A comparison between the photophysical and photosensitising properties of tetraphenyl porphycenes and porphyrins

Rubio, Noemí; Prat, Ferran; Bou, Núria; Borrell, José I.; Teixidó, Jordi; Villanueva, Ángeles; Juarranz, Ángeles; Cañete, Magdalena; Stockert, Juan C.; Nonell, Santi

doi:10.1039/b415314f

Cited by 48 publications

(77 citation statements)

References 64 publications

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“…The remaining complexes use most of the transition metals, particularly in the M(II) oxidation state. The general procedure for the synthesis of such complexes consists in treating the corresponding porphycene with a soluble salt of the desired metal (such as Fe acetylacetonate or Ni(OAc) 2 ) in an inert solvent at reflux and in the presence, when necessary, of the extra ligands needed [71,93,112,124,131,[158][159][160][161].…”

Section: Peripheral Functionalization 233 Modification Of the Corementioning

confidence: 99%

“…Decades of research on porphyrins have provided clues for the design of PSs approaching the ideal above: red shifts in the absorption spectrum (bathochromism) can be achieved by enlarging the size of the aromatic macrocycle thus destabilizing the highest occupied molecular orbital (HOMO) [77][78][79][80][81][82][83][84], by suitable peripheral functionalization [71,83,85,86], or by introducing heteroatoms in the macrocycle core, particularly nitrogens [79,83,[87][88][89][90][91][92][93][94].…”

Section: Introductionmentioning

confidence: 99%

“…2), which results in 20-fold larger absorption coefficients in the red part of the spectrum. Several 2,7,12,17-tetraalkyl-substituted porphycenes (e.g., methyl, ethyl, n-propyl, methoxyethyl) [63][64][65], as well as the tetraphenyl derivative (TPPo) [66][67][68] and its palladium(II) complex (PdTPPo) [69][70][71] were found to be photoactive and to induce efficient cell damage in vitro and in vivo [64,[72][73][74][75]. This review aims to summarize the chemistry of porphycenes, and their photophysical and biological properties for PDT applications.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Porphycenes: Facts and Prospects in Photodynamic Therapy of Cancer

Stockert¹,

Cañete²,

Juarranz³

et al. 2007

CMC

177

130

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The photodynamic process induces cell damage and death by the combined effect of a photosensitizer (PS), visible light, and molecular oxygen, which generate singlet oxygen ((1)O(2)) and other reactive oxygen species that are responsible for cytotoxicity. The most important application of this process with increasing biomedical interest is the photodynamic therapy (PDT) of cancer. In addition to hematoporphyrin-based drugs, 2nd generation PSs with better photochemical properties are now studied using cell cultures, experimental tumors and clinical trials. Porphycene is a structural isomer of porphyrin and constitutes an interesting new class of PS. Porphycene derivatives show higher absorption than porphyrins in the red spectral region (lambda > 600 nm, epsilon > 50000 M-(1)cm(-1)) owing to the lower molecular symmetry. Photophysical and photobiological properties of porphycenes make them excellent candidates as PSs, showing fast uptake and diverse subcellular localizations (mainly membranous organelles). Several tetraalkylporphycenes and the tetraphenyl derivative (TPPo) induce photodamage and cell death in vitro. Photodynamic treatments of cultured tumor cells with TPPo and its palladium(II) complex induce cytoskeletal changes, mitotic blockage, and dose-dependent apoptotic or necrotic cell death. Some pharmacokinetic and phototherapeutic studies on experimental tumors after intravenous or topical application of lipophilic alkyl-substituted porphycene derivatives are known. Taking into account all these features, porphycene PSs should be very useful for PDT of cancer and other biomedical applications.

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Section: Peripheral Functionalization 233 Modification Of the Corementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Porphycenes: Facts and Prospects in Photodynamic Therapy of Cancer

Stockert¹,

Cañete²,

Juarranz³

et al. 2007

CMC

177

130

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“…The indium porphyrins of 2 and 4 exhibited the highest activity of the singlet oxygen production than others. The result that the metal porphyrins, 2, 4, and 5, exhibit the higher activity for the singlet oxygen production than the free-based porphyrins, 1 and 3, suggests the heavy atom effect, which is also reported with the Pd porphyrin [48].…”

Section: Singlet Oxygen Productionmentioning

confidence: 49%

Syntheses and photodynamic properties of glucopyranoside-conjugated indium(III) porphyrins as a bifunctional agent

Nakai

Maeda

Mashima

et al. 2013

J. Porphyrins Phthalocyanines

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Malignant tumor is the most common cause of death, and great efforts have been made to develop new ways for the cancer treatments and the rapid diagnoses. The cancer treatments including surgery, chemotherapy, radiotherapy, immunotherapy, photodynamic therapy (PDT), etc., are in widespread clinical use. Since these treatments are often accompanied with serious side effects, improvements are important to diminish the undesirable side effects. We have focused on the improvement of photodynamic therapy (PDT). In the PDT procedure, the photosensitizer is administrated to patients by intravenous injection, tumor is irradiated with light at the highest uptake of the photosensitizer by tumor, and singlet oxygen produced by the excited photosensitizer results in tumor apoptosis [1][2][3][4]. Therefore, PDT is promising as the less toxic cancer treatment than chemotherapy if the selective uptake of the photosensitizer by tumor is achieved. ABSTRACT: The glucopyranoside-conjugated porphyrins, H 2 TPP{p-O-(CH 2 ) 2 -O-OAcGlc} (1), [InTPP{p-O-(CH 2 ) 2 -O-OAcGlc}]NO 3 (2), H 2 TPP{p-O-(CH 2 ) 2 -O-Glc} (3), [InTPP{p-O-(CH 2 ) 2 -O-Glc}]-NO 3 (4) and ZnTPP{p-O-(CH 2 ) 2 -O-OAcGlc} (5) were synthesized, and characterized by 1 H NMR, 13 C NMR, ESI-MS, UV-vis spectroscopies and elemental analyses. In the 1 H NMR spectrum of 2, two sets of signals were observed for H-atoms of the phenyl group of porphyrin, indicating that 2 has the axial chirality due to a NO 3 ion coordinating to the indium atom. Abilities of the singlet oxygen production of these porphyrins, investigated by using 1,3-diphenylisobenzofuran (DPBF) as a quencher, were higher than those of the free-based and zinc porphyrins, reflecting the heavy atom effect. The photodynamic properties of these porphyrin derivatives were investigated against COLO 679. All of the glucopyranosideconjugated porphyrins exhibited the high photocytotoxicity compared with Laserphyrin ® . Above all, 4 exhibited the highest photocytotoxicity, coinciding with the high abilities of this complex for the singlet oxygen production and the cell permeability.

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“…The four bands for TPP are related to the presence of extra two hydrogens in the free base porphyrin that lead to a reduction of the overall porphyrin symmetry from the D 4 h type of metalloporphyrins to D 2 h. 30 The structural changes in the basic structure of InTPP compared with those in TPP lead to a blue shift in the peak position of the long-wavelength Q band (646 nm for TPP versus 600 nm for InTPP). 21 This blue shift is attributable to a distortion of the ligand plane caused by the central ion, 31,32 and is also considered to be a measure of the degree of interaction between the central ion and the conjugated system. 29 The transient absorption spectrum obtained with laser flash photolysis of InTPP in DMSO is shown in Figure 3.…”

Section: Photophysical Resultsmentioning

confidence: 99%

Photodynamic activity of chloro(5,10,15,20-tetraphenylporphyrinato)indium(III)

Silva¹,

Pelegrino²,

Tedesco³

et al. 2008

J. Braz. Chem. Soc.

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A atividade fotodinâmica do cloro (5,10,15,20-tetrafenilporfirinato) de índio(III) (InTPP) in vitro foi investigado para possível uso em terapia fotodinâmica (PDT). O rendimento quântico de oxigênio singlete do InTPP (Φ ∆ = 0,72) em DMSO foi maior que da 5,10,15,20-tetrafenilporfirina (TPP) (Φ ∆ = 0,52). Os sítios de ligação entre os fotossensibilizadores e albumina bovina (BSA) são independentes e com células vermelhas de sangue humano (RBC) são cooperativos, com um e quatro sítios de ligação por molécula, respectivamente. As constantes de associação com BSA são (1,15 ± 0,07) × 10 5 e (2,6 ± 0,1) × 10 4 L mol -1 e com RBC são (2,40 ± 0,05) × 10 7 L mol -1 e (7,2 ± 0,2) × 10 4 L mol ) of photosensitizers were used. InTPP was 1.37-1.5 times more effective in the photooxidation of RBC than Photofrin®. Our results indicate that InTPP should be used in future studies of PDT.

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A comparison between the photophysical and photosensitising properties of tetraphenyl porphycenes and porphyrins

Cited by 48 publications

References 64 publications

Porphycenes: Facts and Prospects in Photodynamic Therapy of Cancer

Porphycenes: Facts and Prospects in Photodynamic Therapy of Cancer

Syntheses and photodynamic properties of glucopyranoside-conjugated indium(III) porphyrins as a bifunctional agent

Photodynamic activity of chloro(5,10,15,20-tetraphenylporphyrinato)indium(III)

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