Baicalin loaded in folate-PEG modified liposomes for enhanced stability and tumor targeting

Colloids and Surfaces B: Biointerfaces

Volumn 140, Issue , 2016, Pages 74-82

  Chen, Yiyin ^a   Van Minh, Le ^a,e   Liu, Jianwen ^a   Angelov, Borislav ^b   Drechsler, Markus ^c   Garamus, Vasil M ^d   Willumeit Römer, Regine ^d   Zou, Aihua ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Czech Republic)

^c UNIVERSITY OF BAYREUTH   (Germany)

^d INSTITUTE OF MATERIALS RESEARCH   (Germany)

^e NGUYEN TAT THANH UNIVERSITY   (Viet Nam)

Author keywords

Baicalin; Cryo TEM; Folate receptor; Liposomes; SAXS; Targeting drug delivery

Indexed keywords

BIOCHEMISTRY; EFFICIENCY; FLAVONOIDS; HIGH RESOLUTION TRANSMISSION ELECTRON MICROSCOPY; MEDICINE; TRANSMISSION ELECTRON MICROSCOPY; TUMORS; X RAY SCATTERING;

BAICALIN; CRYO-TEM; FOLATE RECEPTOR; SAXS; TARGETING DRUG DELIVERIES;

LIPOSOMES;

BAICALIN; FOLATE RECEPTOR; FOLIC ACID; LIPOSOME; MACROGOL; FLAVONOID; MACROGOL DERIVATIVE; NONSTEROID ANTIINFLAMMATORY AGENT; POLY(ETHYLENE GLYCOL)-FOLATE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL TRANSPORT; CHEMICAL MODIFICATION; CONTROLLED STUDY; CRYOELECTRON MICROSCOPY; CYTOTOXICITY TEST; DRUG STABILITY; DRUG TARGETING; FEMALE; HELA CELL LINE; HUMAN; HUMAN CELL; IN VITRO STUDY; LIPOSOMAL DELIVERY; MTT ASSAY; PARTICLE SIZE; PRIORITY JOURNAL; RADIATION SCATTERING; TRANSMISSION ELECTRON MICROSCOPY; ZETA POTENTIAL; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CELL SURVIVAL; CHEMISTRY; CONFOCAL MICROSCOPY; DRUG EFFECTS; DRUG RELEASE; METABOLISM; PATHOLOGY; SMALL ANGLE SCATTERING; ULTRASTRUCTURE; UTERINE CERVIX TUMOR; X RAY DIFFRACTION;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CELL SURVIVAL; CRYOELECTRON MICROSCOPY; DRUG LIBERATION; DRUG STABILITY; FEMALE; FLAVONOIDS; FOLATE RECEPTORS, GPI-ANCHORED; FOLIC ACID; HELA CELLS; HUMANS; LIPOSOMES; MICROSCOPY, CONFOCAL; MICROSCOPY, ELECTRON, TRANSMISSION; POLYETHYLENE GLYCOLS; SCATTERING, SMALL ANGLE; UTERINE CERVICAL NEOPLASMS; X-RAY DIFFRACTION;

EID: 84951753939     PISSN: 09277765     EISSN: 18734367     Source Type: Journal    
DOI: 10.1016/j.colsurfb.2015.11.018     Document Type: Article

References (65)

1. Shieh D.E., Liu L.T., Lin C.C. Antioxidant and free radical scavenging effects of baicalein, baicalin and wogonin. Anticancer Res. 2000, 20:2861-2865.
2. Ikemoto S., Sugimura K., Yoshida N., Yasumoto R., Wada S., Yamamoto K., Kishimoto T. Antitumor effects of Scutellariae radix and its components baicalein, baicalin, and wogonin on bladder cancer cell lines. Urology 2000, 55:951-955.
3. Chan F.L., Choi H.L., Chen Z.Y., Chan P.S.F., Huang Y. Induction of apoptosis in prostate cancer cell lines by a flavonoid: baicalin. Cancer Lett. 2000, 160:219-228.
4. Yang B.L., Chen H.J., Chen Y.G., Gu Y.F., Zhang S.P., Lin Q., Sun Y. Inhibitory effects of baicalin on orthotopic xenografts of colorectal cancer cells that are deficient in a mismatch repair gene in nude mice. Int. J. Colorectal Dis. 2013, 28:547-553.
5. Chen J.C., Li Z.L., Chen A.Y., Ye X.Q., Luo H.T., Rankin G.O., Chen Y.C. Inhibitory effect of baicalin and baicalein on ovarian cancer cells. Int. J. Mol. Sci. 2013, 14:6012-6025.
6. Gao J.Y., Zhao H.Y., Hylands P.J., Corcorana O. Secondary metabolite mapping identifies Scutellaria inhibitors of human lung cancer cells. J. Pharm. Biomed. Anal. 2010, 53:723-728.
7. Parajuli P., Joshee N., Rimando A.M., Mittal S., Yadav A.K. In vitro antitumor mechanisms of various Scutellaria extracts and constituent flavonoids. Planta Med. 2009, 75:41-48.
8. Motoo Y., Sawabu N. Antitumor effects of saikosaponins, baicalin and baicalein on human hepatoma cell lines. Cancer Lett. 1994, 86:91-95.
9. Jang S.I., Kim H.J., Hwang K.M., Jekal S.J., Pae H.O., Choi B.M., Yun Y.G., Kwon T.O., Chung H.T., Kim Y.C. Hepatoprotective effect of baicalin, a major flavone from Scutellaria radix, on acetaminophen-induced liver injury in mice. Immunopharmacol. Immunotoxicol. 2003, 25:585-594.
10. Wan J.Y., Gong X., Zhou Q.X., Zhang L., Li H.Z., Zhou Y.F. Protective effect of baicalin against lipopolysaccharide/d-galactosamine-induced liver injury in mice by up-regulation of heme oxygenase-1. Eur. J. Pharm. 2008, 587:302-308.
11. Park S.W., Lee C.H., Kim Y.S., Kang S.S., Jeon S.J., Son K.H., Lee S.M. Protective effect of baicalin against carbon tetrachloride-induced acute hepatic injury in mice. J. Pharm. Sci. 2008, 106:136-143.
12. Shen Y.C., Chiou W.F., Chiou W.F., Chen C.F. Mechanisms in mediating the anti-inflammatory effects of baicalin and baicalein in human leukocytes. Eur. J. Pharm. 2003, 465:171-181.
13. Tsai P.L., Tsai T.H. Pharmacokinetics of baicalin in rats and its interactions with cyclosporin A, quinidine and SKF-525A: a microdialysis study. Planta Med. 2004, 70:1069-1074.
14. Wang Y.Y. Advances in research of baicalin absorption and pharmacokinetics. Chin. J. Curr. Pract. Med. 2005, 4:44-45.
15. Xing J., Chen X., Zhong D. Absorption and enterohepatic circulation of baicalin in rat. Life Sci. 2005, 78:140-146.
16. Hao J.F., Wang F.G., Wang X.D., Zhang D.R., Zhang D.R., Bi Y.P., Gao Y.S., Zhao X.M., Zhang Q. Development and optimization of baicalin-loaded solid lipid nanoparticles prepared by coacervation method using central composite design. Eur. J. Pharm. Sci. 2012, 47:497-505.
17. Li B.B., He M., Li W., Luo Z.B., Guo Y., Li Y.J., Zang C.B., Wang B., Li F., Li S.L., Ji P. Dissolution and pharmacokinetics of baicalin-polyvinylpyrrolidone coprecipitate. J. Pharm. Pharmacol. 2013, 65:1670-1678.
18. Jin S.Y., Han J., Jin S.X., Lv Q.Y., Bai J.X., Chen H.G., Li R.S., Wu W., Yuan H.L. Characterization and evaluation in vivo of baicalin-nanocrystals prepared by an ultrasonic-homogenization-fluid bed drying method. Chin. J. Nat. Med. 2014, 12:71-80.
19. Liu Z.F., Yang Z.H., Zhang S.Y. Study on preparation and main drug content determination of baicalin liposomes. Xiandai Yiyao Weisheng 2010, 26:2411-2412.
20. Chen Y.Y., Angelova A., Angelov B., Drechsler M., Garamus V.M., Willumeit-Römer R., Zou A.H. Sterically stabilized spongosomes for multidrug delivery of anticancer nanomedicines. J. Mater. Chem. B 2015, 3:7734-7744.
21. Angelova A., Angelov B., Drechsler M., Garamus V.M., Lesieur S. Int. J. Pharm. 2013, 454:625-632.
22. Wang H., Yan X., Li G.L., Pilz-Allen C., Möhwald H., Shchukin D. Sono-assembly of highly biocompatible polysaccharide capsules for hydrophobic drug delivery. Adv. Healthc. Mater. 2014, 3:825-831.
23. Zhao F., Shen G., Chen C., Xing R., Zou Q., Ma G., Yan X. Nanoengineering of stimuli-responsive protein-based biomimetic protocells as versatile drug delivery tools. Chem. Eur. J. 2014, 20:6880-6887.
24. Zhang H., Fei J., Yan X., Wang A., Li J. Enzyme-responsive release of doxorubicin from monodisperse dipeptide-based nanocarriers for highly efficient cancer treatment in vitro. Adv. Funct. Mater. 2015, 25:1193-1204.
25. Matsumura Y., Maeda H. A new concept for macromolecular therapeutics in cancer chemotherapy: mechanism of tumoritropic accumulation of proteins and the antitumor agent smancs. Cancer Res. 1986, 46:6387-6392.
26. Wang A.Z., Langer R., Farokhzad O.C. Nanoparticle delivery of cancer drugs. Annu. Rev. Med. 2012, 63:185-198.
27. Perrault S.D., Walkey C., Jennings T., Fischer H.C., Chan W.C.W. Mediating tumor targeting efficiency of nanoparticles through design. Nano Lett. 2009, 9:1909-1915.
28. Zauner W., Farrow N.A., Haines A.M.R. In vitro uptake of polystyrene microspheres: effect of particle size, cell line and cell density. J. Control. Release 2001, 71:39-51.
29. Rejman J., Oberle V., Zuhorn I.S., Hoekstra D. Size-dependent internalization of particles via the pathways of clathrin-and caveolae-mediated endocytosis. J. Biochem. 2004, 377:159-169.
30. Jain R.K., Stylianopoulos T. Delivering nanomedicine to solid tumors. Nat. Rev. Clin. Oncol. 2010, 7:653-664.
31. Bae Y.H., Park K. Targeted drug delivery to tumors: myths, reality and possibility. J. Control. Release 2011, 153:198-205.
32. Gruner B.A., Weitman S.D. The folate receptor as a potential therapeutic anticancer target. Investig. New Drugs 1998, 16:205-219.
33. Kim S.H., Kim J.K., Lim S.J., Park J.S., Lee M.K., Kim C.K. Folate-tethered emulsion for the target delivery of retinoids to cancer cells. Eur. J. Pharm. Biopharm. 2008, 68:618-625.
34. Stella B., Arpicco S., Peracchia M.T., Desmaele D., Hoebeke J., Renoir M., D'Angelo J., Cattel L., Couvreur P. J. Pharm. Sci. 2000, 89:1452.
35. Roger E., Kalscheuer S., Kirtane A., Guru B.R., Grill A.E., Whittum-Hudson J., Panyam J. Mol. Pharm. 2012, 9:2103.
36. Curiel D.T. Strategies to adapt adenoviral vectors for targeted delivery. Ann. N. Y. Acad. Sci. 1999, 886:158-171.
37. Gabizon A., Shmeeda H., Horowitz A.T., Zalipsky S. Tumor cell targeting of liposome-entrapped drugs with phospholipid-anchored folic acid-PEG conjugates. Adv. Drug Deliv. Rev. 2004, 56:1177-1192.
38. Hilgenbrink A.R., Low P.S. Folate receptor-mediated drug targeting: from therapeutics to diagnostics. J. Pharm. Sci. 2005, 94:2135-2146.
39. Ke C.Y., Mathias C.J., Green M.A. The folate receptor as a molecular target for tumor-selective radionuclide delivery. Nucl. Med. Biol. 2003, 30:811-817.
40. Kim S.H., Jeong J.H., Mok H., Lee S.H., Kim S.W., Park T.G. Folate receptor targeted delivery of polyelectrolyte complex micelles prepared from ODN-PEG-folate conjugate and cationic lipids. Biotechnol. Prog. 2007, 23:232-237.
41. Leamon C.P., Reddy J.A., Vlahov I.R., Vetzel M., Parker N., Nicoson J.S., Xu L.C., Westrick E. Synthesis and biological evaluation of EC72: a new folate-targeted chemotherapeutic. Bioconjug. Chem. 2005, 16:803-811.
42. Zhang Q., Xiang G.Y., Zhang Y.J., Yang K.Y., Fan W., Lin J.L., Zeng F.B., Wu J.Z. Increase of doxorubicin sensitivity for folate receptor positive cells when given as prodrug N-(phenylacetyl) doxorubicin in combination with folate-conjugated PGA. J. Pharm. Sci. 2006, 95:2266-2275.
43. Niu L., Meng L., Lu Q. Folate-conjugated PEG on single walled carbon nanotubes for targeting delivery of doxorubicin to cancer cells. Macomol. Biosci. 2013, 13:735-744.
44. Wang H., Zhao P.Q., Niu R.F., Liang X.F., Gong X.Q., Song T., Niu R.F., Chang J. Folate-PEG coated cationic modified chitosan-cholesterol liposomes for tumor-targeted drug delivery. Biomaterials 2010, 31:4129-4138.
45. Kiliçay E., Demirbilek M., Türk M., Güven E., Hazer B., Denkbas E.B. Preparation and characterization of poly (2-hydroxybutyrate-co-3-hydroxyhexanoate) (PHBHHX) based nanoparticles for targeted cancer therapy. Eur. J. Pharm. Sci. 2011, 44:310-320.
46. Desk Reference of Clinical Pharmocology Manuchair Ebadi 2008, 123. Taylor&Francis, ISBN 1-4200-4743-4. 2nd ed.
47. Kuang Y., Liu J., Liu Z.L., Zhuo R.X. Cholesterol-based anionic long-circulating cisplatin liposomes with reduced renal toxicity. Biomaterials 2012, 33:1596-1606.
48. H.J.M. Kempen, Synthetic glycolipids, a process for the preparation, thereof and several uses for these, synthetic glycolipids, U.S. Patents (1988) 4751219.
49. Xiang G.Y., Wu J., Lee R.J., Lu Y.H., Liu Z.L. Synthesis and evaluation of a novel ligand for folate-mediated targeting liposomes. Int. J. Pharm. 2008, 356:29-36.
50. Wu J., Liu Q., Lee R.J. A folate receptor-targeted liposomal formulation for paclitaxel. Int. J. Pharm. 2006, 316:148-153.
51. Gabizon A., Horowitz A.T., Goren D., Tzemach D., Shavit F.M., Qazen M.M., Zalipsky S. Targeting folate receptor with folate linked to extremities of poly(ethylene glycol)-grafted liposomes: in vitro studies. Bioconjug. Chem. 1999, 10:289-298.
52. Mourtas S., Kastellorizios M., Antimisiaris S.G., Klepetsanis P., Farsari E., Amanatides E., Mataras D., Pistillo B.R., Favia P., Sardella E., d'Agostino R. Covalent immobilization of liposomes on plasma functionalized metallic surfaces. Colloids Surf. B Biointerface 2011, 84:214-220.
53. Kastelloriziosa M., Faviac P., Michanetzis G.P.A.K., Pistillo B.R., Mourtas S., Klepetsanis P., Sardella E., d'Agostino R., Missirlis Y.F., Antimisiarisa S.G. Haemocompatibility improvement of metallic surfaces by covalent immobilization of heparin-liposomes. Int. J. Pharm. 2012, 432:91-98.
54. Gao W., Xiang B., Meng T.T., Liu F., Qi X.R. Chemotherapeutic drug delivery to cancer cells using a combination of folate targeting and tumor microenvironment-sensitive polypeptides. Biomaterials 2013, 34:4137-4149.
55. Förster S., Timmann A., Meyer A. J. Phys. Chem. B 2005, 109:1347-1360.
56. Yang T., Cui F.D., Chio M.K., Cho J.W., Chung S.J., Shim C.K., Kim D.D. Enhanced solubility and stability of PEGylated liposomal paclitaxel: in vitro and in vivo evaluation. Int. J. Pharm. 2007, 338:317-326.
57. Kraft J.C., Freeling J.P., Wang Z.Y., Ho R.J.Y. Emerging research and clinical development trends of liposome and lipid nanoparticle drug delivery systems. J. Pharm. Sci. 2014, 103:29-52.
58. Sułkowski W.W., Pentak D., Nowak K., Sułkowska A. The influence of temperature, cholesterol content and pH on liposome stability. J. Mol. Struct. 2005, 744:737-747.
59. Ikumi S., Yasuyuki S. Characterization of novel mixed polyethyleneglycol modified liposomes. Biol. Pharm. Bull. 2007, 30:208-211.
60. Lasic D.D. Recent developments in medical applications of liposomes: sterically stabilized liposomes in cancer therapy and gene delivery in vivo. J. Control. Release 1997, 48:203-222.
61. Feng X., Chu Z.Y., Zhai Y.J., Zhang H. Solubility of baicalin and freeze-dried powder preparation for injection. J. Liaoning Univ. TCM 2010, 12:49-51.
62. He L., Ding M.G., Lu X.X., Li Z.H., Yuan F., Long X.Y. Physicochemical properties of baicalin in different pH phosphate buffer solution. Northwest Pharm. J. 2012, 27:208-211.
63. Chen Y.J., Jia Y., Liu S.Z. Preparation of baicalin flexible nano-liposome. Chin. J. Exp. Tradit. Med. Formul. 2011, 17:1-4.
64. Xiong X., Liu S.Z., Xu J.Y., Chen Y.J. Preparation of baicalin lipid carrier gel and evaluation of its in vitro transdermal property. Chin. J. Exp. Tradit. Med. Formul. 2012, 18:28-30.
65. Alfonso G.B., Matthisa N., Bengt F. In search of the holy grail: folate-targetd nanoparticles for cancer therapy. Biochem. Pharmacol. 2011, 81:976-984.