Tumour-localizing and -photosensitising properties of meso-tetra(4-nido-carboranylphenyl)porphyrin (H2TCP)

Clara Fabris, M. Graça H Vicente, Erhong Hao, Elisabetta Friso, Lara Borsetto, Giulio Jori, Giovanni Miotto, Paolo Colautti, Davide Moro, Juan Esposito, Alice Ferretti, Carlo Riccardo Rossi, Donato Nitti, Guido Sotti, Marina Soncin

Research output: Contribution to journalArticle

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Abstract

A water-soluble meso-substituted porphyrin (H2TCP) bearing 36 boron atoms, which appeared to be an efficient photodynamic sensitiser (singlet oxygen quantum yield = 0.44), was studied for its accumulation by murine melanotic melanoma cells (B16F1). The amount of H2TCP in the cells increased with the porphyrin dose in the incubation medium up to, and at least, 100 μM concentrations with no significant cytotoxic effect in the dark. Moreover, the H2TCP uptake increased with the incubation time reaching a plateau value corresponding with the recovery of 0.4 nmol of H2TCP per mg of cell proteins after 24 h incubation. Fluorescence microscopy observations showed that the porphyrin was largely localized intracellularly, exhibiting a discrete distribution in the cytoplasm with a pattern which was closely similar to that observed for the endosomal probe Lucifer yellow. The photosensitising efficiency of the H2TCP toward B16F1 cells was studied for different irradiation (1-15 min) and incubation (1-24 h) times. Nearly complete (>95%) cell mortality was obtained upon incubation with 20 μM H2TCP and 10 min irradiation with red light (600-700 nm, 20 mW/cm2). The porphyrin was also accumulated in appreciable amounts by the tumour tissue after intravenous injection to C57BL/6 mice bearing a subcutaneously transplanted melanotic melanoma. Maximum accumulation in the tumour was achieved by administration of H2TCP dissolved in the ternary mixture 20% dimethylsulfoxide (DMSO)-30% polyethyleneglycol (PEG 400)-50% water. Thus, this porphyrin could act as both a photodynamic therapy agent and a radiosensitising agent for boron neutron capture therapy.

Original languageEnglish
Pages (from-to)131-138
Number of pages8
JournalJournal of Photochemistry and Photobiology B: Biology
Volume89
Issue number2-3
DOIs
Publication statusPublished - Dec 14 2007

Fingerprint

porphyrins
Porphyrins
Tumors
tumors
Bearings (structural)
neoplasms
cells
Boron
Neoplasms
melanoma
boron
Melanoma
therapy
irradiation
Boron Neutron Capture Therapy
Irradiation
Radiation-Sensitizing Agents
therapeutics
Singlet Oxygen
Photodynamic therapy

Keywords

  • Boron neutron capture therapy
  • Carborane
  • Melanotic melanoma
  • Photodynamic therapy
  • Porphyrin

ASJC Scopus subject areas

  • Plant Science
  • Bioengineering
  • Physical and Theoretical Chemistry

Cite this

Tumour-localizing and -photosensitising properties of meso-tetra(4-nido-carboranylphenyl)porphyrin (H2TCP). / Fabris, Clara; Vicente, M. Graça H; Hao, Erhong; Friso, Elisabetta; Borsetto, Lara; Jori, Giulio; Miotto, Giovanni; Colautti, Paolo; Moro, Davide; Esposito, Juan; Ferretti, Alice; Rossi, Carlo Riccardo; Nitti, Donato; Sotti, Guido; Soncin, Marina.

In: Journal of Photochemistry and Photobiology B: Biology, Vol. 89, No. 2-3, 14.12.2007, p. 131-138.

Research output: Contribution to journalArticle

Fabris, C, Vicente, MGH, Hao, E, Friso, E, Borsetto, L, Jori, G, Miotto, G, Colautti, P, Moro, D, Esposito, J, Ferretti, A, Rossi, CR, Nitti, D, Sotti, G & Soncin, M 2007, 'Tumour-localizing and -photosensitising properties of meso-tetra(4-nido-carboranylphenyl)porphyrin (H2TCP)', Journal of Photochemistry and Photobiology B: Biology, vol. 89, no. 2-3, pp. 131-138. https://doi.org/10.1016/j.jphotobiol.2007.09.012
Fabris, Clara ; Vicente, M. Graça H ; Hao, Erhong ; Friso, Elisabetta ; Borsetto, Lara ; Jori, Giulio ; Miotto, Giovanni ; Colautti, Paolo ; Moro, Davide ; Esposito, Juan ; Ferretti, Alice ; Rossi, Carlo Riccardo ; Nitti, Donato ; Sotti, Guido ; Soncin, Marina. / Tumour-localizing and -photosensitising properties of meso-tetra(4-nido-carboranylphenyl)porphyrin (H2TCP). In: Journal of Photochemistry and Photobiology B: Biology. 2007 ; Vol. 89, No. 2-3. pp. 131-138.
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abstract = "A water-soluble meso-substituted porphyrin (H2TCP) bearing 36 boron atoms, which appeared to be an efficient photodynamic sensitiser (singlet oxygen quantum yield = 0.44), was studied for its accumulation by murine melanotic melanoma cells (B16F1). The amount of H2TCP in the cells increased with the porphyrin dose in the incubation medium up to, and at least, 100 μM concentrations with no significant cytotoxic effect in the dark. Moreover, the H2TCP uptake increased with the incubation time reaching a plateau value corresponding with the recovery of 0.4 nmol of H2TCP per mg of cell proteins after 24 h incubation. Fluorescence microscopy observations showed that the porphyrin was largely localized intracellularly, exhibiting a discrete distribution in the cytoplasm with a pattern which was closely similar to that observed for the endosomal probe Lucifer yellow. The photosensitising efficiency of the H2TCP toward B16F1 cells was studied for different irradiation (1-15 min) and incubation (1-24 h) times. Nearly complete (>95{\%}) cell mortality was obtained upon incubation with 20 μM H2TCP and 10 min irradiation with red light (600-700 nm, 20 mW/cm2). The porphyrin was also accumulated in appreciable amounts by the tumour tissue after intravenous injection to C57BL/6 mice bearing a subcutaneously transplanted melanotic melanoma. Maximum accumulation in the tumour was achieved by administration of H2TCP dissolved in the ternary mixture 20{\%} dimethylsulfoxide (DMSO)-30{\%} polyethyleneglycol (PEG 400)-50{\%} water. Thus, this porphyrin could act as both a photodynamic therapy agent and a radiosensitising agent for boron neutron capture therapy.",
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