Paclitaxel-loaded phosphonated calixarene nanovesicles as a modular drug delivery platform

Scientific Reports

Volumn 6, Issue , 2016, Pages

  Mo, Jingxin ^a,b   Eggers, Paul K ^c   Yuan, Zhi Xiang ^d   Raston, Colin L ^e   Lim, Lee Yong ^a  

^a UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

^b SUN YAT SEN UNIVERSITY   (China)

^c UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

^d SICHUAN AGRICULTURAL UNIVERSITY   (China)

^e Institute for NanoScale Science and Technology   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CALIXARENE; FOLIC ACID; NANOMATERIAL; PACLITAXEL;

A-549 CELL LINE; CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; DRUG SCREENING; HUMAN; NEOPLASMS; PH; TUMOR CELL LINE;

A549 CELLS; ANTINEOPLASTIC AGENTS; CALIXARENES; CELL LINE, TUMOR; CELL SURVIVAL; DRUG SCREENING ASSAYS, ANTITUMOR; FOLIC ACID; HUMANS; HYDROGEN-ION CONCENTRATION; NANOSTRUCTURES; NEOPLASMS; PACLITAXEL;

EID: 84962207578     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep23489     Document Type: Article

References (32)

1. Torchilin, V. P. Recent advances with liposomes as pharmaceutical carriers. Nat Rev Drug Discov 4, 145-160, doi: 10. 1038/nrd1632 (2005).
2. Jiang, L. et al. Anti-Cancer Efficacy of Paclitaxel Loaded in pH Triggered Liposomes. J Biomed Nanotechnol 12, 79-90, doi: 10. 1166/ jbn. 2016. 2123 (2016).
3. Jiang, L. et al. Overcoming drug-resistant lung cancer by paclitaxel loaded dual-functional liposomes with mitochondria targeting and pH-response. Biomaterials 52, 126-139, doi: 10. 1016/j. biomaterials. 2015. 02. 004 (2015).
4. Bae, Y., Jang, W. D., Nishiyama, N., Fukushima, S. & Kataoka, K. Multifunctional polymeric micelles with folate-mediated cancer cell targeting and pH-triggered drug releasing properties for active intracellular drug delivery. Mol Biosyst 1, 242-250, doi: 10. 1039/ b500266d (2005).
5. Wang, Y. et al. Polysorbate 80 coated poly (varepsilon-caprolactone)-poly (ethylene glycol)-poly (varepsilon-caprolactone) micelles for paclitaxel delivery. Int J Pharm 434, 1-8, doi: 10. 1016/j. ijpharm. 2012. 05. 015 (2012).
6. Gao, X. et al. Combined Delivery and Anti-Cancer Activity of Paclitaxel and Curcumin Using Polymeric Micelles. J Biomed Nanotechnol 11, 578-589, doi: 10. 1166/jbn. 2015. 1964 (2015).
7. Rui, Y., Wang, S., Low, P. S. & Thompson, D. H. Diplasmenylcholine-Folate Liposomes: An Efficient Vehicle for Intracellular Drug Delivery. J Am Chem Soc 120, 11213-11218, doi: 10. 1021/ja9742949 (1998).
8. Zhao, X. B. & Lee, R. J. Tumor-selective targeted delivery of genes and antisense oligodeoxyribonucleotides via the folate receptor. Adv Drug Deliver Rev 56, 1193-1204, doi: 10. 1016/j. addr. 2004. 01. 005 (2004).
9. Lu, Y. & Low, P. S. Folate-mediated delivery of macromolecular anticancer therapeutic agents. Adv Drug Deliver Rev 54, 675-693, doi: 10. 1016/S0169-409X(02)00042-X (2002).
10. Yoo, H. S. & Park, T. G. Folate-receptor-targeted delivery of doxorubicin nano-aggregates stabilized by doxorubicin-PEG-folate conjugate. J Control Release 100, 247-256, doi: 10. 1016/j. jconrel. 2004. 08. 017 (2004).
11. Muller, C. & Schibli, R. Folic acid conjugates for nuclear imaging of folate receptor-positive cancer. J Nucl Med 52, 1-4, doi: 10. 2967/ jnumed. 110. 076018 (2011).
12. Tran, P. H., Tran, T. T. & Lee, B. J. Biodistribution and pharmacokinetics in rats and antitumor effect in various types of tumorbearing mice of novel self-assembled gelatin-oleic acid nanoparticles containing paclitaxel. J Biomed Nanotechnol 10, 154-165, doi: 10. 1166/jbn. 2014. 1660 (2014).
13. Martin, A. D. et al. Synthesis and Toxicology of p-Phosphonic Acid Calixarenes and O-Alkylated Analogues as Potential Calixarene-Based Phospholipids. ChemPlusChem 77, 308-313, doi: 10. 1002/cplu. 201100081 (2012).
14. James, E. et al. Antioxidant phospholipid calix[4]arene mimics as micellular delivery systems. Org Biomol Chem 11, 6108-6112, doi: 10. 1039/C3OB41178H (2013).
15. Eggers, P. K. et al. Composite fluorescent vesicles based on ionic and cationic amphiphilic calix[4]arenes. Rsc Adv 2, 6250-6257, doi: 10. 1039/C2ra20491f (2012).
16. Mo, J. et al. Shear induced carboplatin binding within the cavity of a phospholipid mimic for increased anticancer efficacy. Sci. Rep. 5, doi: 10. 1038/srep10414 (2015).
17. Gupta, N., Hatoum, H. & Dy, G. K. First line treatment of advanced non-small-cell lung cancer-specific focus on albumin bound paclitaxel. Int J Nanomed 9, 209-221, doi: 10. 2147/IJN. S41770 (2014).
18. Wang, C. et al. Synthesis, characterization, and application of amino-terminated poly(ethylene glycol)-block-poly(epsiloncaprolactone) copolymer for paclitaxel. J Nanosci Nanotechno 13, 68-76, doi: 10. 1166/jnn. 2013. 6695 (2013).
19. Wang, C. et al. Characterization, pharmacokinetics and disposition of novel nanoscale preparations of paclitaxel. Int J Pharm 414, 251-259, doi: 10. 1016/j. ijpharm. 2011. 05. 014 (2011).
20. Guo, J. et al. Poly-,.-Polyasparthydrazide-Based Nanogels for Potential Oral Delivery of Paclitaxel: In vitro and In vivo Properties. J Biomed Nanotechnol 11, 2231-2242, doi: 10. 1166/jbn. 2015. 2118 (2015).
21. Ye, L. et al. Antitumor effect and toxicity of Lipusu in rat ovarian cancer xenografts. Food Chem Toxicol 52, 200-206, doi: 10. 1016/j. fct. 2012. 11. 004 (2013).
22. Xu, X. et al. Clinical comparison between paclitaxel liposome (Lipusu(R)) and paclitaxel for treatment of patients with metastatic gastric cancer. Asian Pac J Cancer P 14, 2591-2594 (2013).
23. Lim, R. K. & Lin, Q. Bioorthogonal chemistry: recent progress and future directions. Chem Commun (Camb) 46, 1589-1600, doi: 10. 1039/b925931g (2010).
24. Li, X., Guo, J., Asong, J., Wolfert, M. A. & Boons, G.-J. Multifunctional Surface Modification of Gold-stabilized Nanoparticles by Bioorthogonal Reactions. J Am Chem Soc 133, 11147-11153, doi: 10. 1021/ja2012164 (2011).
25. Mo, J. X., Eggers, P. K., Raston, C. L. & Lim, L. Y. Development and validation of a LC/TOF MS method for the determination of carboplatin and paclitaxel in nanovesicles. Anal Bioanal Chem 406, 2659-2667, doi: 10. 1007/s00216-014-7684-0 (2014).
26. Tannock, I. F. & Rotin, D. Acid pH in tumors and its potential for therapeutic exploitation. Cancer Res 49, 4373-4384 (1989).
27. Kumler, W. D. & Eiler, J. J. The Acid Strength of Mono and Diesters of Phosphoric Acid. The n-Alkyl Esters from Methyl to Butyl, the Esters of Biological Importance, and the Natural Guanidine Phosphoric Acids. J Am Chem Soc 65, 2355-2361, doi: 10. 1021/ ja01252a028 (1943).
28. Leamon, C. P., Cooper, S. R. & Hardee, G. E. Folate-liposome-mediated antisense oligodeoxynucleotide targeting to cancer cells: evaluation in vitro and in vivo. Bioconjugate Chem 14, 738-747, doi: 10. 1021/bc020089t (2003).
29. Saul, J. M., Annapragada, A., Natarajan, J. V. & Bellamkonda, R. V. Controlled targeting of liposomal doxorubicin via the folate receptor in vitro. J Control Release 92, 49-67, doi: 10. 1016/S0168-3659(03)00295-5 (2003).
30. Kramer, R. A., Zakher, J. & Kim, G. Role of the glutathione redox cycle in acquired and de novo multidrug resistance. Science 241, 694-697 (1988).
31. Pizzato, M. et al. Evidence for nonspecific adsorption of targeted retrovirus vector particles to cells. Gene Ther 8, 1088-1096, doi: 10. 1038/sj. gt. 3301494 (2001).
32. Schatzel, K., Neumann, W.-G., Muller, J. & Materzok, B. Optical tracking of single Brownian particles. Appl. Opt. 31, 770-778, doi: 10. 1364/ao. 31. 000770 (1992).