US5936087A Expired / Lapsed US ⏱️ 0.0 years remaining

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

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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 05:49

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