PEI-derivatized fullerene drug delivery using folate as a homing device targeting to tumor

Biomaterials

Volumn 34, Issue 1, 2013, Pages 251-261

  Shi, Jinjin ^a   Zhang, Hongling ^a   Wang, Lei ^a   Li, Lulu ^a   Wang, Honghong ^a   Wang, Zhenzhen ^a   Li, Zhi ^a   Chen, Chengqun ^a   Hou, Lin ^a   Zhang, Chaofeng ^a   Zhang, Zhenzhong ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

Docetaxel; Drug delivery; Folic acid; Nanoparticle; PEI derivatized fullerene; Tumor targeting

Indexed keywords

ANTI-TUMOR EFFICACY; AZIRIDINES; BLOOD CIRCULATION; DOCETAXEL; DRUG DELIVERY SYSTEM; ETHYLENE DIAMINE; FOLIC ACIDS; IN-VITRO; IN-VIVO; SIDE EFFECT; TOXIC EFFECT; TUMOR MODELS; TUMOR-TARGETING;

AMIDES; CARDIOVASCULAR SYSTEM; CATIONIC POLYMERIZATION; CELL DEATH; CELL MEMBRANES; DRUG PRODUCTS; FULLERENES; NANOPARTICLES; ORGANIC ACIDS; TUMORS;

DRUG DELIVERY;

AZIRIDINE; DOCETAXEL; ETHYLENEDIAMINE; FOLIC ACID; FULLERENE DERIVATIVE; NANOPARTICLE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL HOMING; CELL MEMBRANE; CIRCULATION; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG CONJUGATION; DRUG DELIVERY SYSTEM; DRUG EFFICACY; DRUG PENETRATION; DRUG STRUCTURE; DRUG TARGETING; ENCAPSULATION; FEMALE; INFRARED SPECTROSCOPY; MOLECULARLY TARGETED THERAPY; MOUSE; NEOPLASM; NONHUMAN; POLYMERIZATION; PRIORITY JOURNAL;

ADMINISTRATION, INTRAVENOUS; ANIMALS; APOPTOSIS; BODY WEIGHT; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG DELIVERY SYSTEMS; ENDOCYTOSIS; FEMALE; FOLIC ACID; FULLERENES; HUMANS; MALE; MICE; MICE, INBRED BALB C; NEOPLASMS; PARTICLE SIZE; POLYETHYLENEIMINE; SPECTROPHOTOMETRY, ULTRAVIOLET; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TAXOIDS; TISSUE DISTRIBUTION; TUMOR BURDEN; XENOGRAFT MODEL ANTITUMOR ASSAYS;

MURINAE;

EID: 84868101208     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2012.09.039     Document Type: Article

References (48)

1. Langer R. Drug delivery and targeting. Nature 1998, 392(6679 Suppl.):5-10.
2. 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(12 Pt 1):6387-6392.
3. Moghimi S.M., Hunter A.C., Murray J.C. Long-circulating and target-specific nanoparticles: theory to practice. Pharmacol Rev 2001, 53(2):283-318.
4. Peer D., Karp J.M., Hong S., Farokhzad O.C., Margalit R., Langer R. Nanocarriers as an emerging platform for cancer therapy. Nat Nanotechnol 2007, 2(12):751-760.
5. Moghimi S.M., Hunter A.C., Murray J.C. Nanomedicine: current status and future prospects. FASEB J 2005, 19(3):311-330.
6. Youns M., Hoheisel J.D., Efferth T. Therapeutic and diagnostic applications of nanoparticles. Curr Drug Targets 2011, 12(3):357-365.
7. Sanchez L., Otero R., Gallego J.M., Miranda R., Martin N. Ordering fullerenes at the nanometer scale on solid surfaces. Chem Rev 2009, 109(5):2081-2091.
8. Nosik D.N., Lialina I.K., Kalnina L.B., Lobach O.A., Chataeva M.S., Rasnetsov L.D. The antiretroviral agent Fullevir. Vopr Virusol 2009, 54(5):41-43.
9. Durdagi S., Mavromoustakos T., Chronakis N., Papadopoulos M.G. Computational design of novel fullerene analogues as potential HIV-1 PR inhibitors: analysis of the binding interactions between fullerene inhibitors and HIV-1 PR residues using 3D QSAR, molecular docking and molecular dynamics simulations. Bioorg Med Chem 2008, 16(23):9957-9974.
10. Horie M., Fukuhara A., Saito Y., Yoshida Y., Sato H., Ohi H., et al. Antioxidant action of sugar-pendant C60 fullerenes. Bioorg Med Chem Lett 2009, 19(20):5902-5904.
11. Isakovic A., Markovic Z., Todorovic-Markovic B., Nikolic N., Vranjes-Djuric S., Mirkovic M., et al. Distinct cytotoxic mechanisms of pristine versus hydroxylated fullerene. Toxicol Sci 2006, 91(1):173-183.
12. Chen Y.W., Hwang K.C., Yen C.C., Lai Y.L. Fullerene derivatives protect against oxidative stress in RAW 264.7 cells and ischemia-reperfused lungs. Am J Physiol Regul Integr Comp Physiol 2004, 287(1):R21-R26.
13. Isakovic A., Markovic Z., Nikolic N., Todorovic-Markovic B., Vranjes-Djuric S., Harhaji L., et al. Inactivation of nanocrystalline C60 cytotoxicity by gamma-irradiation. Biomaterials 2006, 27(29):5049-5058.
14. Mikata Y., Takagi S., Tanahashi M., Ishii S., Obata M., Miyamoto Y., et al. Detection of 1270 nm emission from singlet oxygen and photocytotoxic property of sugar-pendant 60 fullerenes. Bioorg Med Chem Lett 2003, 13(19):3289-3292.
15. Montellano A., Da Ros T., Bianco A., Prato M. Fullerene C(6)(0) as a multifunctional system for drug and gene delivery. Nanoscale 2011, 3(10):4035-4041.
16. Ashcroft J.M., Tsyboulski D.A., Hartman K.B., Zakharian T.Y., Marks J.W., Weisman R.B., et al. Fullerene (C60) immunoconjugates: interaction of water-soluble C60 derivatives with the murine anti-gp240 melanoma antibody. Chem Commun (Camb) 2006, 28:3004-3006.
17. Zakharian T.Y., Seryshev A., Sitharaman B., Gilbert B.E., Knight V., Wilson L.J. A fullerene-paclitaxel chemotherapeutic: synthesis, characterization, and study of biological activity in tissue culture. J Am Chem Soc 2005, 127(36):12508-12509.
18. Partha R., Mitchell L.R., Lyon J.L., Joshi P.P., Conyers J.L. Buckysomes: fullerene-based nanocarriers for hydrophobic molecule delivery. ACS Nano 2008, 2(9):1950-1958.
19. Chaudhuri P., Paraskar A., Soni S., Mashelkar R.A., Sengupta S. Fullerenol-cytotoxic conjugates for cancer chemotherapy. ACS Nano 2009, 3(9):2505-2514.
20. Zhou W., Yuan X., Wilson A., Yang L., Mokotoff M., Pitt B., et al. Efficient intracellular delivery of oligonucleotides formulated in folate receptor-targeted lipid vesicles. Bioconjug Chem 2002, 13(6):1220-1225.
21. Ratnam M., Hao H., Zheng X., Wang H., Qi H., Lee R., et al. Receptor induction and targeted drug delivery: a new antileukaemia strategy. Expert Opin Biol Ther 2003, 3(4):563-574.
22. Yao V., Berkman C.E., Choi J.K., O'Keefe D.S., Bacich D.J. Expression of prostate-specific membrane antigen (PSMA), increases cell folate uptake and proliferation and suggests a novel role for PSMA in the uptake of the non-polyglutamated folate, folic acid. Prostate 2010, 70(3):305-316.
23. Petersen L.F., Brockton N.T., Bakkar A., Liu S., Wen J., Weljie A.M., et al. Elevated physiological levels of folic acid can increase in vitro growth and invasiveness of prostate cancer cells. BJU Int 2012, 109(5):788-795.
24. Weitman S.D., Weinberg A.G., Coney L.R., Zurawski V.R., Jennings D.S., Kamen B.A. Cellular localization of the folate receptor: potential role in drug toxicity and folate homeostasis. Cancer Res 1992, 52(23):6708-6711.
25. Chilcott J., Lloyd Jones M., Wilkinson A. Docetaxel for the adjuvant treatment of early node-positive breast cancer: a single technology appraisal. Health Technol Assess 2009, 13(Suppl. 1):7-13.
26. Anton A., Ruiz A., Segui M.A., Calvo L., Munoz M., Lao J., et al. Phase I clinical trial of liposomal-encapsulated doxorubicin citrate and docetaxel, associated with trastuzumab, as neo-adjuvant treatment in stages II and IIIA, HER2-overexpressing breast cancer patients. GEICAM 2003-03 study. Ann Oncol 2009, 20(3):454-459.
27. Abe H., Ogawa H., Okino T., Kato M., Sako H., Sano H., et al. Bi-weekly docetaxel in the adjuvant treatment of node-positive or high-risk breast cancer patients: phase I study of the Shiga Breast Cancer Study Group. Breast Cancer 2009, 16(1):37-41.
28. Yardley D.A., Burris H.A., Farley C.P., Barton J.H., Peacock N.W., Spigel D.R., et al. A phase II feasibility trial of dose-dense docetaxel followed by doxorubicin/cyclophosphamide as adjuvant or neoadjuvant treatment for women with node-positive or high-risk node-negative breast cancer. Clin Breast Cancer 2008, 8(3):242-248.
29. Sun B., Feng S.S. Trastuzumab-functionalized nanoparticles of biodegradable copolymers for targeted delivery of docetaxel. Nanomedicine (Lond) 2009, 4(4):431-445.
30. Muthu M.S., Kulkarni S.A., Raju A., Feng S.S. Theranostic liposomes of TPGS coating for targeted co-delivery of docetaxel and quantum dots. Biomaterials 2012, 33(12):3494-3501.
31. Lee S., Murthy N. Targeted delivery of catalase and superoxide dismutase to macrophages using folate. Biochem Biophys Res Commun 2007, 360(1):275-279.
32. Rao B.M., Chakraborty A., Srinivasu M.K., Devi M.L., Kumar P.R., Chandrasekhar K.B., et al. A stability-indicating HPLC assay method for docetaxel. J Pharm Biomed Anal 2006, 41(2):676-681.
33. Moes J.J., Koolen S.L., Huitema A.D., Schellens J.H., Beijnen J.H., Nuijen B. Pharmaceutical development and preliminary clinical testing of an oral solid dispersion formulation of docetaxel (ModraDoc001). Int J Pharm 2011, 420(2):244-250.
34. Hu Z., Guan W., Wang W., Zhu Z., Wang Y. Folacin C60 derivative exerts a protective activity against oxidative stress-induced apoptosis in rat pheochromocytoma cells. Bioorg Med Chem Lett 2010, 20(14):4159-4162.
35. Wang Z.R., Chen D., Zhou J., Tang G.P. Aspirin-PEI-beta-CyD as a novel non-viral vector for gene transfer. Zhejiang Da Xue Xue Bao Yi Xue Ban 2009, 38(1):46-52.
36. Zhao L., Chen H., Chen D., Hu Y.P., Yu H., Wang Q.Q., et al. Platinum tetrachloride coupled PEG-PEI as drug carrier and gene delivery vector. Zhejiang Da Xue Xue Bao Yi Xue Ban 2009, 38(1):59-66.
37. Chen M.L., Chen X.W., Wang J.H. Functionalization of MWNTs with hyperbranched PEI for highly selective isolation of BSA. Macromol Biosci 2010, 10(8):906-915.
38. Wilbur D.S., Chyan M.K., Hamlin D.K., Kegley B.B., Risler R., Pathare P.M., et al. Reagents for astatination of biomolecules: comparison of the in vivo distribution and stability of some radioiodinated/astatinated benzamidyl and nido-carboranyl compounds. Bioconjug Chem 2004, 15(1):203-223.
39. Zhang Z., Jia J., Lai Y., Ma Y., Weng J., Sun L., et al. Conjugating folic acid to gold nanoparticles through glutathione for targeting and detecting cancer cells. Bioorg Med Chem 2010, 18(15):5528-5534.
40. Hou Z., Zhan C., Jiang Q., Hu Q., Li L., Chang D., et al. Both FA- and mPEG-conjugated chitosan nanoparticles for targeted cellular uptake and enhanced tumor tissue distribution. Nanoscale Res Lett 2011, 6(1):563.
41. Niu R., Zhao P., Wang H., Yu M., Cao S., Zhang F., et al. Preparation, characterization, and antitumor activity of paclitaxel-loaded folic acid modified and TAT peptide conjugated PEGylated polymeric liposomes. J Drug Target 2011, 19(5):373-381.
42. Liu Z., Sun X., Nakayama-Ratchford N., Dai H. Supramolecular chemistry on water-soluble carbon nanotubes for drug loading and delivery. ACS Nano 2007, 1(1):50-56.
43. Murakami T., Ajima K., Miyawaki J., Yudasaka M., Iijima S., Shiba K. Drug-loaded carbon nanohorns: adsorption and release of dexamethasone in vitro. Mol Pharm 2004, 1(6):399-405.
44. Wang L., Zhang M., Zhang N., Shi J., Zhang H., Li M., et al. Synergistic enhancement of cancer therapy using a combination of docetaxel and photothermal ablation induced by single-walled carbon nanotubes. Int J Nanomed 2011, 6:2641-2652.
45. Min M., Wang X., Yang Y., Liu Z., Zhou Z., Zhu M., et al. Fabrication of micro-nano structure nanofibers by solvent etching. J Nanosci Nanotechnol 2011, 11(8):6919-6925.
46. Kubota R., Tahara M., Shimizu K., Sugimoto N., Hirose A., Nishimura T. Time-dependent variation in the biodistribution of C(6)(0) in rats determined by liquid chromatography-tandem mass spectrometry. Toxicol Lett 2011, 206(2):172-177.
47. Nikolic N., Vranjes-Ethuric S., Jankovic D., Ethokic D., Mirkovic M., Bibic N., et al. Preparation and biodistribution of radiolabeled fullerene C60 nanocrystals. Nanotechnology 2009, 20(38):385102.
48. Qingnuan L., Yan X., Xiaodong Z., Ruili L., Qieqie D., Xiaoguang S., et al. Preparation of (99m)Tc-C(60)(OH)(x) and its biodistribution studies. Nucl Med Biol 2002, 29(6):707-710.