Synthesis, photophysical properties and biological evaluation of β-alkylaminoporphyrin for photodynamic therapy

An updated overview on the development of new photosensitizers for anticancer photodynamic therapy

“…For example, a novel porphyrin-based PS (5,10,15,20-tetrakis[(5-diethylamino)pentyl] porphyrin, TDPP, 1 ) with four diethylaminopentyl side-chains recently reported by Li et al 72 showed a high 1 O 2 yield with the ability to kill human esophageal cancer cell lines (Eca-109) and significantly reduce the growth of Eca-109 xenograft tumors in BABL/c nude mice. Among a series of β -alkylaminoprophyrins reported later by Chen's group 73 , derivative 2 showed higher phototoxicity than Hp monomethyl ether and the lowest toxicity in the dark. Another new porphyrin derivative 3 bearing ethylenediaminetetraacetic acid showed intense in vitro phototoxicity on HepG2 and BGC823 cell lines, and further inhibited the growth of BGC823 tumors in nude mice 74 , Mechanism studies indicated that 3 can induce cell death via the mitochondrial apoptotic pathway mainly triggered by lysosomal photodamage.…”

“…Side-chains containing functional groups, such as nitrogen atoms 72. , 73. , carboxylic acid 74 and sugar 75 , are frequently incorporated into the porphyrin skeleton.…”

Porphyrin Macrocycles: General Properties and Theranostic Potential

“…Numerous studies have reported that structural modifications by attaching functional groups with different polarities to the macrocycle, or introducing metal ions into the tetrapyrrole macrocycles, increase the stability and diminish the aggregation tendency of PS molecules. On the other hand, attaching functional groups with rich π electron content to peripheral macrocycles determines the red shift of maximum PS absorption together with spectral optimization [ 153 , 154 , 155 , 156 , 157 , 158 , 159 ].…”

Chemical approaches for the enhancement of porphyrin skeleton-based photodynamic therapy

“…Hudson et al 55 synthesised phosphorous (27a) and nitrogen (27 b) centred lipophilic cationic porphyrins displaying LD 90 values of 5.9 and 6.1 mM (irradiation with 3.6 J/cm 2 of 630 nm light), respectively, during in vitro photodynamic assays against human colorectal adenocarcinoma cells (HT-29). Liao et al 56 reported hybrids of b-alkylaminoporphyrins and different amines or substituted phenyl groups. Compound 28 showed better phototoxicity against HeLa cells (IC 50 ¼ 4.38 mM, 650 nm, 16 J/cm 2 ).…”