Synthesis, properties, and photodynamic properties in vitro of heavy-chalcogen analogues of tetramethylrosamine.
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.
Detty
Michael R
MR
Institute for Lasers, Photonics, and Biophotonics, Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY 14260, USA. mdetty@buffalo.edu
Prasad
Paras N
PN
Donnelly
David J
DJ
Ohulchanskyy
Tymish
T
Gibson
Scott L
SL
Hilf
Russell
R
D000818:Animals; D045744:Cell Line, Tumor; D002470:Cell Survival; D018011:Chalcogens / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology*; D042541:Intracellular Space / Q000648:ultrastructure; D013058:Mass Spectrometry; D018613:Microscopy, Confocal; D015394:Molecular Structure; D017319:Photosensitizing Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats; D012235:Rhodamines; D012643:Selenium / Q000737:chemistry; D018036:Selenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013455:Sulfur / Q000737:chemistry
D018011:Chalcogens; D006575:Heterocyclic Compounds, 3-Ring; D017319:Photosensitizing Agents; D012235:Rhodamines; D018036:Selenium Compounds; C412715:tetramethylrosamine; C493770:tetramethylrosamine selenium; C493769:tetramethylrosamine sulfur; D013455:Sulfur; D012643:Selenium