Skip to main content
SpringerLink
Log in

Apoptotic effects of 1,5-bis-(5-nitro-2-furanyl)-1, K]4-pentadien-3-one on Drosophila SL2 cells

  • Original Paper
  • Published:
Molecular & Cellular Toxicology Aims and scope Submit manuscript

Abstract

In recent years, concerns over the potential impact of synthetic pesticides on the environment have promoted the research and development of environmentally friendly “green” pesticides. In the current study, we utilized a green biomimetic insecticide, 1,5-bis-(5-nitro-2-furanyl)-1,4-pentadien-3-one (compound C), to examine its cytotoxicity on an insect cell line, Drosophila melanogaster (SL2). Results from MTT assay showed cells treated with 100 µM of compound C for 48 h significantly inhibited the growth of SL2 cells by 87.71±0.96%. We subsequently attempted to illustrate the act on mechanism of compound C at the cellular level and found that it initiated apoptosis through a mitochondrial-dependent mechanism that increased the activity of caspase-3 and altered the cell cycle. These results suggest that the green biomimetic insecticide, compound C, is a novel and potent inducer of insect cell apoptosis.

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. Gavrilescu, M. Fate of pesticides in the environment and its bioremediation. Eng Life Sci 5:497–526 (2005).

    Article  CAS  Google Scholar 

  2. Crouse, G. D. Pesticide leads from nature. Chem Tech 28:36–45 (1998).

    CAS  Google Scholar 

  3. Liu, C. L. & Li, Z. M. Agrochemicals discovered and developed from natural leads-fungicides. Pesticides 42:1–4 (2003).

    Google Scholar 

  4. Gao, P., Hou, T. P., Gao, R., Cui, Q. & Liu, S. G. Ac-tivity of the botanical aphicides 1,5-diphenyl-1-penta-none and 1,5-diphenyl-2-penten-1-one on two species of aphididnae. Pest Manag Sci 57:307–310 (2001).

    Article  CAS  PubMed  Google Scholar 

  5. Hou, T. P., Cui, Q., Xiang, R. L., Hou, R. T. & Liu, S. G. Study on extraction isolation of killing aphid compo-nents from Stellera chamaejasme L.. J Sichuan Univ: Natural Science Edition 38:743–747 (2001).

    Google Scholar 

  6. Hou, T. P., Cui, Q., Chen, S. H., Hou, R. T. & Liu, S. G. New compounds against aphids from Stellera chamae-jasme L.. Chin J Org Chem 22:67–70 (2002).

    CAS  Google Scholar 

  7. Cui, Z. N., Zhang, L. H., Ling, J. & Yang, Y. Synthesis, insecticidal activity and 3D-QSAR studies on diacylhy-drazine derivatives containing furan. Chin J Org Chem 10:1482–1491 (2010).

    Google Scholar 

  8. Cao, M. et al. Synthesis and biological activities of perfluoroisopropyl-substituted furanacyl thiourea com-pounds. Agrochemicals 51:488–490 (2012).

    CAS  Google Scholar 

  9. Hu, Y. G. et al. Synthesis and antitumor activity of some 2-Amino-furo(2,3-d)-yrimidin-4(3H)-one deriva-tives. Chin J Org Chem 32:1468–1472 (2012).

    Article  CAS  Google Scholar 

  10. Chen, L., Wang, X. L., Lu, T. & Hou, T. P. Lead opti-mization and insecticidal activity of analogues of da-phneolone isolated from Stellera chamaejasme L.. Pest Manag Sci 63:928–934 (2007).

    Article  CAS  PubMed  Google Scholar 

  11. Lu, T., Chen, L. & Hou, T. P. Synthesis and structure-ac-tivity study of botanical aphicides 1,5-diphenyl-1-pen-tanone analogues. Pestic Biochem Physiol 89:60–64 (2007).

    Article  Google Scholar 

  12. Jin, H. Structural optimization and bioactivities of daph-neone analogues. in: Sichuan Univ, Ph.D. (2009).

    Google Scholar 

  13. Kumarswamy, R., Seth, R. K., Dwarakanath, B. S. & Chandna, S. Mitochondrial regulation of insect cell apoptosis: evidence for permeability transition pore-in-dependent cytochrome-c release in the Lepidopteran Sf9 cells. Int J Biochem Cell 41:1430–1440 (2009).

    Article  CAS  Google Scholar 

  14. Scarlett, J. L. et al. Changes in mitochondrial mem-brane potential during stauros porine-induced apopto-sis in jurkat cells. FEBS Lett 475:267–272 (2000).

    Article  CAS  PubMed  Google Scholar 

  15. Salehzadeh, A. et al. The effects of phytochemical pes-ticides on the growth of cultured invertebrate and verte-brate cells. Pest Manag Sci 58:268–276 (2002).

    Article  CAS  PubMed  Google Scholar 

  16. William, G. & Rocktown, N. J. 2,2-dimethyl-2,3-dihy-drobenzofuranyl-7-n-methylcarbamate, US 3474171 A (1969).

    Google Scholar 

  17. Motohiro, T., Shinzo, K., Ikuya, O., Kathleen, A. D. & John, E. C. Potency and selectivity of trifluoroacetylim-ino and pyrazinoylimino nicotinic insecticides and their fit at a unique binding site niche. J Med Chem 51:4213–4218 (2008).

    Article  Google Scholar 

  18. Chen, L. et al. Synthesis and biological activity of tong-haosu analogs containing phenoxy-phenyl moiety. Chin J Chem 22:984–989 (2004).

    Article  CAS  Google Scholar 

  19. Lorraine, M. Studying stress: the importance of organ-ism-level responses. Ecol Appl 9:431–440 (1999).

    Article  Google Scholar 

  20. Smagghe, G., Goodman, C. L. & Stanley, D. Insect cell culture and applications to research and pest manage-ment. In Vitro Cell Dev Biol-Animal 45:93–105 (2009).

    Article  Google Scholar 

  21. Francesca, F., Fiorenza, M. & Giuseppina, M. Cytotox-icity induced by nivalenol, deoxyivaleol, and fumonisin B1 in the SF-9 insect cell line. In Vitro Cell Dev Bi-ol-Animal 40:166–171 (2004).

    Article  Google Scholar 

  22. Zhang, X. G., Tao, K. & Hou, T. P. Investigation of 1-(4-morpholinophenyl)-3-(4-fluorophenyl)-propenone and 1-(4-morpholinophenyl)-3-(3-fluorophenyl)-pro-penone as new apoptosis inducers on Spodoptera frugiperda (Sf9) cells. Toxicol Mech Methods 22:315–320 (2012).

    Article  PubMed  Google Scholar 

  23. Murray, A. W. Revisiting the cell cycle: cyclins revisit-ed. Cell 116:221–234 (2004).

    Article  CAS  PubMed  Google Scholar 

  24. Mossman, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cy-totoxicity assays. J Immunol Methods 65:55–63 (1983).

    Article  Google Scholar 

  25. Wang, J., Li, X. R., Liu, Y. B. & Zhao, X. Salt stress induces programmed cell death in Thellungiella halophila suspension-cultured cells. J Plant Physiol 167:1145–1151 (2010).

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Key laboratory of Bio-resource and eco-environment of Ministry of education, College of life Sciences, Sichuan University, Chengdu, 610064, China

    Yuan-Hang Ren, Hong Jin, Ke Tao & Tai-Ping Hou

Authors
  1. Yuan-Hang Ren
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hong Jin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ke Tao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tai-Ping Hou
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ke Tao.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ren, YH., Jin, H., Tao, K. et al. Apoptotic effects of 1,5-bis-(5-nitro-2-furanyl)-1, K]4-pentadien-3-one on Drosophila SL2 cells. Mol. Cell. Toxicol. 11, 187–192 (2015). https://doi.org/10.1007/s13273-015-0017-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13273-015-0017-3

Keywords

Search

Navigation