Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groups

Cormick, M. Paula; Rovera, Marisa; Durantini, Edgardo N.

doi:10.1016/j.jphotochem.2007.08.013

Cited by 35 publications

(11 citation statements)

References 35 publications

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“…Similar values of Ф Δ were reported for a dicationic amphiphilic phthalocyanine and a tetracationic zinc(II) tetramethyltetrapyridino [3,4-b:3′,4′-g: 3″,4″-l: 3′′′,4′′′-q]porphyrazinium [32,40]. However, the Φ Δ sensitized by (NCH 3 ) 4 ZnPc 4+ was very low as a consequence of its partial aggregation in this medium [37,41]. However, the photophysics of the phthalocyanines established in solution can significantly change in the microbial suspensions.…”

Section: Photodynamic Propertiessupporting

confidence: 77%

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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Section: Photodynamic Propertiessupporting

confidence: 77%

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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“…The shift of the Q band to red is an important property for photodynamic therapy (PDT) and photo sensing application. Peripherally substituted phthalocyanines isn't resistant against high concentration of sulfuric acid, so their "di-", "tri-", "tetra-" protonated forms cannot be prepared [69,70]. In our study, we investigated protonation behavior of the compound (5) by using sulfuric acid in DMSO.…”

Section: Uvevis Absorption Spectra Of the Compound (4e8)mentioning

confidence: 99%

Synthesis, characterization and spectroscopic studies of novel peripherally tetra-imidazole substituted phthalocyanine and its metal complexes, the computational and experimental studies of the novel phthalonitrile derivative

Akçay

Bayrak

Karslıoğlu

et al. 2012

Journal of Organometallic Chemistry

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“…Several studies showed that phthalocyanines are efficient in the photodynamic inactivation of both Gram-positive and -negative bacteria (9)(10)(11)(12)(13).…”

Section: Introductionmentioning

confidence: 99%

Phthalocyanine Thio‐Pyridinium Derivatives as Antibacterial Photosensitizers^†

Pereira

Carvalho

Faustino

et al. 2012

Photochem & Photobiology

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This study describes the synthesis of three new tetra‐ and octa‐thio‐pyridinium phthalocyanine derivatives. PSs 3a and 4a were prepared from the tetramerization of phthalonitriles 1 and 2, respectively, whereas PS 5 was prepared from the nucleophilic substitution of the 8 beta fluor atoms of hexadecafluorophthalocyaninatozinc(II) by mercaptopyridine, followed by cationization. The recombinant bioluminescent Escherichia coli strain was used to assess, in real time, the photoinactivation efficiency of these cationic phthalocyanines, under white and red light. The cellular localization and uptake were also determined to assess the potential of the new phthalocyanines as antibacterial agents. Derivative 3a was the most effective PS, causing a 5 logs reduction in bioluminescence after 30 min of irradiation under white or red lights. The photoinactivation efficiency of the phthalocyanine 4a was similar (5 logs reduction in bioluminescence) to that of 3a when irradiated with white light, but the efficiency of inactivation was reduced (2.1 logs reduction in bioluminescence) under red light. The tetra‐substituted phthalocyanine 3a also generates high amounts of singlet oxygen, does not aggregate in PBS and is highly fluorescent, which makes it an effective PS and a promising fluorescent labeling.

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Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groups

Cited by 35 publications

References 35 publications

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

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

Synthesis, characterization and spectroscopic studies of novel peripherally tetra-imidazole substituted phthalocyanine and its metal complexes, the computational and experimental studies of the novel phthalonitrile derivative

Phthalocyanine Thio‐Pyridinium Derivatives as Antibacterial Photosensitizers^†

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Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groups

Cited by 35 publications

References 35 publications

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

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

Synthesis, characterization and spectroscopic studies of novel peripherally tetra-imidazole substituted phthalocyanine and its metal complexes, the computational and experimental studies of the novel phthalonitrile derivative

Phthalocyanine Thio‐Pyridinium Derivatives as Antibacterial Photosensitizers†

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Phthalocyanine Thio‐Pyridinium Derivatives as Antibacterial Photosensitizers^†