N-conjugates of 2,5-disubstituted pyrrole and glutathione. Evaluation of their potency as antioxidants against photosensitization of NCTC 2544 keratinocytes by excess endogenous protoporphyrin IX.
A novel glutathione compound in which the amino group has been derivatized by a 2,5-dimethyl pyrrole is shown to be very effective against cell photosensitization in vitro. Protoporphyrin IX either added to the medium or produced endogenously by incubation of NCTC 2544 keratinocytes with 5-aminolevulinic acid has been chosen as the photosensitizer. The antioxidant effectiveness of glutathione-pyrrole derivatives against protoporphyrin photosensitization depends critically on the type of 2,5 substitution on the pyrrole ring. This structure-function relationship may be attributed to the difference in compartmentation and/or uptake of the various glutathione-pyrrole derivatives under study. The 2,5-dimethyl pyrrole derivative is much more effective than glutathione as a protective agent against phototoxic reactions induced by protoporphyrin IX.
Gaullier
J M
JM
Laboratoire de Photobiologie (INSERM U312), Muséum National d'Histoire Naturelle, Paris, France.
Valla
A
A
Bazin
M
M
Giraud
M
M
Dubertret
L
L
Santus
R
R
D000622:Aminolevulinic Acid / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D005978:Glutathione / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D015603:Keratinocytes / Q000166:cytology / Q000187:drug effects*; D008027:Light; D015394:Molecular Structure; D017319:Photosensitizing Agents / Q000494:pharmacology*; D011524:Protoporphyrins / Q000494:pharmacology*; D011758:Pyrroles / Q000737:chemistry / Q000494:pharmacology*
D000975:Antioxidants; D017319:Photosensitizing Agents; D011524:Protoporphyrins; D011758:Pyrroles; D000622:Aminolevulinic Acid; C028025:protoporphyrin IX; D005978:Glutathione