Improved oral delivery of resveratrol from N-trimethyl chitosan-g-palmitic acid surface-modified solid lipid nanoparticles

Colloids and Surfaces B: Biointerfaces

Volumn 139, Issue , 2016, Pages 52-61

  Ramalingam, Prakash ^a   Ko, Young Tag ^a  

^a Gachon University College of Medicine   (South Korea)

Author keywords

N trimethyl chitosan; Oral bioavailability; Palmitic acid; Resveratrol; Solid lipid nanoparticles

Indexed keywords

AGGLOMERATION; BIOCHEMISTRY; CHITIN; CHITOSAN; HYDROPHOBICITY; NANOPARTICLES; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RESVERATROL; SATURATED FATTY ACIDS; SURFACE TREATMENT;

CLINICAL APPLICATION; N-TRIMETHYL CHITOSANS; ORAL BIOAVAILABILITIES; ORAL DRUG DELIVERY SYSTEM; PHYSICOCHEMICAL PROPERTY; RELATIVE BIOAVAILABILITY; SOLID LIPID NANOPARTICLE (SLN); SOLID LIPID NANOPARTICLES;

PALMITIC ACID;

CHITOSAN DERIVATIVE; GELUCIRE; GLYCEROL PALMITOSTEARATE; N TRIMETHYL CHITOSAN; PALMITIC ACID; POLYSORBATE 80; RESVERATROL; SOLID LIPID NANOPARTICLE; UNCLASSIFIED DRUG; CHITOSAN; DIACYLGLYCEROL; DRUG CARRIER; FAT; GELUCIRE 50-13; N-TRIMETHYL CHITOSAN CHLORIDE; NANOPARTICLE; OIL; POLYSORBATE; STILBENE DERIVATIVE;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG DELIVERY SYSTEM; DRUG DOSAGE FORM COMPARISON; DRUG FORMULATION; DRUG STABILITY; EMBRYO; IN VITRO STUDY; IN VIVO STUDY; INFRARED SPECTROSCOPY; MALE; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; PHYSICAL CHEMISTRY; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SINGLE DRUG DOSE; SUSTAINED DRUG RELEASE; ANIMAL; BAGG ALBINO MOUSE; BIOAVAILABILITY; BLOOD; CHEMICAL PHENOMENA; CHEMISTRY; DRUG RELEASE; KINETICS; NIH 3T3 CELL LINE; SOLUBILITY;

ADMINISTRATION, ORAL; ANIMALS; BIOLOGICAL AVAILABILITY; CHITOSAN; DIGLYCERIDES; DRUG CARRIERS; DRUG COMPOUNDING; DRUG LIBERATION; FATS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; KINETICS; MALE; MICE; MICE, INBRED BALB C; NANOPARTICLES; NIH 3T3 CELLS; OILS; PALMITIC ACID; POLYSORBATES; SOLUBILITY; STILBENES;

EID: 84949636103     PISSN: 09277765     EISSN: 18734367     Source Type: Journal    
DOI: 10.1016/j.colsurfb.2015.11.050     Document Type: Article

References (52)

1. 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.
2. Karthikeyan S., Prasad N.R., Ganamani A., Balamurugan E. Anticancer activity of resveratrol-loaded gelatin nanoparticles on NCI-H460 non-small cell lung cancer cells. Biomed. Prev. Nutr. 2013, 3:64-73.
3. Baur J.A., Sinclair D.A. Therapeutic potential of resveratrol: the in vivo evidence. Nat. Rev. Drug Discov. 2006, 5:493-506.
4. Orallo F. Comparative studies of the antioxidant effects of cis-and trans-resveratrol. Curr. Med. Chem. 2006, 13:87-98.
5. Bradamante S., Barenghi L., Villa A. Cardiovascular protective effects of resveratrol. Cardiovasc. Drug Rev. 2004, 22:169-188.
6. Jang M., Cai L., Udeani G.O., Slowing K.V., Thomas C.F., Beecher C.W., Fong H.H., Farnsworth N.R., Kinghorn A.D., Mehta R.G. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 1997, 275:218-220.
7. López-Nicolás J.M., Rodríguez-Bonilla P., García-Carmona F. Complexation of pinosylvin, an analogue of resveratrol with high antifungal and antimicrobial activity, by different types of cyclodextrins. J. Agric. Food Chem. 2009, 57:10175-10180.
8. Hausenblas H.A., Schoulda J.A., Smoliga J.M. Resveratrol treatment as an adjunct to pharmacological management in type 2 diabetes mellitus-systematic review and meta-analysis. Mol. Nutr. Food Res. 2015, 59:147-159.
9. Ghanim H., Sia C.L., Korzeniewski K., Lohano T., Abuaysheh S., Marumganti A., Chaudhuri A., Dandona P. A resveratrol and polyphenol preparation suppresses oxidative and inflammatory stress response to a high-fat, high-carbohydrate meal. J. Clin. Endocrinol. Metab. 2011, 96:1409-1414.
10. Summerlin N., Soo E., Thakur S., Qu Z., Jambhrunkar S., Popat A. Resveratrol nanoformulations: Challenges and opportunities. Int. J. Pharm. 2015, 479:282-290.
11. Singh G., Pai R.S. Recent advances of resveratrol in nanostructured based delivery systems and in the management of HIV/AIDS. J. Control. Release 2014, 194:178-188.
12. Peng H., Xiong H., Li J., Xie M., Liu Y., Bai C., Chen L. Vanillin cross-linked chitosan microspheres for controlled release of resveratrol. Food Chem. 2010, 121:23-28.
13. 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.
14. Sessa M., Tsao R., Liu R., Ferrari G., Donsì F. Evaluation of the stability and antioxidant activity of nanoencapsulated resveratrol during in vitro digestion. J. Agric. Food Chem. 2011, 59:12352-12360.
15. Shao J., Li X., Lu X., Jiang C., Hu Y., Li Q., You Y., Fu Z. Enhanced growth inhibition effect of Resveratrol incorporated into biodegradable nanoparticles against glioma cells is mediated by the induction of intracellular reactive oxygen species levels. Colloids Surf. B: Biointerfaces 2009, 72:40-47.
16. Boocock D.J., Faust G.E., Patel K.R., Schinas A.M., Brown V.A., Ducharme M.P., Booth T.D., Crowell J.A., Perloff M., Gescher A.J. Phase I dose escalation pharmacokinetic study in healthy volunteers of resveratrol, a potential cancer chemopreventive agent. Cancer Epidemiol. Biomark. Prev. 2007, 16:1246-1252.
17. Mehnert W., Mäder K. Solid lipid nanoparticles: production, characterization and applications. Adv. Drug Deliv. Rev. 2001, 47:165-196.
18. MuÈller R.H., MaÈder 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.
19. Wissing S., Kayser O., Müller R. Solid lipid nanoparticles for parenteral drug delivery. Adv. Drug Deliv. Rev. 2004, 56:1257-1272.
20. Neves A.R., Lúcio M., Martins S., Lima J.L.C., Reis S. Novel resveratrol nanodelivery systems based on lipid nanoparticles to enhance its oral bioavailability. Int. J. Nanomed. 2013, 8:177.
21. Ramalingam P., Ko Y.T. Enhanced oral delivery of curcumin from N-trimethyl chitosan surface-modified solid lipid nanoparticles: pharmacokinetic and brain distribution evaluations. Pharm. Res. 2014, 32:389-402.
22. Venishetty V.K., Chede R., Komuravelli R., Adepu L., Sistla R., Diwan P.V. Design and evaluation of polymer coated carvedilol loaded solid lipid nanoparticles to improve the oral bioavailability: a novel strategy to avoid intraduodenal administration. Colloids Surf. B: Biointerfaces 2012, 95:1-9.
23. Fan T., Chen C., Guo H., Xu J., Zhang J., Zhu X., Yang Y., Zhou Z., Li L., Huang Y. Design and evaluation of solid lipid nanoparticles modified with peptide ligand for oral delivery of protein drugs. Eur. J. Pharm. Biopharm. 2014, 88:518-528.
24. Masuko T., Minami A., Iwasaki N., Majima T., Nishimura S.-I., Lee Y.C. Thiolation of chitosan. Attachment of proteins via thioether formation. Biomacromolecules 2005, 6:880-884.
25. Lee C.-M., Jeong H.-J., Kim S.-L., Kim E.-M., Kim D.W., Lim S.T., Jang K.Y., Jeong Y.Y., Nah J.-W., Sohn M.-H. SPION-loaded chitosan-linoleic acid nanoparticles to target hepatocytes. Int. J. Pharm. 2009, 371:163-169.
26. Cheong S.-J., Lee C.-M., Kim S.-L., Jeong H.-J., Kim E.-M., Park E.-H., Kim D.W., Lim S.T., Sohn M.-H. Superparamagnetic iron oxide nanoparticles-loaded chitosan-linoleic acid nanoparticles as an effective hepatocyte-targeted gene delivery system. Int. J. Pharm. 2009, 372:169-176.
27. Wydro P., Krajewska B., Hac-Wydro K. Chitosan as a lipid binder: a langmuir monolayer study of chitosan-lipid interactions. Biomacromolecules 2007, 8:2611-2617.
28. Mao S., Shuai X., Unger F., Wittmar M., Xie X., Kissel T. Synthesis, characterization and cytotoxicity of poly(ethylene glycol)-graft-trimethyl chitosan block copolymers. Biomaterials 2005, 26:6343-6356.
29. Chen F., Zhang Z.-R., Yuan F., Qin X., Wang M., Huang Y. In vitro and in vivo study of N-trimethyl chitosan nanoparticles for oral protein delivery. Int. J. Pharm. 2008, 349:226-233.
30. Subbiah R., Ramalingam P., Ramasundaram S., Park K., Ramasamy M.K., Choi K.J. N, N, N-Trimethyl chitosan nanoparticles for controlled intranasal delivery of HBV surface antigen. Carbohydr. Polym. 2012, 89:1289-1297.
31. He W., Du Y., Dai W., Wu Y., Zhang M. Effects of N-trimethyl chitosan chloride as an absorption enhancer on properties of insulin liquid suppository in vitro and in vivo. J. Appl. Polym. Sci. 2006, 99:1140-1146.
32. Chen H., Wu J., Sun M., Guo C., Yu A., Cao F., Zhao L., Tan Q., Zhai G. N-trimethyl chitosan chloride-coated liposomes for the oral delivery of curcumin. J. Liposome Res. 2012, 22:100-109.
33. Cafaggi S., Russo E., Stefani R., Leardi R., Caviglioli G., Parodi B., Bignardi G., De Totero D., Aiello C., Viale M. Preparation and evaluation of nanoparticles made of chitosan or N-trimethyl chitosan and a cisplatin-alginate complex. J. Control. Release 2007, 121:110-123.
34. Germershaus O., Mao S., Sitterberg J., Bakowsky U., Kissel T. Gene delivery using chitosan, trimethyl chitosan or polyethylenglycol-graft-trimethyl chitosan block copolymers: establishment of structure-activity relationships in vitro. J. Control. Release 2008, 125:145-154.
35. Sayin B., Somavarapu S., Li X.W., Sesardic D., Şenel S., Alpar O.H. TMC-MCC (N-trimethyl chitosan-mono-N-carboxymethyl chitosan) nanocomplexes for mucosal delivery of vaccines. Eur. J. Pharm. Sci. 2009, 38:362-369.
36. Yin L., Ding J., He C., Cui L., Tang C., Yin C. Drug permeability and mucoadhesion properties of thiolated trimethyl chitosan nanoparticles in oral insulin delivery. Biomaterials 2009, 30:5691-5700.
37. Lee C.-M., Jang D., Kim J., Cheong S.-J., Kim E.-M., Jeong M.-H., Kim S.-H., Kim D.W., Lim S.T., Sohn M.-H. Oleyl-chitosan nanoparticles based on a dual probe for optical/MR imaging in vivo. Bioconjug. Chem. 2011, 22:186-192.
38. Chen X., Ding S., Qu G., Zhang C. Synthesis of novel chitosan derivatives for micellar solubilization of cyclosporine A. J. Bioact. Compat. Polym. 2008, 23:563-578.
39. Bei Y.-Y., Yuan Z.-Q., Zhang L., Zhou X.-F., Chen W.-L., Xia P., Liu Y., You B.-G., Hu X.-J., Zhu Q.-L. Novel self-assembled micelles based on palmitoyl-trimethyl-chitosan for efficient delivery of harmine to liver cancer. Expert Opin. Drug Deliv. 2014, 11:843-854.
40. Du Y.-Z., Wang L., Yuan H., Wei X.-H., Hu F.-Q. Preparation and characteristics of linoleic acid-grafted chitosan oligosaccharide micelles as a carrier for doxorubicin. Colloids Surf. B: Biointerfaces 2009, 69:257-263.
41. Hu F.-Q., Liu L.-N., Du Y.-Z., Yuan H. Synthesis and antitumor activity of doxorubicin conjugated stearic acid-g-chitosan oligosaccharide polymeric micelles. Biomaterials 2009, 30:6955-6963.
42. Hu F.-Q., Zhang Y.-Y., You J., Yuan H., Du Y.-Z. pH triggered doxorubicin delivery of PEGylated glycolipid conjugate micelles for tumor targeting therapy. Mol. Pharm. 2012, 9:2469-2478.
43. Ramalingam P., Ko Y.T. A validated LC-MS/MS method for quantitative analysis of curcumin in mouse plasma and brain tissue and its application in pharmacokinetic and brain distribution studies. J. Chromatogr. B 2014, 969:101-108.
44. Das S., Chaudhury A. Recent advances in lipid nanoparticle formulations with solid matrix for oral drug delivery. AAPS Pharm. Sci. Technol. 2011, 12:62-76.
45. Hazzah H.A., Farid R.M., Nasra M., Hazzah W.A., El-Massik M.A., Abdallah O.Y. Gelucire-based nanoparticles for curcumin targeting to oral mucosa: preparation, characterization, and antimicrobial activity assessment. J. Pharm. Sci. 2015, 104:3913-3924.
46. Cho H.-J., Park J.W., Yoon I.-S., Kim D.-D. Surface-modified solid lipid nanoparticles for oral delivery of docetaxel: enhanced intestinal absorption and lymphatic uptake. Int. J. Nanomed. 2014, 9:495.
47. Chalikwar S.S., Belgamwar V.S., Talele V.R., Surana S.J., Patil M.U. Formulation and evaluation of nimodipine-loaded solid lipid nanoparticles delivered via lymphatic transport system. Colloids Surf. B: Biointerfaces 2012, 97:109-116.
48. Thanou M., Verhoef J., Junginger H. Oral drug absorption enhancement by chitosan and its derivatives. Adv. Drug Deliv. Rev. 2001, 52:117-126.
49. Cao J., Sun J., Wang X., Li X., Deng Y. N-Trimethyl chitosan-coated multivesicular liposomes for oxymatrine oral delivery. Drug Dev. Ind. Pharm. 2009, 35:1339-1347.
50. Huang A., Makhlof A., Ping Q., Tozuka Y., Takeuchi H. N-trimethyl chitosan-modified liposomes as carriers for oral delivery of salmon calcitonin. Drug Deliv. 2011, 18:562-569.
51. Jose S., Anju S., Cinu T., Aleykutty N., Thomas S., Souto E. In vivo pharmacokinetics and biodistribution of resveratrol-loaded solid lipid nanoparticles for brain delivery. Int. J. Pharm. 2014, 474:6-13.
52. Teskač K., Kristl J. The evidence for solid lipid nanoparticles mediated cell uptake of resveratrol. Int. J. Pharm. 2010, 390:61-69.