Skip to main content
SpringerLink
Log in

Novel polyzwitterion shell with adaptable surface chemistry engineered to enhance anti-fouling and intracellular imaging of detonation nanodiamonds under tumor pHe

  • Research Article
  • Published:
Frontiers of Materials Science Aims and scope Submit manuscript

Abstract

In this work, zwitterionic polymer (polyzwitterion) coating nanodiamonds (ND) with tumorous pH responsiveness were prepared for efficient application of commercial NDs in tumor cells imaging. Poly(carboxybetaine methacrylate) was firstly grafted on the pristine NDs (PCBMA-@-NDs) by surface-initiated reversible addition-fragmentation chain transfer (RAFT) polymerization. To achieve pH responsiveness and activated interaction with tumor cells, PCBMA-@-NDs were subsequently modified with benzene sulfonamide (PCBSA-@-NDs) via one step carbodiimide chemistry. The surface polymer functionalization was characterized by FTIR, 1H NMR and TGA, and PCBMA-@-NDs and PCBSA-@-NDs showed great dispersibility, enhanced fluorescence intensity and excellent antifouling property in contrast to pristine NDs. Moreover, PCBSA-@-NDs was able to switch zwitterionic surface (at pH 7.4) reversibly into positive charge (at pH 6.5) via protonated or deprotonated acylsulfonamide. As expected, PCBSA-@-NDs demonstrated higher cell affinity and better imaging performance than those of zwitterionic NDs at tumor slight acid environment, proven by fluorescence microscopy and flow cytometry. Overall, we provide a feasible and valuable strategy to construct smart NDs, thus encouraging the application of cost-effective fluorescence nanomaterials in biomedical fields.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Nam J, Won N, Bang J, et al. Surface engineering of inorganic nanoparticles for imaging and therapy. Advanced Drug Delivery Reviews, 2013, 65(5): 622–648

    Article  CAS  Google Scholar 

  2. Chang S L Y, Reineck P, Williams D, et al. Dynamic self-assembly of detonation nanodiamond in water. Nanoscale, 2020, 12(9): 5363–5367

    Article  CAS  Google Scholar 

  3. Patel K D, Singh R K, Kim H W. Carbon-based nanomaterials as an emerging platform for theranostics. Materials Horizons, 2019, 6(3): 434–469

    Article  CAS  Google Scholar 

  4. Radtke M, Bernardi E, Slablab A, et al. Nanoscale sensing based on nitrogen vacancy centers in single crystal diamond and nanodiamonds: achievements and challenges. Nano Futures, 2019, 3(4): 042004

    Article  CAS  Google Scholar 

  5. Mochalin V N, Shenderova O, Ho D, et al. The properties and applications of nanodiamonds. Nature Nanotechnology, 2012, 7(1): 11–23

    Article  CAS  Google Scholar 

  6. Sotoma S, Akagi K, Hosokawa S, et al. Comprehensive and quantitative analysis for controlling the physical/chemical states and particle properties of nanodiamonds for biological applications. RSC Advances, 2015, 5(18): 13818–13827

    Article  CAS  Google Scholar 

  7. Passeri D, Rinaldi F, Ingallina C, et al. Biomedical applications of nanodiamonds: An overview. Journal of Nanoscience and Nanotechnology, 2015, 15(2): 972–988

    Article  CAS  Google Scholar 

  8. Zhu Y, Li J, Li W, et al. The biocompatibility of nanodiamonds and their application in drug delivery systems. Theranostics, 2012, 2(3): 302–312

    Article  CAS  Google Scholar 

  9. Reina G, Zhao L, Bianco A, et al. Chemical functionalization of nanodiamonds: Opportunities and challenges ahead. Angewandte Chemie International Edition, 2019

  10. Tinwala H, Wairkar S. Production, surface modification and biomedical applications of nanodiamonds: A sparkling tool for theranostics. Materials Science & Engineering C: Materials for Biological Applications, 2019, 97: 913–931

    Article  CAS  Google Scholar 

  11. Boudou J P, David M O, Joshi V, et al. Hyperbranched polyglycerol modified fluorescent nanodiamond for biomedical research. Diamond and Related Materials, 2013, 38: 131–138

    Article  CAS  Google Scholar 

  12. Zhao J, Lu M, Lai H, et al. Delivery of amonafide from fructose-coated nanodiamonds by oxime ligation for the treatment of human breast cancer. Biomacromolecules, 2018, 19(2): 481–489

    Article  CAS  Google Scholar 

  13. Lu M, Wang Y K, Zhao J, et al. PEG grafted-nanodiamonds for the delivery of gemcitabine. Macromolecular Rapid Communications, 2016, 37(24): 2023–2029

    Article  CAS  Google Scholar 

  14. Wang D, Tong Y, Li Y, et al. PEGylated nanodiamond for chemotherapeutic drug delivery. Diamond and Related Materials, 2013, 36: 26–34

    Article  Google Scholar 

  15. Chen B, Zhang Y, Zhang J, et al. PEGylated polyvinylidene fluoride membranes via grafting from a graphene oxide additive for improving permeability and antifouling properties. RSC Advances, 2019, 9(32): 18688–18696

    Article  CAS  Google Scholar 

  16. Moore E, Delalat B, Vasani R, et al. Surface-initiated hyper-branched polyglycerol as an ultralow-fouling coating on glass, silicon, and porous silicon substrates. ACS Applied Materials & Interfaces, 2014, 6(17): 15243–15252

    Article  CAS  Google Scholar 

  17. Shiraishi K, Yokoyama M. Toxicity and immunogenicity concerns related to PEGylated-micelle carrier systems: a review. Science and Technology of Advanced Materials, 2019, 20(1): 324–336

    Article  CAS  Google Scholar 

  18. Kim H, Man H B, Saha B, et al. Multiscale Simulation as a framework for the enhanced design of nanodiamond-polyethyle-nimine-based gene delivery. The Journal of Physical Chemistry Letters, 2012, 3(24): 3791–3797

    Article  CAS  Google Scholar 

  19. Xu D, Liu M, Zhang Q, et al. Preparation of water dispersible and biocompatible nanodiamond-poly (amino acid) composites through the ring-opening polymerization. Materials Science & Engineering C: Materials for Biological Applications, 2018, 91: 496–501

    Article  CAS  Google Scholar 

  20. Chen H B, Gu Z J, An H W, et al. Precise nanomedicine for intelligent therapy of cancer. Science China: Chemistry, 2018, 61(12): 1503–1552

    Article  CAS  Google Scholar 

  21. Zhai S, Ma Y, Chen Y, et al. Synthesis of an amphiphilic block copolymer containing zwitterionic sulfobetaine as a novel pH-sensitive drug carrier. Polymer Chemistry, 2014, 5(4): 1285–1297

    Article  CAS  Google Scholar 

  22. Merz V, Lenhart J, Vonhausen Y, et al. Zwitterion-functionalized detonation nanodiamond with superior protein repulsion and colloidal stability in physiological media. Small, 2019, 15(48): 1901551

    Article  CAS  Google Scholar 

  23. Park J, Nam J, Won N, et al. Compact and stable quantum dots with positive, negative, or zwitterionic surface: specific cell interactions and non-specific adsorptions by the surface charges. Advanced Functional Materials, 2011, 21(9): 1558–1566

    Article  CAS  Google Scholar 

  24. Lim E K, Chung B H, Chung S J. Recent advances in pH-sensitive polymeric nanoparticles for smart drug delivery in cancer therapy. Current Drug Targets, 2018, 19(4): 300–317

    Article  CAS  Google Scholar 

  25. Stuart M A C, Huck W T S, Genzer J, et al. Emerging applications of stimuli-responsive polymer materials. Nature Materials, 2010, 9(2): 101–113

    Article  Google Scholar 

  26. Mura S, Nicolas J, Couvreur P. Stimuli-responsive nanocarriers for drug delivery. Nature Materials, 2013, 12(11): 991–1003

    Article  CAS  Google Scholar 

  27. Piao J G, Gao F, Li Y, et al. pH-sensitive zwitterionic coating of gold nanocages improves tumor targeting and photothermal treatment efficacy. Nano Research, 2018, 11(6): 3193–3204

    Article  CAS  Google Scholar 

  28. Abel B A, Sims M B, McCormick C L. Tunable pH- and CO2-responsive sulfonamide-containing polymers by RAFT polymerization. Macromolecules, 2015, 48(16): 5487–5495

    Article  CAS  Google Scholar 

  29. Mizuhara T, Saha K, Moyano D F, et al. Acylsulfonamide-functionalized zwitterionic gold nanoparticles for enhanced cellular uptake at tumor pH. Angewandte Chemie International Edition, 2015, 54(22): 6567–6570

    Article  CAS  Google Scholar 

  30. Ranneh A H, Takemoto H, Sakuma S, et al. An ethylenediamine-based switch to render the polyzwitterion cationic at tumorous pH for effective tumor accumulation of coated nanomaterials. Angewandte Chemie International Edition, 2018, 57(18): 5057–5061

    Article  CAS  Google Scholar 

  31. Zhang Z, Chen S, Jiang S. Dual-functional biomimetic materials: Nonfouling poly(carboxybetaine) with active functional groups for protein immobilization. Biomacromolecules, 2006, 7(12): 3311–3315

    Article  CAS  Google Scholar 

  32. Jiang S, Cao Z. Ultralow-fouling, functionalizable, and hydrolyzable zwitterionic materials and their derivatives for biological applications. Advanced Materials, 2010, 22(9): 920–932

    Article  CAS  Google Scholar 

  33. Gutch P K, Singh R, Shaik M. Polymeric decontaminant: N,N-dichloro poly 2,6-dimethyl 1, 4-phenylene oxide sulfonamide: synthesis, characterization and efficacy against simulant of sulfur mustard. Journal of Polymer Materials, 2011, 28(1): 5–13

    CAS  Google Scholar 

  34. Neagu V, Vasiliu S, Racovita S. Adsorption studies of some inorganic and organic salts on new zwitterionic ion exchangers with carboxybetaine moieties. Chemical Engineering Journal, 2010, 162(3): 965–973

    Article  CAS  Google Scholar 

  35. Chen J, Liu M, Huang Q, et al. Facile preparation of fluorescent nanodiamond-based polymer composites through a metal-free photo-initiated RAFT process and their cellular imaging. Chemical Engineering Journal, 2018, 337: 82–90

    Article  CAS  Google Scholar 

  36. Abraham S, So A, Unsworth L D. Poly(carboxybetaine methacrylamide)-modified nanoparticles: a model system for studying the effect of chain chemistry on film properties, adsorbed protein conformation, and clot formation kinetics. Biomacromolecules, 2011, 12(10): 3567–3580

    Article  CAS  Google Scholar 

  37. Hui Y Y, Cheng C L, Chang H C. Nanodiamonds for optical bioimaging. Journal of Physics D: Applied Physics, 2010, 43(37): 374021

    Article  Google Scholar 

  38. Kang R H, Baek S W, Ryu T K, et al. Fabrication of blue-fluorescent nanodiamonds modified with alkyl isocyanate for cellular bioimaging. Colloids and Surfaces B: Biointerfaces, 2018, 167: 191–196

    Article  CAS  Google Scholar 

  39. Sethuraman V A, Na K, Bae Y H. pH-responsive sulfonamide/PEI system for tumor specific gene delivery: An in vitro study. Biomacromolecules, 2006, 7(1): 64–70

    Article  CAS  Google Scholar 

  40. Wang Z, Ma G, Zhang J, et al. Surface protonation/deprotonation controlled instant affinity switch of nano drug vehicle (NDV) for pH triggered tumor cell targeting. Biomaterials, 2015, 62: 116–127

    Article  CAS  Google Scholar 

  41. Ou H, Cheng T, Zhang Y, et al. Surface-adaptive zwitterionic nanoparticles for prolonged blood circulation time and enhanced cellular uptake in tumor cells. Acta Biomaterialia, 2018, 65: 339–348

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge the financial support from the National Natural Science Foundation of China (Project U1704150) and the Scientific and Technological Projects of Henan province (182102410017).

Author information

Authors and Affiliations

  1. School of Chemical Engineering & Pharmaceutics, Henan University of Science & Technology, Luoyang, 471023, China

    Biyu Zhou, Junbo Li, Binzhong Lu, Leitao Zhang, Ju Liang & Xin Li

  2. School of Medicine, Henan University of Science & Technology, Luoyang, 471023, China

    Wenlan Wu

  3. College of Food and Bioengineering, Henan University of Science & Technology, Luoyang, 471023, China

    Junpeng Yi

Authors
  1. Biyu Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Junbo Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Binzhong Lu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Wenlan Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Leitao Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ju Liang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Junpeng Yi
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Xin Li
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Junbo Li.

Additional information

Disclosure of potential conflicts of interests

The authors declare no potential conflicts of interests.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhou, B., Li, J., Lu, B. et al. Novel polyzwitterion shell with adaptable surface chemistry engineered to enhance anti-fouling and intracellular imaging of detonation nanodiamonds under tumor pHe. Front. Mater. Sci. 14, 402–412 (2020). https://doi.org/10.1007/s11706-020-0527-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11706-020-0527-3

Keywords

Search

Navigation