article · 01/01/2009
Photosensitizing properties of chlorins in solution and in membrane-mimicking systems
Résumé
The photosensitizing properties of three chlorins, meso-tetra(3-hydroxyphenyl) chlorin (m-THPC), chlorin e6 (Ce6) and meso-tetraphenylchlorin substituted by two adjacent sulfonated groups (TPCS(2a)) are compared in solution and when incorporated in dioleoyl-sn-phosphatidylcholine (DOPC) liposomes. In solution, the three chlorins possess a similar efficacy to generate singlet oxygen (quantum yield similar to 0.65). The formation of conjugated dienes was used to determine their ability to induce the peroxidation of methyl linoleate as a target of singlet oxygen. In ethanol solution, the apparent quantum yield for this process is the same for the three chlorins and its value agrees with that expected from the known rates for the decay of singlet oxygen and its reaction with methyl linoleate. When incorporated in liposomes, the order of efficacy is m-THPC > TPCS(2a) > Ce6. This order is tentatively assigned to the relative embedment of the photosensitizer within the lipidic bilayer, TPCS(2a) and Ce6 being anchored by their negative chains nearer to the water-lipid interface. The photoinduced permeation of the lipidic bilayer by these chlorins was investigated by measuring the release of carboxy fluorescein entrapped into DOPC liposomes. The charged chlorins, in particular TPCS(2a), are the most efficient, a result discussed in relation with the technology of photochemical internalization, PCI.
Citer cet article
Mojzisova, H., Bonneau, S., Maillard, P., Berg, K., & Brault, D. (2009). Photosensitizing properties of chlorins in solution and in membrane-mimicking systems. Photochem Photobiol Sci., 8(6), 778-87. https://doi.org/10.1039/b822269j@article{Mojzisova2009_154,
author = {Mojzisova, Halina and Bonneau, Stephanie and Maillard, Philippe and Berg, Kristian and Brault, Daniel},
year = {2009},
month = {1},
title = {Photosensitizing properties of chlorins in solution and in membrane-mimicking systems},
journal = {Photochem Photobiol Sci.},
volume = {8},
number = {6},
pages = {778-87},
abstract = {The photosensitizing properties of three chlorins, meso-tetra(3-hydroxyphenyl) chlorin (m-THPC), chlorin e6 (Ce6) and meso-tetraphenylchlorin substituted by two adjacent sulfonated groups (TPCS(2a)) are compared in solution and when incorporated in dioleoyl-sn-phosphatidylcholine (DOPC) liposomes. In solution, the three chlorins possess a similar efficacy to generate singlet oxygen (quantum yield similar to 0.65). The formation of conjugated dienes was used to determine their ability to induce the peroxidation of methyl linoleate as a target of singlet oxygen. In ethanol solution, the apparent quantum yield for this process is the same for the three chlorins and its value agrees with that expected from the known rates for the decay of singlet oxygen and its reaction with methyl linoleate. When incorporated in liposomes, the order of efficacy is m-THPC > TPCS(2a) > Ce6. This order is tentatively assigned to the relative embedment of the photosensitizer within the lipidic bilayer, TPCS(2a) and Ce6 being anchored by their negative chains nearer to the water-lipid interface. The photoinduced permeation of the lipidic bilayer by these chlorins was investigated by measuring the release of carboxy fluorescein entrapped into DOPC liposomes. The charged chlorins, in particular TPCS(2a), are the most efficient, a result discussed in relation with the technology of photochemical internalization, PCI.},
url = {http://www.dx.doi.org/10.1039/b822269j},
doi = {10.1039/b822269j},
issn = {1474-905X},
}TY - JOUR
AU - Mojzisova, Halina
AU - Bonneau, Stephanie
AU - Maillard, Philippe
AU - Berg, Kristian
AU - Brault, Daniel
PY - 2009
DA - 2009/01/01
TI - Photosensitizing properties of chlorins in solution and in membrane-mimicking systems
JO - Photochem Photobiol Sci.
VL - 8
IS - 6
SN - 1474-905X
AB - The photosensitizing properties of three chlorins, meso-tetra(3-hydroxyphenyl) chlorin (m-THPC), chlorin e6 (Ce6) and meso-tetraphenylchlorin substituted by two adjacent sulfonated groups (TPCS(2a)) are compared in solution and when incorporated in dioleoyl-sn-phosphatidylcholine (DOPC) liposomes. In solution, the three chlorins possess a similar efficacy to generate singlet oxygen (quantum yield similar to 0.65). The formation of conjugated dienes was used to determine their ability to induce the peroxidation of methyl linoleate as a target of singlet oxygen. In ethanol solution, the apparent quantum yield for this process is the same for the three chlorins and its value agrees with that expected from the known rates for the decay of singlet oxygen and its reaction with methyl linoleate. When incorporated in liposomes, the order of efficacy is m-THPC > TPCS(2a) > Ce6. This order is tentatively assigned to the relative embedment of the photosensitizer within the lipidic bilayer, TPCS(2a) and Ce6 being anchored by their negative chains nearer to the water-lipid interface. The photoinduced permeation of the lipidic bilayer by these chlorins was investigated by measuring the release of carboxy fluorescein entrapped into DOPC liposomes. The charged chlorins, in particular TPCS(2a), are the most efficient, a result discussed in relation with the technology of photochemical internalization, PCI.
SP - 778
EP - 87
DO - 10.1039/b822269j
UR - http://www.dx.doi.org/10.1039/b822269j
ER -