Novel porphyrin–psoralen conjugates: synthesis, DNA interaction and cytotoxicity studies

Abstract

A Cu(i)-catalyzed azide-alkyne cycloaddition reaction (CuAAC) has been utilized to prepare novel triazole-linked cationic porphyrin-psoralen conjugates that exhibited significant photocytotoxicity against A549 cancer cells (IC50 = 84 nM).

Synthesis, characterization and biomolecule-binding properties of novel tetra-platinum(ii)-thiopyridylporphyrins

“…The photostability of 3 and 4 was studied by monitoring the decrease of the absorbance of their Soret-bands, after different times of white light irradiation (400-800 nm) delivered by an illumination system at a fluence rate of 50 mW cm −2 . 15,37 In PBS solutions both compounds at 1.5 µM showed high photostability over the investigated irradiation period (30 min; Table SI 1 †).…”

“Click”-reaction: An alternative tool for new architectures of porphyrin based derivatives

“…This reaction has been applied in many tetrapyrrolic entities such as porphyrins [55], phthalocyanines [55] and more recently corroles [56,57]. Concerning the applications of click-made porphyrins many studies have been made on photodynamic therapy (PDT) [58][59][60][61], polymers [62][63][64][65], self-assembly [66][67][68], biochemistry [69][70][71][72] and materials chemistry [73][74][75][76]. The scope of this work is to present click reactions that are carried out on porphyrin compounds.…”

“…Porphyrin-galactose 50 and porphyrin-lactose 51[108].Kumar and his coworkers synthesized novel water soluble conjugates (cationic porphyrin-b-carboline) 52[109] and porphyrin-psoralen[70] 53 which exhibited high photocytotoxicity towards A549 cancer cells and could be potential candidates (Figure 24). For the preparation of both these complexes they used CuSO 4 , SA, DMF/H 2 O, 80 o C, 168 h. At lower temperatures, the reaction was very sluggish and yields were reduced.…”

“…For the preparation of both these complexes they used CuSO 4 , SA, DMF/H 2 O, 80 o C, 168 h. At lower temperatures, the reaction was very sluggish and yields were reduced. Porphyrin-b-carboline 52[109] and porphyrin-psoralen 53[70] conjugates.In the following report[61] a click approach for the synthesis of super-paramagnetic iron oxide-porphyrin conjugates was described as well as the characterization and the evaluation of the phototoxicity of the designed nanoconjugates 54 (Figure 25). of this work proved that upon light irradiation the porphyrin nanoconstructs act as promising theranostic nanoagents for the treatment of cancer cells by PDT and for the tracking of therapeutic agents through MRI and/or fluorescence-based techniques.…”

Water-soluble porphyrin-phosphonate conjugates as potential photodynamic therapy photosensitizers

“…Due to the nontargeted distributions of the photosensitizers (PSs), which lead to unwanted photodynamic effects in normal tissues [3], PDT has been mostly limited to cure melanomas and solid tumors like the bladder and the esophagus [4], which occurred in externally accessible cavities. To overcome these limitations, especially the undesirable side-effects, PSs have been conjugated with some biological molecules, such as carbohydrates [5,6], monoclonal antibodies [7,8], peptides [9][10][11], oligo-nucleotides [12] and some other natural products [13], to improve their biocompatibility, selectivity, efficacy and stability.…”