Skip to main content
SpringerLink
Log in

Synthesis and Spectroscopic Studies of Phenanthroimidazole-Imine Derivatives and Evaluation of Their Antioxidant Activity

  • ORIGINAL ARTICLE
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

The phenanthroimidazole derivatives are used in the drug industry in large scale. In this study four new phenanthroimidazole-imine derivatives were synthesized and their spectroscopic studies as well as their antioxidant behaviors were examined. Structural analyses were made by FT-IR, 1H-NMR, 13C-NMR, LC-MS spectroscopy techniques. UV–vis absorption and emission spectroscopy techniques have been used to determine the photophysical characteristics of four newly synthesized phenanthroimidazoles. The maximum absorption and emission wavelengths, molar extinction coefficients (ε), singlet energy levels (Es), Stokes’ shift values (Δλ) of phenanthroimidazole-imine derivatives are given. Additionally, the antioxidant behavior of all compounds were investigated which the ascorbic acid used as standard molecule in present study.

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

Scheme 1
Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Gülçin İ (2012) Antioxidant activity of food constituents: an overview. Arch Toxicol 86:345–391

    Article  PubMed  Google Scholar 

  2. Youssef KM, El-Sherbeny MA, El-Shafie FS, Farag HA, Al-Deeb OA, Awadalla SA (2004) Synthesis of curcumin analogues as potential antioxidant cancer chemopreventive agents. Arch Pharm Med Chem 337:42–54

    Article  CAS  Google Scholar 

  3. Ghibu S, Richard C, Vergely C, Zeller M, Cottin Y, Rochette L (2009) Antioxidant properties of an endogenous thiol: alpha-lipoic acid, useful in the prevention of cardiovascular diseases. J Cardiovasc Pharmacol 54:391–398

    Article  CAS  PubMed  Google Scholar 

  4. Uttara B, Singh AV, Zamboni P, Mahajan RT (2009) Oxidative stress and neurodegenerative diseases: a review of upstream and downstream antioxidant therapeutic options. Curr Neuropharmacol 7:65–74

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Feng Y, Wang X (2012) Antioxidant therapies for Alzheimer’s disease. Oxid Med Cell Longev. https://doi.org/10.1155/2012/472932

    PubMed  PubMed Central  Google Scholar 

  6. Dias V, Junn E, Mouradian MM (2013) The role of oxidative stress in Parkinson’s disease. J Parkinsons Dis 3:461–491. https://doi.org/10.3233/JPD-130230

    CAS  PubMed  PubMed Central  Google Scholar 

  7. Nıeto N, Torres MI, FernáNdez MI, GıróN MD, RíOs A, SuáRez MD, Gıl A (2000) Experimental ulcerative colitis impairs antioxidant defense system in rat intestine. Dig Dis Sci 45:1820–1827

    Article  PubMed  Google Scholar 

  8. Masaki H (2010) Role of antioxidants in the skin: anti-aging effects. J Dermatol Sci 58:85–90

    Article  CAS  PubMed  Google Scholar 

  9. Halliwell B (1997) Antioxidants in human health and disease. Ann Rev Nutr 16:33–50

    Article  Google Scholar 

  10. Evans R, Miller NJ, Paganga Ne AG (1996) Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 20:933–956

    Article  Google Scholar 

  11. Sorrenti V, Salerno L, Di Giacomo C, Acquaviva R, Siracusa MA, Vanella A (2006) Imidazole derivatives as antioxidants and selective inhibitors of nNOS. Nitric Oxide 14:45–50

    Article  CAS  PubMed  Google Scholar 

  12. Estevão MS, Carvalho LC, Ribeiro D, Couto D, Freitas M, Gomes A, Ferreira LM, Fernandes E, Marques MMB (2010) Antioxidant activity of unexplored indole derivatives: synthesis and screening. Eur J Med Chem 45:4869–4878

    Article  PubMed  Google Scholar 

  13. Bubols GB, Vianna DR, Medina-Remón A, von Poser G, Lamuela-Ravento RM, Eifler-Lima VL, Garcia SC (2013) The antioxidant activity of coumarins and flavonoids. Mini Rev Med Chem 13:318–334

    CAS  PubMed  Google Scholar 

  14. Pietta PG (2000) Flavonoids as antioxidants. J Nat Prod 63:1035–1042

    Article  CAS  PubMed  Google Scholar 

  15. Liu J, Qiu J, Wang M, Wang L, Su L, Gao J, Gu Q, Xu J, Huang S-L, Gu L-Q, Huang Z-S, Li D (2014) Synthesis and characterization of 1H-phenanthro[9,10-d]imidazole derivatives as multifunctional agents for treatment of Alzheimer’s disease. Biochim Biophys Acta 1840:2886–2903

    Article  CAS  PubMed  Google Scholar 

  16. Chau A, Cote B, Ducharme Y, Frenette R, Friesen R, Gagnon M, Giroux A, Martins E, Yu H, Wu T (2008) 2-(Phenyl or heterocyclic)-1H-phenanthro[9,10-D]imidazoles as MPGES-1 inhibitors. US7442716 B2

  17. Côté B, Boulet L, Brideau C et al (2007) Substituted phenanthrene imidazoles as potent, selective, and orally active mPGES-1 inhibitors. Biorg Med Chem Lett 17:6816–6820

    Article  Google Scholar 

  18. Kieltyka R, Fakhoury J, Moitessier N, Sleiman HF (2008) Platinum phenanthroimidazole complexes as G-quadruplex DNA selective binders. Chem Eur J 14:1145–1154

    Article  CAS  PubMed  Google Scholar 

  19. Sendra JM, Sentandreu E, Navarro JL (2006) Reduction kinetics of the free stable radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) for determination of the antiradical activity of citrus juices. Eur Food Res Technol 223:615–624

    Article  CAS  Google Scholar 

  20. Kedare SB, Singh RP (2011) Genesis and development of DPPH method of antioxidant assay. J Food Sci Technol 48:412–422

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. Satapathy R, Wu YH, Lin HC (2012) Novel dithieno-benzo-imidazole-based Pb2+ sensors: substituent effects on sensitivity and reversibility. Chem Comm 48:5668–5670

    Article  CAS  PubMed  Google Scholar 

  22. Zheng K, Lin W, Tan L (2012) A phenanthtoimidazole-based fluorescent chemosensor for imaging hydrogen sulfide in living cells. Org Biomol Chem 10: 9683–9688

    Article  CAS  PubMed  Google Scholar 

  23. De Lange MCC, Thorn Leeson D, Van Kuijk KAB, Huizer AH, Vaxma CAGO (1993) On the source of the anomalous fluorescence of 4- (dialkylamino) benzonitrile in aromatic hydrocarbon solvents: the role of exciplexes. Chem Phys 174:425–440

    Article  Google Scholar 

  24. Plotnikov VG, Sazhnikov VA, Alfimov MV (2007) Intermolecular interactions and spectral and luminescent properties of optical molecular sensors. High Energy Chem 41:299–311

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Funding for this research was provided by the project 2013-096, Scientific Research Funds of Manisa Celal Bayar University

Author information

Authors and Affiliations

  1. Faculty of Arts and Science, Department of Chemistry, Manisa Celal Bayar University, Muradiye, Manisa, 45040, Turkey

    Sibel Gülle

  2. Faculty of Engineering, Department of Metallurgy and Materials Engineering, Manisa Celal Bayar University, Muradiye, Manisa, 45040, Turkey

    Seçil Çelik Erbaş

  3. Faculty of Science, Department of Biology, Ege University, 35100,, Bornova, Izmir, Turkey

    Ataç Uzel

Authors
  1. Sibel Gülle
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Seçil Çelik Erbaş
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ataç Uzel
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Sibel Gülle.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gülle, S., Erbaş, S.Ç. & Uzel, A. Synthesis and Spectroscopic Studies of Phenanthroimidazole-Imine Derivatives and Evaluation of Their Antioxidant Activity. J Fluoresc 28, 217–223 (2018). https://doi.org/10.1007/s10895-017-2184-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-017-2184-1

Keywords

Search

Navigation