Photophysical properties of glucoconjugated chlorins and porphyrins and their associations with cyclodextrins.
Glucoconjugated analogues of the meta-hydroxyphenyl porphyrin (m-THPP) and meta-hydroxyphenyl chlorin (m-THPC) has been recently synthesized. The characteristics of their triplet states have been determined with regard to their involvement in the photodynamic (PDT) efficiency. In the case of porphyrin derivatives, triplet quantum yields (Phi(T)) were ranging from 0.42 to 0.55 and triplet life times (tau(T)) from 1 to 5 micros. High reaction rate constants (k(q)) with molecular oxygen (k(q): 1.2-1.6 x 10(9)s(-1)) have been found. The triplet lifetimes of chlorin derivatives were about four times higher than those of porphyrins whereas the Phi(T) and k(q) values remained quite similar. Singlet oxygen yields of glucosylated and non-glucosylated porphyrins and chlorins were not significantly different within experimental errors (Phi(Delta)((1)O(2)): 0.41-0.58). Furthermore, it has been shown that glucoconjugated photosensitizers could undergo associations with the methyl-beta-cyclodextrin (Me-beta-CD) which exhibit high triplet lifetimes and singlet oxygen yields ranging from 0.27 to 0.48.
Bautista-Sanchez
Antonia
A
Laboratoire de Chimie Analytique, EA 3343, Faculté de Pharmacie Paris XI, 5 rue J.-B. Clément, F-92296 Chatenay-Malabry, France.
Kasselouri
Athena
A
Desroches
Marie-Catherine
MC
Blais
Jocelyne
J
Maillard
Philippe
P
de Oliveira
Daniela Manfrim
DM
Tedesco
Antonio C
AC
Prognon
Patrice
P
Delaire
Jacques
J
D002942:Circular Dichroism; D003505:Cyclodextrins / Q000737:chemistry*; D006001:Glycoconjugates / Q000737:chemistry*; D017319:Photosensitizing Agents / Q000737:chemistry; D011166:Porphyrins / Q000737:chemistry*; D026082:Singlet Oxygen / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D047392:beta-Cyclodextrins / Q000737:chemistry
D003505:Cyclodextrins; D006001:Glycoconjugates; D017319:Photosensitizing Agents; D011166:Porphyrins; D047392:beta-Cyclodextrins; C108732:methyl-beta-cyclodextrin; D026082:Singlet Oxygen; C006969:chlorin