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US5132432A Expired / Lapsed US ⏱️ 0.0 years remaining

Chemically reactive pyrenyloxy sulfonic acid dyes

Assignee: Molecular Probes Inc
•
Filing: 1989-09-22
•
Granted: 1992-07-21
•
Expires: 2009-09-22
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Abstract

Abstract The invention relates to novel fluorescent dyes based on the following pyrenyloxy sulfonic acid structure: ##STR1## wherein at least one of R 1 , R 2 , R 3 , and R 4 is --OCH 2 C(O)OCH 3 , --OCH 2 CON(O)H, --OCH 2 CON 3 , --OCH 2 CONHNH 2 , ##STR2## or --CH 2 CONH(CH 2 ) n NH 2 where n is an integer from 1 to 10; at least one of R 1 , R 2 , R 3 , and R 4 is sulfonic acid or alkali salts of sulfonic acid; and all other of R 1 , R 2 , R 3 , and R 4 are hydrogen or a hydroxyl group. The new reagents contain functional groups typically found in biomolecules or polymers. The spectral properties of the fluorescent dyes are sufficiently different in wavelengths and intensity from fluorescein as to permit simultaneous use of both dyes with minimum interference. The dyes have narrower spectral band-widths and smaller Stokes' shifts than other reactive dyes with similar spectral properties, do not show appreciable sensitivity to pH, have higher solubilities in aqueous solvents and have good quantum yields and photostability.

Inventors

  • 👤 Richard P. Haugland
  • 👤 James E. Whitaker

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 23:55
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/30; C07D207/34; C07D207/36; C07D207/40; C07D207/404; C07C; C07C309/00; C07C309/01; C07C309/28; C07C309/41; C07C309/43; C07D207/04; C07D207/10; C07D207/16; C09; C09B; C09B57/00; C09B57/001; C07C2603/00; C07C2603/02; C07C2603/40; C07C2603/42; C07C2603/50

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 144 words
A fluorescent dye having the structure: ##STR9## wherein (a) at least one of R 1 , R 2 , R 3 , and R 4 has the structure --O--R 5 wherein R 5 includes a chemically reactive functional group selected from the group consisting of --CH 2 C(O)OCH 3 , --CH 2 C(O)OH, --CH 2 CON 3 , --CH 2 CONHNH 2 , ##STR10## and --CH 2 CONH(CH 2 ) n NH 2 where n is an integer from 1 to 10; (b) at least one of R 1 , R 2 , R 3 , and R 4 is selected from the group consisting of sulfonic acid and alkali salts of sulfonic acid; and (c) all other of R 1 , R 2 , R 3 , and R 4 are selected from the group consisting of a hydrogen and a hydroxyl group.
Claim 2
Dependent Claim 144 words
A fluorescent dye having the structure: ##STR9## wherein (a) at least one of R 1 , R 2 , R 3 , and R 4 has the structure --O--R 5 wherein R 5 includes a chemically reactive functional group selected from the group consisting of --CH 2 C(O)OCH 3 , --CH 2 C(O)OH, --CH 2 CON 3 , --CH 2 CONHNH 2 , ##STR10## and --CH 2 CONH(CH 2 ) n NH 2 where n is an integer from 1 to 10; (b) at least one of R 1 , R 2 , R 3 , and R 4 is selected from the group consisting of sulfonic acid and alkali salts of sulfonic acid; and (c) all other of R 1 , R 2 , R 3 , and R 4 are selected from the group consisting of a hydrogen and a hydroxyl group.
Claim 3
Dependent Claim 40 words
A fluorescent dye as recited in claim 1 wherein R 1 has the structure --OCH 2 C(O)OCH 3 and R 2 , R 3 , and R 4 have the structure --SO 3 X, wherein X is an alkali metal.
Claim 4
Dependent Claim 39 words
A fluorescent dye as recited in claim 1 wherein R 1 has the structure --OCH 2 C(O)OH and R 2 , R 3 , and R 4 have the structure --SO 3 X, wherein X is an alkali metal.
Claim 5
Dependent Claim 40 words
A fluorescent dye as recited in claim 1 wherein R 1 has the structure --OCH 2 CON 3 and R 2 , R 3 , and R 4 have the structure --SO 3 X, wherein X is an alkali metal.
Claim 6
Dependent Claim 40 words
A fluorescent dye as recited in claim 1 wherein R 1 has the structure --OCH 2 CONHNH 2 and R 2 , R 3 , and R 4 have the structure --SO 3 X, wherein X is an alkali metal.
Claim 7
Dependent Claim 37 words
A fluorescent dye as recited in claim 1 wherein R 1 has the structure ##STR11## and R 2 , R 3 , and R 4 have the structure --SO 3 X, wherein X is an alkali metal.
Claim 8
Dependent Claim 54 words
A fluorescent dye as recited in claim 1 wherein R 1 has the structure --OCH 2 CONH(CH 2 ) n NH 2 , where n is an integer from 1 to 10, and R 2 , R 3 , and R 4 have the structure --SO 3 X, wherein X is an alkali metal.
Claim 9
Dependent Claim 41 words
A fluorescent dye as recited in claim 1 wherein R 1 has the structure --OCH 2 C(O)OH, R 2 is a hydroxyl group, and R 3 and R 4 have the structure --SO 3 X, wherein X is an alkali metal.
Claim 10
Dependent Claim 38 words
A fluorescent dye as recited in claim 1 wherein R 1 and R 2 have the structure --OCH 2 C(O)OH and R 3 and R 4 have the structure --SO 3 X, wherein X is an alkali metal.

References Cited (Backward Citations)

US2122828A Cited
US3996345A Cited
US4213904A Cited
US4520110A Cited
US4542104A Cited
US4844841A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1995-07-21 1996-01-20 1996-07-21 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1999-07-21 2000-01-20 2000-07-21 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2003-07-21 2004-01-20 2004-07-21 $7700.00 Window Closed / Lapsed

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