Halogen atom effect on photophysical and photodynamic characteristics of derivatives of 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin

Serra, Arménio C.; Piñeiro, Marta; Gonsalves, Α. Μ. d’A. Rocha; Abrantes, Ana Margarida; Laranjo, Mafalda; Santos, Antônio Cardozo dos; Botelho, Maria Filomena

doi:10.1016/j.jphotobiol.2008.04.006

Cited by 55 publications

(21 citation statements)

References 33 publications

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“…The introduction of heavy atoms such as iodine and bromine to photosensitizers is able to enhance their singlet oxygen generation ability by improving the ISC and the triplet lifetime of the photosensitizers [15], [16], [33], [34], [35]. In this study, however, mono-iodo substitution in compound 3 did not result in higher singlet oxygen generation rate than compound 1 and 2 .…”

Section: Resultsmentioning

confidence: 52%

“…glycerol) to the phthalocyanine macrocycle are also known to increase and red-shift their absorption maxima [10]. Meanwhile, non-peripheral substitution in 2 , compared to the peripheral substitution in 1 , was expected to reduce aggregation and to shift the absorption spectrum towards NIR [11], [12], [14] while, 3 was designed with an iodine atom added to enhance intersystem crossing (ISC) efficiency and singlet oxygen quantum yield [15], [16], [17], [18], [19], [20].…”

Section: Introductionmentioning

confidence: 99%

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Improved Photodynamic Efficacy of Zn(II) Phthalocyanines via Glycerol Substitution

et al. 2014

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Phthalocyanines are excellent photosensitizers for photodynamic therapy as they have strong absorbance in the near infra-red region which is most relevant for in vivo activation in deeper tissular regions. However, most phthalocyanines present two major challenges, ie, a strong tendency to aggregate and low water-solubility, limiting their effective usage clinically. In the present study, we evaluated the potential enhancement capability of glycerol substitution on the photodynamic properties of zinc (II) phthalocyanines (ZnPc). Three glycerol substituted ZnPc, 1–3, (tetra peripherally, tetra non-peripherally and mono iodinated tri non-peripherally respectively) were evaluated in terms of their spectroscopic properties, rate of singlet oxygen generation, partition coefficient (log P), intracellular uptake, photo-induced cytotoxicity and vascular occlusion efficiency. Tetrasulfonated ZnPc (ZnPcS4) was included as a reference compound. Here, we showed that 1–3 exhibited 10–100 nm red-shifted absorption peaks with higher molar absorptivity, and at least two-fold greater singlet oxygen generation rates compared to ZnPcS4. Meanwhile, phthalocyanines 1 and 2 showed more hydrophilic log P values than 3 consistent with the number of glycerol attachments but 3 was most readily taken up by cells compared to the rest. Both phthalocyanines 2 and 3 exhibited potent phototoxicity against MCF-7, HCT-116 and HSC-2 cancer cell-lines with IC50 ranging 2.8–3.2 µM and 0.04–0.06 µM respectively, while 1 and ZnPcS4 (up to 100 µM) failed to yield determinable IC50 values. In terms of vascular occlusion efficiency, phthalocyanine 3 showed better effects than 2 by causing total occlusion of vessels with diameter <70 µm of the chorioallantoic membrane. Meanwhile, no detectable vascular occlusion was observed for ZnPcS4 with treatment under similar experimental conditions. These findings provide evidence that glycerol substitution, in particular in structures 2 and 3, is able to improve the photodynamic properties of ZnPc.

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Section: Resultsmentioning

confidence: 52%

Section: Introductionmentioning

confidence: 99%

Improved Photodynamic Efficacy of Zn(II) Phthalocyanines via Glycerol Substitution

et al. 2014

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“…While there is considerable attention in the synthesis of new PSs with improved PDT characteristics, porphyrin derivatives are particularly strong under investigations in preclinical and clinical PDT of tumors [14][15][16]. In the present research, the antitumor activity of TDPP, a porphyrin derivative, was evaluated in vitro and in vivo.…”

Section: Discussionmentioning

confidence: 97%

Antitumor effects evaluation of a novel porphyrin derivative in photodynamic therapy

Magetic

et al. 2015

Tumor Biol.

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In this paper, the antitumor activity of a novel porphyrin-based photosensitizer 5,10,15,20-tetrakis[(5-diethylamino)pentyl] porphyrin (TDPP) was reported in vitro and in vivo. The photophysical and cellular properties of TDPP were investigated. The singlet oxygen generation quantum yield of TDPP was detected; it showed a high singlet oxygen quantum yield of 0.52. The intracellular distribution of photosensitizer was detected with laser scanning confocal microscopy. The efficiency of TDPP-photodynamic therapy (PDT) in vitro was analyzed by 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay and in situ trypan blue exclusion test. Treated with a 630-nm laser, TDPP can kill cultured human esophageal cancer cell line (Eca-109) cells and reduce the growth of Eca-109 xenograft tumors significantly in BABL/c nude mice. And histopathological study was also used to confirm the antitumor effect. It has the perspective to be developed as a new antitumor drug in photodynamic therapy and deserves further investigation.

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“…5,10,15,20-Tetrakis(2-bromo-5-hydroxyphenyl)porphyrin has hydrogen atoms replaced by bromine atoms that increase the efficacy in the formation of cytotoxic species. This compound has IC50 values 6 times lower than Photofrin ® against WiDr cells [58]. In order to increase the selectivity another approach was tried.…”

Section: Future Photosensitizers: Development Of New Drugsmentioning

confidence: 99%

A look at clinical applications and developments of photodynamic therapy

et al. 2008

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The battle against cancer is so important that all possible weapons must be considered. Photodynamic therapy (PDT) is a therapeutic approach which has proved its capacity to give many excellent results, but it is having some difficulty in being imposed. The simplicity of the mechanism of action of this technique has been compromised by the multidisciplinary approach required for its implementation, which makes its adoption for more general use by health professionals difficult. This review aims to give a perspective of the performance of current approved PDT drugs, and their clinical applications against cancer.Basic investigation in PDT, particularly in the design of new sensitizers, is still ongoing, and needs to be further exploited. Emergent and diversified solutions with excellent results in pre-clinical phases are described to raise the multidisciplinary interest required to boost the clinical use of PDT.

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Halogen atom effect on photophysical and photodynamic characteristics of derivatives of 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin

Cited by 55 publications

References 33 publications

Improved Photodynamic Efficacy of Zn(II) Phthalocyanines via Glycerol Substitution

Improved Photodynamic Efficacy of Zn(II) Phthalocyanines via Glycerol Substitution

Antitumor effects evaluation of a novel porphyrin derivative in photodynamic therapy

A look at clinical applications and developments of photodynamic therapy

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