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PEI-NIR Heptamethine Cyanine Nanotheranostics for Tumor Targeted Gene Delivery
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    PEI-NIR Heptamethine Cyanine Nanotheranostics for Tumor Targeted Gene Delivery
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    • Eduardo De los Reyes-Berbel
      Eduardo De los Reyes-Berbel
      Department of Organic Chemistry, Biotechnology Institute, Faculty of Sciences, University of Granada, 18071 Granada, Spain
    • Rafael Salto-Gonzalez
      Rafael Salto-Gonzalez
      Department of Biochemistry and Molecular Biology II, School of Pharmacy, University of Granada, 18071 Granada, Spain
    • Mariano Ortega-Muñoz
      Mariano Ortega-Muñoz
      Department of Organic Chemistry, Biotechnology Institute, Faculty of Sciences, University of Granada, 18071 Granada, Spain
    • Francisco Jose Reche-Perez
      Francisco Jose Reche-Perez
      Department of Biochemistry and Molecular Biology II, School of Pharmacy, University of Granada, 18071 Granada, Spain
    • Ana Belen Jodar-Reyes
      Ana Belen Jodar-Reyes
      Biocolloid and Fluid Physics Group, Department of Applied Physics, Faculty of Sciences, University of Granada, 18071 Granada, Spain
    • Fernando Hernandez-Mateo
      Fernando Hernandez-Mateo
      Department of Organic Chemistry, Biotechnology Institute, Faculty of Sciences, University of Granada, 18071 Granada, Spain
    • Maria Dolores Giron-Gonzalez*
      Maria Dolores Giron-Gonzalez
      Department of Biochemistry and Molecular Biology II, School of Pharmacy, University of Granada, 18071 Granada, Spain
      *E-mail: [email protected]
    • Francisco Santoyo-Gonzalez*
      Francisco Santoyo-Gonzalez
      Department of Organic Chemistry, Biotechnology Institute, Faculty of Sciences, University of Granada, 18071 Granada, Spain
      *E-mail: [email protected]
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    Bioconjugate Chemistry

    Cite this: Bioconjugate Chem. 2018, 29, 8, 2561–2575
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.bioconjchem.8b00262
    Published June 28, 2018
    Copyright © 2018 American Chemical Society

    Abstract

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    Polymer-based nanotheranostics are appealing tools for cancer treatment and diagnosis in the fast-growing field of nanomedicine. A straightforward preparation of novel engineered PEI-based nanotheranostics incorporating NIR fluorescence heptamethine cyanine dyes (NIRF-HC) to enable them with tumor targeted gene delivery capabilities is reported. Branched PEI-2 kDa (b2kPEI) is conjugated with IR-780 and IR-783 dyes by both covalent and noncovalent simple preparative methodologies varying their stoichiometry ratio. The as-prepared set of PEI-NIR-HC nanocarriers are assayed in vitro and in vivo to evaluate their gene transfection efficiency, cellular uptake, cytotoxicity, internalization and trafficking mechanisms, subcellular distribution, and tumor specific gene delivery. The results show the validity of the approach particularly for one of the covalent IR783-b2kPEI conjugates that exhibit an enhanced tumor uptake, probably mediated by organic anion transporting peptides, and favorable intracellular transport to the nucleus. The compound behaves as an efficient nanotheranostic transfection agent in NSG mice bearing melanoma G361 xenographs with concomitant imaging signal and gene concentration in the targeted tumor. By this way, advanced nanotheranostics with multifunctional capabilities (gene delivery, tumor-specific targeting, and NIR fluorescence imaging) are generated in which the NIRF-HC dye component accounts for simultaneous targeting and diagnostics, avoiding additional incorporation of additional tumor-specific targeting bioligands.

    Copyright © 2018 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.bioconjchem.8b00262.

    • Commercial chemical and biological reagents used, general chemical synthetic procedures, purification and physicochemical characterization of NIRHF-HC-based probes and their polyplexes, NMR spectra, and in vitro and in vivo biological essays (PDF)

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    Cited By

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    This article is cited by 12 publications.

    1. Syed Muhammad Usama, Chen-Ming Lin, Kevin Burgess. On the Mechanisms of Uptake of Tumor-Seeking Cyanine Dyes. Bioconjugate Chemistry 2018, 29 (11) , 3886-3895. https://doi.org/10.1021/acs.bioconjchem.8b00708
    2. Mingzhi Zhu, Pei Wang, Biaoqi Chen, Linrong Shi, Ruimin Long, Shibin Wang, Yuangang Liu. Active-oxygenating hollow Prussian blue nanosystems loaded with biomacromolecules for photodynamic/photothermal therapy of cancer and alleviating hypoxic tumors. Materials & Design 2024, 237 , 112618. https://doi.org/10.1016/j.matdes.2023.112618
    3. Panoraia Siafaka, Emre Şefik Çağlar, Evren Atlıhan Gündoğdu, Neslihan Üstündağ Okur. New Era on Combining Both Imaging and Drug Delivery to Treat Cancer. Current Pharmaceutical Biotechnology 2023, 24 (7) , 832-855. https://doi.org/10.2174/1389201023666220617152334
    4. Chaoqun Zhang, Jie Song, Xin Shen, Qian Li, Feng Su, Suming Li. Fluorescent nanoprobe prepared from hyaluronic acid modified iron selenide nanoparticles for real-time detection of hyaluronidase as tumor marker. Journal of Pharmaceutical and Biomedical Analysis Open 2023, 1 , 100001. https://doi.org/10.1016/j.jpbao.2023.100001
    5. Ottorino Lucchi, Davide Fabbri, Francisco Santoyo‐Gonzalez, Fernando Hernandez‐Mateo, F. Javier Lopez‐Jaramillo, Mariano Ortega‐Muñoz. Divinyl Sulfone. 2021, 1-8. https://doi.org/10.1002/047084289X.rd476.pub2
    6. Atanas Kurutos, Jasmina Nikodinovic-Runic, Aleksandar Veselinovic, Jovana B. Veselinović, Fadhil S. Kamounah, Tatjana Ilic-Tomic. RNA-targeting low-molecular-weight fluorophores for nucleoli staining: synthesis, in silico modelling and cellular imaging. New Journal of Chemistry 2021, 45 (29) , 12818-12829. https://doi.org/10.1039/D1NJ01659H
    7. Francisco J. Reche-Perez, Simona Plesselova, Eduardo De los Reyes-Berbel, Mariano Ortega-Muñoz, Francisco J. Lopez-Jaramillo, Fernando Hernandez-Mateo, Francisco Santoyo-Gonzalez, Rafael Salto-Gonzalez, Maria D. Giron-Gonzalez. Single chain variable fragment fused to maltose binding protein: a modular nanocarrier platform for the targeted delivery of antitumorals. Biomaterials Science 2021, 9 (5) , 1728-1738. https://doi.org/10.1039/D0BM01903H
    8. Yang Li, Yiming Zhou, Xiuli Yue, Zhifei Dai. Cyanine conjugates in cancer theranostics. Bioactive Materials 2021, 6 (3) , 794-809. https://doi.org/10.1016/j.bioactmat.2020.09.009
    9. Atanas Kurutos, Yutaka Shindo, Yuki Hiruta, Kotaro Oka, Daniel Citterio. Near-infrared pH responsive heptamethine cyanine platforms: Modulating the proton acceptor. Dyes and Pigments 2020, 181 , 108611. https://doi.org/10.1016/j.dyepig.2020.108611
    10. Atanas Kurutos, Tatjana Ilic-Tomic, Fadhil S. Kamounah, Aleksey A. Vasilev, Jasmina Nikodinovic-Runic. Non-cytotoxic photostable monomethine cyanine platforms: Combined paradigm of nucleic acid staining and in vivo imaging. Journal of Photochemistry and Photobiology A: Chemistry 2020, 397 , 112598. https://doi.org/10.1016/j.jphotochem.2020.112598
    11. Tingting Xu, Di Chang, Yu Cai, Shudan Min, Yuanyuan Ma, Hui Mao, Shenghong Ju. Targeting of an antecedent proteinase by an activatable probe with deep tissue penetration facilitates early visualization and dynamic malignancy evaluation of orthotopic pancreatic ductal adenocarcinoma (PDAC). Biomaterials Science 2019, 7 (8) , 3320-3333. https://doi.org/10.1039/C9BM00441F
    12. Arthur H. G. David, Pablo García‐Cerezo, Araceli G. Campaña, Francisco Santoyo‐González, Victor Blanco. [2]Rotaxane End‐Capping Synthesis by Click Michael‐Type Addition to the Vinyl Sulfonyl Group. Chemistry – A European Journal 2019, 25 (24) , 6170-6179. https://doi.org/10.1002/chem.201900156

    Bioconjugate Chemistry

    Cite this: Bioconjugate Chem. 2018, 29, 8, 2561–2575
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.bioconjchem.8b00262
    Published June 28, 2018
    Copyright © 2018 American Chemical Society

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