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US5936087A
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Dibenzorhodamine dyes
Assignee: Applied Biosystems LLC
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Filing: 1997-11-25
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Granted: 1999-08-10
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Expires: 2017-11-25
Abstract
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 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.
Inventors
- 👤 Scott C. Benson
- 👤 Joe Y. L. Lam
- 👤 Steven Michael Menchen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 13:03
CPC Classifications
C; C09; C09B; C09B11/00; C09B11/04; C09B11/10; C09B11/24; C07; C07D; C07D209/00; C07D209/56; C07D209/58; C07D209/60; C07D221/00; C07D221/02; C07D221/04; C07D221/06; C07D221/10; C07D311/00; C07D311/02; C07D311/78; C07D491/00; C07D491/12; C07D491/14; C07D491/147; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H19/10; C07H19/16; C07H19/20; C07H21/00; C07H21/04; C09B11/02; C12; C12Q; C12Q1/00; C12Q1/68; C12Q1/6869; Y; Y10; Y10T; Y10T436/00; Y10T436/14; Y10T436/142222; Y10T436/143333
Claims Analysis
Total Claims: 41
Claim 1
Independent Claim
13 words
A dibenzorhodamine compound having the structure ##STR21## including nitrogen- and aryl-substituted forms thereof.
Claim 2
Dependent Claim
13 words
A dibenzorhodamine compound having the structure ##STR21## including nitrogen- and aryl-substituted forms thereof.
Claim 3
Dependent Claim
64 words
The compound of claim 1 comprising a first bridging group which when taken together with the C-12-bonded nitrogen and the C-12 and C-13 carbons forms a first ring structure having from 4 to 7 members; and/or a second bridging group which when taken together with the C-2-bonded-nitrogen and the C-1 and C-2 carbons forms a second ring structure having from 4 to 7 members.
Claim 4
Dependent Claim
19 words
The compound of claim 2 wherein one or both of the first and second ring structures has five members.
Claim 5
Dependent Claim
16 words
The compound of claim 3 wherein the five membered ring structure includes one gem disubstituted carbon.
Claim 6
Dependent Claim
12 words
The compound of claim 4 wherein the gem substituents are lower alkyl.
Claim 7
Dependent Claim
11 words
The compound of claim 5 wherein the gem substituents are methyl.
Claim 8
Dependent Claim
13 words
The compound of claim 3 wherein the five membered ring is not aromatic.
Claim 9
Dependent Claim
18 words
The compound of claim 3 wherein the five membered ring is substituted with linking group or water-solubilizing group.
Claim 10
Dependent Claim
15 words
The compound of claim 2 wherein the first and second ring structures are the same.
Claim 11
Dependent Claim
14 words
The compound of claim 2 wherein the first and second ring structures are different.
Claim 12
Dependent Claim
30 words
The compound of claim 1 comprising a C-7 substituent selected from the group consisting of acetylene, lower alkyl, lower alkene, cyano, phenyl, heterocyclic aromatic, electron-rich heterocycle, and substituted forms thereof.
Claim 13
Dependent Claim
19 words
The compound of claim 11 wherein the C-7 substituent is phenyl having the structure ##STR22## including aryl-substituted forms thereof.
Claim 14
Dependent Claim
44 words
The compound of claim 12 wherein substituents at any one of positions C-14 to C-18 are selected from the group consisting of chlorine, fluorine, lower alkyl, carboxylic acid, sulfonic acid, --CH 2 OH, alkoxy, phenoxy, linking group, water solubilizing group, and substituted forms thereof.
Claim 15
Dependent Claim
22 words
The compound of claim 11 wherein a substituent at position C-18 is selected from the group consisting of carboxylic acid and sulfonate.
Claim 16
Dependent Claim
14 words
The compound of claim 13 wherein a substituent at position C-18 is carboxylic acid.
Claim 17
Dependent Claim
15 words
The compound of claim 12 wherein a substituent at positions C-14 and C-17 is chlorine.
Claim 18
Dependent Claim
15 words
The compound of claim 12 wherein a substituent at positions C-14 to C-17 is chlorine.
Claim 19
Dependent Claim
15 words
The compound of claim 12 wherein a substituent at positions C-14 to C-17 is fluorine.
Claim 20
Dependent Claim
40 words
The compound of claim 12 wherein a substituent at one of positions C-15 and C-16 is linking group and the other is hydrogen, a substituent at positions C-14 and C-17 is chlorine, and a substituent at position C-18 is carboxy.
Claim 21
Dependent Claim
37 words
The compound of claim 1 comprising one or more nitrogen substituents selected from the group consisting of lower alkyl, lower alkene, lower alkyne, phenyl, aromatic, electron-rich heterocycle, polycyclic aromatic, water-solubilizing group, linking group, including substituted forms thereof.
Claim 22
Dependent Claim
23 words
The compound of claim 20 wherein the nitrogen substituents are selected from the group consisting of lower alkyl, phenyl, and substituted forms thereof.
Claim 23
Dependent Claim
28 words
The compound of claim 21 wherein the nitrogen substituents are selected from the group consisting of substituted lower alkyl and substituted phenyl, wherein the substituent is linking group.
Claim 24
Dependent Claim
27 words
The compound of claim 21 wherein the nitrogen substituents are selected from the group consisting of substituted lower alkyl and substituted phenyl, wherein the substituent is sulfonate.
Claim 25
Dependent Claim
12 words
The compound of claim 20 wherein the nitrogen substituents are water-solubilizing group.
Claim 26
Dependent Claim
25 words
The compound of claim 24 wherein the water-solubilizing group is selected from the group consisting of sulfonate, phosphate, quaternary amine, sulfate, polyhydroxyl, and water-soluble polymer.
Claim 27
Dependent Claim
65 words
The compound of claim 1 comprising a third bridging group which when taken together with the C-12-bonded nitrogen and the C-11 and C-12 carbons forms a third ring structure having from 5 to 7 members; and/or a fourth bridging group which when taken together with the C-2-bonded nitrogen and the C-2 and C-3 carbons forms a fourth ring structure having from 5 to 7 members.
Claim 28
Dependent Claim
19 words
The compound of claim 26 wherein one or both of the third and fourth ring structures has six members.
Claim 29
Dependent Claim
16 words
The compound of claim 27 wherein the six membered ring structure includes one gem disubstituted carbon.
Claim 30
Dependent Claim
12 words
The compound of claim 28 wherein the gem substituents are lower alkyl.
Claim 31
Dependent Claim
11 words
The compound of claim 29 wherein the gem substituents are methyl.
Claim 32
Dependent Claim
13 words
The compound of claim 27 wherein the six membered ring is not aromatic.
Claim 33
Dependent Claim
66 words
The compound of claim 1 comprising one or more substituents at one or more of positions C-1, C-3 to C-6, C-8 to C-11, and C-13, selected from the group consisting of fluorine, chlorine, lower alkyl, lower alkene, lower alkyne, sulfate, sulfonate, sulfone, sulfonamide, sulfoxide, amino, ammonium, amido, nitrile, lower alkoxy, phenoxy, aromatic, phenyl, polycyclic aromatic, electron-rich heterocycle, water-solubilizing group, and linking group, including substituted forms thereof.
Claim 34
Dependent Claim
13 words
The compound of claim 32 wherein the one or more substituents are sulfonate.
Claim 35
Dependent Claim
9 words
The compound of claim 1 having the structure ##STR23##
Claim 36
Dependent Claim
8 words
The compound of claim 1 having the structure
Claim 37
Dependent Claim
8 words
The compound of claim 1 having the structure
Claim 38
Dependent Claim
8 words
The compound of claim 1 having the structure
Claim 39
Dependent Claim
8 words
The compound of claim 1 having the structure
Claim 40
Dependent Claim
8 words
The compound of claim 1 having the structure
Claim 41
Dependent Claim
8 words
The compound of claim 1 having the structure
References Cited (Backward Citations)
DE4137934A1
Cited
US5750409A
Cited
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