Nanoscale delivery of resveratrol towards enhancement of supplements and nutraceuticals

Nutrients

Volumn 8, Issue 3, 2016, Pages

  Neves, Ana Rute ^a   Martins, Susana ^a   Segundo, Marcela A ^a   Reis, Salette ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

Biocompatibility; Intestinal permeability; Lipidnanoparticles; Nanodeliverysystems; Oralbioavailability; Resveratrol

Indexed keywords

NUTRACEUTICAL; RESVERATROL; SOLID LIPID NANOPARTICLE; DRUG CARRIER; LIPID; NANOPARTICLE; STILBENE DERIVATIVE;

ARTICLE; BIOAVAILABILITY; BIOCOMPATIBILITY; CELL VIABILITY; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; DRUG STABILITY; ELECTRIC RESISTANCE; ELECTROPHORETIC LIGHT SCATTERING; ENTRAPMENT EFFICIENCY; HUMAN; HUMAN CELL; INTESTINE MUCOSA PERMEABILITY; LIGHT SCATTERING; MTT ASSAY; NANOENCAPSULATION; NANOSCALE DELIVERY SYSTEM; PARTICLE SIZE; PHOTODEGRADATION; PHOTON CORRELATION SPECTROSCOPY; PHYSICAL PARAMETERS; POLYDISPERSITY INDEX; TRANSEPITHELIAL ELECTRICAL RESISTANCE; ZETA POTENTIAL; CACO-2 CELL LINE; CHEMISTRY; DIETARY SUPPLEMENT; DRUG FORMULATION; INTESTINAL SECRETIONS; INTESTINE ABSORPTION; INTESTINE MUCOSA; METABOLISM; NANOTECHNOLOGY; ORAL DRUG ADMINISTRATION; PERMEABILITY; TIME FACTOR;

ADMINISTRATION, ORAL; CACO-2 CELLS; DIETARY SUPPLEMENTS; DRUG CARRIERS; DRUG COMPOUNDING; DRUG STABILITY; HUMANS; INTESTINAL ABSORPTION; INTESTINAL MUCOSA; INTESTINAL SECRETIONS; LIPIDS; NANOPARTICLES; NANOTECHNOLOGY; PERMEABILITY; STILBENES; TIME FACTORS;

EID: 84960096002     PISSN: None     EISSN: 20726643     Source Type: Journal    
DOI: 10.3390/nu8030131     Document Type: Article

References (68)

1. Baur, J.A.; Sinclair, D.A. Therapeutic potential of resveratrol: The in vivo Evidence. Nat. Rev. Drug Discov. 2006, 5, 493–506.
2. Delmas, D.; Aires, V.; Limagne, E.; Dutartre, P.; Mazue, F.; Ghiringhelli, F.; Latruffe, N. Transport, stability, and biological activity of resveratrol. Ann. N. Y. Acad. Sci. 2011, 1215, 48–59.
3. Neves, A.R.; Lucio, M.; Lima, J.L.; Reis, S. Resveratrol in medicinal chemistry: A critical review of its pharmacokinetics, drug-delivery, and membrane interactions. Curr. Med. Chem. 2012, 19, 1663–1681.
4. Walle, T.; Hsieh, F.; DeLegge, M.H.; Oatis, J.E.; Walle, U.K. High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab. Dispos. 2004, 32, 1377–1382.
5. Almeida, L.; Vaz-da-Silva, M.; Falcao, A.; Soares, E.; Costa, R.; Loureiro, A.I.; Fernandes-Lopes, C.; Rocha, J.F.; Nunes, T.; Wright, L. et al. Pharmacokinetic and safety profile of trans-resveratrol in a rising multiple-dose study in healthy volunteers. Mol. Nutr. Food Res. 2009, 53, S7–S15.
6. Kapetanovic, I.M.; Muzzio, M.; Huang, Z.; Thompson, T.N.; McCormick, D.L. Pharmacokinetics, oral bioavailability, and metabolic profile of resveratrol and its dimethylether analog, pterostilbene, in rats. Cancer Chemother. Pharmacol.2011, 68, 593–601.
7. Chen, X.; He, H.; Wang, G.; Yang, B.; Ren, W.; Ma, L.; Yu, Q. Stereospecific determination of cis- and trans-resveratrol in rat plasma by HPLC: Application to pharmacokinetic studies. Biomed. Chromatogr. 2007, 21, 257–265.
8. Trela, B.C.; Waterhouse, A.L. Resveratrol: Isomeric molar absorptivities and stability. J. Agric. Food Chem. 1996, 44, 1253–1257.
9. Amri, A.; Chaumeil, J.C.; Sfar, S.; Charrueau, C. Administration of resveratrol: What formulation solutions to bioavailability limitations? J. Control. Release 2012, 158, 182–193.
10. Johnson, J.J.; Nihal, M.; Siddiqui, I.A.; Scarlett, C.O.; Bailey, H.H.; Mukhtar, H.; Ahmad, N. Enhancing the bioavailability of resveratrol by combining it with piperine. Mol. Nutr. Food Res. 2011, 55, 1169–1176.
11. Amiot, M.J.; Romier, B.; Dao, T.M.; Fanciullino, R.; Ciccolini, J.; Burcelin, R.; Pechere, L.; Emond, C.; Savouret, J.F.; Seree, E. Optimization of trans-resveratrol bioavailability for human therapy. Biochimie 2013, 95, 1233–1238.
12. Bonechi, C.; Martini, S.; Ciani, L.; Lamponi, S.; Rebmann, H.; Rossi, C.; Ristori, S. Using liposomes as carriers for polyphenolic compounds: The Case of Trans-Resveratrol. PLoS ONE 2012, 7, e41438.
13. Sun, Y.; Xia, Z.; Zheng, J.; Qiu, P.; Zhang, L.; Mc Clements, D.J.; Xiao, H. Nanoemulsion-based delivery systems for nutraceuticals: Influence of carrier oil type on bioavailability of pterostilbene. J. Funct. Foods 2015, 13, 61–70.
14. Augustin, M.A.; Abeywardena, M.Y.; Patten, G.; Head, R.; Lockett, T.; De Luca, A.; Sanguansri, L. Effects of microencapsulation on the gastrointestinal transit and tissue distribution of a bioactive mixture of fish oil, tributyrin and resveratrol. J. Funct. Foods 2011, 3, 25–37.
15. Summerlin, N.; Soo, E.; Thakur, S.; Qu, Z.; Jambhrunkar, S.; Popat, A. Resveratrol nanoformulations: Challenges and opportunities. Int. J. Pharm. 2015, 479, 282–290.
16. Da Rocha Lindner, G.; Bonfanti Santos, D.; Colle, D.; Gasnhar Moreira, E.L.; Daniel Prediger, R.; Farina, M.; Khalil, N.M.; Mara Mainardes, R. Improved neuroprotective effects of resveratrol-loaded polysorbate 80-coated poly(lactide) nanoparticles in MPTP-induced Parkinsonism. Nanomedicine (Lond.) 2015, 10, 1127–1138.
17. Guo, W.; Li, A.; Jia, Z.; Yuan, Y.; Dai, H.; Li, H. Transferrin modified PEG-PLA-resveratrol conjugates: in vitro and in vivo studies for glioma. Eur. J. Pharmacol. 2013, 718, 41–47.
18. Musazzi, U.M.; Youm, I.; Murowchick, J.B.; Ezoulin, M.J.; Youan, B.B. Resveratrol-loaded nanocarriers: Formulation, optimization, characterization and in vitro toxicity on cochlear cells. Colloids Surf. B Biointerfaces 2014, 118, 234–242.
19. Sanna, V.; Siddiqui, I.A.; Sechi, M.; Mukhtar, H. Resveratrol-loaded nanoparticles based on poly(epsilon-caprolactone) and poly(d,l-lactic-co-glycolic acid)-poly(ethylene glycol) blend for prostate cancer treatment. Mol. Pharm. 2013, 10, 3871–3881.
20. Singh, G.; Pai, R.S. Optimized PLGA nanoparticle platform for orally dosed trans-resveratrol with enhanced bioavailability potential. Expert Opin. Drug Deliv. 2014, 11, 647–659.
21. Lu, X.; Ji, C.; Xu, H.; Li, X.; Ding, H.; Ye, M.; Zhu, Z.; Ding, D.; Jiang, X.; Ding, X.; Guo, X. Resveratrol-loaded polymeric micelles protect cells from Abeta-induced oxidative stress. Int. J. Pharm. 2009, 375, 89–96.
22. Penalva, R.; Esparza, I.; Larraneta, E.; Gonzalez-Navarro, C.J.; Gamazo, C.; Irache, J.M. Zein-based nanoparticles improve the oral bioavailability of resveratrol and its anti-inflammatory effects in a mouse model of endotoxic shock.J. Agric. Food Chem. 2015, 63, 5603–5611.
23. Sessa, M.; Balestrieri, M.L.; Ferrari, G.; Servillo, L.; Castaldo, D.; D’Onofrio, N.; Donsi, F.; Tsao, R. Bioavailability of encapsulated resveratrol into nanoemulsion-based delivery systems. Food Chem. 2014, 147, 42–50.
24. Ansari, K.A.; Vavia, P.R.; Trotta, F.; Cavalli, R. Cyclodextrin-based nanosponges for delivery of resveratrol: in vitrocharacterisation, stability, cytotoxicity and permeation study. AAPS Pharm. Sci. Tech. 2011, 12, 279–286.
25. Silva, F.; Figueiras, A.; Gallardo, E.; Nerin, C.; Domingues, F.C. Strategies to improve the solubility and stability of stilbene antioxidants: A comparative study between cyclodextrins and bile acids. Food Chem. 2014, 145, 115–125.
26. Venuti, V.; Cannava, C.; Cristiano, M.C.; Fresta, M.; Majolino, D.; Paolino, D.; Stancanelli, R.; Tommasini, S.; Ventura, C.A. A characterization study of resveratrol/sulfobutyl ether-beta-cyclodextrin inclusion complex and in vitroanticancer activity. Colloids Surf. B Biointerfaces 2014, 115, 22–28.
27. Catania, A.; Barrajon-Catalan, E.; Nicolosi, S.; Cicirata, F.; Micol, V. Immunoliposome encapsulation increases cytotoxic activity and selectivity of curcumin and resveratrol against HER2 overexpressing human breast cancer cells.Breast Cancer Res. Treat. 2013, 141, 55–65.
28. Coimbra, M.; Isacchi, B.; van Bloois, L.; Torano, J.S.; Ket, A.; Wu, X.; Broere, F.; Metselaar, J.M.; Rijcken, C.J.; Storm, G. et al. Improving solubility and chemical stability of natural compounds for medicinal use by incorporation into liposomes. Int. J. Pharm. 2011, 416, 433–442.
29. Lu, X.Y.; Hu, S.; Jin, Y.; Qiu, L.Y. Application of liposome encapsulation technique to improve anti-carcinoma effect of resveratrol. Drug Dev. Ind. Pharm. 2012, 38, 314–322.
30. Narayanan, N.K.; Nargi, D.; Randolph, C.; Narayanan, B.A. Liposome encapsulation of curcumin and resveratrol in combination reduces prostate cancer incidence in PTEN knockout mice. Int. J. Cancer 2009, 125, 1–8.
31. Wang, X.X.; Li, Y.B.; Yao, H.J.; Ju, R.J.; Zhang, Y.; Li, R.J.; Yu, Y.; Zhang, L.; Lu, W.L. The use of mitochondrial targeting resveratrol liposomes modified with a dequalinium polyethylene glycol-distearoylphosphatidyl ethanolamine conjugate to induce apoptosis in resistant lung cancer cells. Biomaterials 2011, 32, 5673–5687.
32. Soo, E.; Thakur, S.; Qu, Z.; Jambhrunkar, S.; Parekh, H.S.; Popat, A. Enhancing delivery and cytotoxicity of resveratrol through a dual nanoencapsulation approach. J. Colloid Interface Sci. 2016, 462, 368–374.
33. Jose, S.; Anju, S.S.; Cinu, T.A.; Aleykutty, N.A.; Thomas, S.; Souto, E.B. In vivo pharmacokinetics and biodistribution of resveratrol-loaded solid lipid nanoparticles for brain delivery. Int. J. Pharm. 2014, 474, 6–13.
34. Gokce, E.H.; Korkmaz, E.; Dellera, E.; Sandri, G.; Bonferoni, M.C.; Ozer, O. Resveratrol-loaded solid lipid nanoparticles versus nanostructured lipid carriers: Evaluation of antioxidant potential for dermal applications. Int. J. Nanomed. 2012, 7, 1841–1850.
35. Teskac, K.; Kristl, J. The evidence for solid lipid nanoparticles mediated cell uptake of resveratrol. Int. J. Pharm. 2010,390, 61–69.
36. Neves, A.R.; Lucio, M.; Martins, S.; Lima, J.L.; Reis, S. Novel resveratrol nanodelivery systems based on lipid nanoparticles to enhance its oral bioavailability. Int. J. Nanomed. 2013, 8, 177–187.
37. Pandita, D.; Kumar, S.; Poonia, N.; Lather, V. Solid lipid nanoparticles enhance oral bioavailability of resveratrol, a natural polyphenol. Food Res. Int. 2014, 62, 1165–1174.
38. Muchow, M.; Maincent, P.; Muller, R.H. Lipid nanoparticles with a solid matrix (SLN, NLC, LDC) for oral drug delivery. Drug Dev. Ind. Pharm. 2008, 34, 1394–1405.
39. Shidhaye, S.S.; Vaidya, R.; Sutar, S.; Patwardhan, A.; Kadam, V.J. Solid lipid nanoparticles and nanostructured lipid carriers—Innovative generations of solid lipid carriers. Curr. Drug Deliv. 2008, 5, 324–331.
40. Beloqui, A.; Solinis, M.A.; Rodriguez-Gascon, A.; Almeida, A.J.; Preat, V. Nanostructured lipid carriers: Promising drug delivery systems for future clinics. Nanomedicine 2016, 12, 143–161.
41. Muller, R.H.; Radtke, M.; Wissing, S.A. Nanostructured lipid matrices for improved microencapsulation of drugs. Int. J. Pharm. 2002, 242, 121–128.
42. Artursson, P.; Palm, K.; Luthman, K. Caco-2 monolayers in experimental and theoretical predictions of drug transport. Adv. Drug Deliv. Rev. 2001, 46, 27–43.
43. Corti, G.; Maestrelli, F.; Cirri, M.; Zerrouk, N.; Mura, P. Development and evaluation of an in vitro method for prediction of human drug absorption II. Demonstration of the method suitability. Eur. J. Pharm. Sci. 2006, 27, 354–362.
44. Schwebel, H.J.; van Hoogevest, P.; Leigh, M.L.; Kuentz, M. The apparent solubilizing capacity of simulated intestinal fluids for poorly water-soluble drugs. Pharm. Dev. Technol. 2011, 16, 278–286.
45. Frank, K.J.; Westedt, U.; Rosenblatt, K.M.; Holig, P.; Rosenberg, J.; Magerlein, M.; Brandl, M.; Fricker, G. Impact of FaSSIF on the solubility and dissolution-/permeation rate of a poorly water-soluble compound. Eur. J. Pharm. Sci.2012, 47, 16–20.
46. Neves, A.R.; Queiroz, J.F.; Weksler, B.; Romero, I.A.; Couraud, P.O.; Reis, S. Solid lipid nanoparticles as a vehicle for brain-targeted drug delivery: Two New Strategies of Functionalization with Apolipoprotein E. Nanotechnology 2015, 26, 495103.
47. Acosta, E. Bioavailability of nanoparticles in nutrient and nutraceutical delivery. Curr. Opin. Colloid Interface Sci. 2009,14, 3–15.
48. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to Proliferation and Cytotoxicity Assays. J. Immunol. Methods 1983, 65, 55–63.
49. Delie, F.; Rubas, W. A human colonic cell line sharing similarities with enterocytes as a model to examine oral absorption: Advantages and Limitations of the Caco-2 Model. Crit. Rev. Ther. Drug Carrier Syst. 1997, 14, 221–286.
50. Behrens, I.; Kissel, T. Do cell culture conditions influence the carrier-mediated transport of peptides in Caco-2 cell monolayers? Eur. J. Pharm. Sci. 2003, 19, 433–442.
51. Neves, A.R.; Reis, S.; Segundo, M.A. Development and validation of a HPLC method using a monolithic column for quantification of trans-resveratrol in lipid nanoparticles for intestinal permeability studies. J. Agric. Food Chem. 2015,63, 3114–3120.
52. Muller, R.H.; Mader, K.; Gohla, S. Solid lipid nanoparticles (SLN) for controlled drug delivery - a review of the state of the art. Eur. J. Pharm. Biopharm. 2000, 50, 161–177.
53. Müller, R.H.; Jacobs, C.; Kayser, O. Nanosuspensions as particulate drug formulations in therapy: Rationale for development and what we can expect for the future. Adv. Drug Deliv. Rev. 2001, 47, 3–19.
54. Des Rieux, A.; Fievez, V.; Momtaz, M.; Detrembleur, C.; Alonso-Sande, M.; van Gelder, J.; Cauvin, A.; Schneider, Y.J.; Preat, V. Helodermin-loaded nanoparticles: Characterization and transport across an in vitro model of the follicle-associated epithelium. J. Control. Release 2007, 118, 294–302.
55. Florence, A.T. Nanoparticle uptake by the oral route: Fulfilling its potential? Drug Discov. Today Technol. 2005, 2, 75–81.
56. Des Rieux, A.; Ragnarsson, E.G.; Gullberg, E.; Preat, V.; Schneider, Y.J.; Artursson, P. Transport of nanoparticles across an in vitro model of the human intestinal follicle associated epithelium. Eur. J. Pharm. Sci. 2005, 25, 455–465.
57. Yin Win, K.; Feng, S.-S. Effects of particle size and surface coating on cellular uptake of polymeric nanoparticles for oral delivery of anticancer drugs. Biomaterials 2005, 26, 2713–2722.
58. Stervbo, U.; Vang, O.; Bonnesen, C. A review of the content of the putative chemopreventive phytoalexin resveratrol in red wine. Food Chem. 2007, 101, 449–457.
59. Vian, M.A.; Tomao, V.; Gallet, S.; Coulomb, P.O.; Lacombe, J.M. Simple and rapid method for cis- and trans-resveratrol and piceid isomers determination in wine by high-performance liquid chromatography using chromolith columns. J. Chromatogr. A 2005, 1085, 224–229.
60. Figueiras, T.S.; Neves-Petersen, M.T.; Petersen, S.B. Activation energy of light induced isomerization of resveratrol. J. Fluoresc. 2011, 21, 1897–1906.
61. Camont, L.; Cottart, C.H.; Rhayem, Y.; Nivet-Antoine, V.; Djelidi, R.; Collin, F.; Beaudeux, J.L.; Bonnefont-Rousselot, D. Simple spectrophotometric assessment of the trans-/cis-resveratrol ratio in aqueous solutions. Anal. Chim. Acta2009, 634, 121–128.
62. Detoni, C.B.; Souto, G.D.; da Silva, A.L.; Pohlmann, A.R.; Guterres, S.S. Photostability and skin penetration of different E-resveratrol-loaded supramolecular structures. Photochem. Photobiol. 2012, 88, 913–921.
63. Hubatsch, I.; Ragnarsson, E.G.; Artursson, P. Determination of drug permeability and prediction of drug absorption in Caco-2 monolayers. Nat. Protoc. 2007, 2, 2111–2119.
64. Artursson, P.; Karlsson, J. Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochem. Biophys. Res. Commun. 1991, 175, 880–885.
65. Willenberg, I.; Michael, M.; Wonik, J.; Bartel, L.C.; Empl, M.T.; Schebb, N.H. Investigation of the absorption of resveratrol oligomers in the Caco-2 cellular model of intestinal absorption. Food Chem. 2015, 167, 245–250.
66. Teng, Z.; Yuan, C.; Zhang, F.; Huan, M.; Cao, W.; Li, K.; Yang, J.; Cao, D.; Zhou, S.; Mei, Q. Intestinal absorption and first-pass metabolism of polyphenol compounds in rat and their transport dynamics in Caco-2 cells. PLoS ONE 2012,7, e29647.
67. Ward, P.D.; Tippin, T.K.; Thakker, D.R. Enhancing paracellular permeability by modulating epithelial tight junctions.Pharm. Sci. Technol. Today 2000, 3, 346–358.
68. Neves, A.R.; Queiroz, J.F.; Costa Lima, S.A.; Figueiredo, F.; Fernandes, R.; Reis, S. Cellular uptake and transcytosis of lipid-based nanoparticles across the intestinal barrier: Relevance for Oral Drug Delivery. J. Colloid Interface Sci. 2016,463, 258–265.