Electrostatically Self-assembled Quinazoline-based Anticancer Drugs on Negatively-charged Nanodiamonds for Overcoming the Chemoresistances in Lung Cancer Cells

  • Anh Thu Ngoc Lam
  • Jin-Ha Yoon
  • Nguyen Hoang Ly
  • Sang-Woo Joo
Original Article
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Abstract

The nanodiamond (ND) conjugates of gefitinib (GF) and erlotinib (EL) were assembled for in vitro lung cancer treatments. The carboxylate infrared bands along with the negative surface charge of -28.3 (±2.1) mV were found efficient to conjugate the nitrogen-containing quinazoline ring drugs, due to the electrostatic interactions, resulting from the surface changes to -12.0 (±1.2) mV and -9.1 (±1.2) mV after adsorption of GF and EL on NDs, respectively. The physicochemical properties of NDs were characterized by transmission electron microcopy, X-ray diffraction, X-ray photoelectron, infrared and Raman spectroscopic tools. The size distributions of NDs after the self-assembly of GF and EL could be checked by dynamic light scattering measurements. The uptake of NDs in cancer cells was estimated by fluorescence microscopy. Cell viability appeared to decrease by 30-50% at 50 and 100 nM of GF and EL, respectively, after the treatment of PEG-assembled NDs compared to the cases using free drugs. Our ND conjugates may be potentially useful for overcoming the chemoresistances in lung cancer cells.

Keywords

Nanodiamonds Quinazoline Electrostatic interaction In vitro cell viability Lung cancer cells Drug resistance 

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References

  1. 1.
    Lim, T., Lee, S.Y., Yang, J., Hwang, S.Y. & Ahn, Y. Microfluidic biochips for simple impedimetric detection of thrombin based label-free DNA aptamers. Bio-Chip J. 11, 109–115 (2017).Google Scholar
  2. 2.
    Pyun, J.-C., Jose, J. & Park, M. Development of a wash-free immunoassay using Escherichia coli cells with autodisplayed Z-domains. Analyst 142, 1720–1728 (2017).CrossRefGoogle Scholar
  3. 3.
    Jeon, H., Lee, M., Jang, W. & Kwon, Y. Intein-mediated protein engineering for biosensor fabrication. Bio-Chip J. 10, 277–287 (2016).Google Scholar
  4. 4.
    Park, M., Jung, H., Jeong, Y. & Jeong, K.-H. Plasmonic schirmer strip for human tear-based gouty arthritis diagnosis using surface-enhanced Raman scattering, ACS Nano 11, 438–443 (2017).CrossRefGoogle Scholar
  5. 5.
    Lim, D.G. et al. Combinatorial nanodiamond in pharmaceutical and biomedical applications. Int. J. Pharm. 514, 41–51 (2016).CrossRefGoogle Scholar
  6. 6.
    Moore, L. et al. Biocompatibility assessment of detonation nanodiamond in non-human primates and rats using histological, hematologic, and urine analysis. ACS Nano 10, 7385–7400 (2016).CrossRefGoogle Scholar
  7. 7.
    Bertrand, J.R. et al. Plasma hydrogenated cationic detonation nanodiamonds efficiently deliver to human cells in culture functional siRNA targeting the Ewing sarcoma junction oncogene. Biomaterials 45, 93–98 (2015).CrossRefGoogle Scholar
  8. 8.
    Wang, D., Li, Y., Tian, Z., Cao, R. & Yang, B. Transferrin-conjugated nanodiamond as an intracellular transporter of chemotherapeutic drug and targeting therapy for cancer cells. Ther. Deliv. 5, 511–524 (2014).CrossRefGoogle Scholar
  9. 9.
    Lam, R. & Ho, D. Nanodiamonds as vehicles for systemic and localized drug delivery. Expert. Opin. Drug Deliv. 6, 883–895 (2009).CrossRefGoogle Scholar
  10. 10.
    Gibson, N.M., Luo, T.J.M., Shenderova, O., Koscheev, A.P. & Brenner, D.W. Electrostatically mediated adsorption by nanodiamond and nanocarbon particles. J. Nanopart. Res. 14, 700 (2012).CrossRefGoogle Scholar
  11. 11.
    Xiao, J. et al. Nanodiamonds-mediated doxorubicin nuclear delivery to inhibit lung metastasis of breast cancer. Biomaterials 34, 9648–9656 (2013).CrossRefGoogle Scholar
  12. 12.
    Wang, D. et al. PEGylated nanodiamond for chemotherapeutic drug delivery. Diam. Relat. Mater. 36, 26–34 (2013).CrossRefGoogle Scholar
  13. 13.
    Liu, K.K. et al. Covalent linkage of nanodiamond-paclitaxel for drug delivery and cancer therapy. Nanotechnology 21, 315106 (2010).CrossRefGoogle Scholar
  14. 14.
    Solarska-Ściuk, K. et al. Effect of functionalized and non-functionalized nanodiamond on the morphology and activities of antioxidant enzymes of lung epithelial cells (A549). Chem. Biol. Interact. 222, 135–147 (2014).CrossRefGoogle Scholar
  15. 15.
    Chu, H.L. et al. Development of a growth-hormoneconjugated nanodiamond complex for cancer therapy. ChemMedChem 9, 1023–1029 (2014).CrossRefGoogle Scholar
  16. 16.
    Chang, C.C. et al. Laser induced popcornlike conformational transition of nanodiamond as a nanoknife. Appl. Phys. Lett. 93, 033905 (2008).CrossRefGoogle Scholar
  17. 17.
    Kaur, R. & Badea, I. Nanodiamonds as novel nanomaterials for biomedical applications: drug delivery and imaging systems. Int. J. Nanomed. 8, 203–220 (2013).CrossRefGoogle Scholar
  18. 18.
    Zhu, Y. et al. The biocompatibility of nanodiamonds and their application in drug delivery systems. Theranostics 2, 302–312 (2012).CrossRefGoogle Scholar
  19. 19.
    Mochalin, V.N. et al. Adsorption of drugs on nanodiamond: toward development of a drug delivery platform. Mol. Pharm. 10, 3728–3735 (2013).CrossRefGoogle Scholar
  20. 20.
    Brugger, W. & Thomas, M. EGFR-TKI resistant nonsmall cell lung cancer (NSCLC): new developments and implications for future treatment. Lung Cancer 77, 2–8 (2012).CrossRefGoogle Scholar
  21. 21.
    Sharma, S.V., Bell, D.W., Settleman, J. & Haber, D.A. Epidermal growth factor receptor mutations in lung cancer. Nat. Rev. Cancer 7, 169–181 (2007).CrossRefGoogle Scholar
  22. 22.
    Nobili, S., Landini, I., Mazzei, T. & Mini, E. Overcoming tumor multidrug resistance using drugs able to evade P-glycoprotein or to exploit its expression. Med. Res. Rev. 32, 1220–1262 (2012).CrossRefGoogle Scholar
  23. 23.
    Lam, A.T.N. et al. Adsorption and desorption of tyrosine kinase inhibitor erlotinib on gold nanoparticles. J. Colloids Interface Sci. 425, 96–101 (2014).CrossRefGoogle Scholar
  24. 24.
    Lam, A.T.N. et al. Colloidal gold nanoparticle conjugates of gefitinib. Col. Surf. B 123, 61–67 (2014).CrossRefGoogle Scholar
  25. 25.
    Xiao, J. et al. Nanodiamonds-mediated doxorubicin nuclear delivery to inhibit lung metastasis of breast cancer. Biomaterials 34, 9648–9656 (2013).CrossRefGoogle Scholar
  26. 26.
    Li, W.M., Mayer, L.D. & Bally, M.B. Prevention of antibody-mediated elimination of ligand-targeted liposomes by using poly(ethylene glycol)-modified lipids. J. Pharmacol. Exp. Ther. 300, 976–983 (2002).CrossRefGoogle Scholar
  27. 27.
    Varsányi, G. Assignments for vibrational spectra of seven hundred benzene derivatives. Halsted Press Book 1, 27–28 (1974).Google Scholar
  28. 28.
    Mochalin, V.N., Shenderova, O., Ho, D. & Gogotsi, Y. The properties and applications of nanodiamonds. Nat. Nanotechnol. 7, 11–23 (2012).CrossRefGoogle Scholar
  29. 29.
    Ferrari, A.C. & Robertson, J. Raman spectroscopy of amorphous, nanostructured, diamond-like carbon, and nanodiamond. Phil. Trans. R. Soc. Lond. A 362, 2477–2512 (2004).CrossRefGoogle Scholar
  30. 30.
    Nguyen, T., Tekrony, A., Yaehne, K. & Cramb, D.T. Designing a better theranostic nanocarrier for cancer applications. Nanomedicine 9, 2371–2386 (2014).CrossRefGoogle Scholar
  31. 31.
    Jeong, S. et al. Low-toxicity chitosan gold nanoparticles for small hairpin RNA delivery in human lung adenocarcinoma cells. J. Mater. Chem. 21, 13853–13859 (2011).CrossRefGoogle Scholar
  32. 32.
    Kim, H. et al. Multiscale simulation as a framework for the enhanced design of nanodiamond-polyethylenimine-based gene delivery. J. Phys. Chem. Lett. 3, 3791–3797 (2012).CrossRefGoogle Scholar
  33. 33.
    Fröhlich, E. The role of surface charge in cellular uptake and cytotoxicity of medical nanoparticles. Int. J. Nanomed. 7, 5577–5591 (2012).CrossRefGoogle Scholar
  34. 34.
    Choi, S.Y. et al. Cellular uptake and cytotoxicity of positively charged chitosan gold nanoparticles in human lung adenocarcinoma cells. J. Nanopart. Res. 14, 1234 (2012).CrossRefGoogle Scholar
  35. 35.
    Reina, G. et al. Rhodamine/nanodiamond as a system model for drug carrier. J. Nanosci. Nanotechnol. 15, 1022–1029 (2015).CrossRefGoogle Scholar
  36. 36.
    Kemnitz, K., Tamai, N., Yamazaki, I., Nakashima, N. & Yoshihara, K. Fluorescence decays and spectral properties of rhodamine B in submono-, mono-, and multilayer systems. J. Phys. Chem. 90, 5094–5101 (1986).CrossRefGoogle Scholar
  37. 37.
    Van der Auweraer, M., Verschuere, B. & De Schryver, F.C. Absorption and fluorescence properties of rhodamine B derivatives forming Langmuir-Blodgett films. Langmuir 4, 583–588 (1988).CrossRefGoogle Scholar
  38. 38.
    Man, H.B. et al. Synthesis of nanodiamond-daunorubicin conjugates to overcome multidrug chemoresistance in leukemia. Nanomedicine 10, 359–369 (2014).CrossRefGoogle Scholar
  39. 39.
    Coldren, C.D. et al. Baseline gene expression predicts sensitivity to gefitinib in non-small cell lung cancer cell lines. Mol. Cancer Res. 4, 521–528 (2006).CrossRefGoogle Scholar
  40. 40.
    Perevedentseva, E. et al. Nanodiamond internalization in cells and the cell uptake mechanism. J. Nanoparticle. Res. 15, 1834 (2013).CrossRefGoogle Scholar
  41. 41.
    Choi, S.Y. et al. In vitro toxicity of serum protein-adsorbed citrate-reduced gold nanoparticles in human lung adenocarcinoma cells. Toxicology In Vitro 26, 229–237 (2012).CrossRefGoogle Scholar
  42. 42.
    Sadauskas, E. et al. Kupffer cells are central in the removal of nanoparticles from the organism. Part. Fibre Toxicol. 4, 10 (2007).CrossRefGoogle Scholar
  43. 43.
    Chol, H.S. et al. Renal clearance of quantum dots. Nat. Biotechnol. 25, 1165–1170 (2007).CrossRefGoogle Scholar

Copyright information

© The Korean BioChip Society and Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  • Anh Thu Ngoc Lam
    • 1
  • Jin-Ha Yoon
    • 1
  • Nguyen Hoang Ly
    • 1
  • Sang-Woo Joo
    • 1
    • 2
  1. 1.Department of ChemistrySoongsil UniversitySeoulRepublic of Korea
  2. 2.Department of Information Communication, Materials Engineering, Chemistry Convergence TechnologySoongsil UniversitySeoulRepublic of Korea

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