Synthesis and photodynamic properties of adamantylethoxy Zn(II) phthalocyanine derivatives in different media and in human red blood cells

Ochoa, Ana Laura; Tempesti, Tomás Cristian; Spesia, Mariana B.; Milanesio, M. Elisa; Durantini, Edgardo N.

doi:10.1016/j.ejmech.2012.02.005

Cited by 28 publications

(26 citation statements)

References 42 publications

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“…They were similar to aspirin (2%) ( p ≤ 0.05) and not comparable to Triton X-100 (100%), used as a positive control. Fisher and collaborators [ 48 ] reported that hemolysis values below 10% are considered non-hemolytic, which frame these compounds within an acceptable toxicity profile [ 48 , 49 , 50 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antiplatelet Activity of Antithrombotic Thiourea Compounds: Biological and Structure-Activity Relationship Studies

et al. 2015

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The incidence of hematological disorders has increased steadily in Western countries despite the advances in drug development. The high expression of the multi-resistance protein 4 in patients with transitory aspirin resistance, points to the importance of finding new molecules, including those that are not affected by these proteins. In this work, we describe the synthesis and biological evaluation of a series of N,N'-disubstituted thioureas derivatives using in vitro and in silico approaches. New designed compounds inhibit the arachidonic acid pathway in human platelets. The most active thioureas (compounds 3d, 3i, 3m and 3p) displayed IC50 values ranging from 29 to 84 µM with direct influence over in vitro PGE2 and TXA2 formation. In silico evaluation of these compounds suggests that direct blockage of the tyrosyl-radical at the COX-1 active site is achieved by strong hydrophobic contacts as well as electrostatic interactions. A low toxicity profile of this series was observed through hemolytic, genotoxic and mutagenic assays. The most active thioureas were able to reduce both PGE2 and TXB2 production in human platelets, suggesting a direct inhibition of COX-1. These results reinforce their promising profile as lead antiplatelet agents for further in vivo experimental investigations.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Antiplatelet Activity of Antithrombotic Thiourea Compounds: Biological and Structure-Activity Relationship Studies

et al. 2015

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“…The areas of the emission spectra were integrated in the range 650-800 nm. The fluorescence quantum yield (Φ F ) of phthalocyanines were calculated by comparison of the area below the corrected emission spectrum in DMF using Zn(II) 2,9(10),16(17),23( 24)-tet rakis(methoxy)phthalocyanine (M 4 ZnPc) as a reference (Φ F = 0.26) [26].…”

Section: Spectroscopic Studiesmentioning

confidence: 99%

Amphiphilic tricationic Zn(II)phthalocyanine provides effective photodynamic action to eradicate broad-spectrum microorganisms

Baigorria

Durantini

Palma

et al. 2021

Photochem Photobiol Sci

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A novel tricationic Zn(II)phthalocyanine derivative, (NCH 3 ) 3 ZnPc 3+ , was synthesized by ring expansion reaction of boron(III) [2,9(10),16(17)-trinitrosubphthalocyaninato]chloride. First, the reaction of this subphthalocyanine with 2,3-naphthalenedicarbonitrile and Zn(CH 3 COO) 2 catalyzed by 8-diazabicyclo[5.4.0]undec-7-ene was used to obtain the A 3 B-type nitrophthalocyanine. After reduction of nitro groups with Na 2 S and exhaustive methylation of amino groups, (NCH 3 ) 3 ZnPc 3+ was formed in good yields. In addition, the tetracationic analog (NCH 3 ) 4 ZnPc 4+ was synthesized to compare their properties. The absorption and fluorescence spectra showed the Q-bands and the red emission, respectively, which are characteristic of the Zn(II)phthalocyanine derivatives in N,N-dimethylformamide. Furthermore, photodynamic activity sensitized by these compounds was studied in the presence of different molecular probes to sense the formation of reactive oxygen species. (NCH 3 ) 3 ZnPc 3+ efficiently produced singlet molecular oxygen and also it sensitized the formation of superoxide anion radical in the presence of NADH, while the photodynamic activity of (NCH 3 ) 4 ZnPc 4+ was very poor, possibly due to the partial formation of aggregates. Furthermore, the decomposition of L-tryptophan induced by (NCH 3 ) 3 ZnPc 3+ was mainly mediated by a type II mechanism. Antimicrobial photodynamic inactivation sensitized by these phthalocyanines was evaluated in Staphylococcus aureus, Escherichia coli, and Candida albicans, as representative microbial cells. In cell suspensions, (NCH 3 ) 3 ZnPc 3+ was rapidly bound to microbial cells, showing bioimages with red fluorescence emission. After 5 min of irradiation with visible light, (NCH 3 ) 3 ZnPc 3+ was able to completely eliminate S. aureus, E. coli and C. albicans, using 1.0, 2.5 and 5.0 μM phthalocyanine, respectively. In contrast, a low photoinactivation activity was found with (NCH 3 ) 4 ZnPc 4+ as a photosensitizer. Therefore, the amphiphilic tricationic phthalocyanine (NCH 3 ) 3 ZnPc 3+ is a promising photosensitizing structure for application as a broad-spectrum antimicrobial phototherapeutic agent.

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“…Zinc phthalocyanines (ZnPcs) are valuable PSs [5][6][7][8][9][10]. When they functionalized with heterocycles units such as 4-pyridylmethyloxy and pyridyloxy groups [11,12], adamantylethoxy zinc phthalocyanines [13], hexadecafluoro zinc phthalocyanine [14], tetracarboxy zinc phthalocyanine [15] with pentalysine peptidyl moiety (ZnPc-(Lys) 5 ) [16]. A number of cell lines [17][18][19] showed the efficiency of zinc phthalocyanines as photosensitizers as a result of their excellent fluorescence quantum yields [20,21].…”

Section: Introductionmentioning

confidence: 99%

An effective invasive therapeutic approach of fluoro-substituted zinc phthalocyanine derivatives as potential photosensitizer for prostate carcinoma

Youssef¹,

Al-Jameel²,

Al-Magribi³

2020

ScienceAsia

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Fluoro-substituted zinc(II)phthalocyanines (RS) 4 ZnPcs were prepared. All the structures of newly synthesized compounds was evaluated by IR and 1 H NMR spectral analysis. They were tested against human adenocarcinoma prostate cancer cells. A type II membrane antigen highly expressed in prostate cancer, namely prostate-specific membrane antigen, has been an attractive target for imaging and therapy. To investigate the structureactivity relationships of (RS) 4 ZnPcs 4a-c in human adenocarcinoma prostate cancer cell model, 3 fluoro-substituted zinc(II)phthalocyanines with different terminal heteroaromatic rings have been designed and evaluated for their antiproliferative potency in vitro. The detailed LD50 values of the targeted compounds were reported. Our preliminary in vitro studies confirm that (RS) 4 ZnPcs 4a-c could act as an attractive photosensitizer for the early diagnosis of prostate cancer.

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Synthesis and photodynamic properties of adamantylethoxy Zn(II) phthalocyanine derivatives in different media and in human red blood cells

Cited by 28 publications

References 42 publications

Synthesis and Antiplatelet Activity of Antithrombotic Thiourea Compounds: Biological and Structure-Activity Relationship Studies

Synthesis and Antiplatelet Activity of Antithrombotic Thiourea Compounds: Biological and Structure-Activity Relationship Studies

Amphiphilic tricationic Zn(II)phthalocyanine provides effective photodynamic action to eradicate broad-spectrum microorganisms

An effective invasive therapeutic approach of fluoro-substituted zinc phthalocyanine derivatives as potential photosensitizer for prostate carcinoma

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