Nanocomplexes based on amphiphilic hyaluronic acid derivative and polyethylene glycol-lipid for ginsenoside Rg3 delivery

Journal of Pharmaceutical Sciences

Volumn 103, Issue 10, 2014, Pages 3254-3262

  Lee, Jae Young ^a   Yang, Heejung ^b   Yoon, I N Soo ^c   Kim, Sang Bum ^a   Ko, Seung Hak ^d   Shim, Jae Seong ^d,e   Sung, Sang Hyun ^a   Cho, Hyun Jong ^b   Kim, Dae Duk ^a  

^a Seoul National University   (South Korea)

^b Kangwon National University   (South Korea)

^c Mokpo National University   (South Korea)

^d Biogenics Inc   (South Korea)

^e Skin Tech Inc   (South Korea)

Author keywords

Biocompatibility; Cancer; Controlled release; Ginsenoside rg 3; Hyaluronic acid ceramide; Nanocomplex; Pharmacokinetics; Polyethylene glycol lipid; Targeted drug delivery

Indexed keywords

AMPHOPHILE; ANTINEOPLASTIC AGENT; GINSENOSIDE RG 3; GLYCEROPHOSPHOETHANOLAMINE; HYALURONIC ACID DERIVATIVE; MACROGOL 2000; PHOSPHATIDYLCHOLINE; GINSENOSIDE; HYALURONIC ACID; LIPID; MACROGOL DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; AREA UNDER THE CURVE; ARTICLE; BLOOD FLOW; CELL MEMBRANE; CONTROLLED STUDY; DRUG CLEARANCE; DRUG DELIVERY SYSTEM; DRUG HALF LIFE; DRUG STABILITY; HUMAN; HUMAN CELL; HYBRID; LUNG ADENOCARCINOMA; MALE; MEAN RESIDENCE TIME; NONHUMAN; PARTICLE SIZE; RAT; SUSTAINED DRUG RELEASE; ANIMAL; CELL LINE; CHEMISTRY; SPRAGUE DAWLEY RAT;

ANIMALS; CELL LINE; GINSENOSIDES; HUMANS; HYALURONIC ACID; LIPIDS; MALE; POLYETHYLENE GLYCOLS; RATS; RATS, SPRAGUE-DAWLEY;

EID: 84923380372     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.24111     Document Type: Article

References (39)

1. Byrne JD, Betancourt T, Brannon-Peppas L. 2008. Active targeting schemes for nanoparticle systems in cancer therapeutics. Adv Drug Deliv Rev 60(15):1615-1626.
2. Davis ME, Chen ZG, Shin DM. 2008. Nanoparticle therapeutics: An emerging treatmentmodality for cancer.Nat RevDrugDiscov 7(9):771-782.
3. Xu X, Xie K, Zhang XQ, Pridgen EM, Park GY, Cui DS, Shi J, Wu J, Kantoff PW, Lippard SJ, Langer R, Walker GC, Farokhzad OC. 2013.
4. Enhancing tumor cell response to chemotherapy through nanoparticlemediated codelivery of siRNA and cisplatin prodrug. Proc Natl Acad Sci USA 110(46):18638-18119.
5. Lourenco AM, Ferreira LM, Branco PS. 2012. Molecules of natural origin, semi-synthesis and synthesis with anti-inflammatory and anticancer utilities. Curr Pharm Des 18(26):3979-4046.
6. Tavano L, Muzzalupo R, Picci N, de Cindio B. 2014. Co-encapsulation of lipophilic antioxidants into niosomal carriers: Percutaneous permeation studies for cosmeceutical applications. Colloids Surf B Biointerfaces 114:114-119.
7. Zhu JX, Tang D, Feng L, Zheng ZG, Wang RS, Wu AG, Duan TT, He B, Zhu Q. 2013. Development of self-microemulsifying drug delivery system for oral bioavailability enhancement of berberine hydrochloride. Drug Dev Ind Pharm 39(3):499-506.
8. Gong C, Deng S, Wu Q, Xiang M, Wei X, Li L, Gao X, Wang B, Sun L, Chen Y, Li Y, Liu L, Qian Z, Wei Y. 2013. Improving antiangiogenesis and anti-tumor activity of curcumin by biodegradable polymeric micelles. Biomaterials 34(4):1413-1432.
9. Ray L, Kumar P, Gupta KC. 2013. The activity against Ehrlich's ascites tumors of doxorubicin contained in self assembled, cell receptor targeted nanoparticle with simultaneous oral delivery of the green tea polyphenol epigallocatechin-3-gallate. Biomaterials 34(12):3064-3076.
10. Yu H, Teng L, Meng Q, Li Y, Sun X, Lu J, Lee RJ, Teng L. 2013. Development of liposomal Ginsenoside Rg3: Formulation optimization and evaluation of its anticancer effects. Int J Pharm 450(1-2):250-258.
11. Christensen LP. 2009. Ginsenosides chemistry, biosynthesis, analysis, and potential health effects. Adv Food Nutr Res 55:1-99.
12. Guo N, Liu M, Yang D, Huang Y, Niu X, Wu R, Liu Y, Ma G, Dou D. 2013. Quantitative LC-MS/MS analysis of seven ginsenosides and three aconitum alkaloids in Shen-Fu decoction. Chem Cent J 7(1):165-171.
13. Choi YJ, Lee HJ, Kang DW, Han IH, Choi BK, Cho WH. 2013. Ginsenoside Rg3 induces apoptosis in the U87MG human glioblastoma cell line through the MEK signaling pathway and reactive oxygen species. Oncol Rep 30(3):1362-1370.
14. Lee JY, Jung KH, Morgan MJ, Kang YR, Lee HS, Koo GB, Hong SS, Kwon SW, Kim YS. 2013. Sensitization of TRAIL-induced cell death by 20(S)-ginsenoside Rg3 via CHOP-mediated DR5 upregulation in human hepatocellular carcinoma cells. Mol Cancer Ther 12(3):274-285.
15. Bae SH, Zheng YF, Yoo KH, Kim JY, Kim SO, JangMJ, Seo JH, Bae SK. 2013. Stereoselective determination of ginsenosides Rg3 and Rh2 epimers in rat plasma by LC-MS/MS: Application to a pharmacokinetic study. J Sep Sci 36(12):1904-1912.
16. Dong H, Bai LP, Wong VK, Zhou H, Wang JR, Liu Y, Jiang ZH, Liu L. 2011. The in vitro structure-related anti-cancer activity of ginsenosides and their derivatives. Molecules 16(12):10619-10630.
17. Yang H, Yoo G, Kim HS, Kim JY, Kim SO, Yoo YH, Sung SH. 2012. Implication of the stereoisomers of ginsenoside derivatives in the antiproliferative effect of HSC-T6 cells. J Agric Food Chem 60(47):11759-11764.
18. Termsarasab U, Cho HJ, Kim DH, Chong S, Chung SJ, Shim CK, Moon HT, Kim DD. 2013. Chitosan oligosaccharide-arachidic acidbased nanoparticles for anti-cancer drug delivery. Int J Pharm 441 (1-2):373-380.
19. Yoon HY, Koo H, Choi KY, Kwon IC, Choi K, Park JH, Kim K. 2013. Photo-crosslinked hyaluronic acid nanoparticles with improved stability for in vivo tumor-targeted drug delivery. Biomaterials 34(21):5273-5280.
20. Cho HJ, Yoon HY, Koo H, Ko SH, Shim JS, Lee JH, Kim K, Kwon IC, Kim DD. 2011. Self-assembled nanoparticles based on hyaluronic acid-ceramide (HA-CE) and Pluronic ® for tumor-targeted delivery of docetaxel. Biomaterials 32(29):7181-7190.
21. Cho HJ, Yoon HY, Koo H, Ko SH, Shim JS, Cho JH, Park JH, Kim K, Kwon IC, Kim DD. 2012. Hyaluronic acid-ceramide-based optical/ MR dual imaging nanoprobe for cancer diagnosis. J Control Release 162(1):111-118.
22. Cho HJ, Yoon IS, Yoon HY, Koo H, Jin YJ, Ko SH, Shim JS, Kim K, Kwon IC, Kim DD. 2012. Polyethylene glycol-conjugated hyaluronic acid-ceramide self-assembled nanoparticles for targeted delivery of doxorubicin. Biomaterials 33(4):1190-1200.
23. Jin YJ, Termsarasab U, Ko SH, Shim JS, Chong S, Chung SJ, Shim CK, Cho HJ, Kim DD. 2012. Hyaluronic acid derivative-based self-assembled nanoparticles for the treatment of melanoma. Pharm Res 29(12):3443-3454.
24. Lu JM, Yao Q, Chen C. 2009. Ginseng compounds: An update on theirmolecular mechanisms andmedical applications. Curr Vasc Pharmacol 7(3):293-302.
25. Seo JY, Lee JH, Kim NW, Kim YJ, Chang S, Ko NY, Her E, Yoo YH, Kim JW, Lee BY, Lee HY, Kim YM, Choi WS. 2005. Inhibitory effects of a fermented ginseng extract, BST204, on the expression of inducible nitric oxide synthase and nitric oxide production in lipopolysaccharideactivated murine macrophages. J Pharm Pharmacol 57(7):911-918.
26. Park JH, ChoHJ, YoonHY, Yoon IS, Ko SH, ShimJS, Cho JH, Park JH, Kim K, Kwon IC, Kim DD. 2014. Hyaluronic acid derivative-coated nanohybrid liposomes for cancer imaging and drug delivery. J Control Release 174:98-108.
27. Misra S, Heldin P, Hascall VC, Karamanos NK, Skandalis SS, Markwald RR, Ghatak S. 2011. Hyaluronan-CD44 interactions as potential targets for cancer therapy. FEBS J 278(9):1429-1443.
28. Liu Z, Jiao Y,Wang T, Zhang Y, XueW. 2012. Interactions between solubilized polymermolecules and blood components. J Control Release 160(1):14-24.
29. Rausch K, Reuter A, Fischer K, Schmidt M. 2010. Evaluation of nanoparticle aggregation in human blood serum. Biomacromolecules 11(11):2836-2839.
30. Sabín J, Prieto G, Ruso JM, Messina PV, Salgado FJ, Nogueira M, Costas M, Sarmiento F. 2009. Interactions between DMPC liposomes and the serum blood proteins HSA and IgG. J Phys Chem B 113(6):1655-1661.
31. Dos Santos N, Allen C, Doppen AM, AnanthaM, Cox KA, Gallagher RC, KarlssonG, Edwards K,KennerG, Samuels L,Webb MS, Bally MB. 2007. Influence of poly(ethylene glycol) grafting density and polymer length on liposomes: Relating plasma circulation lifetimes to protein binding. Biochim Biophys Acta 1786(6):1367-1377.
32. Park Y, Franses EI. 2010. Effect of a PEGylated lipid on the dispersion stability and dynamic surface tension of aqueous DPPC and on the interactions with albumin. Langmuir 26(10):6932-6942.
33. Hadinoto K, Sundaresan A, Cheow WS. 2013. Lipid-polymer hybrid nanoparticles as a new generation therapeutic delivery platform: A review. Eur J Pharm Biopharm 85(3 Pt A):427-443.
34. Bhadra D, Bhadra S, Jain S, Jain NK. 2003. A PEGylated dendritic nanoparticulate carrier of fluorouracil. Int J Pharm 257(1-2):111-124.
35. Das J, Das S, Samadder A, Bhadra K, Khuda-Bukhsh AR. 2012. Poly (lactide-co-glycolide) encapsulated extract of Phytolacca decandra demonstrates better intervention against induced lung adenocarcinoma in mice and on A549 cells. Eur J Pharm. Sci 47(2):313-324.
36. Dufa ÿWojcicki A, Hillaireau H, Nascimento TL, Arpicco S, Taverna M, Ribes S, Bourge M, Nicolas V, Bochot A, Vauthier C, Tsapis N, Fattal E. 2012. Hyaluronic acid-bearing lipoplexes: Physico-chemical characterization and in vitro targeting of the CD44 receptor. J Control Release 162(3):545-552.
37. Ganesh S, Iyer AK,Morrissey DV, Amiji MM. 2013. Hyaluronic acid based self-assembling nanosystems for CD44 target mediated siRNA delivery to solid tumors. Biomaterials 34(13):3489-3502.
38. Gao LY, Liu XY, Chen CJ,Wang JC, Feng Q, Yu MZ,Ma XF, Pei XW, Niu YJ, Qiu C, Pang WH, Zhang Q. 2014. Core-shell type lipid/rPAAChol polymer hybrid nanoparticles for in vivo siRNA delivery. Biomaterials 35(6):2066-2078.
39. Lorenz C, Hadwiger P, John M, Vornlocher HP, Unverzagt C. 2004. Steroid and lipid conjugates of siRNAs to enhance cellular uptake and gene silencing in liver cells. Bioorg Med Chem Lett 14(19):4975-4977.