Photophysical Properties of Neutral and Cationic Tetrapyridinoporphyrazines

Martí, Cristina; Nonell, Santi; Nicolau, Mónica; Torres, Tomás

doi:10.1562/0031-8655(2000)071<0053:pponac>2.0.co;2

Cited by 16 publications

(35 citation statements)

References 31 publications

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“…Analysis of the photothermal signal was performed by means of two methods proposed by Marti et al [15] and by Small et al [16]. The Marti et al [15] method is based on comparison of the maximal amplitudes (H max ) of the LIOAS signal (describe by Eq.…”

Section: Resultsmentioning

confidence: 99%

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Spectral Properties and Deactivation Processes of Anionic Porphyrin Coupled with TiO2 Nanostructure

et al. 2009

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Meso-tetrakis (4-sulphonatophenyl)porphyrin (TSPP) and its complex with TiO 2 were studied by absorption, fluorescence, and steady-state and time-resolved photothermal spectroscopy. A TiO 2 -TSPP complex was obtained by covalent bonding of anionic porphyrin with the nanostructural form of TiO 2 . The TiO 2 colloidal carriers modifying the thermal energy distribution and considerably influencing the photophysical processes were found to lead to changes in the population of the porphyrin singlet and triplet states, resulting in singlet oxygen generation and/or electron transfer.

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Section: Resultsmentioning

confidence: 99%

“…The Marti et al [15] method is based on comparison of the maximal amplitudes (H max ) of the LIOAS signal (describe by Eq. 1) recorded for the sample (S) and the reference (R) (Fig.…”

Section: Resultsmentioning

confidence: 99%

Spectral Properties and Deactivation Processes of Anionic Porphyrin Coupled with TiO2 Nanostructure

et al. 2009

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“…8 In the case of pyridine derivatives, these compounds can be quaternized, introducing substituents in order to modulate the solubility of the tetracationic derivatives. [9][10][11][12] This procedure permits to form water soluble compounds, some of them solubilized as monomers in aqueous solutions, whereas others mainly remain as aggregates in several media.…”

Section: Introductionmentioning

confidence: 99%

“…ZnTM3,4PyPz was dissolved as a mixture of at least two species in methanol, aqueous sodium dodecylsulfate (SDS), and in methanol-pyridine mixtures. 11 Therefore, this cationic porphyrazine is not an efficient photosensitizer in pure water. 11,13 In the present work, we explore the spectroscopic properties and the photo-oxidation of biological substrates catalyzed by zinc(II)tetramethyltetrapyridino[2,3-b:2′,3′-g:2′′,3′′-l:2′′′,3′′′-q]porphyrazinium (ZnTM2,3PyPz, Scheme 1) in water and in n-heptane/AOT/water micellar system.…”

Section: Introductionmentioning

confidence: 99%

“…11 Therefore, this cationic porphyrazine is not an efficient photosensitizer in pure water. 11,13 In the present work, we explore the spectroscopic properties and the photo-oxidation of biological substrates catalyzed by zinc(II)tetramethyltetrapyridino[2,3-b:2′,3′-g:2′′,3′′-l:2′′′,3′′′-q]porphyrazinium (ZnTM2,3PyPz, Scheme 1) in water and in n-heptane/AOT/water micellar system. The main difference between ZnTM2,3PyPz and ZnTM3,4PyPz sensitizers is found in their solubilities as monomeric species in aqueous solutions.…”

Section: Introductionmentioning

confidence: 99%

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Photosensitization Ability of a Water Soluble Zinc(II)tetramethyltetrapyridinoporphyrazinium Salt in Aqueous Solution and Biomimetic Reverse Micelles Medium

2008

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The spectroscopic properties and the photodynamic activity of a highly water soluble zinc(II)tetramethyltetrapyridino[2,3-b:2',3'-g:2",3"-l:2"',3'''-q]porphyrazinium salt (ZnTM2,3PyPz) were investigated in aqueous homogeneous solution and in biomimetic reverse micelles medium bearing photooxidizable biological substrates. Absorption and fluorescence spectroscopic studies indicate that ZnTM2,3PyPz is dissolved as monomer in water and in n-heptane/sodium bis(2-ethylhexyl)sulfosuccinate (AOT, 0.1 M)/water (W0 = 30) micellar system. Fluorescence quantum yields (phi F) of 0.29 and 0.27 were calculated for ZnTM2,3PyPz in water and in AOT micelles, respectively. Spectroscopic analysis at different AOT concentrations showed interaction between ZnTM2,3PyPz and AOT reverse micelles with a binding constant (Kb) of 1.7 x 10(3) M(-1). The photosensitization ability of ZnTM2,3PyPz was evaluated using 9,10-dimethylanthracene (DMA). Singlet molecular oxygen, O2(1 delta g), production yielded values of phi(delta) = 0.65 for ZnTM2,3PyPz in AOT micelles. Also, ZnTM2,3PyPz induced efficiently the decomposition of the amino acid L-tryptophan (Trp) and the nucleotide guanosine 5'-monophosphate (GMP) in both media. A value of approximately 3.6 x 10(7) s(-1) M(-1) was found for the second order rate constant of Trp (k(r)(Trp)) decomposition in the AOT system, which is near to that found in pure water. Moreover, ZnTM2,3PyPz formed stable complexes with GMP with a binding constant of K(GMP) = 1.0 x 10(3) M(-1). 1H NMR studies indicated that ZnTM2,3PyPz interacts mainly with the guanine moiety more than the sugar part of GMP. On the other hand, the photodynamic activity of ZnTM2,3PyPz produced decomposition of GMP. Quantification of GMP by HPLC indicates that the nucleotide is photooxidized with a k(obs)(GMP) = 2.6 x 10(-4) s(-1) in water. Photooxidation of GMP considerably increases in deuteriated water indicating that ZnTM2,3PyPz appears to perform its photosensitizing action via the intermediacy of O2(1delta g). Also, efficient sensitized decomposition was observed in micellar media resembling that in pure water. These results provide a better understanding of the effective photodynamic action produced by ZnTM2,3PyPz like a potential phototherapeutic agent for the treatment of neoplastic diseases by photodynamic therapy.

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Photoactivity of New Octacationic Magnesium(II) and Zinc(II) Porphyrazines in a Water Solution and G-Quadruplex Binding Ability of Differently Sized Zinc(II) Porphyrazines

et al. 2017

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The new octacations [(2-Mepy)PzM] [M = Mg(HO), Zn], isolated as iodide salts, were obtained from the corresponding neutral complexes [PyPzM] (Py = 2-pyridyl; Pz = porphyrazinato dianion) upon quaternization with CHI of the N atoms of the 2-pyridyl rings under mild experimental conditions. The absorption spectra registered in organic solvents as well as in water (HO) confirm the presence of the complexes in their monomeric form in all cases. The two octacations behave as photosensitizers in a HO/sodium dodecyl sulfate solution for the production of singlet oxygen, O, and exhibit quantum yield values (Φ) 2.2-2.5 higher than those measured for the standard PcAlS, a promising feature of interest for photodynamic therapy. The interaction of the Zn octacation [(2-Mepy)PzZn] with different types of DNA has been studied by means of optical spectroscopic techniques, clearly suggesting that binding of the charged macrocycle to the DNA effectively takes place. In order to assess the effect of the aromatic ring size, the same binding study was performed for the octapyridinated zinc(II) tetraquinoxalinoporphyrazine complex having a much more expanded macrocyclic framework and compared with the behavior of the parent octapyridinated zinc(II) tetrapyrazinoporphyrazine complex having an intermediate macrocycle. The achieved information confirms the relationship between the binding of the charged macrocycle to the DNA and the dimension of the porphyrazine macrocycle.

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Photophysical Properties of Neutral and Cationic Tetrapyridinoporphyrazines

Cited by 16 publications

References 31 publications

Spectral Properties and Deactivation Processes of Anionic Porphyrin Coupled with TiO2 Nanostructure

Spectral Properties and Deactivation Processes of Anionic Porphyrin Coupled with TiO2 Nanostructure

Photosensitization Ability of a Water Soluble Zinc(II)tetramethyltetrapyridinoporphyrazinium Salt in Aqueous Solution and Biomimetic Reverse Micelles Medium

Photoactivity of New Octacationic Magnesium(II) and Zinc(II) Porphyrazines in a Water Solution and G-Quadruplex Binding Ability of Differently Sized Zinc(II) Porphyrazines

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