Ginsenoside compound K-bearing glycol chitosan conjugates: Synthesis, physicochemical characterization, and in vitro biological studies

Carbohydrate Polymers

Volumn 112, Issue , 2014, Pages 359-366

  Mathiyalagan, Ramya ^a   Subramaniyam, Sathiyamoorthy ^a,c   Kim, Yeon Ju ^a   Kim, Youn Chul ^b   Yang, Deok Chun ^a  

^a Kyung Hee University   (South Korea)

^b Wonkwang University   (South Korea)

^c Insilicogen Inc   (South Korea)

Author keywords

Anti cancer efficacy; Compound K; Ginsenosides; Glycol chitosan; Self assembled nanoparticles; Tumor

Indexed keywords

CELL CULTURE; CHITOSAN; CYTOTOXICITY; GLYCOLS; HYDROPHILICITY; NANOPARTICLES; PHYSIOLOGY; TUMORS;

ANTI-CANCER EFFICACY; COMPOUND K; GINSENOSIDES; GLYCOL CHITOSAN; SELF ASSEMBLED NANOPARTICLES;

PHARMACODYNAMICS;

BUFFER; CHITOSAN; GINSENOSIDE; GINSENOSIDE M1; GLYCOL-CHITOSAN; NANOPARTICLE;

CELL SURVIVAL; CHEMISTRY; DRUG DELIVERY SYSTEM; DRUG EFFECTS; DRUG STABILITY; HEPG2 CELL LINE; HUMAN; IN VITRO STUDY; PARTICLE SIZE; PH; PROCEDURES; SYNTHESIS;

BUFFERS; CELL SURVIVAL; CHEMISTRY TECHNIQUES, SYNTHETIC; CHITOSAN; DRUG DELIVERY SYSTEMS; DRUG STABILITY; GINSENOSIDES; HEP G2 CELLS; HUMANS; HYDROGEN-ION CONCENTRATION; IN VITRO TECHNIQUES; NANOPARTICLES; PARTICLE SIZE;

EID: 84903625676     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2014.05.098     Document Type: Article

References (36)

1. Y.W. Cho, S.A. Park, T.H. Han, D.H. Son, J.S. Park, and S.J. Oh et al. In vivo tumor targeting and radionuclide imaging with self-assembled nanoparticles: Mechanisms, key factors, and their implications Biomaterials 28 6 2007 1236 1247 (Pubitemid 44816372)
2. K.T. Choi Botanical characteristics, pharmacological effects and medicinal components of Korean Panax ginseng C A Meyer Acta Pharmacologica Sinica 29 9 2008 1109 1118
3. V.G. Deepagan, T. Thambi, H. Ko, Y.M. Kang, and J.H. Park Amphiphilic polysialic acid derivatives: synthesis, characterization, and in-vitro cytotoxicity Journal of Nanoscience and Nanotechnology 13 11 2013 7312 7318
4. N. Duhem, J. Rolland, R. Riva, P. Guillet, J.M. Schumers, C. Jerome, J.F. Gohy, and V. Preat Tocol modified glycol chitosan for the oral delivery of poorly soluble drugs International Journal of Pharmaceutics 423 2 2012 452 460
5. O. Felt, P. Buri, and R. Gurny Chitosan: A unique polysaccharide for drug delivery Drug Development and Industrial Pharmacy 24 11 1998 979 993 (Pubitemid 28460237)
6. N. Goodarzi, R. Varshochian, G. Kamalinia, F. Atyabi, and R. Dinarvand A review of polysaccharide cytotoxic drug conjugates for cancer therapy Carbohydrate Polymers 92 2 2013 1280 1293
7. 2 solution Carbohydrate Polymers 102 0 2014 901 911
8. H. Hasegawa, J.H. Sung, S. Matsumiya, and M. Uchiyama Main ginseng saponin metabolites formed by intestinal bacteria Planta Medica 62 5 1996 453 457 (Pubitemid 26370341)
9. R. Jayakumar, D. Menon, K. Manzoor, S.V. Nair, and H. Tamura Biomedical applications of chitin and chitosan based nanomaterials - A short review Carbohydrate Polymers 82 2 2010 227 232
10. E.H. Joh, I.A. Lee, I.H. Jung, and D.H. Kim Ginsenoside Rb1 and its metabolite compound K inhibit IRAK-1 activation - The key step of inflammation Biochemical Pharmacology 82 3 2011 278 286
11. D.S. Lee, S. Keo, W. Ko, K.S. Kim, E. Ivanova, and J. Yim et al. Secondary metabolites isolated from Castilleja rubra exert anti-inflammatory effects through NF-κB inactivation on lipopolysaccharide-induced RAW264.7 macrophages Archives of Pharmacal Research 2013 1 8
12. S.J. Lee, H. Koo, H. Jeong, M.S. Huh, Y. Choi, and S.Y. Jeong et al. Comparative study of photosensitizer loaded and conjugated glycol chitosan nanoparticles for cancer therapy Journal of Controlled Release 152 1 2011 21 29
13. S.J. Lee, H. Koo, D.E. Lee, S. Min, S. Lee, and X. Chen et al. Tumor-homing photosensitizer-conjugated glycol chitosan nanoparticles for synchronous photodynamic imaging and therapy based on cellular on/off system Biomaterials 32 16 2011 4021 4029
14. B. Li, D.S. Lee, H.G. Choi, K.S. Kim, G.S. Jeong, and R.B. An et al. Involvement of heme oxygenase-1 induction in the cytoprotective and immunomodulatory activities of Viola patrinii in murine hippocampal and microglia Cells Evidence-Based Complementary and Alternative Medicine 2012 128019
15. B. Li, D.S. Lee, Y. Kang, N.Q. Yao, R.B. An, and Y.C. Kim Protective effect of ganodermanondiol isolated from the Lingzhi mushroom against tert-butyl hydroperoxide-induced hepatotoxicity through Nrf2-mediated antioxidant enzymes Food and Chemical Toxicology 53 2013 317 324
16. A. Maksimenko, M. Alami, F. Zouhiri, J.-D. Brion, A. Pruvost, and J. Mougin et al. Therapeutic modalities of squalenoyl nanocomposites in colon cancer: An ongoing search for improved efficacy ACS Nano 8 3 2014 2018 2032
17. A. Maksimenko, F. Dosio, J. Mougin, A. Ferrero, S. Wack, and L.H. Reddy et al. A unique squalenoylated and nonpegylated doxorubicin nanomedicine with systemic long-circulating properties and anticancer activity Proceedings of the National Academy of Sciences 111 2 2014 E217 E226
18. R. Mathiyalagan, S. Subramaniyam, S. Natarajan, Y.J. Kim, M.S. Sun, and S.Y. Kim et al. Insilico profiling of microRNAs in Korean ginseng (Panax ginseng Meyer) Journal of Ginseng Research 37 2 2013 227 247
19. R. Mathiyalagan, S. Subramaniyam, Y.J. Kim, S. Natarajan, J.W. Min, and S.Y. Kim et al. Synthesis and pharmacokinetic characterization of a pH-sensitive polyethylene glycol ginsenoside CK (PEG-CK) conjugate Bioscience, Biotechnology, and Biochemistry 2014 1 3
20. K.H. Min, K. Park, Y.S. Kim, S.M. Bae, S. Lee, and H.G. Jo et al. Hydrophobically modified glycol chitosan nanoparticles-encapsulated camptothecin enhance the drug stability and tumor targeting in cancer therapy Journal of Controlled Release 127 3 2008 208 218
21. C. Muzzarelli, G. Tosi, O. Francescangeli, and R.A. Muzzarelli Alkaline chitosan solutions Carbohydrate Polymers 338 21 2003 2247 2255 (Pubitemid 38352690)
22. R.A.A. Muzzarelli, J. Boudrant, D. Meyer, N. Manno, M. DeMarchis, and M.G. Paoletti Current views on fungal chitin/chitosan, human chitinases, food preservation, glucans, pectins and inulin: A tribute to Henri Braconnot, precursor of the carbohydrate polymers science, on the chitin bicentennial Carbohydrate Polymers 87 2 2012 995 1012
23. H.Y. Nam, S.M. Kwon, H. Chung, S.Y. Lee, S.H. Kwon, and H. Jeon et al. Cellular uptake mechanism and intracellular fate of hydrophobically modified glycol chitosan nanoparticles Journal of Controlled Release 135 3 2009 259 267
24. S.H. Oh, and B.H. Lee A ginseng saponin metabolite-induced apoptosis in HepG2 cells involves a mitochondria-mediated pathway and its downstream caspase-8 activation and Bid cleavage Toxicology and Applied Pharmacology 194 3 2004 221 229
25. J. Park, Y. Cho, Y. Son, K. Kim, H. Chung, and S. Jeong et al. Preparation and characterization of self-assembled nanoparticles based on glycol chitosan bearing adriamycin Colloid and Polymer Science 284 7 2006 763 770 (Pubitemid 43904810)
26. K. Park, J.H. Kim, Y.S. Nam, S. Lee, H.Y. Nam, and K. Kim et al. Effect of polymer molecular weight on the tumor targeting characteristics of self-assembled glycol chitosan nanoparticles Journal of Controlled Release 122 3 2007 305 314 (Pubitemid 47404663)
27. J.P. Quiñones, K.V. Gothelf, J. Kjems, Á.M.H. Caballero, C. Schmidt, and C.P. Covas Self-assembled nanoparticles of glycol chitosan-ergocalciferol succinate conjugate, for controlled release Carbohydrate Polymers 88 4 2012 1373 1377
28. J.P. Quiñones, K.V. Gothelf, J. Kjems, C. Yang, A.M.H. Caballero, and C. Schmidt et al. Self-assembled nanoparticles of modified-chitosan conjugates for the sustained release of dl-α-tocopherol Carbohydrate Polymers 92 1 2013 856 864
29. N. Sathishkumar, S. Sathiyamoorthy, M. Ramya, D.U. Yang, H.N. Lee, and D.C. Yang Molecular docking studies of anti-apoptotic BCL-2, BCL-XL, and MCL-1 proteins with ginsenosides from Panax ginseng Journal of Enzyme Inhibition and Medicinal Chemistry 27 5 2012 685 692
30. M. Sivasubramanian, T. Thambi, and J.H. Park Mineralized cyclodextrin nanoparticles for sustained protein delivery Carbohydrate Polymers 97 2 2013 643 649
31. T. Thambi, V.G. Deepagan, H. Ko, D.S. Lee, and J.H. Park Bioreducible polymersomes for intracellular dual-drug delivery Journal of Materials Chemistry 22 41 2012 22028 22036
32. T. Thambi, V.G. Deepagan, C.K. Yoo, and J.H. Park Synthesis and physicochemical characterization of amphiphilic block copolymers bearing acid-sensitive orthoester linkage as the drug carrier Polymer 52 21 2011 4753 4759
33. T. Thambi, V.G. Deepagan, H.Y. Yoon, H.S. Han, S.-H. Kim, and S. Son et al. Hypoxia-responsive polymeric nanoparticles for tumor-targeted drug delivery Biomaterials 35 5 2014 1735 1743
34. T. Thambi, H.Y. Yoon, K. Kim, I.C. Kwon, C.K. Yoo, and J.H. Park Bioreducible block copolymers based on poly (ethylene glycol) and poly (γ-benzyl l-glutamate) for intracellular delivery of camptothecin Bioconjugate Chemistry 22 10 2011 1924 1931
35. J.M. Yu, Y.J. Li, L.Y. Qiu, and Y. Jin Self-aggregated nanoparticles of cholesterol-modified glycol chitosan conjugate: Preparation, characterization, and preliminary assessment as a new drug delivery carrier European Polymer Journal 44 3 2008 555 565
36. Z. Zhang, G.J. Du, C.Z. Wang, X.D. Wen, T. Calway, and Z. Li et al. Compound K, a ginsenoside metabolite, inhibits colon cancer growth via multiple pathways including p53-p21 interactions International Journal of Molecular Sciences 14 2 2013 2980 2995