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.
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X. Ai, M. Hu, Z. Wang, et al., Bioconjugate. Chem., 29 (4), 928 – 938 (2018).
S. S. Lucky, K. C. Soo, and Y. Zhang, Chem. Rev., 115(4), 1990 – 2042 (2015).
A. D. Garg and P. Agostinis, Photochem. Photobiol. Sci., 13(3), 474 – 487 (2014).
D. W. Felsher, Nat. Rev. Cancer., 3(5), 375 – 379 (2003).
J. C. S. Simoes, S. Sarpaki, P. Papadimitroulas, et al., J. Med. Chem., 63(23), 14119 – 14150 (2020).
Y. Y. Huang, P. Mroz, T. Zhiyentayev, et al., J. Med. Chem., 53(10), 4018 – 4027 (2010).
E. S. Nyman and P. H. Hynninen, J. Photochem. Photobiol. B, 73(1–2), 1 – 28 (2004).
N. Lin, C. Li, Z.Wang, et al., Photochem. Photobiol. Sci., 14(4), 815 – 832 (2015).
R. Bonnett, Chem. Soc. Rev., 24(1), 19 – 33 (1995).
K. Khorsandi, R. Hosseinzadeh, and F. K. Shahidi, J. Cell. Biochem., 120(4), 4998 – 5009 (2019).
M. T. Martin, I. Prieto, L. Camacho, and D. Mobius, Langmuir., 12(26), 6554 – 6560 (1996).
X. Cui, Y. Li, Y. Li, et al., Dyes Pigm., No. 164, 237 – 243 (2019).
R. H. Jin, S. Aoki, and K. Shima, Chem. Commun., No. 16, 1939 – 1940 (1996).
C. Latouche, M. Pereyre, J. B. Verlhac, et al., Tetrahedron. Lett., 36(10), 1665 – 1666 (1995).
W. G. Roberts, K. M. Smith, J. L. Mccullough, and M. W. Berns, Photochem. Photobiol., 49(4), 431 – 438 (1989).
S. Banfi, E. Caruso, S. Caprioli, et al., Bioorg. Med. Chem., 12(18), 4853 – 4860 (2004).
S. Banfi, E. Caruso, L. Buccafurni, et al., J. Med. Chem., 49(11), 3293 – 3304 (2006).
H. Fischer, R. Gottschlich, and A. Seelig, J. Membr. Biol., 165(3), 201 – 211 (1998).
R. Misra, R. Kumar, T. K. Chandrashekar, et al., J. Am. Chem. Soc., 128(50), 16083 – 16091 (2006).
J. S. Lindsey, I. C. Schreiman, H. C. Hsu, et al., J. Org. Chem., 52(5), 827 – 836 (1987).
N. S. James, R. R. Cheruku, J. R. Missert, et al., Molecules., 23(8), 1842 (2018).
C. Z. Li, L. F. Cheng, Z. Q. Wang, and Y. Gu, Lasers. Med. Sci., 24(2), 167 – 171 (2009).
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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
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DOI: https://doi.org/10.1007/s11094-022-02711-1