:966–971.
6. Rusin A, Krawczyk Z, Grynkiewicz G, Gogler A, Zawisza-Puchałka J, Szeja W. Synthetic derivatives of genistein, their properties and possible applications. Acta Biochim Pol. 2010;57:23–34.
7. Mahmoud AM, Yang W, Bosland MC. Soy isoflavones and prostate cancer: a review of molecular mechanisms. J Steroid Biochem Mol Biol. 2014;140:116–132.
8. Mann GE, Rowlands DJ, Li FY, de Winter P, Siow RC. Activation of endothelial nitric oxide synthase by dietary isoflavones: role of NO in Nrf2-mediated antioxidant gene expression. Cardiovasc Res. 2007;75:261–274.
9. Siriwardhana N, Kalupahana NS, Cekanova M, LeMieux M, Greer B, Moustaid-Moussa N. Modulation of adipose tissue inflammation by bioactive food compounds. J Nutr Biochem. 2013;24:613–623.
10. Lin JY, Tournas JA, Burch JA, Monteiro-Riviere NA, Zielinski J. Topical isoflavones provide effective photoprotection to skin. Photodermatol Photoimmunol Photomed. 2008;24:61–66.
11. Murata M, Midorikawa K, Koh M, Umezawa K, Kawanishi S. Genistein and daidzein induce cell proliferation and their metabolites cause oxidative DNA damage in relation to isoflavone-induced cancer of estrogen-sensitive organs. Biochemistry. 2004;43:2569–2577.
12. Park JS, Park HY, Kim DH, Kim DH, Kim HK. Ortho-Dihydroxyisoflavone derivatives from aged Doenjang (Korean fermented soypaste) and its radical scavenging activity. Bioorg Med Chem Lett. 2008; 18:5006–5009.
13. Park JS, Kim DH, Lee JK, et al. Natural ortho-dihydroxyisoflavone derivatives from aged Korean fermented soybean paste as potent tyrosinase and melanin formation inhibitors. Bioorg Med Chem Lett. 2010;20:1162–1164.
14. Lee DE, Lee KW, Byun S, et al. 7,3′,4′-Trihydroxyisoflavone, a metabolite of the soy isoflavone daidzein, suppresses ultraviolet B-induced skin cancer by targeting Cot and MKK4. J Biol Chem. 2011;286:14246–14256.
15. Vitale DC, Piazza C, Melilli B, Drago F, Salomone S. Isoflavones: estrogenic activity, biological effect and bioavailability. Eur J Drug Metab Pharmacokinet. 2013;38:15–25.
16. Tang J, Xu N, Ji H, Liu H, Wang Z, Wu L. Eudragit nanoparticles containing genistein: formulation, development, and bioavailability assessment. Int J Nanomedicine. 2011;6:2429–2435.
17. Rahimpour Y, Hamishehkar H. Liposomes in cosmeceutics. Expert Opin Drug Deliv. 2012;9:443–455.
18. Papakostas D, Rancan F, Sterry W, Blume-Peytavi U, Vogt A. Nanoparticles in dermatology. Arch Dermatol Res. 2011;303:533–550.
19. Kreilgaard M. Influence of microemulsions on cutaneous drug delivery. Adv Drug Deliv Rev. 2002;54:S77–S98.
20. Aljuffali IA, Hsu CY, Lin YK, Fang JY. Cutaneous delivery of natural antioxidants: the enhancement approaches. Curr Pharm Des. 2015;21:2745–2757.
21. Guterres SS, Alves MP, Pohlmann AR. Polymeric nanoparticles, nanospheres and nanocapsules, for cutaneous applications. Drug Target Insights. 2007;2:147–157.
22. Guo C, Khengar RH, Sun M, Wang Z, Fan A, Zhao Y. Acid-responsive polymeric nanocarriers for topical adapalene delivery. Pharm Res. 2014;31:3051–3059.
23. Loira-Pastoriza C, Sapin-Minet A, Diab R, Grossiord JL, Maincent P. Low molecular weight heparin gels, based on nanoparticles, for topical delivery. Int J Pharm. 2012;426:256–262.
24. Ueda H, Wakabayashi S, Kikuchi J, Ida Y, Kadota K, Tozuka Y. Anomalous role change of tertiary amino and ester groups as hydrogen acceptors in eudragit E based solid dispersion depending on the concentration of naproxen. Mol Pharm. 2015;12:1050–1061.
25. Yen FL, Wu TH, Lin LT, Cham TM, Lin CC. Naringenin-loaded nanoparticles improve the physicochemical properties and the hepatoprotective effects of naringenin in orally-administered rats with CCl(4)-induced acute liver failure. Pharm Res. 2009;26:893–902.
26. COLIPA guidelines: Guidelines for Percutaneous Absorption/Penetration, 1997, Cosmetics Europe. Available from: http://www.jacvam.jp/files/doc/05_01/05_01_Z3.pdf. Accessed March 4, 2015.
27. Yen FL, Wu TH, Tzeng CW, Lin LT, Lin CC. Curcumin nanoparticles improve the physicochemical properties of curcumin and effectively enhance its antioxidant and antihepatoma activities. J Agric Food Chem. 2010;58:7376–7382.
28. Wu TH, Yen FL, Lin LT, Tsai TR, Lin CC, Cham TM. Preparation, physicochemical characterization, and antioxidant effects of quercetin nanoparticles. Int J Pharm. 2008;346:160–168.
29. Zhang W, Li X, Ye T, et al. Design, characterization, and in vitro cellular inhibition and uptake of optimized genistein-loaded NLC for the prevention of posterior capsular opacification using response surface methodology. Int J Pharm. 2013;454:354–366.
30. Naksuriya O, Okonogi S, Schiffelers RM, Hennink WE. Curcumin nanoformulations: a review of pharmaceutical properties and preclinical studies and clinical data related to cancer treatment. Biomaterials. 2014;35:3365–3383.
31. Mora-Huertas CE, Fessi H, Elaissari A. Polymer-based nanocapsules for drug delivery. Int J Pharm. 2010;385:113–142.
32. Sahoo SK, Panyam J, Prabha S, Labhasetwar V. Residual polyvinyl alcohol associated with poly(D,L-lactide-co-glycolide) nanoparticles affects their physical properties and cellular uptake. J Control Release. 2002;82:105–114.
33. Galindo-Rodriguez S, Allémann E, Fessi H, Doelker E. Physicochemical parameters associated with nanoparticle formation in the salting-out, emulsification–diffusion, and nanoprecipitation methods. Pharm Res. 2004;21:1428–1439.
34. Ernsting MJ, Murakami M, Roy A, Li SD. Factors controlling the pharmacokinetics, biodistribution and intratumoral penetration of nanoparticles. J Control Release. 2013;172:782–794.
35. Gohulkumar M, Gurushankar K, Rajendra Prasad N, Krishnakumar N. Enhanced cytotoxicity and apoptosis-induced anticancer effect of silibinin-loaded nanoparticles in oral carcinoma (KB) cells. Mater Sci Eng C Mater Biol Appl. 2014;41:274–282.
36. Tzeng CW, Yen FL, Wu TH, et al. Enhancement of dissolution and antioxidant activity of kaempferol using a nanoparticle engineering process. J Agric Food Chem. 2011;59:5073–5080.
37. Som I, Bhatia K, Yasir M. Status of surfactants as penetration enhancers in transdermal drug delivery. J Pharm Bioallied Sci. 2012;4:2–9.
38. Lane ME. Skin penetration enhancers. Int J Pharm. 2013;447:12–21.
39. Alvarez-Román R, Naik A, Kalia YN, Guy RH, Fessi H. Skin penetration and distribution of polymeric nanoparticles. J Control Release. 2004;99:53–62.
40. Müller RH, Petersen RD, Hommoss A, Pardeike J. Nanostructured lipid carriers (NLC) in cosmetic dermal products. Adv Drug Deliv Rev. 2007;59:522–530.
41. Loo Ch, Basri M, Ismail R, et al. Effect of compositions in nanostructured lipid carriers (NLC) on skin hydration and occlusion. Int J Nanomedicine. 2013;8:13–22.
42. Okonogi S, Riangjanapatee P. Physicochemical characterization of lycopene-loaded nanostructured lipid carrier formulations for topical administration. Int J Pharm. 2015;478:726–735.
43. Rostagno MA, Villares A, Guillamón E, García-Lafuente A, Martínez JA. Sample preparation for the analysis of isoflavones from soybeans and soy foods. J Chromatogr A. 2009;1216:2–29.