Skip to main content
SpringerLink
Log in

Synthesis, Photophysical Properties, and Cytotoxicity of Rhodamine Based Fluorescent Probes

  • Published:
Russian Journal of Bioorganic Chemistry Aims and scope Submit manuscript

Abstract

Rhodamine derivatives are heterocyclic compound, related to the fluorescent probe having a profound application in the field of biotechnology. Herein, we present two new synthesized rhodamine based fluorescent probes from the rhodamine B (probe 1) and rhodamine 6G (probe 2), respectively. The structures of the synthesized probes 1 and 2 were confirmed using 1H NMR and LC-MS spectral techniques. Further, photophysical properties such as absorption, emission and fluorescence lifetime were examined and compared for both the probes under identical conditions. These comparable data provide a possibility to discuss the mechanism which controls the fluorescence properties of probes. The data also showed that the probes in different solvent environment induce a gradual change in the molecular structure and produce a change in fluorescent intensity as a sensory signal. The changes in fluorescence lifetime and quantum yield with the parent compounds are because of change in solvent polarity and also due to the rigidity of the alkyl groups on N atoms in molecular structure. Moreover, the cell imaging and cellular toxicity studies using the probes were performed. Notably, the result obtained in this study suggests that the probe 2 has significant application in the field of cellular imaging or biotechnology.

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.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.

Similar content being viewed by others

REFERENCES

  1. Wang, Z., Yang, M., Chen, C., Zhang, L., and Zeng, H., Sci. Rep., 2016, vol. 6, 29611, pp. 1–7.

    Article  Google Scholar 

  2. Adak, A.K., Dutta, B., Manna, S.K., and Sinha, C., ACS Omega., 2019, vol. 21, pp. 18987–18995.

    Article  Google Scholar 

  3. Abebe, F., Perkins, P., Shaw, R., and Tadesse, S., J. Mol. Struct., 2020, vol. 1205, p. 127594.

    Article  CAS  Google Scholar 

  4. Savarese, M., Aliberti, A., De Santo, I., Battista, E., Causa, F., Netti, P.A., and Rega, N., J. Phys. Chem. A., 2012, vol. 116, pp. 7491–7497.

    Article  CAS  Google Scholar 

  5. Ganbold, E.O., Park, J.H., Dembereldorj, U., Ock, K.S., and Joo, S.W., J. Raman Spectrosc., 2011, vol. 42, pp. 1614–1619.

    Article  CAS  Google Scholar 

  6. Bujdak, J., J. Photochem. Photobiol. C, 2018, vol. 35, pp. 108–133.

    Article  CAS  Google Scholar 

  7. Lewkowicz, A., Bojarski, P., Synak, A., Grobelna, B., Akopova, I., Gryczyński, I., and Kułak, L., J. Phys. Chem. C., 2012, vol. 116, pp. 12304–12311.

    Article  CAS  Google Scholar 

  8. Stewart, B.W. and Wild, C.P., World Cancer Report 2014, IARC, 2014, p. 630.

    Google Scholar 

  9. Singh, K., Rotaru, A.M., and Beharry, A.A., ACS Chem. Biol., 2018, vol. 13, pp. 1785–1798.

    Article  CAS  Google Scholar 

  10. Luo, S., Zhang, E., Su, Y., Cheng, T., and Shi, C., Biomaterials., 2011, vol. 32, pp. 7127–7138.

    Article  CAS  Google Scholar 

  11. Jang, Y.K., Nam, U.C., Kwon, H.L., Hwang, I.H., and Kim, C., Dye Pigment., 2013, vol. 99, pp. 6–13.

    Article  CAS  Google Scholar 

  12. Mahajan, D., Khairnar, N., Bondhopadhaya, B., Sahoo, S.K., Basu, A., Singh, J., Singh, N., Bendre, R., and Kuwar, A., New J. Chem., 2015, vol. 39, pp. 3071–3076.

    Article  CAS  Google Scholar 

  13. Sorokin, P.P. and Lankard, J.R., J. Res. Dev., 1966, vol. 10, pp. 162–163.

    CAS  Google Scholar 

  14. Zhang, X.F., Zhang, Y., and Liu, L., J. Lumin., 2014, vol. 145, pp. 448–453.

    Article  CAS  Google Scholar 

  15. Kojima, H, Hirotani, M, Nakatsubo, N, Kikuchi, K, Urano, Y, Higuchi, T, Hirata, Y, Nagano, T., Anal. Chem., 2001, vol. 73, pp. 1967–1973.

    Article  CAS  Google Scholar 

  16. Saleem, M. and Lee, K.-H., J. Lumin., 2014, vol. 145, pp. 843–848.

    Article  CAS  Google Scholar 

  17. Ettinger, A. and Wittmann, T., Methods Cell Biol., 2014, vol. 123, pp.77–94.

    Article  Google Scholar 

  18. Phull, A.R., Majid, M., ul Haq, I., Khan, M.R., and Kim, S.J., Int. J. Biol. Macromol., 2017, vol. 97, pp. 468–480.

    Article  CAS  Google Scholar 

  19. Li, H., Fan, J., Wang, J., Tian, M., Du, J., Sun, S., Sun, P., and Peng, X., Chem. Commun., 2009, pp. 5904–5906.

  20. Penzkofer, A. and Leupacher, W., J. Lumin., 1987, vol. 37, pp. 61–72.

    Article  CAS  Google Scholar 

  21. Kubin, R.F. and Fletcher, A.N., J. Lumin., 1982, vol. 27, pp. 455–462.

    Article  Google Scholar 

  22. Fischer, M. and Georges, J., Chem. Phys. Lett., 1996, vol. 260, pp. 115–118.

    Article  CAS  Google Scholar 

  23. Drexhage, K.H.H, J. Res. Natl. Bur. Stand. Sect. A. Phys. Chem. 1976, vol. 80, p. 421.

    Article  Google Scholar 

  24. Vogel, M., Rettig, W., Sens, R., and Drexhage, K.H., Chem. Phys. Lett., 1988, vol. 147, pp. 452–460.

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors would like to thank Dr. Rajendran Nagarajan and Mr. Balasaheb D. Vanjare for providing comments regarding the revised manuscript.

Funding

This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF-2019R1I1A3A01059089).

Author information

Authors and Affiliations

  1. Department of Chemistry, Kongju National University, 32588, Gongju, Chungnam, Republic of Korea

    Harini Sampath Kumar & Ki Hwan Lee

  2. Department of Food and Nutrition, Far East University, 27601, Eumseong, Chungbuk, Republic of Korea

    Chang-Shik Choi

Authors
  1. Harini Sampath Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chang-Shik Choi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ki Hwan Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ki Hwan Lee.

Ethics declarations

COMPLIANCE WITH ETHICAL STANDARDS

This article does not contain any studies involving animals or human participants performed by any of the authors.

Conflict of Interests

The authors declare that they no conflict of interests.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Harini Sampath Kumar, Choi, CS. & Lee, K.H. Synthesis, Photophysical Properties, and Cytotoxicity of Rhodamine Based Fluorescent Probes. Russ J Bioorg Chem 47, 691–699 (2021). https://doi.org/10.1134/S1068162021030109

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162021030109

Keywords:

Search

Navigation