Glutathione-responsive core cross-linked micelles for controlled cabazitaxel delivery
Source abstract
Abstract
Stimulus-responsive polymeric micelles (PMs) have recently received attention due to the controlled delivery of drug or gene for application in cancer diagnosis and treatment. In this work, novel glutathione-responsive PMs were prepared to encapsulate hydrophobic antineoplastic drug, cabazitaxel (CTX), to improve its solubility and toxicity. These CTX-loaded micelles core cross-linked by disulfide bonds (DCL-CTX micelles) were prepared by a novel copolymer, lipoic acid grafted mPEG-PLA. These micelles had regular spherical shape, homogeneous diameter of 18.97 ± 0.23 nm, and a narrow size distribution. The DCL-CTX micelles showed high encapsulation efficiency of 98.65 ± 1.77%, and the aqueous solubility of CTX was improved by a factor of 1:1200. In vitro release investigation showed that DCL-CTX micelles were stable in the medium without glutathione (GSH), whereas the micelles had burst CTX release in the medium with 10 mM GSH. Cell uptake results implied that DCL-CTX micelles were internalized into MCF-7 cells through clathrin-mediated endocytosis and released cargo more effectively than Jevtana (commercially available CTX) owing to GSH-stimulated degradation. In MTT assay against MCF-7 cells, these micelles inhibited tumor cell proliferation more effectively than Jevtana due to their GSH-responsive CTX release. All results revealed the potency of GSH-responsive DCL-CTX micelles for stable delivery in blood circulation and for intracellular GSH-trigged release of CTX. Therefore, DCL-CTX micelles show potential as safe and effective CTX delivery carriers and as a cancer chemotherapy formulation.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Nanoparticle-Based Drug Delivery · Lanthanide and Transition Metal Complexes · Dendrimers and Hyperbranched Polymers
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (43)
Show source-provided references
1. Alibolandi M, Ramezani M, Abnous K, Sadeghi F, Hadizadeh F (2015) Comparative evaluation of polymersome versus micelle structures as vehicles for the controlled release of drugs. J Nanopart Res 17:76. https://doi.org/10.1007/s11051-015-2878-810.1007/s11051-015-2878-8 ↗
2. Banerjee P, Satapathy M, Mukhopahayay A, Das P (2014) Leaf extract mediated green synthesis of silver nanoparticles from widely available Indian plants: synthesis, characterization, antimicrobial property and toxicity analysis. Bioresources and Bioprocessing 1(3). https://doi.org/10.1186/s40643-014-0003-y10.1186/s40643-014-0003-y ↗
3. Black SM, Wolf CR (1991) The role of glutathione-dependent enzymes in drug resistance. Pharmacol Ther 51(1):139–154. https://doi.org/10.1016/0163-7258(91)90044-M10.1016/0163-7258(91)90044-M ↗
4. Burt HM, Xichen Zhang, Toleikis P, Embree L, Hunter WL (1999) Development of copolymers of poly(D,L-lactide) and methoxypolyethylene glycol as micellar carriers of paclitaxel. Colloids Surf B Biointerfaces 16:161–171. https://doi.org/10.1016/S0927-7765(99)00067-310.1016/S0927-7765(99)00067-3 ↗
5. Cantin AM, North SL, Hubbard RC, Crystal RG (1987) Normal alveolar epithelial lining fluid contains high levels of glutathione. J Appl Physiol 63(1):152–157. https://doi.org/10.1152/jappl.1987.63.1.15210.1152/jappl.1987.63.1.152 ↗
6. Chan Y, Wong T, Byrne F, Kavallaris M, Bulmus V (2008) Acid-labile core cross-linked micelles for pH-triggered release of antitumor drugs. Biomacromolecules 9(7):1826–1836. https://doi.org/10.1021/bm800043n10.1021/bm800043n ↗
7. Cui C, Xue YN, Wu M, Zhang Y, Yu P, Liu L, Zhuo RX, Huang SW (2013) Cellular uptake, intracellular trafficking, and antitumor efficacy of doxorubicin-loaded reduction-sensitive micelles. Biomaterials 34(15):3858–3869. https://doi.org/10.1016/j.biomaterials.2013.01.10110.1016/j.biomaterials.2013.01.101 ↗
8. Dai Y, Zhang X (2017) Stable and biocompatible genipin-inducing interlayer-crosslinked micelles for sustained drug release. J Nanopart Res 19(164). https://doi.org/10.1007/s11051-017-3866-y10.1007/s11051-017-3866-y ↗
9. Deng B, Ma P, Xie Y (2015) Reduction-sensitive polymeric nanocarriers in cancer therapy: a comprehensive review. Nano 7:12773–12795. https://doi.org/10.1039/C5NR02878G10.1039/C5NR02878G ↗
10. Dey J, Shrivastava S (2012) Can molecules with an anionic head and a poly(ethylene glycol) methyl ether tail self-assemble in water? A surface tension, fluorescence probe, light scattering, and transmission electron microscopic investigation. Soft Matter 8(5):1305–1308. https://doi.org/10.1039/C2SM06931H10.1039/C2SM06931H ↗
11. Diou O, Greco S, Beltran T, Lairez D, Authelin JR, Bazile D (2015) A method to quantify the affinity of cabazitaxel for PLA-PEG nanoparticles and investigate the influence of the nano-assembly structure on the drug/particle association. Pharm Res 32(10):3188–3200. https://doi.org/10.1007/s11095-015-1696-010.1007/s11095-015-1696-0 ↗
12. Galsky MD, Dritselis A, Kirkpatrick P, Oh WK (2010) Cabazitaxel. Nat Rev Drug Discov 9(9):677–678. https://doi.org/10.1038/nrd325410.1038/nrd3254 ↗
13. Han X, Chen D, Sun J, Zhou J, Li D, Gong F, Shen Y (2016) A novel cabazitaxel-loaded polymeric micelle system with superior in vitro stability and long blood circulation time. J Biomater Sci Polym Ed 27:626–642. https://doi.org/10.1080/09205063.2016.114698010.1080/09205063.2016.1146980 ↗
14. Harada A, Kataoka K (1998) Novel polyion complex micelles entrapping enzyme molecules in the Core: preparation of narrowly-distributed micelles from lysozyme and poly(ethylene glycol)-poly(aspartic acid) block copolymer in aqueous medium. Macromolecules 31(2):288–294. https://doi.org/10.1021/ma971277v10.1021/ma971277v ↗
15. Huang SL, Yu XH, Yang L, Song F, Chen G, Lv Z, Li T, Chen D, Zhu W, Yu AA (2014) The efficacy of nimodipine drug delivery using mPEG-PLA micelles and mPEG-PLA/TPGS mixed micelles. Eur J Pharm Sci 63:187–198. https://doi.org/10.1016/j.ejps.2014.07.00710.1016/j.ejps.2014.07.007 ↗
16. Jayaram A, Attard G (2015) Cabazitaxel-a key therapeutic option in prostate cancer. Nat Rev Urol 12(6):312–313. https://doi.org/10.1038/nrurol.2015.9810.1038/nrurol.2015.98 ↗
17. Kakizawa Y, Harada A, Kataoka K (1999) Environment-sensitive stabilization of core-shell structured polyion complex micelle by reversible cross-linking of the core through disulfide bond. J Am Chem Soc 121:11247–11248. https://doi.org/10.1021/ja993057y10.1021/ja993057y ↗
18. Kang MJ, Park SH, Kang MH, Park MJ, Choi YW (2013) Folic acid-tethered Pep-1 peptide-conjugated liposomal nanocarrier for enhanced intracellular drug delivery to cancer cells: conformational characterization and in vitro cellular uptake evaluation. Int J Nanomedicine 8:1155–1165. https://doi.org/10.2147/IJN.S3949110.2217/nnm.13.104 ↗
19. Koo AN, Lee HJ, Kim SE, Chang JH, Park CY, Kim CH, Park JH, Lee SC (2008) Disulfide-cross-linked PEG-poly(amino acid)s copolymer micelles for glutathione-mediated intracellular drug delivery. Chem Commun (Camb) (48):6570–6572. https://doi.org/10.1039/b815918a10.1039/b815918a ↗
20. Lee SY, Kim S, Tyler JY, Park K, Cheng JX (2013) Blood-stable, tumor-adaptable disulfide bonded mPEG-(Cys)4-PDLLA micelles for chemotherapy. Biomaterials 34:552–561. https://doi.org/10.1016/j.biomaterials.2012.09.06510.1016/j.biomaterials.2012.09.065 ↗
21. Li Y, Xiao K, Luo J, Xiao W, Lee JS, Gonik AM, Kato J, Dong TA, Lam KS (2011) Well-defined, reversible disulfide cross-linked micelles for on-demand paclitaxel delivery. Biomaterials 32(27):6633–6645. https://doi.org/10.1016/j.biomaterials.2011.05.05010.1016/j.biomaterials.2011.05.050 ↗
22. Lin MM, Kang YJ, Sohn Y, Kim DK (2015) Dual targeting strategy of magnetic nanoparticle-loaded and RGD peptide-activated stimuli-sensitive polymeric micelles for delivery of paclitaxel. J Nanopart Res 17(248). https://doi.org/10.1007/s11051-015-3033-210.1007/s11051-015-3033-2 ↗
23. Miller T, Breyer S, Colen G, Mier W, Haberkorn U, Geissler S, Voss S, Weigandt M, Goepferich A (2013) Premature drug release of polymeric micelles and its effects on tumor targeting. Int J Pharm 445:117–124. https://doi.org/10.1016/j.ijpharm.2013.01.05910.1016/j.ijpharm.2013.01.059 ↗
24. Mitragotri S, Lahann J (2009) Physical approaches to biomaterial design. Nat Mater 8(1):15–23. https://doi.org/10.1038/nmat234410.1038/nmat2344 ↗
25. Norris LB, Qureshi ZP, Bookstaver PB, Raisch DW, Sartor O, Chen H, Chen F, Bennett CL (2010) Polysorbate 80 hypersensitivity reactions: a renewed call to action. Commun Oncol 7(9):425–428. https://doi.org/10.1016/S1548-5315(11)70418-110.1016/S1548-5315(11)70418-1 ↗
26. Qiu LY, Yan L, Zhang L, Jin YM, Zhao QH (2013) Folate-modified poly(2-ethyl-2-oxazoline) as hydrophilic corona in polymeric micelles for enhanced intracellular doxorubicin delivery. Int J Pharm 456(2):315–324. https://doi.org/10.1016/j.ijpharm.2013.08.07110.1016/j.ijpharm.2013.08.071 ↗
27. Reddy LH, Bazile D (2014) Drug delivery design for intravenous route with integrated physicochemistry, pharmacokinetics and pharmacodynamics: illustration with the case of taxane therapeutics. Adv Drug Deliv Rev 71:34–57. https://doi.org/10.1016/j.addr.2013.10.00710.1016/j.addr.2013.10.007 ↗
28. Rijcken CJ, Snel CJ, Schiffelers RM, Nostrum CFV, Hennink WE (2007) Hydrolysable core-crosslinked thermosensitive polymeric micelles: synthesis, characterisation and in vivo studies. Biomaterials 28(36):5581–5593. https://doi.org/10.1016/j.biomaterials.2007.08.04710.1016/j.biomaterials.2007.08.047 ↗
29. Savic R, Azzam T, Eisenberg A, Maysinger D (2006) Assessment of the integrity of poly(caprolactone)-b-poly(ethylene oxide) micelles under biological conditions: a fluorogenic-based approach. Langmuir 22(8):3570–3578. https://doi.org/10.1021/la053199810.1021/la0531998 ↗
30. Sevier CS, Kaiser CA (2002) Formation and transfer of disulphide bonds in living cells. Nat Rev Mol Cell Biol 3(11):836–847. https://doi.org/10.1038/nrm95410.1038/nrm954 ↗
31. Shao Y, Zhang C, Yao Q, Wang Y, Tian B, Tang X (2014) Improving cabazitaxel chemical stability in parenteral lipid emulsions using cholesterol. Eur J Pharm Sci 52:1–11. https://doi.org/10.1016/j.ejps.2013.09.02410.1016/j.ejps.2013.09.024 ↗
32. Shao YJ, Li S, Tian B, Su LL, Zhang CG, Wang YQ, Tang X, Wang YJ (2015) Evaluation of the stability and pharmacokinetics of cabazitaxel-loaded intravenous lipid microspheres: beneficial effect of cholesterol. Eur J Lipid Sci Technol 117(4):460–470. https://doi.org/10.1002/ejlt.20140016010.1002/ejlt.201400160 ↗
33. Shi LL, Xie HJ, Lu J, Gao Y, Liu JY, Zhang XX, Zhang HJ, Cui JH, Cao QR (2016) Positively charged surface-modified solid lipid nanoparticles promote the intestinal transport of docetaxel through multifunctional mechanisms in rats. Mol Pharm 13(8):2667–2676. https://doi.org/10.1021/acs.molpharmaceut.6b0022610.1021/acs.molpharmaceut.6b00226 ↗
34. Simoes SI, Tapadas JM, Marques CM, Cruz MEM, Martins MBF, Cevc G (2005) Permeabilisation and solubilisation of soybean phosphatidylcholine bilayer vesicles, as membrane models, by polysorbate, Tween 80. Eur J Pharm Sci 26(3-4):307–317. https://doi.org/10.1016/j.ejps.2005.07.00210.1016/j.ejps.2005.07.002 ↗
35. Smith CV, Jones DP, Guenthner TM, Lash LH, Lauterburg BH (1996) Compartmentation of glutathione: implications for the study of toxicity and disease. Toxicol Appl Pharmacol 140(1):1–12. https://doi.org/10.1006/taap.1996.019110.1006/taap.1996.0191 ↗
36. Song Y, Tian Q, Huang Z, Fan D, She Z, Liu X, Cheng X, Yu B, Deng Y (2014) Self-assembled micelles of novel amphiphilic copolymer cholesterol-coupled F68 containing cabazitaxel as a drug delivery system. Int J Nanomedicine 9:2307–2317. https://doi.org/10.2147/IJN.S6122010.2147/IJN.S61220 ↗
37. Tangutur AD, Kumar D, Krishna KV, Kantevari S (2017) Microtubule targeting agents as cancer chemotherapeutics: an over-view of molecular hybrids as stabilising and destabilising agents. Curr Top Med Chem 17:1–1510.2174/1568026617666170104145640 ↗
38. Thurmond KB, Kowalewski T, Wooley KL (1996) Water-soluble Knedel-like structures: the preparation of Shell-cross-linked small particles. J Am Chem Soc 118:7239–7240. https://doi.org/10.1021/ja961299h10.1021/ja961299h ↗
39. Xiao L, Xiong X, Sun X, Zhu Y, Yang H, Chen H, Gan L, Xu H, Yang X (2011) Role of cellular uptake in the reversal of multidrug resistance by PEG-b-PLA polymeric micelles. Biomaterials 32(22):5148–5157. https://doi.org/10.1016/j.biomaterials.2011.03.07110.1016/j.biomaterials.2011.03.071 ↗
40. Xu J, Luan S, Qin B, Wang Y, Wang K, Qi P, Song S (2016) Backbone-hydrazone-containing biodegradable copolymeric micelles for anticancer drug delivery. J Nanopart Res 18(316). https://doi.org/10.1007/s11051-016-3626-410.1007/s11051-016-3626-4 ↗
41. Yared JA, Tkaczuk KH (2012) Update on taxane development: new analogs and new formulations. Drug Des Devel Ther 6:371–384
42. Zhang S, Gao H, Bao G (2015) Physical principles of nanoparticle cellular endocytosis. ACS Nano 9:8655–8671. https://doi.org/10.1021/acsnano.5b0318410.1021/acsnano.5b03184 ↗
43. Zhuang B, Du L, Xu H, Xu X, Wang C, Fan Y, Cong M, Yin J, Li H, Guan H (2016) Self-assembled micelle loading cabazitaxel for therapy of lung cancer. Int J Pharm 499(1-2):146–155. https://doi.org/10.1016/j.ijpharm.2015.12.07310.1016/j.ijpharm.2015.12.073 ↗