Synthesis of unsymmetrical phthalocyanine derivatives and their interaction with mammary MCF7 cells

Conjugation with L,L-diphenylalanine Self-Assemblies Enhances In Vitro Antitumor Activity of Phthalocyanine Photosensitizer

“…This morphological characteristic leads to higher interface area in these materials; thus, these conjugates are presumably more efficient to provide interactions with cell membranes 20 . In addition, the ZnPc3 compound has a high partition coefficient (log P) than the other phthalocyanines, as shown in Table from the literature 11 . In this case, we have observed that a number of protected glycerol groups improved the hydrophobicity of the compounds, which can be associated with higher tendencies to cross the membrane lipid bilayers resulting in increased uptake of the compounds into cells, as shown in vitro photodynamic activities against breast cancer cells by using these compounds 11 .…”

“…In addition, the ZnPc3 compound has a high partition coefficient (log P) than the other phthalocyanines, as shown in Table from the literature 11 . In this case, we have observed that a number of protected glycerol groups improved the hydrophobicity of the compounds, which can be associated with higher tendencies to cross the membrane lipid bilayers resulting in increased uptake of the compounds into cells, as shown in vitro photodynamic activities against breast cancer cells by using these compounds 11 . However, the ZnPc3 alone showed no interaction with MCF-7 cells when compared to the ZnPc1 compound, which had an efficiency of 80%.…”

“…1 . Compounds ZnPc1 and ZnPc2 are tetra substituted with four identical groups (protected and non-protected glycerol, respectively), whereas compounds ZnPc3 and ZnPc4 are non-centrosymmetric (A3B type) 11 and bear three glycerol substituents (protected and non-protected, respectively) and one methyl group.

Figure 1 Zinc phthalocyanines used in this study.

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“…1,3-diphenylisobenzofuran, dimethyl sulfoxide (DMSO) and methyl alcohol were purchased from Synth (Brazil). Zinc phthalocyanine was synthesized as reported elsewhere 11 . Ultrapure water (R > 18 mol L −1 Ωcm −1 ) was obtained from a Milli-Q system.…”

Basic Concepts and Applications of Porphyrins, Chlorins and Phthalocyanines as Photosensitizers in Photonic Therapies

“…A síntese destes compostos pode ser realizada através de um processo não pericíclico denominado ciclotetramerização de seus monômeros; derivados de ftalimidas, anidrido ftálicos, derivados de isoindóis ou ftalonitrilos (Figura 12). 40,41 Apesar do destaque inicial para aplicação na indústria têxtil, estes compostos também demonstraram ser aplicáveis em áreas de alta tecnologia como: displays ópticos, 42 materiais semicondutores, 43 sensores de gás, 44 células solares, 40b,45 tecnologias envolvendo cristais líquidos, 40b,46 catálise, 47 PDT, 48 Para minimizar esse problema, já foram realizadas algumas tentativas de modificações estruturais, geralmente de 2 tipos: (i) Modificações dos substituintes nas posições  e , com a inserções de grupos volumosos hidrofílicos e/ou hidrofóbicos e (ii) Alteração do metal coordenante de modo a permitir a inserção ligantes axiais. Em ambos os casos, a inserção dos grupos é estrategicamente avaliada para minimizar a agregação e, consequentemente, tornar estes compostos solúveis em meios fisiológicos e/ou formulações farmacêuticas visando a rápida absorção pelas células.…”