Y-shaped folic acid-conjugated PEG-PCL copolymeric micelles for delivery of curcumin

Anti-Cancer Agents in Medicinal Chemistry

Volumn 16, Issue , 2016, Pages 599-607

  Feng, Runliang ^a   Zhu, Wenxia ^a   Chu, Wei ^b   Teng, Fangfang ^c   Meng, Ning ^a   Deng, Peizong ^a   Song, Zhimei ^a  

^a UNIVERSITY OF JINAN   (China)

^b INSTITUTE OF BIOPHYSICS   (China)

^c SHANDONG PROVINCIAL HOSPITAL AFFILIATED TO SHANDONG FIRST MEDICAL UNIVERSITY   (China)

Author keywords

Copolymer; Curcumin; Folic acid; Poly (ethylene glycol); Y shaped; caprolactone

Indexed keywords

CURCUMIN; FOLIC ACID; POLYCAPROLACTONE; ANTINEOPLASTIC AGENT; DRUG CARRIER; ETHYLENE GLYCOL DERIVATIVE; FOLATE RECEPTOR; MICELLE; POLY(EPSILON-CAPROLACTONE)-B-POLY(ETHYLENE GLYCOL); POLYESTER;

ACYLATION; ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOCOMPATIBILITY; CHEMICAL PHENOMENA; COMPARATIVE STUDY; CONFOCAL LASER SCANNING MICROSCOPY; CONFOCAL MICROSCOPY; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; DRUG SOLUBILITY; ENCAPSULATION; FLUORESCENCE; HEMOLYSIS ASSAY; HUMAN; HUMAN CELL; IN VITRO STUDY; LIGHT SCATTERING; MICELLE; MORPHOLOGY; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY DIFFRACTION; ZETA POTENTIAL; CELL PROLIFERATION; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; DRUG SCREENING; HELA CELL LINE; HEP-G2 CELL LINE; METABOLISM; PARTICLE SIZE; SOLUBILITY; STRUCTURE ACTIVITY RELATION; SURFACE PROPERTY;

ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; CELL SURVIVAL; CURCUMIN; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG CARRIERS; DRUG SCREENING ASSAYS, ANTITUMOR; ETHYLENE GLYCOLS; FOLATE RECEPTORS, GPI-ANCHORED; FOLIC ACID; HELA CELLS; HEP G2 CELLS; HUMANS; MICELLES; MOLECULAR STRUCTURE; PARTICLE SIZE; POLYESTERS; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; SURFACE PROPERTIES;

EID: 85010303985     PISSN: 18715206     EISSN: 18755992     Source Type: Journal    
DOI: 10.2174/1871520616666160815124014     Document Type: Article

References (48)

1. Singla, A. K.; Garg, A.; Aggarwal, D. Paclitaxel and its formulations. Int. J. Pharm., 2002, 235(1-2), 179-192.
2. Cabral, H.; Kataoka, K. Progress of drug-loaded polymeric micelles into clinical studies. J. Control. Rel., 2014, 190, 465-476.
3. Jain, V.; Jain, S.; Mahajan, S. C. Nanomedicines Based Drug Delivery Systems For Anti-Cancer Targeting And Treatment. Curr. Drug Deliv., 2015, 12 (2), 177-191.
4. Jin, S. E.; Jin, H. E.; Hong, S. S. Targeted delivery system of nanobiomaterials in anticancer therapy: from cells to clinics. Biomed. Res. Int., 2014, 2014, 814208.
5. Chang, S. C.; Chang, P. Y.; Butler, B.; Goldstein, B. Y.; Mu, L.; Cai, L.; You, N. C.; Baecker, A.; Yu, S. Z.; Heber, D.; Lu, Q. Y.; Li, L.; Greenland, S.; Zhang, Z. F. Single nucleotide polymorphisms of one-carbon metabolism and cancers of theesophagus, stomach, and liver in a chinese population. PloS one, 2014, 9 (10), e109235.
6. Zhao, P.; Wang, H.; Yu, M.; Liao, Z.; Wang, X.; Zhang, F.; Ji, W.; Wu, B.; Han, J.; Zhang, H.; Wang, H.; Chang, J.; Niu, R. Paclitaxel loaded folic acid targeted nanoparticles of mixed lipid-shell and polymer-core: in vitro and in vivo evaluation. Eur. J. Pharm. Biopharm., 2012, 81 (2), 248-256.
7. Wang, J.; Liu, W.; Tu, Q.; Wang, J.; Song, N.; Zhang, Y.; Nie, N.; Wang, J. Folate-decorated hybrid polymeric nanoparticles for chemically and physically combined paclitaxel loading and targeted delivery. Biomacromolecules, 2011, 12 (1), 228-234.
8. Park, E. K.; Kim, S. Y.; Lee, S. B.; Lee, Y. M. Folate-conjugated methoxy poly(ethylene glycol)/poly(epsilon-caprolactone) amphiphilic block copolymeric micelles for tumor-targeted drug delivery. J. Control. Release, 2005, 109 (1-3), 158-168.
9. Pan, Z.; Yu, L.; Song, N.; Zhou, L.; Li, J.; Ding, M.; Tan, H.; Fu, Q. Synthesis and characterization of biodegradable polyurethanes with folate side chains conjugated to hard segments. Polym. Chem.-UK, 2014, 5 (8), 2901-2910.
10. Lu, J.; Zhao, W.; Huang, Y.; Liu, H.; Marquez, R.; Gibbs, R. B.; Li, J.; Venkataramanan, R.; Xu, L.; Li, S.; Li, S. Targeted delivery of Doxorubicin by folic acid-decorated dual functional nanocarrier. Mol. Pharm., 2014, 11 (11), 4164-4178.
11. Feng, R. L.; Zhu, W. X.; Song, Z. M.; Zhao, L. Y.; Zhai, G. X. Novel star-type methoxy-poly(ethylene glycol) (PEG)-poly(epsilon-caprolactone) (PCL) copolymeric nanoparticles for controlled release of curcumin. J. Nanopart. Res., 2013, 15 (6), 1748-1759.
12. Zhu, W. X.; Song, Z. M.; Wei, P.; Meng, N.; Teng, F. F.; Yang, F. Y.; Liu, N.; Feng, R. L. Y-shaped biotin-conjugated poly (ethylene glycol)–poly (epsilon-caprolactone) copolymer for the targeted delivery of curcumin. J. Colloid Interface Sci., 2015, 443 (0), 1-7.
13. Salem, A. K.; Cannizzaro, S. M.; Davies, M. C.; Tendler, S. J. B.; Roberts, C. J.; Williams, P. M.; Shakesheff, K. M. Synthesis and Characterisation of a Degradable Poly(lactic acid)−Poly(ethylene glycol) Copolymer with Biotinylated End Groups. Biomacromolecules, 2001, 2 (2), 575-580.
14. Petrova, S.; Riva, R.; Jerome, C.; Lecomte, P.; Mateva, R. Controlled synthesis of AB(2) amphiphilic triarm star-shaped block copolymers by ring-opening polymerization. Eur. Polym. J., 2009, 45 (12), 3442-3450.
15. Yang, X.; Deng, W.; Fu, L.; Blanco, E.; Gao, J.; Quan, D.; Shuai, X. Folate-functionalized polymeric micelles for tumor targeted delivery of a potent multidrug-resistance modulator FG020326. J. Biomed. Mater. Res. A, 2008, 86 (1), 48-60.
16. Hong, G. B.; Zhou, J. X.; Yuan, R. X. Folate-targeted polymeric micelles loaded with ultrasmall superparamagnetic iron oxide: combined small size and high MRI sensitivity. Int. J. Nanomed., 2012, 7, 2863-2872.
17. Song, Z.; Feng, R.; Sun, M.; Guo, C.; Gao, Y.; Li, L.; Zhai, G. Curcumin-loaded PLGA-PEG-PLGA triblock copolymeric micelles: Preparation, pharmacokinetics and distribution in vivo. J. Colloid Interface Sci., 2011, 354 (1), 116-123.
18. Wang, Y. J.; Wang, C.; Gong, C. Y.; Wang, Y. J.; Guo, G.; Luo, F.; Qian, Z. Y. Polysorbate 80 coated poly (ɛ-caprolactone)–poly (ethylene glycol)–poly (ɛ-caprolactone) micelles for paclitaxel delivery. Int. J. Pharm., 2012, 434 (1–2), 1-8.
19. Lee, J. S.; Feijen, J. Polymersomes for drug delivery: design, formation and characterization. J. Control. Release, 2012, 161 (2), 473-483.
20. Song, Z. M.; Feng, R. L.; Sun, M.; Guo, C. Y.; Gao, Y.; Li, L. B.; Zhai, G. X. Curcumin-loaded PLGA-PEG-PLGA triblock copolymeric micelles: Preparation, pharmacokinetics and distribution in vivo. J. Colloid Interface Sci., 2011, 354 (1), 116-123.
21. Meng, H.; Xue, M.; Xia, T.; Ji, Z.; Tarn, D. Y.; Zink, J. I.; Nel, A. E. Use of Size and a Copolymer Design Feature To Improve the Biodistribution and the Enhanced Permeability and Retention Effect of Doxorubicin-Loaded Mesoporous Silica Nanoparticles in a Murine Xenograft Tumor Model. ACS nano, 2011, 5 (5), 4131-4144.
22. Dutta, P.; Dey, J. Drug solubilization by amino acid based polymeric nanoparticles: Characterization and biocompatibility studies. Int. J. Pharm., 2011, 421 (2), 353-363.
23. Shaikh, J.; Ankola, D. D.; Beniwal, V.; Singh, D.; Kumar, M. N. Nanoparticle encapsulation improves oral bioavailability of curcumin by at least 9-fold when compared to curcumin administered with piperine as absorption enhancer. Eur. J. Pharm. Sci., 2009, 37 (3-4), 223-230.
24. Tsai, Y. M.; Chien, C. F.; Lin, L. C.; Tsai, T. H. Curcumin and its nano-formulation: the kinetics of tissue distribution and bloodbrain barrier penetration. Int. J. Pharm., 2011, 416 (1), 331-338.
25. Song, Z. M.; Zhu, W. X.; Liu, N.; Yang, F. Y.; Feng, R. L. Linolenic acid-modified PEG-PCL micelles for curcumin delivery. Int. J. Pharm., 2014, 471 (1-2), 312-321.
26. Manju, S.; Sharma, C. P.; Sreenivasan, K. Targeted coadministration of sparingly soluble paclitaxel and curcumin into cancer cells by surface engineered magnetic nanoparticles. J. Mater. Chem., 2011, 21 (39), 15708-15717.
27. Jia, W. J.; Gu, Y. C.; Gou, M. L.; Dai, M.; Li, X. Y.; Kan, B.; Yang, J. L.; Song, Q. F.; Wei, Y. Q.; Qian, Z. Y. Preparation of Biodegradable Polycaprolactone/Poly (ethylene glycol)/ Polycaprolactone (PCEC) Nanoparticles. Drug Deliv., 2008, 15 (7), 409-416.
28. Letchford, K.; Liggins, R.; Burt, H. Solubilization of hydrophobic drugs by methoxy poly(ethylene glycol)-block-polycaprolactone diblock copolymer micelles: theoretical and experimental data and correlations. J. Pharm. Sci., 2008, 97 (3), 1179-1190.
29. Pillai, J. J.; Thulasidasan, A. K.; Anto, R. J.; Chithralekha, D. N.; Narayanan, A.; Kumar, G. S. Folic acid conjugated cross-linked acrylic polymer (FA-CLAP) hydrogel for site specific delivery of hydrophobic drugs to cancer cells. J. Nanobiotechnol., 2014, 12, 25.
30. Yallapu, M. M.; Jaggi, M.; Chauhan, S. C. β-Cyclodextrincurcumin self-assembly enhances curcumin delivery in prostate cancer cells. Colloids Surf. B Biointerfaces, 2010, 79 (1), 113-125.
31. Mohanty, C.; Sahoo, S. K. The in vitro stability and in vivo pharmacokinetics of curcumin prepared as an aqueous nanoparticulate formulation. Biomaterials, 2010, 31 (25), 6597-6611.
32. Yen, F. L.; Wu, T. H.; Tzeng, C. W.; Lin, L. T.; Lin, C. C. Curcumin nanoparticles improve the physicochemical properties of curcumin and effectively enhance its antioxidant and antihepatoma activities. J. Agric. Food. Chem., 2010, 58 (12), 7376-7382.
33. Sun, B.; Zhao, R.; Kong, F.; Ren, Y.; Zuo, A.; Liang, D.; Zhang, J. Phosphorylatable short peptide conjugation for facilitating transfection efficacy of CS/DNA complex. Int. J. Pharm., 2010, 397 (1-2), 206-210.
34. Cerda-Cristerna, B. I.; Flores, H.; Pozos-Guillen, A.; Perez, E.; Sevrin, C.; Grandfils, C. Hemocompatibility assessment of poly(2-dimethylamino ethylmethacrylate) (PDMAEMA)-based polymers. J. Control. Release, 2011, 153 (3), 269-277.
35. Teiten, M. H.; Dicato, M.; Diederich, M. Hybrid Curcumin Compounds: A New Strategy for Cancer Treatment. Molecules, 2014, 19 (12), 20839-20863.
36. Zang, S.; Liu, T.; Shi, J.; Qiao, L. Curcumin: a promising agent targeting cancer stem cells. Anticancer Agents Med. Chem., 2014, 14 (6), 787-792.
37. Pan, Z. C.; Yu, L. Q.; Song, N. J.; Zhou, L. J.; Li, J. H.; Ding, M. M.; Tan, H.; Fu, Q. Synthesis and characterization of biodegradable polyurethanes with folate side chains conjugated to hard segments. Polym Chem-Uk, 2014, 5 (8), 2901-2910.
38. Lee, H.; Zeng, F.; Dunne, M.; Allen, C. Methoxy poly(ethylene glycol)-block-poly(delta-valerolactone) copolymer micelles for formulation of hydrophobic drugs. Biomacromolecules, 2005, 6 (6), 3119-3128.
39. Sun, Y.; Huang, Y.; Bian, S.; Liang, J.; Fan, Y.; Zhang, X. Reduction-degradable PEG-b-PAA-b-PEG triblock copolymer micelles incorporated with MTX for cancer chemotherapy. Colloids Surf. B Biointerfaces, 2013, 112, 197-203.
40. Hu, Y.; Jiang, X.; Ding, Y.; Zhang, L.; Yang, C.; Zhang, J.; Chen, J.; Yang, Y. Preparation and drug release behaviors of nimodipineloaded poly(caprolactone)-poly(ethylene oxide)-polylactide amphiphilic copolymer nanoparticles. Biomaterials, 2003, 24 (13), 2395-2404.
41. Xu, B.; Yuan, J.; Wang, Z.; Gao, Q. Shell-cross-linked amino acidmodified APLA-b-PEG-Cys copolymer micelle as a drug delivery carrier. J. Microencapsul., 2009, 26 (7), 659-666.
42. Bu, L.; Gan, L.-C.; Guo, X.-Q.; Chen, F.-Z.; Song, Q.; Qi, Z.; Gou, X.-J.; Hou, S.-X.; Yao, Q. Trans-resveratrol loaded chitosan nanoparticles modified with biotin and avidin to target hepatic carcinoma. Int. J. Pharm., 2013, 452 (1–2), 355-362.
43. Canal, F.; Vicent, M. J.; Pasut, G.; Schiavon, O. Relevance of folic acid/polymer ratio in targeted PEG-epirubicin conjugates. J. Control. Release, 2010, 146 (3), 388-399.
44. Qiu, L. Y.; Yan, L.; Zhang, L.; Jin, Y. M.; Zhao, Q. H. Folatemodified poly(2-ethyl-2-oxazoline) as hydrophilic corona in polymeric micelles for enhanced intracellular doxorubicin delivery. Int. J. Pharm., 2013, 456 (2), 315-324.
45. Cheng, C. Y.; Ou, K. L.; Huang, W. T.; Chen, J. K.; Chang, J. Y.; Yang, C. H. Gadolinium-based CuInS2/ZnS nanoprobe for dualmodality magnetic resonance/optical imaging. ACS Appl. Mater. Interfaces, 2013, 5 (10), 4389-4400.
46. Yang, C.; Chen, H.; Zhao, J.; Pang, X.; Xi, Y.; Zhai, G. Development of a folate-modified curcumin loaded micelle delivery system for cancer targeting. Colloids Surf. B Biointerfaces, 2014, 121, 206-213.
47. Zhang, L.; Lu, J.; Jin, Y.; Qiu, L. Folate-conjugated betacyclodextrin-based polymeric micelles with enhanced doxorubicin antitumor efficacy. Colloids Surf. B Biointerfaces, 2014, 122, 260-269.
48. Chu, Y.; Li, D.; Luo, Y. F.; He, X. J.; Jiang, M. Y. Preparation and In Vitro Evaluation of Glycyrrhetinic Acid-Modified Curcumin-Loaded Nanostructured Lipid Carriers. Molecules, 2014, 19 (2), 2445-2457.