Delivery of paclitaxel using PEGylated graphene oxide as a nanocarrier

ACS Applied Materials and Interfaces

Volumn 7, Issue 2, 2015, Pages 1355-1363

  Xu, Zhiyuan ^a,b   Zhu, Shaojia ^b   Wang, Mingwei ^c   Li, Yongjun ^a   Shi, Ping ^b   Huang, Xiaoyu ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

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

^c FUDAN UNIVERSITY SHANGHAI CANCER CENTER   (China)

Author keywords

Drug delivery; Graphene oxide; Paclitaxel; PEG

Indexed keywords

BIOCHEMISTRY; BIOCOMPATIBILITY; CHEMOTHERAPY; DISEASES; DRUG DELIVERY; GRAPHENE; POLYETHYLENE GLYCOLS;

BIOLOGICAL APPLICATIONS; DRUG DELIVERY SYSTEM; FLUORESCEIN ISOTHIOCYANATE; GRAPHENE OXIDES; HUMAN BREAST CANCER; NATURAL GRAPHITE; PACLITAXEL; UTILIZATION RATES;

DRUG THERAPY;

ANTINEOPLASTIC AGENT; DRUG CARRIER; GRAPHITE; OXIDE; PACLITAXEL;

CHEMISTRY; DEVICES; DRUG DELIVERY SYSTEM; HUMAN; MCF 7 CELL LINE; PARTICLE SIZE; PROCEDURES; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; GRAPHITE; HUMANS; MCF-7 CELLS; OXIDES; PACLITAXEL; PARTICLE SIZE;

EID: 84921490510     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am507798d     Document Type: Article

References (37)

1. Yang, X. Y.; Zhang, X. Y.; Liu, Z. F.; Ma, Y. F.; Huang, Y.; Chen, Y. S. High-Efficiency Loading and Controlled Release of Doxorubicin Hydrochloride on Graphene Oxide. J. Phys. Chem. C 2008, 112, 17554-17558.
2. Johnson, J. A.; Lu, Y. A.; Burts, A. O.; Xia, Y.; Durrell, A. C.; Tirrell, D. A.; Grubbs, R. H. Drug-Loaded, Bivalent-Bottle-Brush Polymers by Graft-Through ROMP. Macromolecules 2010, 43, 10326-10335.
3. Huizing, M. T.; Misser, V. H.; Pieters, R. C.; ten Bokkel Huinink, W. W.; Veenhof, C. H.; Vermorken, J. B.; Pinedo, H. N.; Beijnen, J. H. Taxanes: A New Class of Antitumor Agents. Cancer Invest. 1995, 13, 381-404.
4. Wani, M. C.; Taylor, H. L; Wall, M. E.; Coggon, P.; McPhail, A. P. Plant Antitumour Agents. VI. Isolation and Structure of Taxol, A Novel Antileukemic and Antitumor Agent from Taxus Brevioflia. J. Am. Chem. Soc. 1971, 93, 2325-2327.
5. Rowinsky, E. K.; Cazenave, L. A.; Donehower, R. C. Taxol: A Novel Investigational Antimicrotubule Agent. J. Natl. Cancer Inst. 1990, 82, 1247-1259.
6. Wall, E. M.; Wan, M. C. Camptothecin and Taxol: Discovery to Clinic. Cancer Res. 1995, 55, 753-760.
7. Smith, D. C.; Chay, C. H.; Dunn, R. L.; Fardig, J.; Esper, P.; Olson, K. Phase II Trial of Paclitaxel, Estramustine, Etoposide, and Carboplatin in the Treatment of Patients with Hormone-Refractory Prostate Carcinoma. Cancer 2003, 98, 269-276.
8. Nilufer, J. S. F.; Dong, Z.; Wang, Y. L. Taxanes: Promising Anti-Cancer Drugs. Asian Pac. J. Cancer Prev. 2011, 12, 837-851.
9. Singla, A. K.; Garg, A.; Aggarwal, D. Paclitaxel and Its Formulations. Int. J. Pharm. 2002, 235, 179-192.
10. Jin, J. Y.; Lee, W. S.; Joo, K. M.; Maiti, K. K.; Biswas, G.; Kim, W.; Kim, K. T.; Lee, S. J.; Kim, K. H.; Nam, D. H.; Chung, S. K. Preparation of Blood-Brain Barrier-Permeable Paclitaxel-Carrier Conjugate and Its Chemotherapeutic Activity in the Mouse Glioblastoma Model. Med. Chem. Commun. 2011, 2, 270-273.
11. Goldspiel, B. R. Pharmaceutical Issues: Preparation, Administration, Stability, and Compatibility with Other Medications. Ann. Pharmacother. 1994, 28, s23-s26.
12. Weiss, R. B.; Donehower, R. C.; Wiernik, P. H.; Ohnuma, T.; Gralla, R. J.; Trump, D. L.; Baker, J. R.; VanEcho, D. A.; VonHoff, D. D.; Leyland-Jones, B. Hypersensitivity Reactions from Taxol. J. Clin. Oncol. 1990, 8, 1263-1268.
13. Kim, S. C.; Kim, D. W.; Shim, Y. H.; Bang, J. S.; Oh, H. S.; Kim, S. W.; Seo, M. H. In vivo Evaluation of Polymeric Micellar Paclitaxel Formulation: Toxicity and Efficacy. J. Controlled Release 2001, 72, 191-202.
14. Fonseca, C.; Simoes, S.; Gaspar, R. Paclitaxel-Loaded PLGA Nanoparticles: Preparation, Physicochemical Characterization and in vitro Anti-Tumoral Activity. J. Controlled Release 2002, 83, 273-286.
15. Bao, H. Q.; Pan, Y. Z.; Ping, Y.; Sahoo, N. G.; Wu, T. F.; Li, L.; Li, J.; Gan, L. H. Chitosan-Functionalized Graphene Oxide as a Nanocarrier for Drug and Gene Delivery. Small 2011, 7, 1569-1578.
16. Yang, K.; Wan, J. M.; Zhang, S. A.; Zhang, Y. J.; Lee, S. T.; Liu, Z. In vivo Pharmacokinetics, Long-Term Biodistribution, and Toxicology of PEGylated Graphene in Mice. ACS Nano 2011, 5, 516-522.
17. Zhang, Y. B.; Ali, S. F.; Dervishi, E.; Xu, Y.; Li, Z. R.; Casciano, D.; Biris, A. S. Cytotoxicity Effects of Graphene and Single-Wall Carbon Nanotubes in Neural Phaeochromocytoma-Derived PC12 Cells. ACS Nano 2010, 4, 3181-3186.
18. Bitounis, D.; Ali-Boucetta, H.; Hong, B. H.; Min, D. H.; Kostarelos, K. Prospects and Challenges of Graphene in Biomedical Applications. Adv. Mater. 2013, 25, 2258-2268.
19. Du, L. B.; Suo, S.; Luo, D.; Jia, H. Y.; Sha, Y. L.; Liu, Y. Hydroxyethylated Graphene Oxide as Potential Carriers for Methotrexate Delivery. J. Nanopart. Res. 2013, 15, 1708-1714.
20. Makharza, S.; Cirillo, G.; Bachmatiuk, A.; Ibrahim, I.; Ioannides, N.; Trzebicka, B.; Hampel, S.; Rummeli, M. H. Graphene Oxide-Based Drug Delivery Vehicles: Functionalization, Characterization, and Cytotoxicity Evaluation. J. Nanopart. Res. 2013, 15, 2099-2124.
21. Wang, Y.; Li, Z. H.; Wang, J.; Li, J. H.; Lin, Y. H. Graphene and Graphene Oxide: Biofunctionalization and Applications in Biotechnology. Cell 2013, 29, 205-212.
22. He, H. Y.; Klinowski, J.; Forster, M.; Lerf, A. A New Structural Model for Graphite Oxide. Chem. Phys. Lett. 1998, 287, 53-56.
23. Yang, H. F.; Shan, C. S.; Li, F. H.; Han, D. X.; Zhang, Q. X.; Niu, L. Covalent Functionalization of Polydisperse Chemically-Converted Graphene Sheets with Amine-Terminated Ionic Liquid. Chem. Commun. 2009, 3880-3882.
24. Liu, Z.; Robinson, J. T.; Sun, X. M.; Dai, H. J. PEGylated Nanographene Oxide for Delivery of Water-Insoluble Cancer Drugs. J. Am. Chem. Soc. 2008, 130, 10876-10877.
25. Zhang, L. M.; Xia, J. G.; Zhao, Q. H.; Liu, L. W.; Zhang, Z. J. Functional Graphene Oxide as a Nanocarrier for Controlled Loading and Targeted Delivery of Mixed Anticancer Drugs. Small 2010, 6, 537-544.
26. Prentice, D. E.; Majeed, S. K. Oral Toxicity of Polyethylene Glycol (PEG 200) in Monkeys and Rats. Toxicol. Lett. 1978, 2, 119-122.
27. Torchilin, V. P.; Omelyanenko, V. G.; Parisov, M. I.; Bogdanov, A. A.; Trubetskoy, V. S.; Herron, J. N.; Gentry, C. A. Poly(ethylene glycol) on the Liposome Surface: on the Mechanism of Polymer-Coated Liposome Longevity. Biochim. Biophys. Acta 1994, 1195, 11-20.
28. Zalipsky, S. Chemistry of Polyethylene Glycol Conjugates with Biologically Active Molecules. Adv. Drug Delivery Rev. 1995, 16, 157-182.
29. Leung, H. W.; Ballantyne, B.; Hermansky, S. J.; Franta, S. W. Peroral Subchronic, Chronic Toxicity, and Pharmacokinetic Studies of a 100-Kilo Dalton Polymer of Ethylene Oxide (Polyox N-10) in the Fischer 344 Rat. Int. J. Toxicol. 2000, 19, 305-312.
30. Yamaoka, T.; Tabata, Y.; Ikada, Y. Distribution and Tissue Uptake of Poly(ethylene glycol) with Different Molecular Weights after Intravenous Administration to Mice. J. Pharm. Sci. 1994, 83, 601-606.
31. Magri, N. F.; Kingston, D. G. I. Modified Taxols, 4. Synthesis and Biological Activity of Taxols Modified in the Side chain. J. Nat. Prod. 1988, 51, 298-306.
32. Rele, S. M.; Cui, W. X.; Wang, L. C.; Hou, S. J.; Barr-Zarse, G.; Tatton, D.; Gnanou, Y.; Esko, J. D.; Chaikof, E. L. Dendrimer-like PEO Glycopolymers Exhibit Anti-Inflammatory Properties. J. Am. Chem. Soc. 2005, 127, 10132-10133.
33. Mei, B. C.; Susumu, K.; Medintz, I. L.; Delehanty, J. B.; Mountziaris, T. J.; Mattoussi, H. Modular Poly(ethylene glycol) Ligands for Biocompatible Semiconductor and Gold Nanocrystals with Extended pH and Ionic Stability. J. Mater. Chem. 2008, 18, 4949-4958.
34. Fang, M.; Wang, K. G.; Lu, H. B.; Yang, Y. L.; Nutt, S. Covalent Polymer Functionalization of Graphene Nanosheets and Mechanical Properties of Composites. J. Mater. Chem. 2009, 19, 7098-7105.
35. Deutsch, H. M.; Glinski, J. A.; Hernandez, M.; Haugwitqt, R. D.; Narayanan, V. L.; Suffness, M.; Zalkow, L. H. Synthesis of Congeners and Prodrugs. 3. Water- Soluble Prodrugs of Taxol with Potent Antitumor Activity. J. Med. Chem. 1989, 32, 788-792.
36. Peng, C.; Hu, W.; Zhou, Y.; Fan, C. H.; Huang, Q. Intracellular Imaging with a Graphene-Based Fluorescent Probe. Small 2010, 6, 1686-1692.
37. Li, L. L.; Tang, F. Q.; Liu, H. Y.; Hao, N. J.; Chen, D.; Teng, X.; He, J. Q. in vivo Delivery of Silica Nanorattle Encapsulated Docetaxel for Liver Cancer Therapy with Low Toxicity and High Efficacy. ACS Nano 2010, 4, 6874-6882.