Abstract |
Thio and seleno analogues of tetramethylrosamine were prepared by the directed-metalation/cyclization of the corresponding N,N-diethyl 2-(3-dimethylaminophenylchalcogeno)-4-dimethylaminobenzamide to the 2,7-bis-(N,N-dimethylamino)-9H-chalcogenoxanthen-9-one followed by the addition of phenylmagnesium bromide, dehydration, and ion exchange to the chloride salt. The thio and seleno tetramethylrosamines had longer wavelengths of absorption and higher quantum yields for the generation of singlet oxygen than tetramethylrosamine. Both the thio and selenoanalogues of tetramethylrosamine were efficient photosensitizers against R3230AC rat mammary adenocarcinoma cells in vitro.
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Authors | Michael R Detty, Paras N Prasad, David J Donnelly, Tymish Ohulchanskyy, Scott L Gibson, Russell Hilf |
Journal | Bioorganic & medicinal chemistry
(Bioorg Med Chem)
Vol. 12
Issue 10
Pg. 2537-44
(May 15 2004)
ISSN: 0968-0896 [Print] England |
PMID | 15110836
(Publication Type: Journal Article, Research Support, U.S. Gov't, P.H.S.)
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Chemical References |
- Chalcogens
- Heterocyclic Compounds, 3-Ring
- Photosensitizing Agents
- Rhodamines
- Selenium Compounds
- tetramethylrosamine
- tetramethylrosamine selenium
- tetramethylrosamine sulfur
- Sulfur
- Selenium
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Topics |
- Animals
- Cell Line, Tumor
- Cell Survival
- Chalcogens
(chemistry)
- Heterocyclic Compounds, 3-Ring
(chemical synthesis, chemistry, pharmacology)
- Intracellular Space
(ultrastructure)
- Mass Spectrometry
- Microscopy, Confocal
- Molecular Structure
- Photosensitizing Agents
(chemical synthesis, chemistry, pharmacology)
- Rats
- Rhodamines
- Selenium
(chemistry)
- Selenium Compounds
(chemical synthesis, chemistry, pharmacology)
- Sulfur
(chemistry)
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