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Synthesis of Chiral Carbo-Nanotweezers for Enantiospecific Recognition and DNA Duplex Winding in Cancer Cells

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Download Hi-Res ImageDownload to MS-PowerPointCite This:ACS Appl. Mater. Interfaces 2018, 10, 44, 37886-37897
    Research Article

    Synthesis of Chiral Carbo-Nanotweezers for Enantiospecific Recognition and DNA Duplex Winding in Cancer Cells
    Click to copy article linkArticle link copied!

    • Indu Tripathi
      Indu Tripathi
      Departments of Bioengineering, Materials Science and Engineering, University of Illinois at Urbana−Champaign, Urbana, Illinois 61801, United States
      Mills Breast Cancer Institute, Carle Foundation Hospital, 502 North Busey, Urbana, Illinois 61801, United States
      More by Indu Tripathi
    • Santosh K. Misra
      Santosh K. Misra
      Departments of Bioengineering, Materials Science and Engineering, University of Illinois at Urbana−Champaign, Urbana, Illinois 61801, United States
      Mills Breast Cancer Institute, Carle Foundation Hospital, 502 North Busey, Urbana, Illinois 61801, United States
      More by Santosh K. Misra
      Orcidhttp://orcid.org/0000-0002-3313-4895
    • Fatemeh Ostadhossein
      Fatemeh Ostadhossein
      Departments of Bioengineering, Materials Science and Engineering, University of Illinois at Urbana−Champaign, Urbana, Illinois 61801, United States
      Mills Breast Cancer Institute, Carle Foundation Hospital, 502 North Busey, Urbana, Illinois 61801, United States
      More by Fatemeh Ostadhossein
    • Indrajit Srivastava
      Indrajit Srivastava
      Departments of Bioengineering, Materials Science and Engineering, University of Illinois at Urbana−Champaign, Urbana, Illinois 61801, United States
      Mills Breast Cancer Institute, Carle Foundation Hospital, 502 North Busey, Urbana, Illinois 61801, United States
      More by Indrajit Srivastava
      Orcidhttp://orcid.org/0000-0002-6864-0202
    • Dipanjan Pan*
      Dipanjan Pan
      Departments of Bioengineering, Materials Science and Engineering, University of Illinois at Urbana−Champaign, Urbana, Illinois 61801, United States
      Mills Breast Cancer Institute, Carle Foundation Hospital, 502 North Busey, Urbana, Illinois 61801, United States
      *E-mail: [email protected]
      More by Dipanjan Pan
      Orcidhttp://orcid.org/0000-0003-0175-4704
    Other Access OptionsSupporting Information (5)

    ACS Applied Materials & Interfaces

    Cite this: ACS Appl. Mater. Interfaces 2018, 10, 44, 37886–37897
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acsami.8b15618
    Published October 9, 2018
    Copyright © 2018 American Chemical Society
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    Abstract

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    Abstract Image

    Targeting the DNA of tumor cells with small molecules may offer effective clinical strategies for transcriptional inhibition. We unveil synthesis and characterization of ∼20 nm chiral carbon nanoparticles for enantiospecific recognition of DNA. Our approach inculcates chirality in carbon nanoparticles by controlled tethering of minor groove binders, i.e., Tröger’s base (TB). The chiral particles positively enriched the cellular nucleus in MCF-7 breast cancer cells, irrespective of the TB asymmetry tethered on the particle surface, but negatively induced chiral carbon nanoparticles exhibited improved efficiency at inhibiting cell growth. Further studies indicated that these chiral particles act as nanotweezers to perturb the genomic DNA and induce apoptosis cascade in cancer cells.

    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/acsami.8b15618.

    • Anhydrous state morphology, fluorescence emission spectra, cell cycle analysis, AFM height profile of CNTWZs, Z-stacked images (DOCX)

    • Video of confocal slices from untreated MCF-7 cells (AVI)

    • Video of confocal slices from (−) CNTWZ treated MCF-7 cells (AVI)

    • Video of confocal slices from (+) CNTWZ treated MCF-7 cells (AVI)

    • Video of confocal slices from (±) CNTWZ treated MCF-7 cells (AVI)

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    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

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    This article is cited by 15 publications.

    1. Yuwen Wang, Andy Tay. Advances in Enantiomer-Dependent Nanotherapeutics. ACS Nano 2023, 17 (11) , 9850-9869. https://doi.org/10.1021/acsnano.3c02798
    2. Wei Gong, Masoud Kazem-Rostami, Florencia A. Son, Shengyi Su, Kira M. Fahy, Haomiao Xie, Timur Islamoglu, Yan Liu, J. Fraser Stoddart, Yong Cui, Omar K. Farha. Tröger’s Base Chemistry in Solution and in Zr(IV)-Based Metal–Organic Frameworks. Journal of the American Chemical Society 2022, 144 (49) , 22574-22581. https://doi.org/10.1021/jacs.2c08623
    3. Guangmin Li, Xihao Zhang, Xuening Fei, Jiafeng Li, Hongfei Liu, Wei Liu, Yang Yang, Bingjing Li, Mingrui Liu, Gaoling Yang, Ti Zhang. Chiral FA Conjugated CdTe/CdS Quantum Dots for Selective Cancer Ablation. ACS Nano 2022, 16 (8) , 12991-13001. https://doi.org/10.1021/acsnano.2c05517
    4. Guangmin Li, Jiayun Zheng, Jiafeng Li, Jiajia Kang, Xinyu Jin, Anning Guo, Zhibo Chen, Xuening Fei, Kaiyuan Wang, Hongfei Liu, Hongbin Zhao, Wei Liu, Gaoling Yang. Chiral quantum dots for bioapplications. Journal of Materials Chemistry C 2024, 12 (29) , 10825-10836. https://doi.org/10.1039/D4TC01979B
    5. Akanksha Dohare, Niranjan Chatterjee, Santosh K. Misra. In situ carbonization metamorphoses porous silica particles into biodegradable therapeutic carriers of lesser consequence on TGF-β1 mediated fibrosis. Nanoscale 2024, 16 (18) , 8843-8850. https://doi.org/10.1039/D4NR00123K
    6. Piyush Kumar, Santosh K. Misra. Color changing Redox Active Paper Stamps (CoRAPS) for quick and easy detection of bacterial infection. Biochemical Engineering Journal 2023, 198 , 109039. https://doi.org/10.1016/j.bej.2023.109039
    7. Meghan M. Watt, Parikshit Moitra, Zach Sheffield, Fatemeh Ostadhossein, Elizabeth A. Maxwell, Dipanjan Pan. A narrative review on the role of carbon nanoparticles in oncology. WIREs Nanomedicine and Nanobiotechnology 2023, 15 (2) https://doi.org/10.1002/wnan.1845
    8. Anupama Ojha, Sonali Jaiswal, Priyanka Bharti, Sarad Kumar Mishra. Nanoparticles and Nanomaterials-Based Recent Approaches in Upgraded Targeting and Management of Cancer: A Review. Cancers 2023, 15 (1) , 162. https://doi.org/10.3390/cancers15010162
    9. Ming Cheng, Wen Gong, Mingxiang Lu, Junkai Ma, Zhiyan Lu, Haibing Li. Engineering and Application of Pillar[6]arene Functionalized Chiral Surface in Selective Adsorption of R ‐Adrenaline . Chinese Journal of Chemistry 2022, 40 (8) , 925-930. https://doi.org/10.1002/cjoc.202100714
    10. Priyanka Ray, Parikshit Moitra, Dipanjan Pan. Emerging theranostic applications of carbon dots and its variants. VIEW 2022, 3 (2) https://doi.org/10.1002/VIW.20200089
    11. Zaihui Peng, Long Yuan, Juncheng XuHong, Hao Tian, Yi Zhang, Jun Deng, Xiaowei Qi. Chiral nanomaterials for tumor therapy: autophagy, apoptosis, and photothermal ablation. Journal of Nanobiotechnology 2021, 19 (1) https://doi.org/10.1186/s12951-021-00965-7
    12. Yoshimi Ichimaru, Koichi Kato, Yoshinori Okuno, Yoshihiro Yamaguchi, Wanchun Jin, Mikako Fujita, Masami Otsuka, Masanori Imai, Hiromasa Kurosaki. Design and synthesis of an anthranyl bridged optically active dinuclear iron(II)-ligand and evaluation of DNA-cleaving activity. Bioorganic & Medicinal Chemistry Letters 2021, 35 , 127782. https://doi.org/10.1016/j.bmcl.2021.127782
    13. Koichi Kato, Yoshimi Ichimaru, Yoshinori Okuno, Yoshihiro Yamaguchi, Wanchun Jin, Mikako Fujita, Masami Otsuka, Masanori Imai, Hiromasa Kurosaki. DNA-cleavage activity of the iron(II) complex with optically active ligands, meta- and para-xylyl-linked N’,N’-dipyridylmethyl-cyclohexane-1,2-diamine. Bioorganic & Medicinal Chemistry Letters 2021, 36 , 127834. https://doi.org/10.1016/j.bmcl.2021.127834
    14. Indrajit Srivastava, John S. Khamo, Subhendu Pandit, Parinaz Fathi, Xuedong Huang, Anleen Cao, Richard T. Haasch, Shuming Nie, Kai Zhang, Dipanjan Pan. Influence of Electron Acceptor and Electron Donor on the Photophysical Properties of Carbon Dots: A Comparative Investigation at the Bulk‐State and Single‐Particle Level. Advanced Functional Materials 2019, 29 (37) https://doi.org/10.1002/adfm.201902466
    15. Indrajit Srivastava, Dinabandhu Sar, Prabuddha Mukherjee, Aaron S. Schwartz-Duval, Zhaolu Huang, Camilo Jaramillo, Ana Civantos, Indu Tripathi, Jean Paul Allain, Rohit Bhargava, Dipanjan Pan. Enzyme-catalysed biodegradation of carbon dots follows sequential oxidation in a time dependent manner. Nanoscale 2019, 11 (17) , 8226-8236. https://doi.org/10.1039/C9NR00194H
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    ACS Applied Materials & Interfaces

    Cite this: ACS Appl. Mater. Interfaces 2018, 10, 44, 37886–37897
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acsami.8b15618
    Published October 9, 2018
    Copyright © 2018 American Chemical Society
    Request reuse permissions

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