Porphyrin-Triazine Hybrid and Its Zinc Complex: Spectroscopy, Electrochemistry and in vitro Cytotoxic Activities against Head and Neck Squamous Cell Carcinoma

  • Zhouqun Ji Affiliated Hospital of Jiangsu University, Zhenjiang 212000, P. R. China
  • Yingtan Zhai School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, P. R. China
  • Tingting Gu School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, P. R. China
  • Xu Liang School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, P. R. China

Аннотация

Herein, a porphyrin-triazine hybrid 2 and its zinc complex 2-Zn were synthesized and characterized, and the electronic structures were investigated by spectroscopic and electrochemical characterizations. Weak interactions between porphyrin cores and meso-substituted triazine units were confirmed and the influence of solvents on the spectroscopic properties were also discussed. Importantly, these two porphyrins exhibited clearly in vitro cytotoxic activities against head and neck squamous cell carcinoma. Especially, free-base porphyrin-triazine hybrid 2 exhibited much smaller IC50 values by using CAL-27 (0.33±0.06 μg/mL) and CAL-33 (0.021±0.0007 μg/mL), respectively. In addition, their cell photoluminescence properties were also investigated.

Литература

Chizhova N.V., Likhonina A.E., Tesakova, M.V., et al. J. Mol. Struct. 2025, 1335, 141998. https://doi.org/10.1016/j.molstruc.2025.141998

Majumder S., Borah B.P., Bhuyan J. Dalton Trans. 2020, 49, 8419-8432. https://doi.org/10.1039/D0DT00813C

Chen H., Wang Y., Wang W., et al. Nat. Biotechnol. 2025, 43, 1717-1727. https://doi.org/10.1038/s41587-024-02267-3

Hiroto S., Miyake Y., Shinokubo Y. Chem. Rev. 2017, 117, 2910-3043. https://doi.org/10.1021/acs.chemrev.6b00427

Lu H., Kobayashi N. Chem. Rev. 2016, 116, 6184-6261. https://doi.org/10.1021/acs.chemrev.5b00588

Han J.L., Liu Y.D., Peng D.F., et al. Bioconjugate Chem. 2023, 34, 2155-2180. https://doi.org/10.1021/acs.bioconjchem.3c00432

Bortnevskaya Y.S., Zakharov N.S., Senkov V.S., et al. Mol. Pharm. 2025, 22, 3308-3330. https://doi.org/10.1021/acs.molpharmaceut.5c00247

Tyurin V.S,, Shkirdova A.O., Koifman O.I., et al. Molecules 2023, 28(15), 5782. https://doi.org/10.3390/molecules28155782

Brém B., Gal E., Găină L., et al. RSC Med. Chem. 2024, 16, 747-766. https://doi.org/10.1039/D4MD00601A

Balukova A., Bokea K., Barber P. R., et al. Int. J. Mol. Sci. 2024, 25(8), 4222. https://doi.org/10.3390/ijms25084222

Dubey P., Pathak D. P., Ali F., Chauhan G., Kalaiselvan V. Curr. Drug Discov. Technol. 2024, 21, e170723218813. https://doi.org/10.2174/1570163820666230717161610

Kumawat J., Jain S., Misra N., et al. Mini Rev. Med. Chem. 2024, 24, 2019-2071. https://doi.org/10.2174/0113895575309800240526180356

Rathod B., Pawar S., Puri S., et al. ChemistrySelect 2024, 9, e202303655. https://doi.org/10.1002/slct.202303655

Tountas M., Verykios A., Polydorou E., el al. ACS Appl. Mater. Interfaces 2018, 10, 20728-20739. https://doi.org/10.1021/acsami.8b03061

Alpatova V.M., Rys E.G., Kononova E.G., et al. Molecules 2022, 27, 6200. https://doi.org/10.3390/molecules27196200

Lazarides T., Charalambidis G., Vuillamy A., et al. Inorg. Chem. 2011, 50, 8926-8936. https://doi.org/10.1021/ic201052k

Xiao X.C., Liu C.Z., Liu W.K. et al. J. Porphyrins Phthalocyanines 2010, 14, 123-127. https://doi.org/10.1142/S1088424610001805

Regmi N., Sharma M., Kumar S., et al. J. Mol. Struct. 2026, 1350, 14386. https://doi.org/10.1016/j.molstruc.2025.143863

Manathanath M., Sasidharan S., Saudagar P., et al. Polyhedron 2022, 217, 115711. https://doi.org/10.1016/j.poly.2022.115711

Ringot C., Saad N., Granet R., et al. Carbohydr. Polym. 2013, 91, 333-338. https://doi.org/10.1016/j.carbpol.2012.08.013

Liang X., Xu L., Li M. Z., et al. J. Porphyrins Phthalocyanines 2015, 19, 819-829. https://doi.org/10.1142/S1088424615500492

Kadish K.M., Van Caemelbecke E., Royal G. In: The Porphyrin Handbook, Vol. 8 (Kadish K.M., Smith K.M., Guilard R., Eds.), New York: Academic Press, 2000. pp 1-114.

Pavani, C., Iamamoto Ya., Baptista M.S. Photochem. Photobiol. 2012, 88(4), 774-781. https://doi.org/10.1111/j.1751-1097.2012.01102.x

Deda D. K., Pavani Ch., Caritá E., et al. J. Porphyrins Phthalocyanines 2012, 16(1), 55-63. https://doi.org/10.1142/S1088424611004336

Опубликован
2026-06-24
Как цитировать
Ji, Z., Zhai, Y., Gu, T., & Liang, X. (2026). Porphyrin-Triazine Hybrid and Its Zinc Complex: Spectroscopy, Electrochemistry and in vitro Cytotoxic Activities against Head and Neck Squamous Cell Carcinoma. Макрогетероциклы/Macroheterocycles, 19(2), 163-170. https://doi.org/10.6060/mhc267000L
Раздел
Порфирины