Skip to main content
SpringerLink
Log in

Cell growth inhibitory effects of polyphenols with naphthalene skeleton against cisplatin-resistant ovarian cancer cells

  • Note
  • Published:
Applied Biological Chemistry Submit manuscript

Abstract

Cisplatin often shows the drug resistance which could limit the chemotherapeutic efficacy. Thus, it is necessary to develop anticancer agents against cisplatin-resistant cancer cells. To identify pharmacophores exhibiting the cell growth inhibitory effect against cisplatin-resistant A2780/Cis ovarian cancer cells, we prepared 35 synthetic polyphenols bearing naphthalene skeleton including naphthalenyl chalcones, naphthalenyl flavones, naphthalenyl flavanones, 4,5-dihydro-1H-pyrazol-3-yl)naphthalen-2-ols, naphthalen-1-yl-N-phenyl-4,5-dihydro-1H-pyrazole-1-carbothioamides, and 4,5-dihydro-1H-pyrazol-3-yl)naphthalen-1-ol. The correlation between their inhibitory effects and structural properties was evaluated using hologram quantitative structure activity relationship and comparative molecular field analysis. The pharmacophores derived here can lead us to design new polyphenols against the growth of cisplatin-resistant cells.

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

Fig. 1
Fig. 2

References

  1. Sudo T (2012) Molecular-targeted therapies for ovarian cancer: prospects for the future. Int J Clin Oncol 17:424–429

    Article  CAS  Google Scholar 

  2. McGuire WP, Hoskins WJ, Brady MF, Kucera PR, Partridge EE, Look KY, Clarke-Pearson DL, Davidson M (1996) Cyclophosphamide and cisplatin compared with paclitaxel and cisplatin in patients with stage III and stage IV ovarian cancer. N Engl J Med 334:1–6

    Article  CAS  Google Scholar 

  3. Galluzzi L, Vitale I, Michels J, Brenner C, Szabadkai G, Harel-Bellan A, Castedo M, Kroemer G (2014) Systems biology of cisplatin resistance: past, present and future. Cell Death Dis 5:e1257

    Article  CAS  Google Scholar 

  4. Koberle B, Tomicic MT, Usanova S, Kaina B (2010) Cisplatin resistance: preclinical findings and clinical implications. Biochim Biophys Acta 1806:172–182

    PubMed  Google Scholar 

  5. Usanova S, Piée-Staffa A, Sied U, Thomale J, Schneider A, Kaina B, Köberle B (2010) Cisplatin sensitivity of testis tumour cells is due to deficiency in interstrand-crosslink repair and low ERCC1-XPF expression. Mol Cancer 9:248

    Article  Google Scholar 

  6. Shin SY, Jung H, Ahn S, Hwang D, Yoon H, Hyun J, Yong Y, Cho HJ, Koh D, Lee YH, Lim Y (2014) Polyphenols bearing cinnamaldehyde scaffold showing cell growth inhibitory effects on the cisplatin-resistant A2780/Cis ovarian cancer cells. Bioorg Med Chem 22:1809–1820

    Article  CAS  Google Scholar 

  7. Yoon H, Ahn S, Park M, Kim DW, Kim SH, Koh D, Lim Y (2013) 1H and 13C NMR spectral assignments of chalcones bearing pyrazoline-carbothioamide groups. Magn Reson Chem 51:500–508

    Article  CAS  Google Scholar 

  8. Hwang D, Hyun J, Jo G, Koh D, Lim Y (2011) Synthesis and complete assignment of NMR data of 20 chalcones. Magn Reson Chem 49:41–45

    Article  CAS  Google Scholar 

  9. Hwang D, Jo G, Hyun J, Lee SD, Koh D, Lim Y (2012) Synthesis of methoxybenzoflavones and assignments of their NMR data. Magn Reson Chem 50:62–67

    Article  CAS  Google Scholar 

  10. Shin SY, Yoon H, Ahn S, Kim DW, Bae DH, Koh D, Lee YH, Lim Y (2013) Structural properties of polyphenols causing cell cycle arrest at G1 phase in HCT116 human colorectal cancer cell lines. Int J Mol Sci 14:16970–16985

    Article  Google Scholar 

  11. Jung Y, Shin SY, Yong Y, Jung H, Ahn S, Lee YH, Lim Y (2015) Plant-derived flavones as inhibitors of aurora B kinase and their quantitative structure-activity relationships. Chem Biol Drug Des 85:574–585

    Article  CAS  Google Scholar 

  12. Jung KY, Park J, Han YS, Lee YH, Shin SY, Lim Y (2017) Synthesis and biological evaluation of hesperetin derivatives as agents inducing apoptosis. Bioorg Med Chem 25:397–407

    Article  CAS  Google Scholar 

  13. Lee Y, Kim BS, Ahn S, Koh D, Lee YH, Shin SY, Lim Y (2016) Anticancer and structure-activity relationship evaluation of 3-(naphthalen-2-yl)-N,5-diphenyl-pyrazoline-1-carbothioamide analogs of chalcone. Bioorg Chem 68:166–176

    Article  CAS  Google Scholar 

  14. Cho M, Yoon H, Park M, Kim YH, Lim Y (2014) Flavonoids promoting HaCaT migration: I. Hologram quantitative structure-activity relationships. Phytomedicine 21:560–569

    Article  CAS  Google Scholar 

  15. Kim BS, Shin SY, Ahn S, Koh D, Lee YH, Lim Y (2017) Biological evaluation of 2-pyrazolinyl-1-carbothioamide derivatives against HCT116 human colorectal cancer cell lines and elucidation on QSAR and molecular binding modes. Bioorg Med Chem 25:5423–5432

    Article  CAS  Google Scholar 

  16. Rao SD, Pagidas K (2010) Epigallocatechin-3-gallate, a natural polyphenol, inhibits cell proliferation and induces apoptosis in human ovarian cancer cells. Anticancer Res 30:2519–2523

    CAS  PubMed  Google Scholar 

  17. Yang PY, Hu DN, Lin IC, Liu FS (2015) Butein shows cytotoxic effects and induces apoptosis in human ovarian cancer cells. Am J Chin Med 43:769–782

    Article  CAS  Google Scholar 

  18. Gao Y, Rankin GO, Tu Y, Chen YC (2016) Inhibitory effects of the four main theaflavin derivatives found in black tea on ovarian cancer cells. Anticancer Res 36(2):643–651

    CAS  PubMed  PubMed Central  Google Scholar 

  19. Tang JM, Min J, Li BS, Hong SS, Liu C, Hu M, Li Y, Yang J, Hong L (2016) Therapeutic effects of punicalagin against ovarian carcinoma cells in association with β-catenin signaling inhibition. Int J Gynecol Cancer 26:1557–1563

    Article  Google Scholar 

Download references

Acknowledgments

This study was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning (Grant No. NRF-2016R1D1A1A09919045), Republic of Korea. This paper was supported by the KU Research Professor Program of Konkuk University.

Author information

Authors and Affiliations

  1. Department of Biological Sciences, Konkuk University, Seoul, 05029, Republic of Korea

    Soon Young Shin

  2. Division of Bioscience and Biotechnology, BMIC, Konkuk University, Seoul, 05029, Republic of Korea

    Youngshim Lee, Jihyun Park, Doseok Hwang, Geunhyeong Jo & Yoongho Lim

  3. Department of Applied Chemistry, Dongduk Women’s University, Seoul, 02748, Republic of Korea

    Ji Hye Lee & Dongsoo Koh

Authors
  1. Soon Young Shin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Youngshim Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jihyun Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Doseok Hwang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Geunhyeong Jo
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ji Hye Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Dongsoo Koh
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Yoongho Lim
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yoongho Lim.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 948 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shin, S.Y., Lee, Y., Park, J. et al. Cell growth inhibitory effects of polyphenols with naphthalene skeleton against cisplatin-resistant ovarian cancer cells. Appl Biol Chem 61, 697–701 (2018). https://doi.org/10.1007/s13765-018-0403-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13765-018-0403-3

Keywords

Search

Navigation