Skip to main content

Advertisement

Log in

Synthesis and Evaluation of New 5,15-Diarylporphyrin Derivatives for Photodynamic Therapy

  • Published:
Pharmaceutical Chemistry Journal Aims and scope

Two new 5,15-diarylporphyrin derivatives (L1 and L2) were designed and synthesized and their anti-esophageal cancer effects as photosensitizers were evaluated. Both compounds have strong absorption band at 645 – 655 nm in UV-Vis spectra, obvious singlet oxygen generation ability, and fluorescence emission around 657 – 674 nm under laser excitation. Under photodynamic therapy (PDT) conditions, they could significantly inhibit the growth of Eca-109 tumor cells. In particular, compound L1 exhibited excellent photodynamic antiproliferative effect and is worthy of further development.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1.
Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.

Similar content being viewed by others

References

  1. X. Ai, M. Hu, Z. Wang, et al., Bioconjugate. Chem., 29 (4), 928 – 938 (2018).

    Article  CAS  Google Scholar 

  2. S. S. Lucky, K. C. Soo, and Y. Zhang, Chem. Rev., 115(4), 1990 – 2042 (2015).

    Article  CAS  Google Scholar 

  3. A. D. Garg and P. Agostinis, Photochem. Photobiol. Sci., 13(3), 474 – 487 (2014).

    Article  CAS  Google Scholar 

  4. D. W. Felsher, Nat. Rev. Cancer., 3(5), 375 – 379 (2003).

    Article  CAS  Google Scholar 

  5. J. C. S. Simoes, S. Sarpaki, P. Papadimitroulas, et al., J. Med. Chem., 63(23), 14119 – 14150 (2020).

    Article  CAS  Google Scholar 

  6. Y. Y. Huang, P. Mroz, T. Zhiyentayev, et al., J. Med. Chem., 53(10), 4018 – 4027 (2010).

    Article  CAS  Google Scholar 

  7. E. S. Nyman and P. H. Hynninen, J. Photochem. Photobiol. B, 73(1–2), 1 – 28 (2004).

    Article  CAS  Google Scholar 

  8. N. Lin, C. Li, Z.Wang, et al., Photochem. Photobiol. Sci., 14(4), 815 – 832 (2015).

    Article  CAS  Google Scholar 

  9. R. Bonnett, Chem. Soc. Rev., 24(1), 19 – 33 (1995).

    Article  CAS  Google Scholar 

  10. K. Khorsandi, R. Hosseinzadeh, and F. K. Shahidi, J. Cell. Biochem., 120(4), 4998 – 5009 (2019).

    Article  CAS  Google Scholar 

  11. M. T. Martin, I. Prieto, L. Camacho, and D. Mobius, Langmuir., 12(26), 6554 – 6560 (1996).

    Article  CAS  Google Scholar 

  12. X. Cui, Y. Li, Y. Li, et al., Dyes Pigm., No. 164, 237 – 243 (2019).

  13. R. H. Jin, S. Aoki, and K. Shima, Chem. Commun., No. 16, 1939 – 1940 (1996).

  14. C. Latouche, M. Pereyre, J. B. Verlhac, et al., Tetrahedron. Lett., 36(10), 1665 – 1666 (1995).

    Article  CAS  Google Scholar 

  15. W. G. Roberts, K. M. Smith, J. L. Mccullough, and M. W. Berns, Photochem. Photobiol., 49(4), 431 – 438 (1989).

    Article  CAS  Google Scholar 

  16. S. Banfi, E. Caruso, S. Caprioli, et al., Bioorg. Med. Chem., 12(18), 4853 – 4860 (2004).

    Article  CAS  Google Scholar 

  17. S. Banfi, E. Caruso, L. Buccafurni, et al., J. Med. Chem., 49(11), 3293 – 3304 (2006).

    Article  CAS  Google Scholar 

  18. H. Fischer, R. Gottschlich, and A. Seelig, J. Membr. Biol., 165(3), 201 – 211 (1998).

    Article  CAS  Google Scholar 

  19. R. Misra, R. Kumar, T. K. Chandrashekar, et al., J. Am. Chem. Soc., 128(50), 16083 – 16091 (2006).

    Article  CAS  Google Scholar 

  20. J. S. Lindsey, I. C. Schreiman, H. C. Hsu, et al., J. Org. Chem., 52(5), 827 – 836 (1987).

    Article  CAS  Google Scholar 

  21. N. S. James, R. R. Cheruku, J. R. Missert, et al., Molecules., 23(8), 1842 (2018).

    Article  Google Scholar 

  22. C. Z. Li, L. F. Cheng, Z. Q. Wang, and Y. Gu, Lasers. Med. Sci., 24(2), 167 – 171 (2009).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Zhi-Long Chen.

Rights and permissions

Springer Nature or its licensor holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Liu, Y., Ding, YX., Mi, L. et al. Synthesis and Evaluation of New 5,15-Diarylporphyrin Derivatives for Photodynamic Therapy. Pharm Chem J 56, 790–797 (2022). https://doi.org/10.1007/s11094-022-02711-1

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11094-022-02711-1

Keywords

Navigation