Synthesis, Characterization of NR@SiO2/PNIPAm-co-Ppa Composite Nanogel and Study On Its Application in Photodynamic Therapy
Tóm tắt
In the present study, a novel composite nanogel based on fluorescence resonance energy transfer (FRET) and its application for photodynamic therapy is reported. First of all, nanoparticles of silica doped with Nile Red (NR) were prepared by Stöber method, then they were decorated by γ-methacryloxypropyltrimethoxysilane (MPS) to prepare MPS decorated NR@SiO2 nanoparticles, and finally they were copolymerized with N-isopropylacrylamide (NIPAm) and Pyropheophorbide-a (Ppa) by free radical copolymerization, and composite nanogel of NR@SiO2/PNIPAm-co-Ppa was fabricated. The microstructure of the as-prepared nanogel was characterized by Fourier transform infrared spectrum (FTIR), photoluminescence (PL), UV–Visible spectrophotometer (UV–Vis), dynamic light scattering (DLS) and transmission electron microscopy (TEM). PL spectrum indicated that, under irradiation of visible light source, energy can be transferred from NR to Ppa. UV–Vis spectrum demonstrated that aggregation of Ppa is prevented efficiently and Ppa exists as “monomer” state in the composite nanogel. Under irradiation of laser, singlet oxygen (1O2) can be produced efficiently by excited nanogel. The in vitro cytotoxicity test showed that HeLa cells can be killed by the composite nanogel.
Tài liệu tham khảo
citation_journal_title=Chem Soc Rev; citation_title=Supramolecular photosensitizers rejuvenate photodynamic therapy; citation_author=XS Li, SY Lee, JY Yoon; citation_volume=47; citation_publication_date=2018; citation_pages=1174-1188; citation_doi=10.1039/c7cs00594f; citation_id=CR1
citation_journal_title=J Am Chem Soc; citation_title=A Nanoscale Metal-Organic Framework Overcomes Hypoxia for Photodynamic Therapy Primed Cancer Immunotherapy; citation_author=GX Lan, KY Ni, ZW Xu, SS Veroneau, Y Song, WB Lin; citation_volume=140; citation_publication_date=2018; citation_pages=5670-5673; citation_doi=10.1021/jacs.8b01072; citation_id=CR2
citation_journal_title=Chem Soc Rev; citation_title=Overcoming the Achilles' heel of photodynamic therapy; citation_author=WP Fan, P Huang, XY Chen; citation_volume=45; citation_publication_date=2016; citation_pages=6488-6519; citation_doi=10.1039/c6cs00616g; citation_id=CR3
citation_journal_title=Biomaterials; citation_title=Advances in nanomaterials for photodynamic therapy applications: Status and challenges; citation_author=JM Chen, TJ Fan, ZJ Xie, QQ Zeng, P Xue, TT Zheng, Y Chen, XL Luo, H Zhang; citation_volume=237; citation_publication_date=2020; citation_doi=10.1016/j.biomaterials.2020.119827; citation_id=CR4
citation_journal_title=Adv Funct Mater; citation_title=Metal-organic framework nanoparticles in photodynamic therapy: current status and perspectives; citation_author=M Lismont, L Dreesen, S Wuttke; citation_volume=27; citation_publication_date=2017; citation_pages=1606314; citation_doi=10.1002/adfm.201606314; citation_id=CR5
citation_journal_title=J Am Chem Soc; citation_title=Continuous O2-evolving MnFe2O4 nanoparticle-anchored mesoporous silica nanoparticles for efficient photodynamic therapy in hypoxic cancer; citation_author=J Kim, HR Cho, H Jeon, D Kim, C Song, N Lee, SH Choi, T Hyeon; citation_volume=139; citation_publication_date=2017; citation_pages=10992-10995; citation_doi=10.1021/jacs.7b05559; citation_id=CR6
citation_journal_title=Biomater Sci; citation_title=Nanoparticle delivery of Wnt-1 siRNA enhances photodynamic therapy by inhibiting epithelial-mesenchymal transition for oral cancer; citation_author=CA Ma, LL Shi, Y Huang, LY Shen, H Peng, XY Zhu, GY Zhou; citation_volume=5; citation_publication_date=2017; citation_pages=494-501; citation_doi=10.1039/c6bm00833j; citation_id=CR7
citation_journal_title=J Clin Med; citation_title=Photodynamic Therapy Using Talaporfin Sodium for Local Failure after Chemoradiotherapy or Radiotherapy for Esophageal Cancer: A Single Center Experience; citation_author=N Ishida, S Osawa, T Miyazu, M Kaneko, S Tamura, S Tani, M Yamade, M Iwaizumi, Y Hamaya, T Furuta, K Sugimoto; citation_volume=9; citation_publication_date=2020; citation_pages=1509; citation_doi=10.3390/jcm9051509; citation_id=CR8
citation_journal_title=Int J Mol Sci; citation_title=Photodynamic and Cold Atmospheric Plasma Combination Therapy Using Polymeric Nanoparticles for the Synergistic Treatment of Cervical Cancer; citation_author=JH Ha, YJ Kim; citation_volume=22; citation_publication_date=2021; citation_pages=1172; citation_doi=10.3390/ijms22031172; citation_id=CR9
citation_journal_title=New J Chem; citation_title=Facile synthesis of chitosan assisted multifunctional magnetic Fe3O4@SiO2@CS@pyropheophorbide-a fluorescent nanoparticles for photodynamic therapy; citation_author=JJ Cheng, GH Tan, WT Li, HY Zhang, XD Wu, ZQ Wang, YX Jin; citation_volume=40; citation_publication_date=2016; citation_pages=8522-8534; citation_doi=10.1039/c6nj01765g; citation_id=CR10
citation_journal_title=J Pharm Sci; citation_title=Folic acid conjugated pyropheophorbide a as the photosensitizer tested for in vivo targeted photodynamic therapy; citation_author=J Wang, Q Liu, YT Zhang, H Shi, H Liu, WJ Guo, YH Ma, WQ Huang, ZY Hong; citation_volume=106; citation_publication_date=2017; citation_pages=1482-1489; citation_doi=10.1016/j.xphs.2017.02.019; citation_id=CR11
citation_journal_title=Mol Pharmaceutics; citation_title=Aptamer-Pyropheophorbide a Conjugates with Tumor Spheroid Targeting and Penetration Abilities for Photodynamic Therapy; citation_author=HJ Xiong, JH Yan, SD Cai, QY He, NC Wen, Y Wang, YQ Hu, DM Peng, YF Liu, ZB Liu; citation_volume=17; citation_publication_date=2020; citation_pages=2882-2890; citation_doi=10.1021/acs.molpharmaceut.0c00335; citation_id=CR12
citation_journal_title=Langmuir; citation_title=Protoporphyrin IX nanoparticle carrier: preparation, optical properties, and singlet oxygen generation; citation_author=LM Rossi, PR Silva, LLR Vono, AU Fernandes, DB Tada, MS Baptista; citation_volume=24; citation_publication_date=2008; citation_pages=12534-12538; citation_doi=10.1021/la800840k; citation_id=CR13
citation_journal_title=Chem J Chin Univ; citation_title=Preparation of Complex Nanogel with Up-conversion Fluorescence-responsive Performance and Its Fluorescence Energy Transfer Behavior; citation_author=DL Liang, QS Song, YT Yao, B Liu; citation_volume=40; citation_publication_date=2019; citation_pages=583-591; citation_doi=10.7503/cjcu20180470; citation_id=CR14
citation_journal_title=J Fluoresc; citation_title=NIR-Fluorescent Multidye Silica Nanoparticles with Large Stokes Shifts for Versatile Biosensing Applications; citation_author=G Chapman, G Patonay; citation_volume=29; citation_publication_date=2019; citation_pages=293-305; citation_doi=10.1007/s10895-018-02339-z; citation_id=CR15
citation_journal_title=Nat Methods; citation_title=FRET as a biomolecular research tool-understanding its potential while avoiding pitfalls; citation_author=WR Algar, N Hildebrandt, SS Vogel, IL Medintz; citation_volume=16; citation_publication_date=2019; citation_pages=815-829; citation_doi=10.1038/s41592-019-0530-8; citation_id=CR16
citation_journal_title=Adv Funct Mater; citation_title=Hydrogen-Bonded Two-Component Ionic Crystals Showing Enhanced Long-Lived Room-Temperature Phosphorescence via TADF-Assisted Förster Resonance Energy Transfer; citation_author=B Zhou, DP Yan; citation_volume=29; citation_publication_date=2019; citation_pages=1807599; citation_doi=10.1002/adfm.201807599; citation_id=CR17
citation_journal_title=J Am Chem Soc; citation_title=Real-time monitoring the dynamics of coordination-driven self-assembly by fluorescence-resonance energy transfer; citation_author=CB Huang, L Xu, JL Zhu, YX Wang, B Sun, XP Li, HB Yang; citation_volume=139; citation_publication_date=2017; citation_pages=9459-9462; citation_doi=10.1021/jacs.7b04659; citation_id=CR18
citation_journal_title=Biosens Bioelectron; citation_title=Nanostructured biosensor for detecting glucose in tear by applying fluorescence resonance energy transfer quenching mechanism; citation_author=LY Chen, WH Tse, Y Chen, MW McDonald, J Melling, J Zhang; citation_volume=5; citation_publication_date=2017; citation_pages=393-399; citation_doi=10.1016/j.bios.2016.12.044; citation_id=CR19
citation_journal_title=Anal Bioanal Chem; citation_title=A hyaluronic acid fluorescent hydrogel based on fluorescence resonance energy transfer for sensitive detection of hyaluronidase; citation_author=MH Ge, JJ Sun, ML Chen, JJ Tian, HC Yin, J Yin; citation_volume=412; citation_publication_date=2020; citation_pages=1915-1923; citation_doi=10.1007/s00216-020-02443-9; citation_id=CR20
citation_journal_title=Chem Commun; citation_title=A supramolecular hydrogel containing boronic acid-appended receptor for fluorocolorimetric sensing of polyols with a paper platform; citation_author=M Ikeda, K Fukuda, T Tanida, T Yoshii, I Hamachi; citation_volume=48; citation_publication_date=2012; citation_pages=2716-2718; citation_doi=10.1039/C2CC17503G; citation_id=CR21
citation_journal_title=J Colloid Interface Sci; citation_title=Thermo-responsive monodisperse core-shell microspheres with PNIPAM core and biocompatible porous ethyl cellulose shell embedded with PNIPAM gates; citation_author=YL Yu, MJ Zhang, R Xie, XJ Ju, JY Wang, SW Pi, LY Chu; citation_volume=376; citation_publication_date=2012; citation_pages=97-106; citation_doi=10.1016/j.jcis.2012.03.028; citation_id=CR22
citation_journal_title=J Fluoresc; citation_title=Self-Assembly of Colloidal Photonic Crystals of PS@PNIPAM Nanoparticles and Temperature-Responsive Tunable Fluorescence; citation_author=S Yuan, FY Ge, X Yang, SY Guang; citation_volume=26; citation_publication_date=2016; citation_pages=1-8; citation_doi=10.1016/j.jlumin.2012.12.005; citation_id=CR23
citation_journal_title=ACS Appl Mater Interfaces; citation_title=Facile Fabrication of Composite Membranes with Dual Thermo- and pH-Responsive Characteristics; citation_author=B Ma, XJ Ju, F Luo, YQ Liu, Y Wang, Z Liu, W Wang, R Xie, LY Chu; citation_volume=9; citation_publication_date=2017; citation_pages=14409-14421; citation_doi=10.1021/acsami.7b02427; citation_id=CR24
citation_journal_title=J Colloid Interface Sci; citation_title=Controlled growth of monodisperse silica spheres in the micron size range; citation_author=W Stöber, A Fink, E Bohn; citation_volume=26; citation_publication_date=1968; citation_pages=62-69; citation_doi=10.1016/0021-9797(68)90272-5; citation_id=CR25
citation_journal_title=Langmuir; citation_title=Methylene blue-containing silica-coated magnetic particles: A potential magnetic carrier for photodynamic therapy; citation_author=DB Tada, LLR Vono, EL Duarte, R Itri, PK Kiyohara, MS Baptista, LM Rossi; citation_volume=23; citation_publication_date=2007; citation_pages=8194-8199; citation_doi=10.1021/la700883y; citation_id=CR26
citation_journal_title=J Mol Struct; citation_title=A comparison of photosensitizing properties of meso-tetraphenylporphin in acetone and in dimethyl sulfoxide; citation_author=M Korínek, R Dědic, A Molnár, A Svoboda, J Hála; citation_volume=744; citation_publication_date=2005; citation_pages=727-731; citation_doi=10.1016/j.molstruc.2004.11.036; citation_id=CR27
citation_journal_title=J Microbiol Methods; citation_title=An improved 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) reduction assay for evaluating the viability of Escherichia coli cells; citation_author=HW Wang, HR Cheng, FQ Wang, DZ Wei, XD Wang; citation_volume=82; citation_publication_date=2010; citation_pages=330-333; citation_doi=10.1016/j.mimet.2010.06.014; citation_id=CR28
citation_journal_title=Spectrochim Acta Part A; citation_title=Unravel the interaction of protoporphyrin IX with reduced graphene oxide by vital spectroscopic techniques; citation_author=MA Jhonsi, C Nithya, A Kathiravan; citation_volume=178; citation_publication_date=2017; citation_pages=86-93; citation_doi=10.1016/j.saa.2017.01.059; citation_id=CR29
citation_journal_title=Mater Sci Eng C; citation_title=Porous protoporphyrin IX-embedded cellulose diacetate electrospun microfibers in antimicrobial photodynamic inactivation; citation_author=TT Wang, HZ Ke, SP Chen, J Wang, WS Yang, XM Cao, JY Liu, QF Wei, RA Ghiladi, QQ Wang; citation_volume=118; citation_publication_date=2021; citation_doi=10.1016/j.msec.2020.111502; citation_id=CR30
citation_journal_title=Colloid Polym Sci; citation_title=Preparation, self-assembly of SiO2/PNIPAm complex microgels and their manipulation of fluorescence emission for organic dyes; citation_author=QC Zhang, QS Song, ZW Zhang, CY Zhao, HH Ma; citation_volume=298; citation_publication_date=2020; citation_pages=1587-1596; citation_doi=10.1007/s00396-020-04746-w; citation_id=CR31
citation_journal_title=Dyes Pigm; citation_title=A phenoxazine-based fluorescent chemosensor for dual channel detection of Cd2+ and CN ions and its application to bio-imaging in live cells and zebrafish; citation_author=P Ravichandiran, A Boguszewska-Czubara, M Maslyk, AP Bella, PM Johnson, SA Subramaniyan, KS Shim, DJ Yoo; citation_volume=172; citation_publication_date=2020; citation_doi=10.1016/j.dyepig.2019.107828; citation_id=CR32
citation_journal_title=ACS Appl Mater Interfaces; citation_title=Temperature-Controlled Catalysis by Core-Shell-Satellite AuAg@pNIPAM@Ag Hybrid Microgels: A Highly Efficient Catalytic Thermoresponsive Nanoreactor; citation_author=L Tzounis, M Doña, JM Lopez-Romero, A Fery, R Contreras-Caceres; citation_volume=11; citation_publication_date=2019; citation_pages=29360-29372; citation_doi=10.1021/acsami.9b10773; citation_id=CR33
citation_journal_title=Photochem Photobiol Sci; citation_title=One- and two-photon solvatochromism of the fluorescent dye Nile Red and its CF3, F and Br-substituted analogues; citation_author=M Hornum, P Reinholdt, JK Zareba, BB Jensen, D Wustner, M Samoc, P Nielsen, J Kongsted; citation_volume=19; citation_publication_date=2020; citation_pages=1382-1391; citation_doi=10.1039/D0PP00076K; citation_id=CR34
citation_journal_title=J Am Chem Soc; citation_title=Stacking Geometries of Early Protoporphyrin IX Aggregates Revealed by Gas-Phase Infrared Spectroscopy; citation_author=J Seo, J Jang, S Warnke, S Gewinner, W Schollkopf, G Helden; citation_volume=138; citation_publication_date=2016; citation_pages=16315-16321; citation_doi=10.1021/jacs.6b08700; citation_id=CR35
citation_journal_title=J Phys Chem B; citation_title=Aggregation Behavior of Protoporphyrin IX in Aqueous Solutions: Clear Evidence of Vesicle Formation; citation_author=LM Scolaro, M Castriciano, A Romeo, S Patanè, E Cefalì, M Allegrini; citation_volume=106; citation_publication_date=2002; citation_pages=2453-2459; citation_doi=10.1021/jp013155h; citation_id=CR36
citation_journal_title=J Chem Phys; citation_title=Study of the Effects of Substitution on the Absorption Spectra of Porphin; citation_author=M Gouterman; citation_volume=30; citation_publication_date=1959; citation_pages=1139-1161; citation_doi=10.1063/1.1730148; citation_id=CR37
citation_journal_title=J Mol Spectrosc; citation_title=Spectra of porphyrins; citation_author=M Gouterman; citation_volume=6; citation_publication_date=1961; citation_pages=138-163; citation_doi=10.1016/0022-2852(61)90236-3; citation_id=CR38
Hornum M, Mulberg MW, Szomek M, Reinholdt P, Brewer JR, Wustner D, Kongsted J, Nielsen P (2020) Substituted 9-Diethylaminobenzo [a] phenoxazin-5-ones (Nile Red Analogues): Synthesis and Photophysical Properties. J Org Chem 86:1471–1488.
https://doi.org/10.1021/acs.joc.0c02346
citation_journal_title=ACS Appl Mater Interfaces; citation_title=Self-Assembled Oxaliplatin (IV) Prodrug-Porphyrin Conjugate for Combinational Photodynamic and Chemotherapy; citation_author=WQ Lim, G Yang, SZF Phua, HZ Chen, YL Zhao; citation_volume=11; citation_publication_date=2019; citation_pages=16391-16401; citation_doi=10.1021/acsami.9b04557; citation_id=CR40
citation_journal_title=Chem Soc Rev; citation_title=Advancing porphyrin's biomedical utility via supramolecular chemistry; citation_author=MA Rajora, J Lou, G Zheng; citation_volume=46; citation_publication_date=2017; citation_pages=6433-6469; citation_doi=10.1039/c7cs00525c; citation_id=CR41
citation_journal_title=Adv Drug Delivery Rev; citation_title=Towards more accurate bioimaging of drug nanocarriers: turning aggregation-caused quenching into a useful tool; citation_author=JP Qi, XW Hu, XC Dong, Y Lu, HP Lu, WL Zhao, W Wu; citation_volume=143; citation_publication_date=2019; citation_pages=206-225; citation_doi=10.1016/j.addr.2019.05.009; citation_id=CR42
citation_journal_title=ACS Appl Mater Interfaces; citation_title=Water Dispersible and Biocompatible Porphyrin-Based Nanospheres for Biophotonics Applications: A Novel Surfactant and Polyelectrolyte-Based Fabrication Strategy for Modifying Hydrophobic Porphyrins; citation_author=N Sheng, SF Zong, W Cao, JZ Jiang, ZY Wang, YP Cui; citation_volume=7; citation_publication_date=2015; citation_pages=19718-19725; citation_doi=10.1021/acsami.5b05256; citation_id=CR43
citation_journal_title=Prog Polym Sci; citation_title=Poly(N-isopropylacrylamide): experiment, theory and application; citation_author=HG Schild; citation_volume=17; citation_publication_date=1992; citation_pages=163-249; citation_doi=10.1016/0079-6700(92)90023-R; citation_id=CR44