A water-soluble inclusion complex of pedunculoside with the polymer β-cyclodextrin: A novel anti-inflammation agent with low toxicity

PLoS ONE

Volumn 9, Issue 7, 2014, Pages

  Liu, Chang ^a   Zhang, Wang ^a   Yang, Hao ^a   Sun, Weidong ^b   Gong, Xiangdong ^a   Zhao, Junxian ^a   Sun, Yun ^a   Diao, Guowang ^a  

^a YANGZHOU UNIVERSITY   (China)

^b Yangzhou Hospital of Traditional Chinese Medicine   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLSALICYLIC ACID; BETA CYCLODEXTRIN; PEDUNCULOSIDE; TRITERPENOID; UNCLASSIFIED DRUG; ANTIINFLAMMATORY AGENT; CELLULOSE; CYCLODEXTRIN; CYCLODEXTRIN POLYMER; GLUCOSE; TRITERPENE; WATER;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG DOSAGE FORM COMPARISON; DRUG SOLUBILITY; EAR EDEMA; FEMALE; IN VIVO STUDY; INFRARED SPECTROSCOPY; MALE; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; THERMOGRAVIMETRY; TOXICITY TESTING; TOXICOLOGY; ULTRAVIOLET VISIBLE SPECTROSCOPY; WATER SOLUBILITY INCLUSION COMPLEX; X RAY POWDER DIFFRACTION; ANALOGS AND DERIVATIVES; ANIMAL; CHEMISTRY; EDEMA; SOLUBILITY;

ANIMALS; ANTI-INFLAMMATORY AGENTS; CELLULOSE; CYCLODEXTRINS; EDEMA; GLUCOSE; MICE; SOLUBILITY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TRITERPENES; WATER;

EID: 84904173638     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0101761     Document Type: Article

References (46)

1. Yadav VR, Prasad S, Sung B, Kannappan R, Aggarwal BB (2010) Targeting inflammatory pathways by triterpenoids for prevention and treatment of cancer. Toxins 2: 2428-2466.
2. Langenheim JH (1994) Higher plant terpenoids: a phytocentric overview of their ecological roles. Journal of Chemical Ecology 20: 1223-1280.
3. Ajikumar PK, Tyo K, Carlsen S, Mucha O, Phon TH, et al. (2008) Terpenoids: opportunities for biosynthesis of natural product drugs using engineered microorganisms. Molecular Pharmaceutics 5: 167-190. (Pubitemid 351579123)
4. Sawadogo WR, Schumacher M, Teiten M-H, Cerella C, Dicato M, et al. (2013) A survey of marine natural compounds and their derivatives with anti-cancer activity reported in 2011. Molecules 18: 3641-3673.
5. Watson RR, Preedy VR (2012) Bioactive food as dietary interventions for arthritis and related inflammatory diseases. Academic press.
6. Salminen A, Lehtonen M, Suuronen T, Kaarniranta K, Huuskonen J (2008) Terpenoids: natural inhibitors of NF-κB signaling with anti-inflammatory and anticancer potential. Cellular and Molecular Life Sciences 65: 2979-2999.
7. Kulkarni AA, Thatcher TH, Hsiao HM, Olsen KC, Kottmann RM, et al. (2013) The triterpenoid CDDO-Me inhibits bleomycin-induced lung inflammation and fibrosis. PloS one 8: e63798.
8. Li G, Liu D, Zhang Y, Qian Y, Zhang H, et al. (2013) Celastrol inhibits lipopolysaccharide-stimulated rheumatoid fibroblast-like synoviocyte invasion through suppression of TLR4/NF-kappa B-mediated matrix metalloproteinase-9 expression. PloS one 8.
9. Jahromi MF, Gupta M, Manickam M, Ray A, Chansouria J (1999) Hypolipidemic activity of pedunculoside, a constituent of Ilex doniana. Pharmaceutical Biology 37: 37-41. (Pubitemid 29381007)
10. Wang C, Chao ZM, Wu XY, Sun W, Tan ZG, et al. (2012) Extraction and crystal structure of pedunculoside. Chinese Journal of Structural Chemistry 31: 1729-1735.
11. Wen X, Sun H, Liu J, Cheng K, Zhang P, et al. (2008) Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: synthesis, structure- activity relationships, and X-ray crystallographic studies. Journal of Medicinal Chemistry 51: 3540-3554. (Pubitemid 351875009)
12. Cao F, Jia J, Yin Z, Gao Y, Sha L, et al. (2012) Ethylene glycol-linked amino acid diester prodrugs of oleanolic acid for PepT1-mediated transport: synthesis, intestinal permeability and pharmacokinetics. Molecular Pharmaceutics 9: 2127-2135.
13. Szejtli J (1998) Introduction and general overview of cyclodextrin chemistry. Chemical Reviews 98: 1743-1754.
14. May M, Batkai S, Zoerner AA, Tsikas D, Jordan J, et al. (2013) Enhanced human tissue microdialysis using hydroxypropyl-β-cyclodextrin as molecular carrier. PloS one 8: e60628.
15. Boztas AO, Karakuzu O, Galante G, Ugur Z, Kocabas F, et al. (2013) Synergistic interaction of paclitaxel and curcumin with cyclodextrin polymer complexation in human cancer cells. Molecular Pharmaceutics 10: 2676-2683.
16. Mondjinou YA, McCauliff LA, Kulkarni A, Paul L, Hyun S-H, et al. (2013) Synthesis of 2-hydroxypropyl-β-cyclodextrin/pluronic-based polyrotaxanes via heterogeneous reaction as potential niemann-pick type C therapeutics. Biomacromolecules 14: 4189-4197.
17. Li H, Frith J, Cooper-White JJ (2013) Modulation of stem cell adhesion and morphology via facile control over surface presentation of cell adhesion molecules. Biomacromolecules 15: 43-52.
18. May M, Batkai S, Zoerner AA, Tsikas D, Jordan J, et al. (2013) Enhanced human tissue microdialysis using hydroxypropyl-ss-cyclodextrin as molecular carrier. PloS one 8: e60628.
19. Zhang W, Gong X, Liu C, Piao Y, Sun Y, et al. (2014) Water-soluble inclusion complex of fullerene with γ-cyclodextrin polymer for photodynamic therapy. J. Mater. Chem. B DOI: 10.1039/C4TB00560K.
20. Zhang W, Chen M, Zha B, Diao G (2012) Correlation of polymer-like solution behaviors with electrospun fiber formation of hydroxypropyl-β- cyclodextrin and the adsorption study on the fiber. Physical Chemistry Chemical Physics 14: 9729-9737.
21. Silva F, Figueiras A, Gallardo E, Nerín C, Domingues FC (2014) Strategies to improve the solubility and stability of stilbene antioxidants: a comparative study between cyclodextrins and bile acids. Food Chemistry 145: 115-125.
22. Sugiura Y, Tanaka R, Katsuzaki H, Imai K, Matsushita T (2013) The anti-inflammatory effects of phlorotannins from Eisenia arborea on mouse ear edema by inflammatory inducers. Journal of Functional Foods 5: 2019-2023.
23. Ye M, Sun M, Hu F, Kengara FO, Jiang X, et al. (2014) Remediation of organochlorine pesticides (OCPs) contaminated site by successive methyl-β-cyclodextrin (MCD) and sunflower oil enhanced soil washing - portulaca oleracea L. cultivation. Chemosphere 105: 119-125.
24. Yáñez C, Cañete-Rosales P, Castillo JP, Catalán N, Undabeytia T, et al. (2012) Cyclodextrin inclusion complex to improve physicochemical properties of herbicide bentazon: exploring better formulations. PloS one 7: e41072.
25. Renard E, Deratani A, Volet G, Sebille B (1997) Preparation and characterization of water soluble high molecular weight β-cyclodextrin- epichlorohydrin polymers. European Polymer Journal 33: 49-57. (Pubitemid 127400456)
26. Zhang W, Gong X, Cai Y, Zhang C, Yu X, et al. (2013) Investigation of water-soluble inclusion complex of hypericin with β-cyclodextrin polymer. Carbohydrate Polymers 95: 366-370.
27. Zhang W, Chen M, Diao G (2011) Preparation and electrochemical behavior of water-soluble inclusion complex of ferrocene with β-cyclodextrin polymer. Electrochimica Acta 56: 5129-5136.
28. Zhang W, Chen M, Gong X, Diao G (2013) Universal water-soluble cyclodextrin polymer-carbon nanomaterials with supramolecular recognition. Carbon 61: 154-163.
29. Liu C, Zhang W, Wang Q, Sun Y, Diao G (2013) The water-soluble inclusion complex of ilexgenin A with β-cyclodextrin polymer-a novel lipid-lowering drug candidate. Organic & Biomolecular Chemistry 11: 4993-4999.
30. OECD (2002) Acute oral toxicity. Acute oral toxic class method guideline 423 adopted 23.03.1996. In: Eleventh Addendum to the, OECD, Guidelines for the Testing of Chemicals. Organization for Economic Cooperation and Development, Paris.
31. Fan D, Zhou X, Zhao C, Chen H, Zhao Y, et al. (2011) Anti-inflammatory, antiviral and quantitative study of quercetin-3-O-β-D-glucuronide in polygonum perfoliatum L. Fitoterapia 82: 805-810.
32. Saraiva RA, Araruna MKA, Oliveira RC, Menezes KDP, Leite GO, et al. (2011) Topical anti-inflammatory effect of caryocar coriaceum wittm. (caryocaraceae) fruit pulp fixed oil on mice ear edema induced by different irritant agents. Journal of Ethnopharmacology 136: 504-510.
33. Schneider H-J, Hacket F, Rüdiger V, Ikeda H (1998) NMR studies of cyclodextrins and cyclodextrin complexes. Chemical Reviews 98: 1755-1786.
34. Chen M, Diao G, Zhang E (2006) Study of inclusion complex of β-cyclodextrin and nitrobenzene. Chemosphere 63: 522-529.
35. Irie T, Uekama K (1997) Pharmaceutical applications of cyclodextrins. III. Toxicological issues and safety evaluation. Journal of Pharmaceutical Sciences 86: 147-162. (Pubitemid 27078377)
36. Glojnaric I, Cuzic S, Markovic D (2013) Evaluation of Hydroxypropyl-beta-Cyclodextrin (HPßCD) as formulation vehicle for use in general toxicity studies in mice. Toxicology Letters 221: S93-S93.
37. Jiang Y, Jiang X, Law K, Chen Y, Gu J, et al. (2011) Enhanced anti-tumor effect of 9-nitro-camptothecin complexed by hydroxypropyl-β-cyclodextrin and safety evaluation. International Journal of Pharmaceutics 415: 252-258.
38. Irie T, Otagiri M, Sunada M, Uekama K, Ohtani Y, et al. (1982) Cyclodextrin-induced hemolysis and shape changes of human erythrocytes in vitro. Journal of Pharmacobio-dynamics 5: 741-744. (Pubitemid 13219471)
39. Jean-Baptiste E, Blanchemain N, Martel B, Neut C, Hildebrand HF, et al. (2012) Safety, healing, and efficacy of vascular prostheses coated with hydroxypropyl-β-cyclodextrin polymer: experimental in vitro and animal studies. European Journal of Vascular and Endovascular Surgery 43: 188-197.
40. Randhawa P, Shapiro R, Jordan M, Starzl T, Demetris A (1993) The histopathological changes associated with allograft rejection and drug toxicity in renal transplant recipients maintained on FK506: clinical significance and comparison with cyclosporine. The American Journal of Surgical Pathology 17: 60.
41. Arima H, Hirayama F, Okamoto C, Uekama K (2002) Recent aspects of cyclodextrin-based pharmaceutical formulations. Recent Res Dev Chem Pharm Sci 2: 155-193.
42. Huang XX, Zhou CL, Wang H, Chen C, Yu SQ, et al. (2011) Pharmacokinetics, efficacy, and safety evaluation of docetaxel/hydroxypropyl-sulfobutyl-β- cyclodextrin inclusion complex. AAPS pharmscitech 12: 665-672.
43. Xian YF, Mao QQ, Ip SP, Lin ZX, Che CT (2011) Comparison on the anti-inflammatory effect of Cortex Phellodendri Chinensis and Cortex Phellodendri Amurensis in 12-O-tetradecanoyl-phorbol-13-acetate-induced ear edema in mice. Journal of Ethnopharmacology 137: 1425-1430.
44. Liu J, Wang ZT, Ji LL (2007) In vivo and in vitro anti-inflammatory activities of neoandrographolide. The American Journal of Chinese Medicine 35: 317-328. (Pubitemid 46579086)
45. Wilmer JL, Simeonova PP, Germolec DR, Luster MI (1997) Benzene and its principal metabolites modulate proinflammatory cytokines and growth factors in human epidermal keratinocyte cultures. In Vitro Toxicology 10: 429.
46. Tötterman AM, Schipper NG, Thompson DO, Mannermaa JP (1997) Intestinal safety of water-soluble β-cyclodextrins in paediatric oral solutions of spironolactone: effects on human intestinal epithelial caco-2 cells. Journal of Pharmacy and Pharmacology 49: 43-48. (Pubitemid 27051029)