US5227487A
Expired / Lapsed
US
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Certain tricyclic and pentacyclic-hetero nitrogen rhodol dyes
Assignee: Molecular Probes Inc
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Filing: 1990-04-16
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Granted: 1993-07-13
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Expires: 2010-04-16
Abstract
Abstract Novel fluorescent dyes based on the rhodol structure are provided. The new reagents contain functional groups capable of forming a stable fluorescent product with functional groups typically found in biomolecules or polymers including amines, phenols, thiols, acids, aldehydes and ketones. Reactive groups in the rhodol dyes include activated esters, isothiocyanates, amines, hydrazines, halides, acids, azides, maleimides, aldehydes, alcohols, acrylamides and haloacetamides. The products are detected by their absorbance or fluorescence properties. The spectral properties of the fluorescent dyes are sufficiently similar in wavelengths and intensity to fluorescein or rhodamine derivatives as to permit use of the same equipment. The dyes, however, show less spectral sensitivity to pH in the physiological range than does fluorescein, have higher solubility in non-polar solvents and have improved photostability and quantum yields.
Inventors
- 👤 Richard P. Haugland
- 👤 James E. Whitaker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 16:40
CPC Classifications
C; C07; C07D; C07D491/00; C07D491/12; C07D491/14; C07D311/00; C07D311/02; C07D311/78; C07D311/80; C07D311/82; C09; C09B; C09B11/00; C09B11/04; C09B11/10; C09K; C09K11/00; C09K11/06
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
193 words
A fluorescent dye having the structure: ##STR2## wherein R 1 is H, and R 2 is H, CF 3 CO, CH 3 , or C 2 H 5 ; or R 1 in combination with R 2 is (CH 2 ) 3 ; R 3 is H, CH 3 , or C 2 H 5 , and R 4 is H; or R 3 in combination with R 4 is (CH 2 ) 3 ; R 5 is H, CH 2 NH 2 , CH 2 NHCOCH 2 Cl, CH 2 NHCOCH 2 l, CH 2 NHCOCH:CH 2 , or CH 2 NHCOC 6 H 4 N 3 ; R 6 is H, Cl, Br, CH 3 , or C 2 H 5 , or (CH 2 ) n CH 3 where n is an integer from 0 to 15, or (CH 2 ) n CO 2 H, where n is an integer from 0 to 11; and R 7 is H, CO 2 H, ##STR3## NH 2 , NCS, CH 2 NHCOCH 2 Cl, or CH 2 NHCOCH 2 l; such that R 7 is not H if R 5 is H.
Claim 2
Dependent Claim
193 words
A fluorescent dye having the structure: ##STR2## wherein R 1 is H, and R 2 is H, CF 3 CO, CH 3 , or C 2 H 5 ; or R 1 in combination with R 2 is (CH 2 ) 3 ; R 3 is H, CH 3 , or C 2 H 5 , and R 4 is H; or R 3 in combination with R 4 is (CH 2 ) 3 ; R 5 is H, CH 2 NH 2 , CH 2 NHCOCH 2 Cl, CH 2 NHCOCH 2 l, CH 2 NHCOCH:CH 2 , or CH 2 NHCOC 6 H 4 N 3 ; R 6 is H, Cl, Br, CH 3 , or C 2 H 5 , or (CH 2 ) n CH 3 where n is an integer from 0 to 15, or (CH 2 ) n CO 2 H, where n is an integer from 0 to 11; and R 7 is H, CO 2 H, ##STR3## NH 2 , NCS, CH 2 NHCOCH 2 Cl, or CH 2 NHCOCH 2 l; such that R 7 is not H if R 5 is H.
Claim 3
Dependent Claim
55 words
A fluorescent dye as recited in claim 1 wherein R 1 , R 3 , R 4 , R 5 , and R 6 are H; R 2 is selected from the group consisting of H and CF 3 CO; and R 7 is selected from the group consisting of CO 2 H and ##STR4##
Claim 4
Dependent Claim
93 words
A fluorescent dye as recited in claim 1 wherein R 1 is CH 3 ; R 2 is C 2 H 5 ; R 3 , R 4 , and R 5 are H; R 6 is selected from the group consisting of H, Cl, Br, (CH 2 ) n CH 3 wherein n is an integer from 0 to 15, and (CH 2 ) n CO 2 H, where n is an integer from 0 to 11; and R 7 is selected from the group consisting of CO 2 H and ##STR5##
Claim 5
Dependent Claim
76 words
A fluorescent dye as recited in claim 1 wherein R 1 , R 4 , and R 5 are H; R 2 and R 3 are independently selected from the group consisting of CH 3 and C 2 H 5 ; R 6 is selected from the group consisting of H, Cl, Br, CH 3 and C 2 H 5 ; and R 7 is selected from the group consisting of CO 2 H and ##STR6##
Claim 6
Dependent Claim
92 words
A fluorescent dye as recited in claim 1 wherein R 1 in combination with R 2 is (CH 2 ) 3 ; R 3 , R 4 , and R 5 are H; R 6 is selected from the group consisting of H, Cl, Br, (CH 2 ) n CH 3 where n is an integer from 0 to 15, and (CH 2 ) n CO 2 H, where n is an integer from 0 to 11; and R 7 is selected from the group consisting of CO 2 H and ##STR7##
Claim 7
Dependent Claim
130 words
A fluorescent dye as recited in claim 1 wherein R 1 in combination with R 2 , or R 3 in combination with R 4 are (CH 2 ) 3 ; R 5 is selected from the group consisting of H, CH 2 NH 2 , CH 2 NHCOCH 2 Cl, CH 2 NHCOCH 2 l, CH 2 NHCOCH:CH 2 , and CH 2 NHCOC 6 H 4 N 3 ; R 6 is selected from the group consisting of H, Cl, Br, (CH 2 ) n CH 3 where n is an integer from 0 to 15, and (CH 2 ) n CO 2 H where n is an integer from 0 to 11; and R 7 is selected from the group consisting of CO 2 H and ##STR8##
Claim 8
Dependent Claim
64 words
A fluorescent dye as recited in claim 1 wherein R 1 in combination with R 2 , or R 3 in combination with R 4 are (CH 2 ) 3 ; R 5 is H; R 6 is Cl; and R 7 is selected from the group consisting of NH 2 , NCS, CH 2 NHCOCH 2 Cl and CH 2 NHCOCH 2 l.
Claim 9
Dependent Claim
112 words
A fluorescent dye as recited in claim 1 having the formula: ##STR9## wherein R 5 is selected from the group consisting of H, CH 2 NH 2 , CH 2 NHCOCH 2 Cl, CH 2 NHCOCH 2 l, CH 2 NHCOCH:CH 2 , and CH 2 NHCOC 6 H 4 N 3 ; R 6 is selected from the group consisting of H, Cl, Br, (CH 2 ) n CH 3 where n is an integer from 0 to 15, and (CH 2 ) n CO 2 H where n is an integer from 0 to 11; and R 7 is selected from the group consisting of CO 2 H and ##STR10##
Claim 10
Dependent Claim
46 words
A fluorescent dye as recited in claim 1 having the formula: ##STR11## wherein R 5 is H; R 6 is Cl; and R 7 is selected from the group consisting of NH 2 , NCS, CH 2 NHCOCH 2 Cl and CH 2 NHCOCH 2 l.
Claim 11
Dependent Claim
132 words
A fluorescent dye having the structure: ##STR12## wherein R 1 and R 4 are independently hydrogen, alkyl, carboxyalkyl, aminoalkyl, halogen or alkoxy, the alkyl portions of which contain less than 4 carbons; R 2 and R 3 are independently hydrogen, methyl or ethyl, or trifluoroacetyl; and R 1 in combination with R 2 , or R 3 in combination with R 4 are (CH 2 ) 3 ; R 5 is H; R 6 is H, Cl, Br, CH 3 , or CH 2 H 5 , and R 9 is COCH 3 ; or R 6 and R 9 in combination are (CH 2 ) 2 CO; and R 7 is H, CO 2 H or ##STR13## such that R 7 is not H if R 9 is COCH 3 .
Claim 12
Dependent Claim
132 words
A fluorescent dye having the structure: ##STR12## wherein R 1 and R 4 are independently hydrogen, alkyl, carboxyalkyl, aminoalkyl, halogen or alkoxy, the alkyl portions of which contain less than 4 carbons; R 2 and R 3 are independently hydrogen, methyl or ethyl, or trifluoroacetyl; and R 1 in combination with R 2 , or R 3 in combination with R 4 are (CH 2 ) 3 ; R 5 is H; R 6 is H, Cl, Br, CH 3 , or CH 2 H 5 , and R 9 is COCH 3 ; or R 6 and R 9 in combination are (CH 2 ) 2 CO; and R 7 is H, CO 2 H or ##STR13## such that R 7 is not H if R 9 is COCH 3 .
Claim 13
Dependent Claim
77 words
A fluorescent dye as recited in claim 10 wherein R 1 in combination with R 2 , or R 3 in combination with R 4 are (CH 2 ) 3 ; R 5 is H; R 6 is selected from the group consisting of H, Cl, Br, CH 3 , and CH 2 H 5 ; R 7 is selected from the group consisting of CO 2 H and ##STR14## and R 9 is COCH 3 .
Claim 14
Dependent Claim
64 words
A fluorescent dye as recited in claim 10 wherein R 1 in combination with R 2 , or R 3 in combination with R 4 are (CH 2 ) 3 ; R 5 is H; R 7 is selected from the group consisting of H, CO 2 H and ##STR15## and R 6 and R 9 in combination are (CH 2 ) 2 CO.
Claim 15
Dependent Claim
72 words
A fluorescent dye having the structure: ##STR16## wherein R 5 is H; R 6 is H, Cl, Br, CH 3 , or CH 2 H 5 , and R 9 is COCH 3 ; or R 6 and R 9 in combination are (CH 2 ) 2 CO; and R 7 is H, CO 2 H or ##STR17## such that R 7 is not H if R 9 is COCH 3 .
Claim 16
Dependent Claim
72 words
A fluorescent dye having the structure: ##STR16## wherein R 5 is H; R 6 is H, Cl, Br, CH 3 , or CH 2 H 5 , and R 9 is COCH 3 ; or R 6 and R 9 in combination are (CH 2 ) 2 CO; and R 7 is H, CO 2 H or ##STR17## such that R 7 is not H if R 9 is COCH 3 .
Claim 17
Dependent Claim
55 words
A fluorescent dye as recited in claim 13 wherein R 5 is H; R 6 is selected from the group consisting of H, Cl, Br, CH 3 , and CH 2 H 5 ; R 7 is selected from the group consisting of CO 2 H and ##STR18## and R 9 is COCH 3 .
Claim 18
Dependent Claim
42 words
A fluorescent dye as recited in claim 13 wherein R 5 is H; R 7 is selected from the group consisting of H, CO 2 H and ##STR19## and R 6 and R 9 in combination are (CH 2 ) 2 CO.
References Cited (Backward Citations)
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