US4945171A
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Xanthene dyes having a fused (C) benzo ring
Assignee: Molecular Probes Inc
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Filing: 1987-08-10
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Granted: 1990-07-31
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Expires: 2007-08-10
Abstract
Abstract Synthesis and applications of fluorescent dyes which are derivatives of benzo[c]xanthenes is described. The dyes exhibit pH dependent absorption and fluorescence spectra with pKas near the normal physiological range. Unlike fluorescein, the dyes exhibit emission of different characteristic wavelengths dependent on the pH of the medium. This permits several methods of measuring the pH of the medium in contact with the indicator including measuring two emissions with one excitation, selectively exiting the acid and base forms independently and measuring their emission at either single or dual wavelengths, or measuring the characteristic pH dependent absorption or fluorescence excitation spectral. Methods are presented for making the indicators permeant to cell membranes for the measurement of intracellular pH.
Inventors
- 👤 Richard P. Haugland
- 👤 James Whitaker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 07:25
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/10; C09; C09B; C09B11/00; C09B11/28; G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/84
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
52 words
A compound of the formula: ##STR6## wherein: R 1 is hydrogen, acetyl or methyl, R 2 is hydroxyl, acetoxyl, dimethylamino, diethylamino, ethylamino or methoxyl R 3 is hydrogen, hydroxyl, halo, methyl or carboxyethyl R 4 is hydrogen, R 5 is hydrogen, carboxyl or acetoxymethoxycarbonyl, and R 6 is hydrogen, carboxyl or acetoxymethoxycarbonyl.
Claim 2
Dependent Claim
52 words
A compound of the formula: ##STR6## wherein: R 1 is hydrogen, acetyl or methyl, R 2 is hydroxyl, acetoxyl, dimethylamino, diethylamino, ethylamino or methoxyl R 3 is hydrogen, hydroxyl, halo, methyl or carboxyethyl R 4 is hydrogen, R 5 is hydrogen, carboxyl or acetoxymethoxycarbonyl, and R 6 is hydrogen, carboxyl or acetoxymethoxycarbonyl.
Claim 3
Dependent Claim
27 words
The compound of claim 1 wherein R 1 , R 3 , R 4 , R 5 and R 6 are hydrogen, and R 2 is hydroxy.
Claim 4
Dependent Claim
28 words
The compound of claim 1 wherein R 3 , R 4 , R 5 and R 6 are hydrogen, R 1 is acetyl and R 2 is acetoxy.
Claim 5
Dependent Claim
28 words
The compound of claim 1 wherein R 1 , R 3 , R 4 and R 5 are hydrogen, R 2 is hydroxy and R 6 is carboxy.
Claim 6
Dependent Claim
28 words
The compound of claim 1 wherein R 1 , R 3 , R 4 and R 6 are hydrogen, R 2 is hydroxy and R 5 is carboxy.
Claim 7
Dependent Claim
29 words
The compound of claim 1 wherein R 3 , R 4 and R 5 are hydrogen, R 1 is acetyl, R 2 is acetoxy and R 6 is carboxy.
Claim 8
Dependent Claim
29 words
The compound of claim 1 wherein R 3 , R 4 and R 6 are hydrogen, R 1 is acetyl, R 2 is acetoxy and R 5 is carboxy.
Claim 9
Dependent Claim
29 words
The compound of claim 1 wherein R 1 , R 4 and R 5 are hydrogen, R 2 is hydroxy, R 3 is chloro and R 6 is carboxy.
Claim 10
Dependent Claim
29 words
The compound of claim 1 wherein R 1 , R 4 and R 6 are hydrogen, R 2 is hydroxy, R 3 is chloro and R 5 is carboxy.
Claim 11
Dependent Claim
30 words
The compound of claim 1 wherein R 4 and R 5 are hydrogen, R 1 is acetyl, R 2 is acetoxy, R 3 is chloro and R 6 is carboxy.
Claim 12
Dependent Claim
30 words
The compound of claim 1 wherein R 4 and R 6 are hydrogen, R 1 is acetyl, R 2 is acetoxy, R 3 is chloro and R 5 is carboxy.
Claim 13
Dependent Claim
28 words
The compound of claim 1 wherein R 1 , R 3 , R 4 and R 5 are hydrogen, R 2 is N,N-dimethylamino and R 6 is carboxy.
Claim 14
Dependent Claim
28 words
The compound of claim 1 wherein R 1 , R 3 , R 4 and R 6 are hydrogen, R 2 is N,N-dimethylamino and R 5 is carboxy.
Claim 15
Dependent Claim
29 words
The compound of claim 1 wherein R 3 , R 4 and R 5 are hydrogen, R 1 is acetyl, R 2 is N,N-dimethylamino and R 6 is acetoxymethoxycarbonyl.
Claim 16
Dependent Claim
29 words
The compound of claim 1 wherein R 3 , R 4 and R 6 are hydrogen, R 1 is acetyl, R 2 is N,N-dimethylamino and R 5 is acetoxymethoxycarbonyl.
Claim 17
Dependent Claim
28 words
The compound of claim 1 wherein R 1 , R 3 , R 4 and R 5 are hydrogen, R 2 is N,N-diethylamino and R 6 is carboxy.
Claim 18
Dependent Claim
28 words
The compound of claim 1 wherein R 1 , R 3 , R 4 and R 6 are hydrogen, R 2 is N,N-diethylamino and R 5 is carboxy.
Claim 19
Dependent Claim
29 words
The compound of claim 1 wherein R 3 , R 4 and R 5 are hydrogen, R 1 is acetyl, R 2 is N,N-diethylamino and R 6 is acetoxymethoxycarbonyl.
Claim 20
Dependent Claim
29 words
The compound of claim 1 wherein R 3 , R 4 and R 6 are hydrogen, R 1 is acetyl, R 2 is N,N-diethylamino and R 5 is acetoxymethoxycarbonyl.
Claim 21
Dependent Claim
29 words
The compound of claim 1 wherein R 1 , R 4 and R 5 are hydrogen, R 2 is N-ethylamino, R 3 is methyl and R 6 is carboxy.
Claim 22
Dependent Claim
29 words
The compound of claim 1 wherein R 1 , R 4 and R 6 are hydrogen, R 2 is N-ethylamino, R 3 is methyl and R 5 is carboxy.
Claim 23
Dependent Claim
70 words
A compound of the formula: ##STR7## wherein: R 1 is hydrogen, acetyl or methyl, R 2 is N,N-dialkylamine, of which each alkyl group consists of 3 methylene groups which, in conjunction with R 3 and R 4 , complete two six-membered non-aromatic rings chemically bonded to the aromatic ring of benzo[c]xanthene, and R 5 and R 6 , which may be the same or different, are hydrogen, carboxyl or acetoxymethoxycarbonyl.
Claim 24
Dependent Claim
70 words
A compound of the formula: ##STR7## wherein: R 1 is hydrogen, acetyl or methyl, R 2 is N,N-dialkylamine, of which each alkyl group consists of 3 methylene groups which, in conjunction with R 3 and R 4 , complete two six-membered non-aromatic rings chemically bonded to the aromatic ring of benzo[c]xanthene, and R 5 and R 6 , which may be the same or different, are hydrogen, carboxyl or acetoxymethoxycarbonyl.
Claim 25
Dependent Claim
18 words
The compound of claim 22 wherein: R 1 and R 5 are hydrogen; and R 6 is carboxyl.
Claim 26
Dependent Claim
18 words
The compound of claim 22 wherein: R 1 and R 6 are hydrogen; and R 5 is carboxyl.
Claim 27
Dependent Claim
138 words
A compound of the formula: ##STR8## wherein: R 1 is hydrogen, a metal or non-metal salt, an alkyl or aryl ether containing from 1 to 18 carbon atoms, or an ester of an aliphatic acid containing from 1 to 18 carbon atoms; R 2 is hydroxyl, amino, or an amino modified by formation of an alkylether, alkylester, alkylamide or alkylamine derivative containing 1 to 18 carbon atoms; R 5 and R 6 , which may be the same or different, are carboxy, sulfo, or alkylamido containing 1 to 6 carbon atoms; and R 3 , R 4 , R 7 and R 8 , which may be the same or different, are alkoxyl containing from 1 to 6 carbon atoms, alkyl containing from 1 to 6 carbon atoms, haloalkyl containing from 1 to 6 carbon atoms, or halo.
Claim 28
Dependent Claim
138 words
A compound of the formula: ##STR8## wherein: R 1 is hydrogen, a metal or non-metal salt, an alkyl or aryl ether containing from 1 to 18 carbon atoms, or an ester of an aliphatic acid containing from 1 to 18 carbon atoms; R 2 is hydroxyl, amino, or an amino modified by formation of an alkylether, alkylester, alkylamide or alkylamine derivative containing 1 to 18 carbon atoms; R 5 and R 6 , which may be the same or different, are carboxy, sulfo, or alkylamido containing 1 to 6 carbon atoms; and R 3 , R 4 , R 7 and R 8 , which may be the same or different, are alkoxyl containing from 1 to 6 carbon atoms, alkyl containing from 1 to 6 carbon atoms, haloalkyl containing from 1 to 6 carbon atoms, or halo.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-07-30 | 1994-01-29 | 1994-07-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-07-30 | 1998-01-29 | 1998-07-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-07-30 | 2002-01-29 | 2002-07-31 | $7700.00 | Window Closed / Lapsed |