Novel porphyrin–Schiff base conjugates: synthesis, characterization and in vitro photodynamic activities

作者: Ya-Hong Yao , Jun Li , Long-Fei Yuan , Zeng-Qi Zhang , Feng-Xing Zhang

DOI: 10.1039/C6RA05682B

关键词:

摘要: Three novel porphyrin–Schiff base conjugates derived from tetra(4-aminophenyl)porphyrin (TAPP), namely, tetra[4-(4-hydroxy benzylideneamino)]phenyl porphyrin (3a), tetra[4-(2-thienyldeneamino)]phenyl (3b) and tetra[4-(2-pyridyldeneamino)]phenyl (3c), were synthesized characterized by IR, UV-vis, 1H NMR, HRMS elementary analysis. Their biological activities against human epidermoid carcinoma (A431) cells evaluated with an MTT assay. As we expected, the showed negligible cytotoxicity to A431 in absence of light, while their phototoxic improved after irradiated LED lamp (425 nm) increased significantly doses. The fluorescence microscope pictures revealed that three could diffuse into skin cancer cells, demonstrating these compounds are potential candidates for photodynamic therapy agents.

参考文章(38)
Ahmed M. Abu-Dief, Ibrahim M.A. Mohamed, A review on versatile applications of transition metal complexes incorporating Schiff bases Beni-Suef University Journal of Basic and Applied Sciences. ,vol. 4, pp. 119- 133 ,(2015) , 10.1016/J.BJBAS.2015.05.004
SK Bharti, G Nath, R Tilak, SK Singh, None, Synthesis, anti-bacterial and anti-fungal activities of some novel Schiff bases containing 2,4-disubstituted thiazole ring European Journal of Medicinal Chemistry. ,vol. 45, pp. 651- 660 ,(2010) , 10.1016/J.EJMECH.2009.11.008
Jin Matsumoto, Tsutomu Shiragami, Kazutaka Hirakawa, Masahide Yasuda, Water-Solubilization of P(V) and Sb(V) Porphyrins and Their Photobiological Application International Journal of Photoenergy. ,vol. 2015, pp. 1- 12 ,(2015) , 10.1155/2015/148964
Mafalda Laranjo, Arménio C. Serra, Margarida Abrantes, Marta Piñeiro, Ana C. Gonçalves, João Casalta-Lopes, Lina Carvalho, Ana B. Sarmento-Ribeiro, António Rocha-Gonsalves, Filomena Botelho, 2-Bromo-5-hydroxyphenylporphyrins for photodynamic therapy: photosensitization efficiency, subcellular localization and in vivo studies. Photodiagnosis and Photodynamic Therapy. ,vol. 10, pp. 51- 61 ,(2013) , 10.1016/J.PDPDT.2012.05.003
Mahesh Uttamlal, A. Sheila Holmes-Smith, The excitation wavelength dependent fluorescence of porphyrins Chemical Physics Letters. ,vol. 454, pp. 223- 228 ,(2008) , 10.1016/J.CPLETT.2008.02.012
Dalip Kumar, K.P. Chandra Shekar, Bhupendra Mishra, Ryohsuke Kurihara, Maiko Ogura, Takeo Ito, Cationic porphyrin–quinoxaline conjugate as a photochemically triggered novel cytotoxic agent Bioorganic & Medicinal Chemistry Letters. ,vol. 23, pp. 3221- 3224 ,(2013) , 10.1016/J.BMCL.2013.03.126
Xiaoli Liu, Mouming Zhao, Kegang Wu, Xianghua Chai, Hongpeng Yu, Zhihua Tao, Jinshui Wang, None, Immunomodulatory and anticancer activities of phenolics from emblica fruit (Phyllanthus emblica L.) Food Chemistry. ,vol. 131, pp. 685- 690 ,(2012) , 10.1016/J.FOODCHEM.2011.09.063
Myriam Gómez-Tardajos, Juan Pablo Pino-Pinto, Claudia Díaz-Soto, Mario E. Flores, Alberto Gallardo, Carlos Elvira, Helmut Reinecke, Hiroyuki Nishide, Ignacio Moreno-Villoslada, Confinement of 5,10,15,20-tetrakis-(4-sulfonatophenyl)-porphyrin in novel poly(vinylpyrrolidone)s modified with aromatic amines Dyes and Pigments. ,vol. 99, pp. 759- 770 ,(2013) , 10.1016/J.DYEPIG.2013.06.028
V. Vaz Serra, A. Zamarrón, M.A.F. Faustino, M.C. Iglesias-de la Cruz, A. Blázquez, J.M.M. Rodrigues, M.G.P.M.S. Neves, J.A.S. Cavaleiro, A. Juarranz, F. Sanz-Rodríguez, New porphyrin amino acid conjugates: Synthesis and photodynamic effect in human epithelial cells Bioorganic & Medicinal Chemistry. ,vol. 18, pp. 6170- 6178 ,(2010) , 10.1016/J.BMC.2010.06.030