Photodemetalation of silver(II) tetraphenylporphyrin

Kunkely, Horst; Vogler, Arnd

doi:10.1016/j.inoche.2007.01.007

Cited by 19 publications

(7 citation statements)

References 22 publications

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“…After the paramagnetic Cu ion was inserted into the porphyrin ring, there was almost no 1 O 2 generation in Por 2. This phenomenon was consistent with the partial filling of d-orbital in Ag(II)-TPP [21] and Co-TCNPP. [22] The reason for this was probably due to the introduction of 'relaxed' metal into the porphyrin to stimulate the triplet state, which prevented the bimolecular quenching by oxygen.…”

Section: Photogeneration Of Singlet Oxygensupporting

confidence: 86%

Synthesis, DNA binding mode, singlet oxygen photogeneration and DNA photocleavage activity of ruthenium compounds with porphyrin–imidazo[4,5‐f]phenanthroline conjugated ligand

Jiang

Liu

Zhao

et al. 2018

Applied Organom Chemis

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Using 1,10‐phenanothroline‐5,6‐dione and 10,20‐bis(4‐methylphenyl)porphyrin copper as starting materials, a conjugated porphyrin–imidazo[4,5‐f]‐1,10‐phenanothroline ligand (Por 1) was prepared. Subsequently, the copper complex of Por 1 was reacted with Ru(1,10‐phenanothroline)2Cl2 to yield ruthenium compound Por 2. After removal of copper metal under acid condition, the free base porphyrin of Por 2 (Por 3) was prepared. The structure of these compounds was confirmed using UV–visible, 1H NMR, mass and infrared spectroscopies and elemental analysis. Through UV–visible, fluorescence and circular dichroism analyses, the interaction modes between Por 1–3 and calf thymus DNA were investigated. Por 1 interacted with DNA via outside groove face, but Por 2 and Por 3 showed intercalative interaction with DNA. Binding constants between Por 1–3 and DNA were 7.79 × 105, 1.29 × 106 and 1.32 × 106 M−1, respectively. With 5,10,15,20‐tetraphenylporphyrin (H2TPP) as a control, the singlet oxygen (1O2) generation of Por 1–3 was measured using the 1,3‐diphenylisobenzofuran method. The 1O2 generation rate of Por 1–3 followed the order: Por 3 >Por 1 >H2TPPP >Por 2. Por 1 and Por 3 showed better 1O2 quantum yields than Por 2, which were almost threefold higher than that of H2TPP. The DNA cleavage ability of Por 1–3 was analyzed using gel electrophoresis. Por 3 showed higher DNA photocleavage activity, with more than 50% photocleavage rate at 20 μM. These results suggest that amphipathic (hydrophilic/lipophilic) Por 3 with conjugated Por 1 ligand is a potential photosensitizer in cancer therapy.

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Section: Photogeneration Of Singlet Oxygensupporting

confidence: 86%

Synthesis, DNA binding mode, singlet oxygen photogeneration and DNA photocleavage activity of ruthenium compounds with porphyrin–imidazo[4,5‐f]phenanthroline conjugated ligand

Jiang

Liu

Zhao

et al. 2018

Applied Organom Chemis

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“…These spectra are shown in Figure 2. By using 5,10,15,20-tetraphenylporphyrin (H 2 TPP) as a reference (Φ ∆ = 0.55), [18] [19] presumably due to a metal-facilitated relaxation of the porphyrin excited triplet state that precludes bimolecular quenching by oxygen. In contrast, zinc(II) (cyanophenyl)-porphyrinate 3 showed a very high 1 O 2 quantum yield of 0.94, which is almost twice that of the other (cyanophenyl)-porphyrins studied.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, Singlet‐Oxygen Photogeneration, DNA Photocleavage and Two‐Photon‐Absorption Properties of Some (4‐Cyanophenyl)porphyrins

et al. 2009

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“…Notably, porphyrins are able to efficiently sensitize the near-infrared luminescence of lanthanide ions, which can be widely applied from telecommunication to biomedical optical imaging [34,35]. Besides, lanthanide(III) porphyrins may be applied for photocatalytic hydrogen production from water because their reduced metal centers (Ln(II)) formed in photoinduced LMCT processes (typical for OOP complexes [36,37]) have considerably high negative redox potentials (except for europium) [38]. In this section, we survey the photophysical and primary photochemical properties of the complexes between a water-soluble, anionic porphyrin, the 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin (H2TSPP 4-) and three early lanthanide(III) ions (Ln = La, Ce, Nd).…”

Section: Photophysics and Photochemistry Of Water-soluble Out-of-planmentioning

confidence: 99%

Visible light-driven photophysics and photochemistry of water-soluble metalloporphyrins

Horváth

Valicsek

Fodor

et al. 2016

Coordination Chemistry Reviews

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Photodemetalation of silver(II) tetraphenylporphyrin

Cited by 19 publications

References 22 publications

Synthesis, DNA binding mode, singlet oxygen photogeneration and DNA photocleavage activity of ruthenium compounds with porphyrin–imidazo[4,5‐f]phenanthroline conjugated ligand

Synthesis, DNA binding mode, singlet oxygen photogeneration and DNA photocleavage activity of ruthenium compounds with porphyrin–imidazo[4,5‐f]phenanthroline conjugated ligand

Synthesis, Characterization, Singlet‐Oxygen Photogeneration, DNA Photocleavage and Two‐Photon‐Absorption Properties of Some (4‐Cyanophenyl)porphyrins

Visible light-driven photophysics and photochemistry of water-soluble metalloporphyrins

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