Abstract
A series of pH-responsive and dual-modality imaging polyurethane micelles as potential dual-modality optical imaging probes were developed by introducing superparamagnetic iron oxide nanoparticles (Fe3O4) for MRI imaging and fluorescent dye fluorescein isothiocyanate (FITC) for optical imaging. 1,4-bis (hydroxyethyl) piperazine, which has amino groups with isolated electron pairs, was employed as a pH-responsive segment to offer pH-responsive capacity. The pH-responsive polymeric micelle can self-assemble into a core-shell structure at physiological pH, consequently, the Fe3O4 nanoparticles can be well encapsulated into hydrophobic core via the hydrophobic interaction. The morphology of Fe3O4 coated by polyurethane nanoparticles were observed by the Transmission Electron Microscopy (TEM) and the thermal stability was also performed by thermo gravimetric analysis (TGA). Subsequently, the optical property was measured by fluorescence spectrometry and ultraviolet visible spectroscopy. Moreover, the cytotoxicity evaluation was measured using an MTT assay and the result showed the low cytotoxicity of polyurethane micelle, making it a promising candidate as an intelligent vehicle as well as a dual-modality optical imaging probe.
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Kramer-Marek G, Gore J, Korc M (2013) Molecular imaging in pancreatic cancer - a roadmap for therapeutic decisions. Cancer Lett 341:132–138
Sajja HK, East MP, Mao H, Wang AY, Nie SM, Yang L (2009) Development of multifunctional nanoparticles for targeted drug delivery and non-invasive imaging of therapeutic effect. Curr Drug Discov Technol 6:43–51
Grabowski CA, Mukhopadhyay A (2008) Diffusion of polystyrene chains and fluorescent dye molecules in semidilute and concentrated polymer solutions. Macromolecules 41:6191–6194
Du W, Tao HY, Zhao SH, He ZX, Li ZJ (2015) Translational applications of molecular imaging in cardiovascular disease and stem cell therapy. Biochimie 116:43–51
Leng L, Wang YB, He NN, Wang D, Zhao QJ (2014) Molecular imaging for assessment of mesenchymal stem cells mediated breast cancer therapy. Biomaterials 35:5162–5170
Krucker T, Sandanaraj BS (2011) Optical imaging for the new grammar of drug discovery. Phil Trans R Soc A 369:4651–4665
Jane-Wit D, Sadeghi MM (2015) Molecular imaging of vascular inflammation, atherosclerosis, and thrombosis. Molecular and Translational Medicine 1:129–166
Hilderbrand SA, Weissleder R (2010) Near-infrared fluorescence: application to in vivo molecular imaging. Curr Opin Chem Biol 14:71–79
Bauwens M, Mottaghy FM, Bucerius J (2015) PET imaging of the human nicotinic cholinergic pathway in atherosclerosis. Curr Cardiol Rep 17:67
Blodgett TM, Meltzer CC, Townsend DW (2007) PET/CT: form and function. Radiology 242:360–385
Gao JH, Gu HG, Xu B (2009) Multifunctional magnetic nanoparticles: design, synthesis, and biomedical applications. Acc Chem Res 42:1097–1107
Corr SR, Rakovich YP, Gun’ko YK (2008) Multifunctional magnetic-fluorescent Nanocomposites for biomedical application. Nanoscale Res Lett 3:87–104
Liao B, Wang W, Long P, He BQ, Lia FW, Liu QQ (2014) Synthesis of fluorescent carbon nanoparticles grafted with polystyrene and their fluorescent fibers processed by electrospinning. RSC Adv 4:57683–57690
Rutkaite R, Swanson L, Li Y, Aremes SP (2008) Fluorescence studies of pyrene-labelled, pH-responsive diblock copolymer micelles in aqueous solution. Polymer 49:1800–1811
Kikuchi K (2010) Design, synthesis and biological application of chemical probes for bio-imaging. Chemcal Socity Reviews 39:2048–2053
Xu HN, Zhou R, Nioka S, Chance B, Glickson JD, Li LZ (2009) Histological basis of Mr/optical imaging of human melanoma mouse Xenografts spanning a range of metastatic potentials. Adv Exp Med Biol 645:247–253
Planka F, Muellerb S, Uprimnyd C, Hanglerc H, Feuchtnera G (2012) Detection of bioprosthetic valve infection by image fusion of 18fluorodeoxyglucose-positron emission tomography and computed tomography. Interact Cardio Vasc Thorac Surg 14:364–366
Dweck MR, Jones C, Joshi NV, Fletcher AM, Richardson H, White A, Marsden M (2012) Assessment of Valvular calcification and inflammation by positron emission tomography in patients with aortic stenosis. Circulation 125:76–86
Xing HY, Bu WB, Zhang SJ, Zheng XP, Li M, Chen F, He QJ, Zhou LP, Peng WJ, Hua YQ, Shi JL (2012) Multifunctional nanoprobes for upconversion fluorescence, MR and CT trimodal imaging. Biomaterials 33:1079–1089
Lu XM, Jiang RC, Fan Q, Zhang L, Zhang HG, Yang MH, Ma YW, Wang LH, Huang W (2012) Fluorescent-magnetic poly(poly(ethyleneglycol) monomethacrylate)-grafted Fe3O4 nanoparticles from post-atom-transfer-radical-polymerization modification: synthesis, characterization, cellular uptake and imaging. J Mater Chem 22:6965–6973
Lee DE, Kim AY, Yoon HY, Choi KY, Kwon IC, Jeong SY, Park JH, Kim K (2012) Amphiphilic hyaluronic acid-based nanoparticles for tumor-specific optical/MR dual imaging. J Mater Chem 22:10444–10447
Abdalla MO, Karna P, Sajja HK, Mao H, Yates C, Turner T, Aneja R (2011) Enhanced noscapine delivery using uPAR-targeted optical-MR imaging trackable nanoparticles for prostate cancer therapy. J Control Release 149:314–322
Nam T, Park S, Lee SY, Park K, Choi K, Song IC, Han MH, Leary JJ, Yuk SA, Kwon IC, Kim K, Jeong SY (2010) Tumor targeting chitosan nanoparticles for dual-modality optical/MR cancer imaging. Bioconjug Chem 21:578–582
Wadajkar AS, Kadapure T, Zhang Y, Cui W, Nguyen KT, Yang J (2012) Dual-imaging enabled cancer-targeting nanoparticles. Healthcare Materials 1:450–456
Liu F, Urban MW (2010) Recent advances and challenges in designing stimuli-responsive polymers. Prog Polym Sci 35:3–23
Park IK, Singha K, Arote RB, Choi YJ (2010) pH-responsive polymers as Gene carriers. Macromol. Rapid Commun 31:1122–1133
Sun HL, Meng FH, Cheng R, Deng C, Zhong ZY (2014) Reduction and pH dual-bioresponsive crosslinked polymersomes for efficient intracellular delivery of proteins and potent induction of cancer cell apoptosis. Acta Biomater 10:2159–2168
Li YY, Cheng H, Zhu JL, Yuan L, Dai Y, Cheng SX, Zhang XZ, Zhuo RX (2009) Temperature- and ph-sensitive multicolored micellar complexes. Adv. Mater 21:2402–2406
Luo RC, Cao Y, Shi P, Chen CH. Near-Infrared Light Responsive Multi-Compartmental Hydrogel Particles Synthesized Through Droplets Assembly Induced by Superhydrophobic Surface. Small 10: 4886–4894
Shen Y, Zhan Y, Tang J, Xu P, Johnson PA, Radosz M (2008) Multifunctioning pH-responsive nanoparticles from hierarchical self-assembly of polymer brush for cancer drug delivery. AICHE J 54:2979–2989
Li W, Luo T, Yang YJ, Tan XN, Liu LF (2015) Formation of controllable hydrophilic/hydrophobic drug delivery systems by electrospinning of vesicles. Langmuir 31:5141–5146
Li MH, Keller P (2009) Stimuli-responsive polymer vesicles. Soft Matter 5:927–937
Smith AS, Seifert U (2007) Vesicles as a model for controlled (de-) adhesion of cells: a thermodynamic approach. Soft Matter 3:275–289
Li J, Huo MR, Wang J, Zhou JP, Mohammad JM, Zhang YL, Zhu QN, Waddad AY , Zhang Q (2012) Redox-sensitive micelles self-assembled from amphiphilic hyaluronic aciddeoxycholic acid conjugates for targeted intracellular delivery of paclitaxel. Biomaterials 33: 2310–2320
Torchilin VP (2005) Recent advances with liposomes as pharmaceutical carriers. Nat Rev Drug Discov 4:145–160
Yan L, Crayton SH, Thawani JP, Amirshaghaghi A, Tsourkas A, Cheng Z (2015) A pH-responsive drug-delivery platform based on glycol chitosan-coated liposomes. Small 11:4870–4874
Freiberg S, Zhu X (2004) Polymer microspheres for controlled drug release. Int J Pharm 282:1–18
Xia YJ, Ribeiro PF, Pack DW (2013) Controlled protein release from monodisperse biodegradable double-wall microspheres of controllable shell thickness. J Control Release 172:704–714
Liang CZ, Li H, Tao YQ, Peng LH, Gao JQ, Wu JJ, Li FC, Hua JM, Chen QX (2013) Dual release of dexamethasone and TGF-beta 3 from polymeric microspheres for stem cell matrix accumulation in a rat disc degeneration model. Acta Biomater 9:9423–9433
Kazunori K, Glenn SK, Masayuki Y, Teruo O, Yasuhisa S (1993) Block copolymer micelles as vehicles for drug delivery. J Control Release 24:119–132
MacEwan SR, Callahan DJ, Chilkoti A (2010) Stimulus-responsive macromolecules and nanoparticles for cancer drug delivery. Nanomedicine 5:793–806
Muthu MS, Rajesh CV, Mishra A, Singh S (2009) Stimulus-responsive targeted nanomicelles for effective cancer therapy. Nanomedicine 4:657–667
Cayre OJ, Chagneux N, Biggs S (2011) Stimulus responsive core-shell nanoparticles: synthesis and applications of polymer based aqueous systems. Soft Matter 7:2211–2234
Wang G, Zhang PF, Dou HJ, Li WW, Sun K, He XT, Han JS, Xiao HS, Li Y (2012) Efficient incorporation of quantum dots into porous microspheres through a solvent-evaporation approach. Langmuir 28:6141–6150
Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55–63
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This research was supported by a grant from National Natural Science Foundation of China (NSFC) (Nos. 51473023 and 51103014).
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Xia, S., Yang, H., Duan, L. et al. A potential dual-modality optical imaging probe based on the pH-responsive micelle. J Polym Res 23, 179 (2016). https://doi.org/10.1007/s10965-016-1017-2
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DOI: https://doi.org/10.1007/s10965-016-1017-2