Document Detail


On the photobiological properties of chimeras combining quaternary ammonium derivatives of retinoic amides and psoralen. A study with cultured human keratinocytes.
MedLine Citation:
PMID:  14743873     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The effectiveness of the combination of retinoids with 8-methoxypsoralen (8-MOP) and ultraviolet-A (UV-A) light in the treatment of some cutaneous proliferative diseases has motivated the synthesis of new "chimera-type" molecules built from psoralen derivatives and retinoic amides and related molecules. The chimeras result from the combination of 8-(3-bromopropyloxy)-psoralen with amides prepared by reacting 4-amino-pyridine with 13E- and 13Z-retinoic acids or a "retinoid-like" derivative with an alkene chain of only three double bonds. The synthesis of chimeras built with the 8-(3-bromopropyloxy)-psoralen and the amide of cinnamic acid or its 4-methoxy derivative has also been carried out. In contrast to 8-MOP, all the chimeras exhibit strong molar absorptivities in the range 20 000-40 000 M(-1) cm(-1) in the 340-390 nm UV-A region. The "retinoid-like"- and retinoid-psoralen chimeras are characterized by a marked dark toxicity toward proliferating NCTC 2544 keratinocytes (with a lethal dose corresponding to 50% cell survival [LD50] of 1-5 microM) as compared with that of the cinnamic acid derivative-psoralen chimeras (LD50 > or = 50 microM). This toxicity leads to alteration of the mitochondrial membrane potential. At nontoxic concentrations, the chimeras demonstrate effective psoralens + UV-A-induced photocytotoxicity. They are moderate photosensitizers of membrane lipid peroxidation. Cell apoptosis is a major photocytotoxic process as suggested by the fluorescence-activated cell-sorting technique using annexin-fluorescein isothiocyanate and propidium iodide as apoptotic markers.
Authors:
Véronique Lartillot; Arnaud Risler; Zo Andriamialisoa; Michel Giraud; Teresa Sá e Melo; Laurence Michel; René Santus
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Photochemistry and photobiology     Volume:  78     ISSN:  0031-8655     ISO Abbreviation:  Photochem. Photobiol.     Publication Date:  2003 Dec 
Date Detail:
Created Date:  2004-01-27     Completed Date:  2004-03-24     Revised Date:  2005-11-17    
Medline Journal Info:
Nlm Unique ID:  0376425     Medline TA:  Photochem Photobiol     Country:  United States    
Other Details:
Languages:  eng     Pagination:  623-32     Citation Subset:  IM    
Affiliation:
INSERM U532, Institut de Recherche sur la Peau, Hôpital Saint-Louis, Paris cedex, France.
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MeSH Terms
Descriptor/Qualifier:
Antineoplastic Agents / chemistry*,  pharmacology
Cell Survival / drug effects,  radiation effects
Cells, Cultured
Dose-Response Relationship, Drug
Dose-Response Relationship, Radiation
Drug Combinations
Ficusin / therapeutic use
Humans
Keratinocytes / cytology*
Light
Lipid Peroxidation / drug effects,  radiation effects
PUVA Therapy / methods*
Quaternary Ammonium Compounds / therapeutic use
Tretinoin / analogs & derivatives,  therapeutic use
Chemical
Reg. No./Substance:
0/Antineoplastic Agents; 0/Drug Combinations; 0/Quaternary Ammonium Compounds; 302-79-4/Tretinoin; 66-97-7/Ficusin

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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