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Recent Patents on Anti-Cancer Drug Discovery

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ISSN (Print): 1574-8928
ISSN (Online): 2212-3970

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Research Article

In Vitro and In Vivo Evaluation of Novel DTX-Loaded Multifunctional Heparin-Based Polymeric Micelles Targeting Folate Receptors and Endosomes

Author(s): Moloud Kazemi, Jaber Emami*, Farshid Hasanzadeh, Mohsen Minaiyan, Mina Mirian, Afsaneh Lavasanifar and Mojgan Mokhtari

Volume 15, Issue 4, 2020

Page: [341 - 359] Pages: 19

DOI: 10.2174/1574892815666201006124604

Price: $65

Abstract

Background: The development of biocompatible tumor-targeting delivery systems for anticancer agents is essential for efficacious cancer chemotherapy. Nanoparticles, as drug delivery cargoes for cancer therapy, are rapidly improving to overcome the limitations of conventional chemotherapeutic agents. Heparin–modified nanoparticles are currently being considered as one of the favorable carriers for the delivery of chemotherapeutics to cancer tissues.

Objective: This study was aimed at evaluating the in vitro and in vivo antitumor activity of a novel targeted, pH-sensitive, heparin-based polymeric micelle loaded with the poorly water-soluble anticancer drug, docetaxel (DTX). The micelles could overcome the limited water solubility, non-specific distribution, and insufficient drug concentration in tumor tissues.

Methods: DTX-loaded folate targeted micelles were prepared and evaluated for physicochemical properties, drug release, in vitro cellular uptake and cytotoxicity in folate receptor-positive and folate receptor-negative cells. Furthermore, the antitumor activity of DTX-loaded micelles was evaluated in the tumor-bearing mice. Some related patents were also studied in this research.

Results: The heparin-based targeted micelles exhibited higher in vitro cellular uptake and cytotoxicity against folate receptor over-expressed cells due to the specific receptor-mediated endocytosis. DTX-loaded micelles displayed greater antitumor activity, higher anti-angiogenesis effects, and lower systemic toxicity compared with free DTX in a tumor-induced mice model as confirmed by tumor growth monitoring, immunohistochemical evaluation, and body weight shift. DTX-loaded targeting micelles demonstrated no considerable toxicity on major organs of tumor-bearing mice compared with free DTX.

Conclusion: Our results indicated that DTX-loaded multifunctional heparin-based micelles with desirable antitumor activity and low toxicity possess great potential as a targeted drug delivery system in the treatment of cancer.

Keywords: Angiogenesis, breast cancer, docetaxel, drug delivery, folic acid, heparin, polymeric micelle, pH-sensitive.

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[1]
Ferguson T, Wilcken N, Vagg R, Ghersi D, Nowak AK. Taxanes for adjuvant treatment of early breast cancer. Cochrane Database Syst Rev 2007; (4): CD004421.
[http://dx.doi.org/10.1002/14651858.CD004421.pub2] [PMID: 17943815]
[2]
Cortes JE, Pazdur R. Docetaxel. J Clin Oncol 1995; 13(10): 2643-55.
[http://dx.doi.org/10.1200/JCO.1995.13.10.2643] [PMID: 7595719]
[3]
Chevallier B, Fumoleau P, Kerbrat P, et al. Docetaxel is a major cytotoxic drug for the treatment of advanced breast cancer: A phase II trial of the Clinical Screening Cooperative Group of the European Organization for Research and Treatment of Cancer. J Clin Oncol 1995; 13(2): 314-22.
[http://dx.doi.org/10.1200/JCO.1995.13.2.314] [PMID: 7844592]
[4]
Guéritte-Voegelein F, Guénard D, Lavelle F, Le Goff MT, Mangatal L, Potier P. Relationships between the structure of taxol analogues and their antimitotic activity. J Med Chem 1991; 34(3): 992-8.
[http://dx.doi.org/10.1021/jm00107a017] [PMID: 1672159]
[5]
Alam F, Al-Hilal TA, Park J, et al. Multi-stage inhibition in breast cancer metastasis by orally active triple conjugate, LHTD4 (low molecular weight heparin-taurocholate-tetrameric deoxycholate). Biomaterials 2016; 86: 56-67.
[http://dx.doi.org/10.1016/j.biomaterials.2016.01.058] [PMID: 26890038]
[6]
Qin Y-Y, Li H, Guo X-J, et al. Adjuvant chemotherapy, with or without taxanes, in early or operable breast cancer: A meta-analysis of 19 randomized trials with 30698 patients. PLoS One 2011; 6(11): e26946.
[http://dx.doi.org/10.1371/journal.pone.0026946]
[7]
Zhang E, Xing R, Liu S, Li P. Current advances in development of new docetaxel formulations. Expert Opin Drug Deliv 2019; 16(3): 301-12.
[http://dx.doi.org/10.1080/17425247.2019.1583644] [PMID: 30773947]
[8]
Engels FKMR, Mathot RA, Verweij J. Alternative drug formulations of docetaxel: A review. Anticancer Drugs 2007; 18(2): 95-103.
[http://dx.doi.org/10.1097/CAD.0b013e3280113338] [PMID: 17159596]
[9]
Hanif MF, Ahmad R, Khalid K, Tabassum M, Akram F. Targeted delivery of nanoparticle based taxanes for breast cancer treatment: A review. Trends in Drug Delivery 2020; 6(3): 36-51.
[10]
Junshan R, Pengfei D, Limian W, Zhou H. Docetaxel nano-polymer micelle lyophilized preparation and preparation method thereof. US20160128940, 2018.
[11]
De T, Desai NP, Yang A, Yim Z, Soon-Shiong PMD. Compositions of poorly water soluble drugs with increased stability and methods for preparation thereof. EP1928435, 2019.
[12]
Sivaraman MM, Patel H, Patel BV, Kannekanti R, Raheesh M. Pharmaceutical compositions of taxane and its derivatives. WO2018109731, 2018.
[13]
Li J, Bao J, Wang W. Drug formulation based on particulates comprising polysaccharide-vitamin conjugate. US20200093935, 2020.
[14]
Fang XB, Zhang JM, Xie X, et al. pH-sensitive micelles based on acid-labile pluronic F68-curcumin conjugates for improved tumor intracellular drug delivery. Int J Pharm 2016; 502(1-2): 28-37.
[http://dx.doi.org/10.1016/j.ijpharm.2016.01.029] [PMID: 26784981]
[15]
Farokhzad OC, Langer R. Impact of nanotechnology on drug delivery. ACS Nano 2009; 3(1): 16-20.
[http://dx.doi.org/10.1021/nn900002m] [PMID: 19206243]
[16]
Zhao P, Astruc D. Docetaxel nanotechnology in anticancer therapy. ChemMedChem 2012; 7(6): 952-72.
[http://dx.doi.org/10.1002/cmdc.201200052] [PMID: 22517723]
[17]
Tan Q, Liu X, Fu X, Li Q, Dou J, Zhai G. Current development in nanoformulations of docetaxel. Expert Opin Drug Deliv 2012; 9(8): 975-90.
[http://dx.doi.org/10.1517/17425247.2012.696606] [PMID: 22703284]
[18]
Javeri I, Nellaiappan K. Methods for the preparation of liposomes comprising drugs. US9655846, 2017.
[19]
Hennink WE, Shi Y, Van Nostrum CF. Amphiphilic block copolymers for delivery of active agents. US20170231908, 2017.
[20]
She W, Li N, Luo K, et al. Dendronized heparin-doxorubicin conjugate based nanoparticle as pH-responsive drug delivery system for cancer therapy. Biomaterials 2013; 34(9): 2252-64.
[http://dx.doi.org/10.1016/j.biomaterials.2012.12.017] [PMID: 23298778]
[21]
Lee S-W, Yun M-H, Jeong SW, et al. Development of docetaxel-loaded intravenous formulation, Nanoxel-PM™ using polymer-based delivery system. J Control Release 2011; 155(2): 262-71.
[http://dx.doi.org/10.1016/j.jconrel.2011.06.012] [PMID: 21704664]
[22]
Zhang L, Zhang N. How nanotechnology can enhance docetaxel therapy. Int J Nanomedicine 2013; 8: 2927-41.
[http://dx.doi.org/10.2147/IJN.S46921] [PMID: 23950643]
[23]
Manjappa AS, Goel PN, Vekataraju MP, et al. Is an alternative drug delivery system needed for docetaxel? The role of controlling epimerization in formulations and beyond. Pharm Res 2013; 30(10): 2675-93.
[http://dx.doi.org/10.1007/s11095-013-1093-5] [PMID: 23756759]
[24]
Sun Q. Formulations and compositions of docetaxel. WO2019200084, 2019.
[25]
Sun Q. Docetaxel and human serum albumin complexes. WO2016187147, 2016.
[26]
Compostions comprising nanoparticles comprising docetaxel and albumin prepared using anhydrous docetaxel. CA2848021, 2018.
[27]
Naik S, Patel D, Surti N, Misra A. Preparation of PEGylated liposomes of docetaxel using supercritical fluid technology. J Supercrit Fluids 2010; 54(1): 110-9.
[http://dx.doi.org/10.1016/j.supflu.2010.02.005]
[28]
Zhai G, Wu J, Yu B, Guo C, Yang X, Lee RJ. A transferrin receptor-targeted liposomal formulation for docetaxel. J Nanosci Nanotechnol 2010; 10(8): 5129-36.
[http://dx.doi.org/10.1166/jnn.2010.2393] [PMID: 21125861]
[29]
De T, Desai NP, Yang A, Yim Z, Soon-Shiong P. Compostions comprising nanoparticles comprising docetaxel and albumin prepared using anhydrous docetaxel. CA2848021, 2016.
[30]
Marino MT. Liposomal taxanes for treatment of SCLC. WO2019032437, 2019.
[31]
Mcghee W, Blackledge J, Grapperhaus M, Rochon LS, Devarakonda K. Modified docetaxel liposome formulations and uses thereof. CA2976912, 2016.
[32]
Xu Z, Chen L, Gu W, et al. The performance of docetaxel-loaded solid lipid nanoparticles targeted to hepatocellular carcinoma. Biomaterials 2009; 30(2): 226-32.
[http://dx.doi.org/10.1016/j.biomaterials.2008.09.014] [PMID: 18851881]
[33]
Li X, Wang D, Zhang J, Pan W. Preparation and pharmacokinetics of docetaxel based on nanostructured lipid carriers. J Pharm Pharmacol 2009; 61(11): 1485-92.
[http://dx.doi.org/10.1211/jpp.61.11.0007] [PMID: 19903373]
[34]
Chen L, Sha X, Jiang X, Chen Y, Ren Q, Fang X. Pluronic P105/F127 mixed micelles for the delivery of docetaxel against Taxol-resistant non-small cell lung cancer: Optimization and  in vitro, in vivo evaluation. Int J Nanomedicine 2013; 8: 73-84.
[http://dx.doi.org/10.2147/ijn.s38221] [PMID: 23319859]
[35]
Luo Z, Jiang L, Ding C, et al. Surfactant free delivery of docetaxel by poly[(r)-3-hydroxybutyrate-(r)-3-hydroxyhexanoate]-based polymeric micelles for effective melanoma treatments. Adv Healthc Mater 2018; 7(23): e1801221.
[http://dx.doi.org/10.1002/adhm.201801221] [PMID: 30398017]
[36]
Sumer Bolu B, Golba B, Sanyal A, Sanyal R. Trastuzumab targeted micellar delivery of docetaxel using dendron-polymer conjugates. Biomater Sci 2020; 8(9): 2600-10.
[http://dx.doi.org/10.1039/C9BM01764J] [PMID: 32239010]
[37]
Agrawal RD, Tatode AA, Rarokar NR, Umekar MJ. Polymeric micelle as a nanocarrier for delivery of therapeutic agents: A comprehensive review. Drug Deliv Ther 2020; 10(1-s): 191-5.
[http://dx.doi.org/10.22270/jddt.v10i1-s.3850]
[38]
Kim BY, Bae JW, Park KD. Enzymatically in situ shell cross-linked micelles composed of 4-arm PPO-PEO and heparin for controlled dual drug delivery. J Control Release 2013; 172(2): 535-40.
[http://dx.doi.org/10.1016/j.jconrel.2013.05.003] [PMID: 23680287]
[39]
Xu G, Zhu C, Li B, et al. Improving the anti-ovarian cancer activity of docetaxel by self-assemble micelles and thermosensitive hydrogel drug delivery system. J Biomed Nanotechnol 2020; 16(1): 40-53.
[http://dx.doi.org/10.1166/jbn.2020.2867] [PMID: 31996284]
[40]
Lu X, Fang M, Yang Y, et al. PEG-conjugated triacontanol micelles as docetaxel delivery systems for enhanced anti-cancer efficacy. Drug Deliv Transl Res 2020; 10(1): 122-35.
[http://dx.doi.org/10.1007/s13346-019-00667-6] [PMID: 31444736]
[41]
Oh I-h, Cho KJ, Tran TH, Huh KM, Lee Y-k. Biofuntional nanoparticle formation and folate-targeted antitumor effect of heparin-retinoic acid conjugates. Macromol Res 2012; 20(5): 520-7.
[http://dx.doi.org/10.1007/s13233-012-0073-7]
[42]
Jingwei S, Ting C, Tao L, Yiling S. PH-responsive, folic acid-targeting and ursolic acid-supporting silica-chitosan-folic acid nano material and application. CN105853365, 2016.
[43]
Krystofiak ES, Matson VZ, Steeber DA, Oliver JA. Elimination of tumor cells using folate receptor targeting by antibody-conjugated, gold-coated magnetite nanoparticles in a murine breast cancer model. J Nanomater 2012; 2012: 9.
[http://dx.doi.org/10.1155/2012/431012]
[44]
Yili D, Ziyuan L, Bingyun W. The beta-cyclodextrin and its synthetic method of double modified with folic acid and application. CN108047355, 2018.
[45]
Ando M, Goto K. Therapeutic method and medicament for cancer patients by folr1-targeting drug and an antagonist for folic acid metabolism. US20170247449, 2017.
[46]
Fasehee H, Dinarvand R, Ghavamzadeh A, et al. Delivery of disulfiram into breast cancer cells using folate-receptor-targeted PLGA-PEG nanoparticles: In vitro and in vivo investigations. J Nanobiotechnology 2016; 14(1): 32.
[http://dx.doi.org/10.1186/s12951-016-0183-z] [PMID: 27102110]
[47]
Liu J, Chong C, Sullivan DJ. Angiogenesis inhibitors. US9642865, 2017.
[48]
Hwang SR, Seo DH, Al-Hilal TA, et al. Orally active desulfated low molecular weight heparin and deoxycholic acid conjugate, 6ODS-LHbD, suppresses neovascularization and bone destruction in arthritis. J Control Release 2012; 163(3): 374-84.
[http://dx.doi.org/10.1016/j.jconrel.2012.09.013] [PMID: 23041275]
[49]
Li L, Huh KM, Lee Y-K, Kim SY. Design of a multifunctional heparin-based nanoparticle system for anticancer drug delivery. Macromol Res 2010; 18(2): 153-61.
[http://dx.doi.org/10.1007/s13233-009-0134-8]
[50]
Jin-ki H, Han E. Heparin-based nanoparticle and complex for delivering growth factor comprising thereof. KR102016116, 2017.
[51]
Smorenburg SM, Van Noorden CJ. The complex effects of heparins on cancer progression and metastasis in experimental studies. Pharmacol Rev 2001; 53(1): 93-105.
[52]
Jinghua C, Zhi C, Yunshu Y. Heparin disaccharides is grafted the purposes of sulphation polymethyl acyl ethanol amine. CN108403704, 2018.
[53]
Ritchie JP, Ramani VC, Ren Y, et al. SST0001, a chemically modified heparin, inhibits myeloma growth and angiogenesis via disruption of the heparanase/syndecan-1 axis. Clin Cancer Res 2011; 17(6): 1382-93.
[http://dx.doi.org/10.1158/1078-0432.CCR-10-2476] [PMID: 21257720]
[54]
Du H, Liu M, Yu A, Ji J, Zhai G. Insight into the role of dual-ligand modification in low molecular weight heparin based nanocarrier for targeted delivery of doxorubicin. Int J Pharm 2017; 523(1): 427-38.
[http://dx.doi.org/10.1016/j.ijpharm.2017.03.065] [PMID: 28359815]
[55]
Hou L, Fan Y, Yao J, et al. Low molecular weight heparin-all-trans-retinoid acid conjugate as a drug carrier for combination cancer chemotherapy of paclitaxel and all-trans-retinoid acid. Carbohydr Polym 2011; 86(3): 1157-66.
[http://dx.doi.org/10.1016/j.carbpol.2011.06.008]
[56]
Park K, Kim K, Kwon IC, et al. Preparation and characterization of self-assembled nanoparticles of heparin-deoxycholic acid conjugates. Langmuir 2004; 20(26): 11726-31.
[http://dx.doi.org/10.1021/la048646i] [PMID: 15595804]
[57]
Park K, Lee GY, Park R-W, Kim I-S, Kim SY, Byun Y. Combination therapy of heparin-deoxycholic acid conjugate and doxorubicin against squamous cell carcinoma and B16F10 melanoma. Pharm Res 2008; 25(2): 268-76.
[http://dx.doi.org/10.1007/s11095-007-9366-5] [PMID: 17619999]
[58]
Park K, Lee GY, Kim Y-S, et al. Heparin-deoxycholic acid chemical conjugate as an anticancer drug carrier and its antitumor activity. J Control Release 2006; 114(3): 300-6.
[http://dx.doi.org/10.1016/j.jconrel.2006.05.017] [PMID: 16884806]
[59]
Hou L, Yao J, Zhou J, Zhang Q. Pharmacokinetics of a paclitaxel-loaded low molecular weight heparin-all-trans-retinoid acid conjugate ternary nanoparticulate drug delivery system. Biomaterials 2012; 33(21): 5431-40.
[http://dx.doi.org/10.1016/j.biomaterials.2012.03.070] [PMID: 22521488]
[60]
Park K, Kim Y-S, Lee GY, et al. Tumor endothelial cell targeted cyclic RGD-modified heparin derivative: Inhibition of angiogenesis and tumor growth. Pharm Res 2008; 25(12): 2786-98.
[http://dx.doi.org/10.1007/s11095-008-9643-y] [PMID: 18581207]
[61]
Wang X, Li J, Wang Y, et al. HFT-T, a targeting nanoparticle, enhances specific delivery of paclitaxel to folate receptor-positive tumors. ACS Nano 2009; 3(10): 3165-74.
[http://dx.doi.org/10.1021/nn900649v] [PMID: 19761191]
[62]
Wu W, Yao W, Wang X, Xie C, Zhang J, Jiang X. Bioreducible heparin-based nanogel drug delivery system. Biomaterials 2015; 39: 260-8.
[http://dx.doi.org/10.1016/j.biomaterials.2014.11.005] [PMID: 25468376]
[63]
Bae KH, Mok H, Park TG. Synthesis, characterization, and intracellular delivery of reducible heparin nanogels for apoptotic cell death. Biomaterials 2008; 29(23): 3376-83.
[http://dx.doi.org/10.1016/j.biomaterials.2008.04.035] [PMID: 18474396]
[64]
Kazemi M, Emami J, Hasanzadeh F, Minaiyan M, Mirian M, Lavasanifar A. Pegylated multifunctional pH-responsive targeted polymeric micelles for ovarian cancer therapy: Synthesis, characterization and pharmacokinetic study. Int J Polym Mate 2020; pp. 1-15.
[65]
Emami J, Kazemi M, Hasanzadeh F, Minaiyan M, Mirian M, Lavasanifar A. Novel pH-triggered biocompatible polymeric micelles based on heparin-α-tocopherol conjugate for intracellular delivery of docetaxel in breast cancer. Pharm Dev Technol 2020; 25(4): 492-509.
[http://dx.doi.org/10.1080/10837450.2019.1711395] [PMID: 31903817]
[66]
Yan X, Yang Y, He L, Peng D, Yin D. Gambogic acid grafted low molecular weight heparin micelles for targeted treatment in a hepatocellular carcinoma model with an enhanced anti-angiogenesis effect. Int J Pharm 2017; 522(1-2): 110-8.
[http://dx.doi.org/10.1016/j.ijpharm.2017.02.051] [PMID: 28242375]
[67]
Emami J, Rezazadeh M, Rostami M, et al. Co-delivery of paclitaxel and α-tocopherol succinate by novel chitosan-based polymeric micelles for improving micellar stability and efficacious combination therapy. Drug Dev Ind Pharm 2015; 41(7): 1137-47.
[http://dx.doi.org/10.3109/03639045.2014.935390] [PMID: 25019502]
[68]
Emami J, Rezazadeh M, Hasanzadeh F, et al. Development and in vitro/in vivo evaluation of a novel targeted polymeric micelle for delivery of paclitaxel. Int J Biol Macromol 2015; 80: 29-40.
[http://dx.doi.org/10.1016/j.ijbiomac.2015.05.062] [PMID: 26093319]
[69]
Emami J, Rezazadeh M, Sadeghi H, Khadivar K. Development and optimization of transferrin-conjugated nanostructured lipid carriers for brain delivery of paclitaxel using Box-Behnken design. Pharm Dev Technol 2017; 22(3): 370-82.
[http://dx.doi.org/10.1080/10837450.2016.1189933] [PMID: 27689412]
[70]
Rezazadeh M, Emami J, Hasanzadeh F, et al. In vivo pharmacokinetics, biodistribution and anti-tumor effect of paclitaxel-loaded targeted chitosan-based polymeric micelle. Drug Deliv 2016; 23(5): 1707-17.
[http://dx.doi.org/10.3109/10717544.2014.954281] [PMID: 25188785]
[71]
Enteshari S, Varshosaz J, Minayian M, Hassanzadeh F. Antitumor activity of raloxifene-targeted poly(styrene maleic acid)-poly (amide-ether-ester-imide) co-polymeric nanomicelles loaded with docetaxel in breast cancer-bearing mice. Inves new drugs 2018; 36(2): 206-16.
[72]
Silkevin, adam C, Thomas B, Tomas V, Joseph ES. Block copolymers for stable micelles. JP2015214584, 2016.
[73]
Li L, Huh KM, Lee Y-K, Kim SY. Biofunctional self-assembled nanoparticles of folate-PEG–heparin/PBLA copolymers for targeted delivery of doxorubicin. J Mater Chem 2011; 21(39): 15288-97.
[http://dx.doi.org/10.1039/c1jm11944c]
[74]
Lu J, Zhao W, Huang Y, et al. Targeted delivery of Doxorubicin by folic acid-decorated dual functional nanocarrier. Mol Pharm 2014; 11(11): 4164-78.
[http://dx.doi.org/10.1021/mp500389v] [PMID: 25265550]
[75]
Liu J, Huang Y, Kumar A, et al. pH-sensitive nano-systems for drug delivery in cancer therapy. Biotechnol Adv 2014; 32(4): 693-710.
[http://dx.doi.org/10.1016/j.biotechadv.2013.11.009] [PMID: 24309541]
[76]
Reshetnyak YK, Andreev OA, Engelman DM. Environmentally sensitive compositions and methods of use thereof. US20180221500, 2018.
[77]
Messersmith PB, He L, Fullenkamp DE. pH responsive self-healing hydrogels formed by boronate-catechol complexation. US20170129999, 2017.
[78]
Chiu H-C, Chiang W-H, Hung C-C, Yu T-W. Preparation of pH-responsive nanoparticles and promoted delivery of anticancer drugs into deep tumor tissues and application thereof. US9980919, 2018.
[79]
Lang T, Dong X, Zheng Z, et al. Tumor microenvironment-responsive docetaxel-loaded micelle combats metastatic breast cancer. Sci Bull (Beijing) 2019; 64(2): 91-100.
[http://dx.doi.org/10.1016/j.scib.2018.12.025]
[80]
Liu Y, Wang W, Yang J, Zhou C, Sun J. pH-sensitive polymeric micelles triggered drug release for extracellular and intracellular drug targeting delivery. Asian J Pharm 2013; 8(3): 159-67.
[http://dx.doi.org/10.1016/j.ajps.2013.07.021]
[81]
Felber AE, Dufresne M-H, Leroux J-C. pH-sensitive vesicles, polymeric micelles, and nanospheres prepared with polycarboxylates. Adv Drug Deliv Rev 2012; 64(11): 979-92.
[http://dx.doi.org/10.1016/j.addr.2011.09.006] [PMID: 21996056]
[82]
Tran TH, Ramasamy T, Choi JY, et al. Tumor-targeting, pH-sensitive nanoparticles for docetaxel delivery to drug-resistant cancer cells. Int J Nanomedicine 2015; 10: 5249-62.
[http://dx.doi.org/10.2147/ijn.s89584] [PMID: 26346426]
[83]
Kanamala M, Wilson WR, Yang M, Palmer BD, Wu Z. Mechanisms and biomaterials in pH-responsive tumour targeted drug delivery: A review. Biomaterials 2016; 85: 152-67.
[http://dx.doi.org/10.1016/j.biomaterials.2016.01.061] [PMID: 26871891]
[84]
Javid A, Ahmadian S, Saboury AA, Kalantar SM, Rezaei-Zarchi S. Novel biodegradable heparin-coated nanocomposite system for targeted drug delivery. RSC Advances 2014; 4(26): 13719-28.
[http://dx.doi.org/10.1039/C3RA43967D]
[85]
Li N-N, Zheng B-N, Lin J-T, Zhang L-M. New heparin-indomethacin conjugate with an ester linkage: Synthesis, self aggregation and drug delivery behavior. Mater Sci Eng C 2014; 34: 229-35.
[http://dx.doi.org/10.1016/j.msec.2013.09.024] [PMID: 24268254]
[86]
Tran TH, Bae BC, Lee YK, Na K, Huh KM. Heparin-folate-retinoic acid bioconjugates for targeted delivery of hydrophobic photosensitizers. Carbohydr Polym 2013; 92(2): 1615-24.
[http://dx.doi.org/10.1016/j.carbpol.2012.10.075] [PMID: 23399198]
[87]
Jung MJ, Lee SS, Hwang YH, et al. MRI of transplanted surface-labeled pancreatic islets with heparinized superparamagnetic iron oxide nanoparticles. Biomaterials 2011; 32(35): 9391-400.
[http://dx.doi.org/10.1016/j.biomaterials.2011.08.070] [PMID: 21903255]
[88]
Arbab AS, Yocum GT, Kalish H, et al. Efficient magnetic cell labeling with protamine sulfate complexed to ferumoxides for cellular MRI. Blood 2004; 104(4): 1217-23.
[http://dx.doi.org/10.1182/blood-2004-02-0655] [PMID: 15100158]
[89]
Guangxi Z, Mengrui L. The chondroitin sulfate of modified with folic acid-deoxycholic acid polymer and its synthetic method and application. CN105380902, 2018.
[90]
Sajjad M, Khan MI, Naveed S, et al. Folate-functionalized thiomeric nanoparticles for enhanced docetaxel cytotoxicity and improved oral bioavailability. AAPS PharmSciTech 2019; 20(2): 81.
[http://dx.doi.org/10.1208/s12249-019-1297-z] [PMID: 30645705]
[91]
Poltavets YI, Zhirnik AS, Zavarzina VV, et al. In vitro anticancer activity of folate-modified docetaxel-loaded PLGA nanoparticles against drug-sensitive and multidrug-resistant cancer cells. Cancer Nanotechnol 2019; 10(1): 2.
[http://dx.doi.org/10.1186/s12645-019-0048-x]
[92]
Alam F, Al-Hilal TA, Chung SW, et al. Functionalized heparin-protamine based self-assembled nanocomplex for efficient anti-angiogenic therapy. J Control Release 2015; 197: 180-9.
[http://dx.doi.org/10.1016/j.jconrel.2014.11.009] [PMID: 25445701]
[93]
Hong G, Yuan R, Liang B, Shen J, Yang X, Shuai X. Folate-functionalized polymeric micelle as hepatic carcinoma-targeted, MRI-ultrasensitive delivery system of antitumor drugs. Biomed Microdevices 2008; 10(5): 693-700.
[http://dx.doi.org/10.1007/s10544-008-9180-9] [PMID: 18350380]
[94]
Tong SW, Xiang B, Dong DW, Qi XR. Enhanced antitumor efficacy and decreased toxicity by self-associated docetaxel in phospholipid-based micelles. Int J Pharm 2012; 434(1-2): 413-9.
[http://dx.doi.org/10.1016/j.ijpharm.2012.06.014] [PMID: 22698861]
[95]
Varshosaz J, Hasanzadeh F, Hashemi-Beni B, Minaiyan M, Enteshari S. Tissue distribution and systemic toxicity evaluation of raloxifene targeted polymeric micelles of poly (styrene-maleic acid)-poly (amide-ether-ester-imide)-poly (ethylene glycol) loaded with docetaxel in breast cancer bearing mice. Recent Patents Anticancer Drug Discov 2019; 14: 280-91.
[96]
Lu RM, Chang YL, Chen MS, Wu HC. Single chain anti-c-Met antibody conjugated nanoparticles for in vivo tumor-targeted imaging and drug delivery. Biomaterials 2011; 32(12): 3265-74.
[http://dx.doi.org/10.1016/j.biomaterials.2010.12.061] [PMID: 21306768]
[97]
Chung SW, Lee M, Bae SM, et al. Potentiation of anti-angiogenic activity of heparin by blocking the ATIII-interacting pentasaccharide unit and increasing net anionic charge. Biomaterials 2012; 33(35): 9070-9.
[http://dx.doi.org/10.1016/j.biomaterials.2012.09.002] [PMID: 23010574]
[98]
Carmeliet P, Jain RK. Angiogenesis in cancer and other diseases. Nature 2000; 407(6801): 249-57.
[http://dx.doi.org/10.1038/35025220] [PMID: 11001068]
[99]
Hasan J, Shnyder SD, Clamp AR, et al. Heparin octasaccharides inhibit angiogenesis in vivo. Clin Cancer Res 2005; 11(22): 8172-9.
[http://dx.doi.org/10.1158/1078-0432.CCR-05-0452] [PMID: 16299249]
[100]
Shen X, Fang J, Lv X, et al. Heparin impairs angiogenesis through inhibition of microRNA-10b. J Biol Chem 2011; 286(30): 26616-27.
[http://dx.doi.org/10.1074/jbc.M111.224212] [PMID: 21642433]
[101]
Norrby K. Low-molecular-weight heparins and angiogenesis. APMIS 2006; 114(2): 79-102.
[http://dx.doi.org/10.1111/j.1600-0463.2006.apm_235.x] [PMID: 16519745]

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