Dibenzorhodamine dyes

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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548416, 549382, C07D22118, C07D31178

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active

059360879

ABSTRACT:
Dibenzorhodamine compounds having the structure ##STR1## are disclosed, including nitogen- and aryl-substituted forms thereof. In addition, two intermediates useful for synthesizing such compounds are disclosed, a first intermediate having the structure ##STR2## including nitrogen- and aryl-substituted forms thereof, and a second intermediate having the structure ##STR3## including nitrogen- and aryl-substituted forms thereof, wherein substituents at positions C-14 to C18 taken separately are selected from the group consisting of hydrogen, chlorine, fluorine, lower alkyl, carboxylic acid, sulfonic acid, --CH.sub.2 OH, alkoxy, phenoxy, linking group, and substituted forms thereof. The invention further includes energy transfer dyes comprising the dibenzorhodamine compounds, nucleosides labeled with the dibenzorhodamine compounds, and nucleic acid analysis methods employing the dibenzorhodamine compounds.

REFERENCES:
patent: 5750409 (1998-05-01), Hermann et al.
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Arden-Jacob, Jutta; Reihe Chemie;Neue langwellige Xanthen-Farbstoffe fur Fluoreszenzsonden und Farbstofflaser; Verlag Shaker, pub.; Prof. Dr. K.H. Drexhage and Prof. Dr. G. von Bunau, eds.; pp. 1-169, (Dec. 12, 1992).
Sauer et al., "New Fluorescent Dyes in the Red Region for Biodiagnostics," Jnl. of Fluorescence, 5(3):247-261 (1995).
Gee et al., "Novel Derivatization of Protein Thiols With Fluorinated Fluoresceins," Tetrahedron Letters 3(44):7905-7908 (1996).
Haugland et al., "New Fluorescein, Rhodamine and Texa Red Analogs with Higher Fluorescence and Improved Photostability," Proceedings of the Xth International Congress, Histochemistry and Cytochemistry , pp. 273 (1996).
Sun et al., "Synthesis of Fluorinated Fluoresceins," J. Org. Chem. 62(19):6469-6475 (1997).
Lieberwirth et al., 1997 "Development of New Multiplex Dyes: Intramolecular Fluorescence Quenching of Rhomadine Dyes," Jnl. of Fluorescence 7(1):59S-61S.
Sauer et al., 1995 Physikalisch-Chemisches Institut, Heidelberg, Germany and Arden-Jacob et al., Institut fur Physikalische Chemie, Siegen, Germany; "Design of Multiplex Dyes for the Detection of Different Biomolecules" .

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