Title: Calcium phosphate-reinforced reduction-sensitive hyaluronic acid micelles for
|
|
- Anastasia Cain
- 5 years ago
- Views:
Transcription
1 Title: Calcium phosphate-reinforced reduction-sensitive hyaluronic acid micelles for delivering paclitaxel in cancer therapy Bing Deng a,1, Mengxin Xia a,1, Jin Qian a, Rui Li a, Lujia Li a,b, Jianliang Shen c, Guowen Li b, Yan Xie a,* a Research Center for Health and Nutrition, Shanghai University of Traditional Chinese Medicine, Shanghai 0, China b Pharmacy Department, Shanghai TCM-integrated Hospital, Shanghai University of Traditional Chinese Medicine, Shanghai 000, China c Department of Nanomedicine, Houston Methodist Research Institute, Houston 00, USA These authors contributed equally to this work. * Corresponding author: Yan Xie, Ph.D. Professor Research Center for Health and Nutrition Shanghai University of Traditional Chinese Medicine 0 Cailun Road Shanghai, China 0 rosexie_1@hotmail.com; yxie@shutcm.edu.cn Phone: +(1) Fax: +(1) 1
2 Materials Hyaluronic acid (HA, Mw = kda) was purchased from Bloomage Freda Biopharm Co., Ltd. (Shandong, China). 1-Ethyl- (-dimethylaminopropyl) carbodiimide (EDC), N- Hydroxysuccinimide (NHS), N-hydroxysulfosuccinimide (Sulfo-NHS), deoxycholic acid (DOCA), dicyclohexylcarbodiimide (DCC), and glutathione (GSH) were purchased from Aladdin Reagent Inc. (Shanghai, China). Cystamine was purchased from TCI Development Co., Ltd. (Shanghai, China). Pyrene was purchased from Sigma-Aldrich (Shanghai, China).,-Diamidino--phenylindole (DAPI) was purchased from Dojindo Molecular Technologies, Inc. (Kumamoto, Japan). Dulbecco s Modified Eagle s Medium (DMEM) and Minimum Essential Medium (MEM) were purchased from Thermo-Fisher Biochemical Product (Waltham, MA, USA). Fetal bovine serum (FBS) was obtained from Gibco Laboratory (Grand Island, NY, USA). Monoclonal rabbit anti-cd antibody (Alexa Fluor ) was perchased from Abcam (Cambridge, United Kingdom). The human breast cancer (MDA-MB- 1) cell line and human hepatoma (HepG) cell line were purchased from Institute of Biochemistry and Cell Biology, SIBS, CAS (Shanghai, China). All other chemicals were of analytical grade.. Synthesis of HA-SS-DOCA conjugates.1. Synthesis of cystamine modified HA (HA-CYS) The synthesis of cystamine modified HA (HA-CYS) was carried out as previously described with some modifications. 1 First, 0.0 mm (moles of the carboxyl group) of HA was dissolved in 0 ml PBS solution (0.01 M, ph.). EDC (.0 mm) and sulfo-nhs (0.0 mm) were added to the HA solution and stirred for 0 min to activate the carboxylic group of HA. Then,.0 mm of cystamine was added and the reaction was allowed to proceed under stirring for h at room temperature. The resulting solution was dialyzed (MWCO 00) exhaustively against 0.1 M NaCl and then distilled water to remove the unreacted CYS, EDC, and sulfo- NHS coupling agents. Finally, the solution was freeze-dried to obtain HA-CYS powder and
3 stored in a desiccator until further use... Synthesis of NHS ester of deoxycholic acid (DOCA-NHSE) The carboxylic group of deoxycholic acid was activated as reported previously., Briefly, DOCA ( mm) was mixed with DCC (1 mm) and NHS (1 mm) in 0 ml of tetrahydrofuran (THF). The mixture was reacted for h at room temperature, and then the precipitated dicyclohexylurea was removed by filtration. The filtrate was poured into cold n- hexane and the DOCA-NHSE precipitate was filtered off and washed thoroughly with cold n- hexane, followed by vacuum drying at room temperature. The DOCA-NHSE was stored at - 0 C before use... Synthesis and characterization of amphiphilic HA-SS-DOCA conjugates The amphiphilic HA-SS-DOCA conjugates were prepared by chemical grafting DOCA- NHSE to HA-CYS through amide formation as previously reported. 1, In brief, HA-CYS (0. mm) was dissolved in ml formamide, and DOCA-NHSE (0.0 mm) dissolved in ml N, N-dimethylformamide (DMF) were added drop wise to the solution. The reaction was performed for h at room temperature with gentle stir. The resulting solution was dialyzed against the excess amount of water/ethanol (1:1, v/v) for 1 day and distilled water for days. After being freeze dried, the final products were obtained as a white flocculence powder and stored at C until further use. 1 H NMR spectra of HA-SS-DOCA conjugates were acquired on a Bruker-00 1 H NMR spectrometer. HA-CYS, DOCA-NHSE, and HA-SS-DOCA conjugates were dissolved in D O, DMSO-d, and D O/CD OD (1:1, v/v), respectively. The DS (defined as the number of DOCA per 0 sugar residues of HA) values for HA-SS-DOCA, was obtained from the ratio of integration between the characteristic peaks of the 1 st methyl group in DOCA (0. ppm, [H]) and the N-acetyl group in HA (.01 ppm, [H]). FT-IR was taken on a Nicolet is spectrophotometer (Thermo-Fisher Scientific Inc., Waltham, MA, USA) over the region from 000 to 00 cm -1. The critical micelle concentration (CMC) of amphiphilic HA-SS-DOCA
4 conjugates was evaluated by fluorescence spectroscopy using pyrene as the probe.. Preparation and characterization of micelles.1. Preparation of HA-SS-DOCA micelles The HA-SS-DOCA micelles were prepared by sonication. Briefly, mg of HA-SS-DOCA conjugates were dissolved in ml of distilled water followed by sonicating at 0 W for min in an ice bath by a probe-type ultrasonicator (JY-D, Ningbo Scentz Biotechnology Co., Ltd., Ningbo, China). The resulting micellar solution was filtrated through a 0. μm pore-sized membrane... Reduction triggered destabilization of HA-SS-DOCA micelle The disassembly of HA-SS-DOCA micelles in response to GSH was monitored by Dynamic light scattering (DLS) measurement (Malvern Instruments Ltd., Worcestershire, UK). Briefly, 0 mm GSH was added in the solution of HA-SS-DOCA micelles, and HA-SS-DOCA micelles without addition of GSH were used as a control. To record the disassembly of micelles, the size distribution was monitored at different time points by the above measurement.. CD expression analysis CD expression levels were determined by immunocytostaining. 0. MDA-MB-1 cells and HepG cells were seperately seeded in glass bottom culture dishes and cultured in DMEM and MEM respectively with % FBS overnight. Then cells were washed with cold phosphate buffer saline (PBS) for three times, and fixed with % formaldehyde ( min) away from light. After washed off with PBS, cells were treated with 1% Triton-0 for min and washed with PBS again for three times. After that, cells were incubated with anti-cd antibody ( μg/ml) overnight, washed off with PBS and stained by DAPI ( μm, min). Next, all reagents were removed and cells were examined under an inverted confocal laser scanning microscope (CLSM, Leica, Wetzler, Germany).. Results and discussion
5 Synthesis of HA-SS-DOCA conjugates In the present study, amphiphilic reduction-sensitive HA-SS-DOCA conjugates were successfully synthesized as previously reported with some modification. 1 In this case, the hydrophobic DOCA groups were conjugated to an HA backbone using cystamine containing a disulfide bond as the reduction-sensitive connecting bridge. The chemical structures of HA-SS-DOCA conjugates were confirmed by 1 H NMR and FT- IR spectra. As shown in Fig. S1A, the structure of HA-CYS (b) was confirmed by the characteristic peaks at.0 ppm of HA and the cystamine was found at the range of.-. ppm. The presence of DOCA moieties in the HA-SS-DOCA conjugates (c) was evaluated by the characteristic peaks appearing at 0.-. ppm. As expected, the characteristic peaks ( cm -1 and cm -1 ) of DOCA that corresponds to C-H vibrations were also appeared in the FT-IR spectra of HA-SS-DOCA (Fig. S1B (c)), indicating that DOCA was introduced to HA. Meanwhile, the appearance of peaks at 1 cm -1 (amide I band), 1 cm -1 (amide Ⅱ band), and 1 cm -1 (C=O) in the IR spectrum of HA-SS-DOCA confirms the formation of an amide linkage between amino groups of CYS and carboxyl groups of HA as well as DOCA. These results indicated that the HA-SS-DOCA conjugates had been successfully synthesized. The critical micelle concentration (CMC) is a principal parameter used to evaluate the 1 stability of the aggregates in the blood circulation system post administration. 1 The fluorescence intensity ratio (I/I) was plotted according to the concentrations of HA- SS-DOCA conjugates (Fig. S), and the CMC value of HA-SS-DOCA conjugates was mg/ml. Such a low CMC value suggested that the HA-SS-DOCA conjugates could easily form self-assembled micelles, and guarantee the micelles to retain their original morphology under highly diluted conditions before reaching the targeting site... Characterization of HA-SS-DOCA micelles Reduction-sensitive HA-SS-DOCA micelles could be easily self-assembled in aqueous condition owing to the amphiphilic property of HA-SS-DOCA conjugates. DLS measurement
6 (Table S1) confirmed that the micelles possessed narrow size distribution with a broad range particle size from. to 1. nm. Interestingly, the micelles particle size decreased as the DS of DOCA increased, which was likely due to the increasing hydrophobic interaction between DOCA groups offered a tight micellar inner core. 1, The zeta potential of the micelles in distilled water is negative owing to the carboxylic group of HA, from -. to -. mv, which provided a repelling force between the particles and increased the stability of the micelles. The TEM image of HA-SS-DOCA micelles (Fig. SA) showed that the micelles were almost spherical in shape. Nevertheless, the size obtained from TEM was smaller than that from DLS, which was likely ascribed to that the samples for TEM undergo a shrinkage caused by water evaporation under air drying. To investigate the disassembly of HA-SS-DOCA micelles and evaluate the reduction responsive behaviors in response to GSH, the change of size distribution of HA-SS-DOCA micelles in 0 mm and 0 mm GSH, was monitored for h using DLS measurement. As shown in Fig. SB and SC, the particle size of HA-SS-DOCA micelles showed negligible size variation incubated with 0 mm GSH for h. On the contrary, aggregation of micelles was observed when incubated with 0 mm GSH, i.e., the diameter of HA-SS-DOCA micelles increased from. nm to 0. nm within h, indicating the rapid disassembly of micelles under reducing environment. The particle size change in 0 mm GSH confirmed that the HA-SS-DOCA micelles are sensitive to reducing condition... CD expression As shown in Fig. S, obvious green fluorescence of anti-cd antibody was observed in MDA-MB-1 cells, while this fluorescence was hardly observed in HepG cells, indicating that CD was high-expressed on MDA-MB-1 cells but was low-expressed on HepG cells. Considering hyaluronic acid can specifically bind with CD receptor, MDA-MB-1 cell was used as CD high expressive cell line and HepG cell as CD low expressive cell line (negative control) to investigate the targeted delivery of mineralized micelles in the following
7 study. References (1) Li, J.; Huo, M.; Wang, J.; Zhou, J.; Mohammad, J. M.; Zhang, Y.; Zhu, Q.; Waddad, A. Y.; Zhang, Q. Redox-sensitive micelles self-assembled from amphiphilic hyaluronic acid-deoxycholic acid conjugates for targeted intracellular delivery of paclitaxel. Biomaterials 01,, -0. () Hamidi, M.; Azadi, A.; Rafiei, P. Hydrogel nanoparticles in drug delivery. Adv. Drug Deliv. Rev. 00, 0, 1-1. () Kim, S. K.; Kim, K.; Lee, S.; Park, K.; Park, J. H.; Kwon, I. C.; Choi, K.; Kim, C.-Y.; Byun, Y. Evaluation of absorption of heparin-doca conjugates on the intestinal wall using a surface plasmon resonance. J. Pharm. Biomed. Anal. 00,, 1-0. () Han, S.-Y.; Han, H. S.; Lee, S. C.; Kang, Y. M.; Kim, I.-S.; Park, J. H. Mineralized hyaluronic acid nanoparticles as a robust drug carrier. J. Mater. Chem. 0, 1, () Yu, C.; Gao, C.; Lü, S.; Chen, C.; Huang, Y.; Liu, M. Redox-responsive shell-sheddable micelles selfassembled from amphiphilic chondroitin sulfate-cholesterol conjugates for triggered intracellular drug release. Chem. Eng. J. 01,, 0-. () Huang, J. B.; Zhang, H.; Yu, Y.; Chen, Y.; Wang, D.; Zhang, G. Q.; Zhou, G. C.; Liu, J. J.; Sun, Z. G.; Sun, D. X.; Lu, Y.; Zhong, Y. Q. Biodegradable self-assembled nanoparticles of poly (D,L-lactide-coglycolide)/hyaluronic acid block copolymers for target delivery of docetaxel to breast cancer. Biomaterials 01,, 0-. 0
8 Supplementary Figure Captions Fig. S1. (A) 1 H NMR spectra of HA (a), HA-CYS conjugate (b), and HA-SS-DOCA conjugate (c). (B) FT-IR spectrum of HA (a), DOCA (b), and HA-SS-DOCA (c). Fig. S. CMC determination of HA-SS-DOCA conjugates. Fluorescence intensity ratio (I/I) versus HA-SS-DOCA concentration was plotted and CMC was estimated from the threshold concentration of self-assembled micelles. Fig. S. (A) TEM images of blank HA-SS-DOCA micelles. (B) Time dependent changes of the mean diameter of HA-SS-DOCA micelles with or without GSH addition. (C) Size distribution of HA-SS-DOCA micelles after incubated with 0 mm (a) or 0 mm (b) GSH for h, respectively. Fig. S. Release behavior of PTX from HA-SS-DOCA micelles in PBS with 0 mm or 0 mm GSH. Data expressed as the mean ± SD (n = ). Fig. S. CLSM images of (A) MDA-MB-1 cells and (B) HepG cells after incubation of anti-cd antibody overnight. Images from left to right show the green fluorescence of anti- CD antibody, the blue fluorescence of DAPI, and the merged fluorescence of anti-cd antibody and DAPI. Fig. S. Confocal laser scanning microscopy (CLSM) images of MDA-MB-1 cancer cells after h incubation with (A) C, (B) C loaded micelles, and (C) C loaded mineralized micelles, respectively. Scale bars correspond to μm in all the images. Fig. S. Optical microscopy images of H&E staining major organs and tumor after treated with different PTX formulations and % glucose as control. Magnification: 0.
9 Table S1 Characteristics of HA-SS-DOCA conjugates (n = ). Samples a Feed ratio b DS a Size (nm) c PDI d Zeta (mv) HA-SS-DOCA ± ± ± 1. HA-SS-DOCA ± ± ± 0.1 HA-SS-DOCA. 0.. ± ± ± 0. a Degree of substitution of deoxycholic acid. b Molar feed ratio of DOCA-NHSE to sugar residuals of HA polymer. c Mean diameters of micelles. d Polydispersity index of micelles size.
10 Fig. S1
11 Fig. S
12 Fig. S 1
13 Fig. S 1
14 Fig. S 1
15 Fig. S 1
16 Fig. S 1
Dual-Responsive Polymer Micelles for. Target-Cell-Specific Anticancer Drug Delivery
Dual-Responsive Polymer Micelles for Target-Cell-Specific Anticancer Drug Delivery Xing Guo, Chunli Shi, Guang Yang, Jie Wang, Zhenghong Cai, and Shaobing Zhou,, * Key Laboratory of Advanced Technologies
More informationSupporting information
S1 Supporting information Biodegradable Injectable Polymer Systems Exhibiting Temperature-Responsive Irreversible Sol-to-Gel Transition by Covalent Bond Formation Yasuyuki YOSHIDA 1,2, Keisuke KAWAHARA
More informationFabrication of Bio-based Polyelectrolyte Capsules and Their Application for Glucose-Triggered Insulin Delivery
Supporting Information for Fabrication of Bio-based Polyelectrolyte Capsules and Their Application for Glucose-Triggered Insulin Delivery Dongjian Shi a*, Maoshuang Ran a, Li Zhang a, He Huang a, Xiaojie
More informationCharacterization and Modification of Low Molecular Water-Soluble Chitosan for Pharmaceutical Application
Characterization and Modification of Low Molecular Water-Soluble Chitosan Bull. Korean Chem. Soc. 2003, Vol. 24, No. 9 1303 Characterization and Modification of Low Molecular Water-Soluble Chitosan for
More informationA ph-sensitive prodrug micelle self-assembled from multi-doxorubicin-tailed. PCFM Lab of Ministry of Education, School of Chemistry and Chemical
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 A ph-sensitive prodrug micelle self-assembled from multi-doxorubicin-tailed polyethylene glycol
More information# Supplementary Material (ESI) for Molecular BioSystems # This journal is The Royal Society of Chemistry 2005
Supporting Information Multifunctional Polymeric Micelles with Folate-Mediated Cancer Cell Targeting and ph-triggered Drug Releasing Properties for Active Intracellular Drug Delivery Younsoo Bae, Woo-Dong
More informationGeneral and Facile Surface Functionalization of Hydrophobic Nanocrystals with Poly(amino acid) for Cell Luminescence Imaging
General and Facile Surface Functionalization of Hydrophobic Nanocrystals with Poly(amino acid) for Cell Luminescence Imaging Sheng Huang, Min Bai, Leyu Wang* State Key Laboratory of Chemical Resource Engineering,
More informationCoordination-responsive Selenium-containing Polymer Micelles for. Supporting information
Electronic Supplementary Material (ESI) for Chemical Science Coordination-responsive Selenium-containing Polymer Micelles for Controlled Drug Release Wei Cao, a Yang Li, b Yu Yi, a Shaobo Ji, a Lingwu
More informationFluorescent Carbon Dots as Off-On Nanosensor for Ascorbic Acid
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Fluorescent Carbon Dots as Off-On Nanosensor for Ascorbic Acid Jun Gong, Xin Lu, Xueqin An*
More informationph and Reduction Dual Responsive Polyurethane Triblock Copolymers for Efficient Intracellular Drug Delivery
Supporting Information ph and Reduction Dual Responsive Polyurethane Triblock Copolymers for Efficient Intracellular Drug Delivery Shuangjiang Yu a, Chaoliang He* a, Jianxun Ding a,b, Yilong Cheng a,b,
More informationThiol-Activated gem-dithiols: A New Class of Controllable. Hydrogen Sulfide (H 2 S) Donors
Thiol-Activated gem-dithiols: A New Class of Controllable Hydrogen Sulfide (H 2 S) Donors Yu Zhao, Jianming Kang, Chung-Min Park, Powell E. Bagdon, Bo Peng, and Ming Xian * Department of Chemistry, Washington
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for Chemical Communications. This journal is The Royal Society of Chemistry 2018 Electronic Supplementary Information A ratiometric fluorescence probe for peroxynitrite
More informationSupporting Information
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2017 Supporting Information Cancer-mitochondria-targeted photodynamic therapy with supramolecular
More informationSupporting Information
Supporting Information A single design strategy for dual sensitive ph probe with a suitable range to map ph in living cells Kang-Kang Yu, Ji-Ting Hou, Kun Li, * Qian Yao, Jin Yang, Ming-Yu Wu, Yong-Mei
More informationA ph-dependent Charge Reversal Peptide for Cancer Targeting
Supporting Information A ph-dependent Charge Reversal Peptide for Cancer Targeting Naoko Wakabayashi 1, Yoshiaki Yano 1, Kenichi Kawano 1, and Katsumi Matsuzaki 1 1 Graduate School of Pharmaceutical Sciences,
More informationSupporting Information
Supporting Information ph- and Amylase-Responsive Carboxymethyl Starch/Poly(2-Isobutyl-acrylic acid) Hybrid Microgels as Effective Enteric Carriers for Oral Insulin Delivery Liang Liu, a,b Ying Zhang,
More informationSupplementary Information for
Supplementary Information for Acid-Resistant Mesoporous Metal Organic Framework Toward Oral Insulin Delivery: Protein Encapsulation, Protection & Release Yijing Chen, Peng Li, Justin A. Modica, Riki J.
More informationA Single fluorescent probe for Dual-imaging Viscosity and H 2 O 2 in Mitochondria with Different Fluorescence Signals in Living Cells
Supporting Information for A Single fluorescent probe for Dual-imaging Viscosity and H 2 O 2 in Mitochondria with Different Fluorescence Signals in Living Cells Mingguang Ren, Beibei Deng, Kai Zhou, Xiuqi
More informationSupporting Information. for. Advanced Functional Materials, adfm Wiley-VCH 2006
Supporting Information for Advanced Functional Materials, adfm.200500627 Wiley-VCH 2006 69451 Weinheim, Germany Supporting information for: Self-assembly of a Novel Micelle Structure from Graft and Diblock
More informationSupporting Information
Supporting Information The Effects of Spacer Length and Composition on Aptamer-Mediated Cell-Specific Targeting with Nanoscale PEGylated Liposomal Doxorubicin Hang Xing +, [a] Ji Li +, [a] Weidong Xu,
More informationBiodegradable Zwitterionic Nanogels with Long. Circulation for Antitumor Drug Delivery
Supporting Information Biodegradable Zwitterionic Nanogels with Long Circulation for Antitumor Drug Delivery Yongzhi Men, Shaojun Peng, Peng Yang, Qin Jiang, Yanhui Zhang, Bin Shen, Pin Dong, *, Zhiqing
More informationSupplementary Materials for
advances.sciencemag.org/cgi/content/full/2/12/e1601838/dc1 Supplementary Materials for General and programmable synthesis of hybrid liposome/metal nanoparticles Jin-Ho Lee, Yonghee Shin, Wooju Lee, Keumrai
More informationSupporting Information. Maximizing the Supported Bilayer Phenomenon: LCP Liposomes Comprised Exclusively
S-1 Supporting Information Maximizing the Supported Bilayer Phenomenon: LCP Liposomes Comprised Exclusively of PEGylated Phospholipids for Enhanced Systemic and Lymphatic Delivery Matthew T. Haynes and
More informationDevelopment of a near-infrared fluorescent probe for monitoring hydrazine in serum and living cells
Supporting Information for Development of a near-infrared fluorescent probe for monitoring hydrazine in serum and living cells Sasa Zhu, Weiying Lin,* Lin Yuan State Key Laboratory of Chemo/Biosensing
More informationSupporting Information
Supporting Information Polymer Micelles Stabilization-n-Demand through Reversible Photocrosslinking 1. Synthesis and Characterization of Diblock Copolymers Materials. Cu(I)Br, 2-Bromo-2-methylpropionyl
More informationL-Carnosine-Derived Fmoc-Tripeptides Forming ph- Sensitive and Proteolytically Stable Supramolecular
Supporting Information: L-Carnosine-Derived Fmoc-Tripeptides Forming ph- Sensitive and Proteolytically Stable Supramolecular Hydrogels Rita Das Mahapatra, a Joykrishna Dey* a, and Richard G. Weiss b a
More informationElectronic Supplementary Material
Electronic Supplementary Material PAMAM Dendrimers Bearing Electron-Donating Chromophores: Fluorescence and Electrochemical Properties Bing-BingWang a, Xin Zhang a, Ling Yang a, Xin-Ru Jia* a, Yan Ji a,
More informationSupporting Information for:
Supporting Information for: Tunable Heptamethine-Azo Dye Conjugate as an IR Fluorescent Probe for the Selective Detection of Mitochondrial Glutathione over Cysteine and Homocysteine Soo-Yeon Lim, 1 Keum-Hee
More informationSupporting Information For
Supporting Information For MicroRNA-Catalyzed Cancer Therapeutics Based on DNA-Programmed Nanoparticle Complex Xucheng Luo, 1 Zhi Li, 1 Ganglin Wang, 1 Xuewen He, 2,3 Xiaoqin Shen, 1 Quanhong Sun, 1 Li
More informationSupporting Information
Electronic Supplementary Material (ESI) for Nanoscale. This journal is The Royal Society of Chemistry 2017 Supporting Information X-Ray Responsive Nanoparticles with Triggered Release of Nitrite, a Precursor
More informationProteomic profiling of small-molecule inhibitors reveals dispensability of MTH1 for cancer cell survival
Supplementary Information for Proteomic profiling of small-molecule inhibitors reveals dispensability of MTH1 for cancer cell survival Tatsuro Kawamura 1, Makoto Kawatani 1, Makoto Muroi, Yasumitsu Kondoh,
More informationCytosolar delivery of large proteins using nanoparticlestabilized
Electronic Supplementary Material (ESI) for Nanoscale. This journal is The Royal Society of Chemistry 2016 Supporting Information Cytosolar delivery of large proteins using nanoparticlestabilized nanocapsules
More informationSupporting Information. Design of LVFFARK and LVFFARK-Functionalized Nanoparticles. for Inhibiting Amyloid β-protein Fibrillation and Cytotoxicity
Supporting Information Design of LVFFARK and LVFFARK-Functionalized Nanoparticles for Inhibiting Amyloid β-protein Fibrillation and Cytotoxicity Neng Xiong, Xiao-Yan Dong, Jie Zheng, Fu-Feng Liu, * and
More informationSimultaneous Blood Brain Barrier Crossing and Protection for Stroke Treatment Based on Edaravone-Loaded Ceria Nanoparticles
Supporting Information Simultaneous Blood Brain Barrier Crossing and Protection for Stroke Treatment Based on Edaravone-Loaded Ceria Nanoparticles Qunqun Bao, Ping Hu, * Yingying Xu, Tiansheng Cheng, Chenyang
More informationEFFECT OF COMPRESSED CO 2 ON THE PROPERTIES OF AOT IN ISOOCTANE REVERSE MICELLAR SOLUTION AND ITS APPLICATION TO RECOVER NANOPARTICLES
EFFECT OF COMPRESSED CO 2 ON THE PROPERTIES OF AOT IN ISOOCTANE REVERSE MICELLAR SOLUTION AND ITS APPLICATION TO RECOVER NANOPARTICLES Dongxia Liu, Jianling Zhang, Tiancheng Mu, Jing Chen, Weize Wu, Jun
More informationB16-F10 (Mus musculus skin melanoma), NCI-H460 (human non-small cell lung cancer
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Experimental Methods Cell culture B16-F10 (Mus musculus skin melanoma), NCI-H460 (human non-small
More informationSupporting Information. Silver Nanoparticle-Gated Mesoporous Silica-Coated Gold Nanorods. Low Premature Release and Multifunctional
Supporting Information Silver Nanoparticle-Gated Mesoporous Silica-Coated Gold Nanorods (AuNR@MS@AgNPs): Low Premature Release and Multifunctional Cancer Theranostic Platform Zhehua Zhang, a, Changhui
More informationSupporting information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting information Experimental Section Synthesis and modification of SBA-15. In a typical
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information Single mammalian cell encapsulation
More informationUV Tracer TM Maleimide NHS ester
UV Tracer TM Maleimide HS ester Product o.: 1020 Product ame: UV-Tracer TM Maleimide-HS ester Chemical Structure: Chemical Composition: C 41 H 67 5 18 Molecular Weight: 1014.08 Appearance: Storage: Yellow
More informationPlasmonic blood glucose monitor based on enzymatic. etching of gold nanorods
Plasmonic blood glucose monitor based on enzymatic etching of gold nanorods Xin Liu, Shuya Zhang, Penglong Tan, Jiang Zhou, Yan Huang, Zhou Nie* and Shouzhuo Yao State Key Laboratory of Chemo/Biosensing
More informationSupporting Information Nitric oxide releasing photoresponsive nanohybrids as excellent therapeutic agent for cervical cancer cell lines
upporting Information itric oxide releasing photoresponsive nanohybrids as excellent therapeutic agent for cervical cancer cell lines Priya udhesh a, Kaviyarasan Tamilarasan a, Palaniappan Arumugam a and
More informationSYNTHESIS AND CHARACTERIZATION OF SEVERAL AMPHIPHILIC CHITOSAN DERIVATIVES NADHRATUN NAIIM MOBARAK & MD. PAUZI ABDULLAH
SYNTHESIS AND CHARACTERIZATION OF SEVERAL AMPHIPHILIC CHITOSAN DERIVATIVES NADHRATUN NAIIM MOBARAK & MD. PAUZI ABDULLAH School of Chemistry Science and Food Technology, Faculty of Science and Technology,
More informationSupplementary data. High-Performance Ultrafiltration Membranes Based on Polyethersulfone/Graphene Oxide Composites
Supplementary data High-Performance Ultrafiltration Membranes Based on Polyethersulfone/Graphene Oxide Composites Fengmin Jin a, Wei Lv b,a, Chen Zhang a, Zhengjie Li a, Rongxin Su a, Wei Qi a, Quan-Hong
More informationElectronic Supporting Information for
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Electronic Supporting Information for Rhodamine based Turn-On Fluorescent Probe for Pb(II)
More informationSupporting Information. A Two-In-One Fluorescent Sensor With Dual Channels to. Discriminate Zn 2+ and Cd 2+
Electronic Supplementary Material (ESI) for RS Advances Supporting Information A Two-In-One Fluorescent Sensor With Dual hannels to Discriminate Zn 2 and d 2 Li-Kun Zhang, a Guang-Fu Wu, a Ying Zhang,
More informationA New Design for Light-Breakable Polymer Micelles
Supporting Information A New Design for Light-Breakable Polymer Micelles 1. Synthesis and Characterization of Diblock Copolymer Materials. Dioxane and THF were purified by distillation from sodium with
More informationHeparin Sodium ヘパリンナトリウム
Heparin Sodium ヘパリンナトリウム Add the following next to Description: Identification Dissolve 1 mg each of Heparin Sodium and Heparin Sodium Reference Standard for physicochemical test in 1 ml of water, and
More informationSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Supporting Information Enzyme-activatable Probe with a Self-immolative Linker for Rapid and Sensitive
More informationSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Supporting Information Facile Three-Step Synthesis and Photophysical Properties of [8]-, [9]-,
More informationTunable Hydrophobicity in DNA Micelles Anaya, Milena; Kwak, Minseok; Musser, Andrew J.; Muellen, Klaus; Herrmann, Andreas; Müllen, Klaus
University of Groningen Tunable Hydrophobicity in DNA Micelles Anaya, Milena; Kwak, Minseok; Musser, Andrew J.; Muellen, Klaus; Herrmann, Andreas; Müllen, Klaus Published in: Chemistry DOI: 10.1002/chem.201001816
More informationPreparation and Characterization of Candesartan Cilexetil Solid Lipid Nanoparticulate Capsules
Research Article Preparation and Characterization of Candesartan Cilexetil Solid Lipid Nanoparticulate Capsules *Surya Kiran Vuddisa, Subramanian S., Sindhu Raavi Department of Pharmaceutics, PSG College
More informationSupporting information for the manuscript
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A. This journal is The Royal Society of Chemistry 2014 Supporting information for the manuscript Toward enhanced photoactivity
More informationPreparation of ph Sensitive Pluronic-Docetaxel Conjugate Micelles to Balance the Stability and Controlled Release Issues
Materials 2015, 8, 379-391; doi:10.3390/ma8020379 Article OPEN ACCESS materials ISSN 1996-1944 www.mdpi.com/journal/materials Preparation of ph Sensitive Pluronic-Docetaxel Conjugate Micelles to Balance
More informationSupporting Information
Supporting Information For Intracellularly Acid-Switchable Multifunctional Micelles for Combinational Photo/Chemotherapy of the Drug Resistant Tumor Tingting Wang +,#, Dangge Wang +,#, Haijun Yu +, *,
More informationA pillar[2]arene[3]hydroquinone which can self-assemble to a molecular zipper in the solid state
A pillar[2]arene[3]hydroquinone which can self-assemble to a molecular zipper in the solid state Mingguang Pan, Min Xue* Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China Fax:
More informationColloids and Surfaces A: Physicochem. Eng. Aspects 278 (2006) 60 66
Colloids and Surfaces A: Physicochem. Eng. Aspects 278 (2006) 60 66 Synthesis and characterization of polyion complex micelles between poly(ethylene glycol)-grafted poly(aspartic acid) and cetyltrimethyl
More informationSupporting Information
Supporting Information Cancer Cell Membrane-Biomimetic Nanoprobes with Two-Photon Excitation and Near-Infrared Emission for Intravital Tumor Fluorescence Imaging Yanlin Lv 1,2,, Ming Liu 3,4,, Yong Zhang
More information2,6,9-Triazabicyclo[3.3.1]nonanes as overlooked. amino-modification products by acrolein
Supplementary Information 2,6,9-Triazabicyclo[3.3.1]nonanes as overlooked amino-modification products by acrolein Ayumi Tsutsui and Katsunori Tanaka* Biofunctional Synthetic Chemistry Laboratory, RIKEN
More informationProtein-Mediated Anti-Adhesion Surface against Oral Bacteria
Electronic Supplementary Material (ESI) for Nanoscale. This journal is The Royal Society of Chemistry 2018 Supporting Information Protein-Mediated Anti-Adhesion Surface against Oral Bacteria Xi Liu a,b,
More informationSupporting Information for. A Lipophilic Pt(IV) Oxaliplatin Derivative Enhances Antitumor activity
Supporting Information for A Lipophilic Pt(IV) Oxaliplatin Derivative Enhances Antitumor activity Aiman Abu Ammar, Raji Raveendran, Dan Gibson, Taher Nassar and Simon Benita* The Hebrew University of Jerusalem,
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for Nanoscale. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information MnO 2 -induced synthesis of fluorescent polydopamine nanparticles
More informationComparison of Young and Old Cardiac Telocytes Using Atomic Force Microscopy
Comparison of Young and Old Cardiac Telocytes Using Atomic Force Microscopy Jiali Luo 1, 2, 3, 4, a, Shanshan Feng 1, 2, 3, 4, b 1Key Laboratory of Regenerative Medicine, Ministry of Education, Jinan University,
More informationSupplementary Figures
Supplementary Figures 7 8 Supplementary Figure Intracellular fusion and degradation. (a) Changes of intracellular metal ion concentrations. Intracellular ion concentrations were normalized by total protein
More informationSupplementary materials. Multivalent mannose displaying nanoparticles constructed from
Supplementary materials Multivalent mannose displaying nanoparticles constructed from poly{styrene-co-[(maleic anhydride)-alt-styrene]} Rongming Su a, Lei Li b, Xiaoping Chen a, Jiahuai Han c, Shoufa Han*,a
More informationab Membrane fluidity kit Instructions for Use For the detection of membrane fluidity in cells
ab189819 Membrane fluidity kit Instructions for Use For the detection of membrane fluidity in cells This product is for research use only and is not intended for diagnostic use. Version 1 Last Updated
More informationSynthesis of organophilic ZIF-71 membranes for pervaporation. solvent separation
Supporting Information Synthesis of organophilic ZIF-71 membranes for pervaporation solvent separation Xueliang Dong, Y. S. Lin* School for Engineering of Matter, Transport and Energy, Arizona State University,
More informationSUPPLEMENTARY INFORMATION
SUPPLEMENTARY INFORMATION DOI: 10.1038/NNANO.2012.80 Protein-Inorganic Hybrid Nanoflowers Jun Ge, Jiandu Lei, and Richard N. Zare Supporting Online Material Materials Proteins including albumin from bovine
More informationOncolytic Adenovirus Complexes Coated with Lipids and Calcium Phosphate for Cancer Gene Therapy
Oncolytic Adenovirus Complexes Coated with Lipids and Calcium Phosphate for Cancer Gene Therapy Jianhua Chen, Pei Gao, Sujing Yuan, Rongxin Li, Aimin Ni, Liang Chu, Li Ding, Ying Sun, Xin-Yuan Liu, Yourong
More informationElectronic Supporting Information
Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers. This journal is the Partner Organisations 2018 Electronic Supporting Information Tetraphenylpyrazine-based luminogens with full-colour
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information ovel pseudo[2]rotaxanes constructed by selfassembly of dibenzyl
More informationSupporting Information
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2018 Copyright WILEY-VCH Verlag GmbH & Co. KGaA, 69469 Weinheim, Germany, 2016. Supporting Information
More informationStudent Handout. This experiment allows you to explore the properties of chiral molecules. You have
Student Handout This experiment allows you to explore the properties of chiral molecules. You have learned that some compounds exist as enantiomers non-identical mirror images, such as your left and right
More informationNaoya Takahashi, Keiya Hirota and Yoshitaka Saga* Supplementary material
Supplementary material Facile transformation of the five-membered exocyclic E-ring in 13 2 -demethoxycarbonyl chlorophyll derivatives by molecular oxygen with titanium oxide in the dark Naoya Takahashi,
More informationThiol-Ene Photoimmobilization of Chymotrypsin on Polysiloxane Gels for Enzymatic Peptide Synthesis
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Supporting information for: Thiol-Ene Photoimmobilization of Chymotrypsin on Polysiloxane Gels
More informationA Long-Term and Slow-Releasing Hydrogen Sulfide Donor Protects against Myocardial. Ischemia/Reperfusion Injury
Supporting Information A Long-Term and Slow-Releasing Hydrogen Sulfide Donor Protects against Myocardial Ischemia/Reperfusion Injury Xiaotian Sun 1 *, Wenshuo Wang 2, Jing Dai 3, Sheng Jin 4, Jiechun Huang
More informationInternational Conference on Biomedical and Biological Engineering (BBE 2016)
International Conference on Biomedical and Biological Engineering (BBE 2016) Injury Mechanism of Sub-Micron Calcium Oxalate Monohydrate and Dihydrate Crystals on Renal Epithelial Cells Poonam BHADJA, Kai
More informationProtection of Photoactivity of Photosensitizers by Amphiphilic Polysaccharide Micelles *
Chinese Journal of Polymer Science Vol. 32, No. 10, (2014), 1413 1418 Chinese Journal of Polymer Science Chinese Chemical Society Institute of Chemistry, CAS Springer-Verlag Berlin Heidelberg 2014 Note
More informationCore-Shell Microneedle Gel for Self-Regulated Insulin Delivery
Supporting Information Core-Shell Microneedle Gel for Self-Regulated Insulin Delivery Jinqiang Wang,,, Yanqi Ye,,, Jicheng Yu,, Anna R. Kahkoska, Xudong Zhang,, Chao Wang,, Wujin Sun,, Ria D. Corder, #
More informationDual aggregation-induced emission for enhanced fluorescence. sensing of furin activity in vitro and in living cells
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information Dual aggregation-induced emission for enhanced fluorescence
More informationAuto-assemblage de copolymères à blocs amphiphiles Suming LI
Auto-assemblage de copolymères à blocs amphiphiles Suming LI Institut Européen des Membranes Université de Montpellier 34095 Montpellier, France Self-assembly of amphiphilic block copolymers Colloidal
More informationSupporting information
Supporting information Conformationally Induced Off-On Cell Membrane Chemosensor Targeting Receptor Protein-Tyrosine Kinases for in Vivo and in Vitro Fluorescence Imaging of Cancers Yang Jiao,, Jiqiu Yin,
More informationElectronic Supplementary Information (ESI) A unique dansyl-based chromogenic chemosensor for rapid and ultrasensitive hydrazine detection
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information (ESI) A unique dansyl-based chromogenic
More informationEUDRAGIT L 100 and EUDRAGIT S 100
Technical Information EUDRAGIT L 100 and EUDRAGIT S 100 Specification and Test Methods Ph. Eur. Methacrylic Acid - Methyl Methacrylate Copolymer (1:1) Methacrylic Acid - Methyl Methacrylate Copolymer (1:2)
More informationSynthesis and Solubility of Hydrophilic Derivatives of β- Sitosterol
J. Ind. Eng. Chem., Vol. 13, No. 3, (2007) 367-372 Synthesis and Solubility of Hydrophilic Derivatives of β- Sitosterol Dae-won Chung and Young Tai Choi Department of Polymer Engineering, College of Engineering,
More informationph Switchable and Fluorescent Ratiometric Squarylium Indocyanine Dyes as Extremely Alkaline Sensors
ph Switchable and Fluorescent Ratiometric Squarylium Indocyanine Dyes as Extremely Alkaline Sensors Jie Li, Chendong Ji, Wantai Yang, Meizhen Yin* State Key Laboratory of Chemical Resource Engineering,
More informationSurface-Enhanced Raman Scattering Active Gold Nanoparticles. with Enzyme-Mimicking Activities for Measuring Glucose and
Surface-Enhanced Raman Scattering Active Gold Nanoparticles with Enzyme-Mimicking Activities for Measuring Glucose and Lactate in Living Tissues Yihui Hu, Hanjun Cheng, Xiaozhi Zhao, Jiangjiexing Wu, Faheem
More informationMOF-Derived Zn-Mn Mixed Hollow Disks. with Robust Hierarchical Structure for High-Performance. Lithium-Ion Batteries
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A. This journal is The Royal Society of Chemistry 2017 Electronic Supplementary Information (ESI) MOF-Derived Zn-Mn Mixed Oxides@Carbon
More informationSupplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2011
Supporting Information Experimental details 1. Materials Ferric chloride (FeCl 3 6H 2 O), Ethylene glycol (EG) and Ammonium hydroxide (NH 3 H 2 O) were obtained from Beijing Chemical Regent Co. Ltd. (Beijing,
More informationNovel ph-responsive nanovectors for controlled release of ionisable drugs
Supplementary Information Novel ph-responsive nanovectors for controlled release of ionisable drugs Francesca Mastrotto, a Stefano Salmaso a, Cameron Alexander, b Giuseppe Mantovani b and Paolo Caliceti
More informationAccessory Publication
10.1071/CH09088_AC CSIRO 2009 Accessory Publication: Australian Journal of Chemistry, 2009, 62(8), 790 793 Thermally Responsive Elastomeric Supramolecular Polymers Featuring Flexible Aliphatic Hydrogen
More informationSupramolecular micelles with dual temperature and redox responses. for multi-controlled drug release
Electronic Supplementary Information for: Supramolecular micelles with dual temperature and redox responses for multi-controlled drug release Weizhong Yuan* ab, Hui Zou a, Wen Guo a,tianxiang Shen a and
More informationEfficient Metal-Free Pathway to Vinyl Thioesters with Calcium Carbide as the Acetylene Source
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information Efficient Metal-Free Pathway to Vinyl Thioesters with Calcium Carbide
More informationSupporting Information
Supporting Information Toward High-Efficient Red Emissive Carbon Dots: Facile Preparation, Unique Properties, and Applications as Multifunctional Theranostic Agents Shan Sun,, Ling Zhang, Kai Jiang, Aiguo
More informationTadpole-shaped Gene Carrier with Distinct Phase. Segregation in A Ternary Polymeric Micelle
Electronic Supplementary Material (ESI) for Soft Matter. This journal is The Royal Society of Chemistry 2015 Supporting Information Tadpole-shaped Gene Carrier with Distinct Phase Segregation in A Ternary
More informationSupporting Information. Gadolinium oxide nanoplates with high longitudinal. relaxivity for magnetic resonance imaging
Electronic Supplementary Material (ESI) for Nanoscale. This journal is The Royal Society of Chemistry 2014 Supporting Information Gadolinium oxide nanoplates with high longitudinal relaxivity for magnetic
More informationSupporting information. Thermosensitive Lipid Bilayer-Coated Mesoporous Carbon. Nanoparticles for Synergistic Thermochemotherapy of Tumor
Supporting information Thermosensitive Lipid Bilayer-Coated Mesoporous Carbon Nanoparticles for Synergistic Thermochemotherapy of Tumor Xian Li, Xiudan Wang, Luping Sha, Da Wang, Wei Shi, Qinfu Zhao*,,
More informationFluorescent probes for detecting monoamine oxidase activity and cell imaging
Fluorescent probes for detecting monoamine oxidase activity and cell imaging Xuefeng Li, Huatang Zhang, Yusheng Xie, Yi Hu, Hongyan Sun *, Qing Zhu * Supporting Information Table of Contents 1. General
More informationNovel D-erythro N-Octanoyl Sphingosine Analogs As Chemo- and Endocrine. Resistant Breast Cancer Therapeutics
Page 11 of 32 Cancer Chemotherapy and Pharmacology Novel D-erythro N-Octanoyl Sphingosine Analogs As Chemo- and Endocrine Resistant Breast Cancer Therapeutics James W. Antoon, Jiawang Liu, Adharsh P. Ponnapakkam,
More informationIMPACT OF FLUORIDE AND SUPEROXIDE DISMUTASE ON THE GOLGI APPARATUS IN RAT RIB-CAGE CHONDROCYTES
13 13 IMPACT OF FLUORIDE AND SUPEROXIDE DISMUTASE ON THE GOLGI APPARATUS IN RAT RIB-CAGE CHONDROCYTES Yanni Yu, a Binjie Meng a Guizhou, China SUMMARY: Chondrocytes of rib-cage cartilage from Wistar rats
More information