Synthesizing and evaluating the photodynamic efficacy of asymmetric heteroleptic A₇B type novel lanthanide bis-phthalocyanine complexes

Abstract

Novel bis-lanthanide Lu(iii) and Eu(iii) phthalocyanine complexes have been designed/synthesized and tested their photodynamic efficacy for A549 and BEAS-2B cells in vitro conditions as candidate photosensitizers in PDT.

Novel axially symmetric and unsymmetric silicon(iv) phthalocyanines having anti-inflammatory groups: synthesis, characterization and their biological properties

“…The solvent was removed under reduced pressure. The resulting crude blue solid was purified by column chromatography (silica gel, CH 2 Cl 2 : EtOH (20 : 1)) to give a blue solid (60 (20 mL) were placed into a flask and argon gas was bubbled through this mixture for 5 min. After the addition of SiCl 2 Pc (370 mg, 0.6 mmol, 1.0 equiv.…”

“…Several different techniques for the determination of the Φ Δ measurement of efficiency have been developed over the past five decades. [60][61][62] In our work, we applied a direct method in DMF. Singletoxygen phosphorescence spectra for all compounds excited with a xenon-arc source at their respective absorption maxima were recorded with a near-IR-sensitive detector.…”

Development of AB3-Type Novel Phthalocyanine and Porphyrin Photosensitizers Conjugated with Triphenylphosphonium for Higher Photodynamic Efficacy

“… 24 Then, excessive 1,6-dibromohexane was reacted with phthalocyanine in the presence of potassium carbonate in dimethylformamide (DMF), leading to brominated phthalocyanine ( AB 3 Br-Pc) using the same synthesis procedure as in porphyrins. Modifications of brominated porphyrin ( AB 3 Br-Por-C4 or AB 3 Br-Por-C6) and phthalocyanine ( AB 3 Br-Pc) derivatives with the mitochondrial target functional group TPP to obtain AB 3 TPP-Por-C4 , AB 3 TPP-Por-C6 , and AB 3 TPP-Pc compounds were made following a procedure applied in one of our previous reports 24 with the reaction of excess TPP in dry DMF ( Schemes 1 and 2 ). The structures illustrated in Schemes 1 and 2 were characterized by 1 H NMR, MALDI-mass, NIR-IR, and UV–vis spectroscopic methods ( Figures S1–S12 ).…”

“…The lowest Φ F value 0.009 belongs to LuPcPox(OAc) and is close to the value (0.004) obtained in DMSO in our previous study. 24 This could be the result of the higher atomic number of lutetium in the cavity of phthalocyanine which may facilitate intersystem crossing to its excited triplet state after excitation. However, the difference and purpose of this study from our previous work are to examine whether there will be a change in the fluorescence property with the addition of the mitochondria targeting the TPP group to the structure.…”

“…In this report, the objective of our study was to present novel AB 3 -type phthalocyanine and porphyrin-based mitochondria-targeted PSs which were conjugated by TPP for the PDT application area. In our previous work 24 which was based on the synthesis and evaluation of the photodynamic efficacy of phthalocyanine-based PS for PDT, especially the LuPcPox(OAc) phthalocyanine derivative having only polyoxyethylene chains ( Figure 1 ) was determined as the best candidate photosensitizer among other phthalocyanine complexes used in that study. This complex without the TPP group induced concentration-dependent cell killing and responded to light irradiation, reducing the IC 50 values down to the nanomolar range.…”