4,7-dichlororhodamine dyes

Details 4,7-dichlororhodamine dyes 4,7-dichlororhodamine dyes

1999-03-27

2000-06-27

Riley, Jezia

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

435 6, 536 221, 536 253, 536 2531, 536 266, 549356, 549381, 549385, 549227, C07H 2102, C07D30900, C07D31178, C07D31188, C12Q 168

Patent

active

060808527

ABSTRACT:
A set of 4,7-dichlororhodamine compounds useful as fluorescent dyes are disclosed having the structures ##STR1## wherein R.sub.1 -R.sub.6 are hydrogen, fluorine, chlorine, lower alkyl, lower alkene, lower alkyne, sulfonate, sulfone, amino, amido, nitrite, lower alkoxy, linking group, or, when taken together, R.sub.1 and R.sub.6 is benzo, or, when taken together, R.sub.4 and R.sub.5 is benzo; R.sub.7 -R.sub.10, R.sub.12 -R.sub.16 and R.sub.18 may be hydrogen, fluorine, chlorine, lower alkyl, lower alkene, lower alkyne, sulfonate, sulfone, amino, amido, nitrite, lower alkoxy, linking group; R.sub.11 and R.sub.17 may be hydrogen, lower alkyl, lower alkene, lower alkyne, phenyl, aryl, linking group; Y.sub.1 -Y.sub.4 are hydrogen, lower alkyl, or cycloalkyl, or, when taken together, Y.sub.1 and R.sub.2, Y.sub.2 and R.sub.1 Y.sub.3 and R.sub.3, and/or Y.sub.4 and R.sub.4 is propano, ethano, or substituted forms thereof, and X.sub.1 -X.sub.3 taken separately are hydrogen, chlorine, fluorine, lower alkyl, carboxylate, sulfonate, hydroxymethyl, and linking group, or any combinations thereof. In another aspect, the invention includes reagents labeled with the 4,7-dichlororhodamine dye compounds, including deoxynucleotides, dideoxynucleotides, and polynucleotides. In an additional aspect, the invention includes methods utilizing such dye compounds and reagents including dideoxy polynucleotide sequencing and fragment analysis methods.

REFERENCES:
patent: 5188934 (1993-02-01), Menchen et al.
patent: 5366860 (1994-11-01), Bergot et al.
patent: 5750409 (1998-05-01), Herrmann et al.
patent: 5770716 (1998-06-01), Khan et al.
patent: 5847162 (1998-12-01), Lee et al.
Vogel et al., "Structural Relaxation of Rhodamine Dyes with Different N-Substitution Patterns: A Study of Fluroescence Decay Times with Quantum Yields," Chemical Physics Letters147 (5):452-460 (Jun. 17, 1988).

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