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WO1998030992B1 - Fluorescent cyanine dyes - Google Patents

Fluorescent cyanine dyes

Info

Publication number
WO1998030992B1
WO1998030992B1 PCT/US1998/000475 US9800475W WO9830992B1 WO 1998030992 B1 WO1998030992 B1 WO 1998030992B1 US 9800475 W US9800475 W US 9800475W WO 9830992 B1 WO9830992 B1 WO 9830992B1
Authority
WO
WIPO (PCT)
Prior art keywords
independently
dye
integer
formula
labeled
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1998/000475
Other languages
French (fr)
Other versions
WO1998030992A3 (en
WO1998030992A2 (en
Filing date
Publication date
Priority claimed from US08/781,326 external-priority patent/US6027709A/en
Priority to CA002278313A priority Critical patent/CA2278313C/en
Priority to AU60206/98A priority patent/AU739930B2/en
Priority to AT98903434T priority patent/ATE236442T1/en
Priority to EP98903434A priority patent/EP1019887B1/en
Priority to JP53116298A priority patent/JP4361138B2/en
Application filed filed Critical
Priority to DE69812982T priority patent/DE69812982T2/en
Publication of WO1998030992A2 publication Critical patent/WO1998030992A2/en
Publication of WO1998030992A3 publication Critical patent/WO1998030992A3/en
Publication of WO1998030992B1 publication Critical patent/WO1998030992B1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Abstract

New fluorescent cyanine dyes having general formula (1), wherein R is -OH, -CO2H, -NH2 or -NCS, and x and y, independently, are integers between 1 and about 10 are useful as reporter groups for labeling biomolecules.

Claims

29
AMENDED CLAIMS
[received by the International Bureau on 17 September 1998 (17.09.98); original claims 3, 5-7 and 11 cancelled; original claim 1 amended; new claims 19-24 added; remaining claims unchanged (8 pages)]
A fluorescent dye having the general formula:
Figure imgf000003_0001
FORMULA 1
wherein R is -NH2 or -NCS, and x and y, independently, are integers between 1 and about 10.
2. A fluorescent dye in accordance with claim 1, wherein R is -OH, x is an integer between 2 and 6 and y is an integer between 2 and 6.
4. N- ( β-hydroxyhexyl) N' - (4-sulfonatobutyl) - 3, 3, 3 ' , 3 ' -tetramethylbenz (e) indodicarbocyanine .
8. A dye-labeled nucleotide analog comprising the general structure
Figure imgf000003_0002
30
wherein each of x and y, independently, is an integer between 1 and 10 and each M, independently, is selected from Li, Na, K, NH_,, (CH3)3NH, (CH3CH2)3NH, (CH3CH2)__jN or (CH3)4N.
9. A dye-labeled nucleotide analog comprising the general structure
Figure imgf000004_0001
wherein each of x and y, independently, is an integer between 1 and 10 and each M, independently, is selected from Li, Na, K, NH4, (CH3)3NH, (CH3CH2)3NH, (CH3CH2)„N or
(CH3)4N.
10. A dye-labeled nucleotide analog in accordance with claim 8 or 9 wherein each of x and y is an integer from 2 to 6. 12. A fluorescent dye labeled DNA chain terminator having the general structure:
31
Figure imgf000005_0001
wherein each of x and y, independently, is an integer selected from 1 to about 10.
13. A fluorescent dye labeled DNA chain terminator having the general structure:
32
Figure imgf000006_0001
wherein each of x and y, independently, is an integer selected from 1 to about 10.
14. A fluorescent dye labeled DNA chain terminator having the general structure:
33
Figure imgf000007_0001
wherein each of x and y, independently, is an integer selected from 1 to about 10.
15. A fluorescent dye labeled DNA chain terminator having the general structure:
34
Figure imgf000008_0001
, N , C H, c
Figure imgf000008_0002
wherein each of x and y, independently, is an integer selected from 1 to about 10.
16. A fluorescent dye-labeled DNA chain terminator in accordance with claim 12, 13, 14 or 15 where each of x and y independently is an integer from 2 to 6.
17. N-(β-hydroxyhexyl) -1, 1, 2-trimethyl-lH- benz (e) indolinium halide.
18. N-(β-hydroxyhexyl)-l, 1, 2-trimethyl-lH- benz (e) indolinium bromide.
19. A phosphoramidite derivative of a dye having the general formula
Figure imgf000009_0001
FORMULA 1
wherein R is O-phosphoramidite and x and y, independently, are integers between 1 and about 10.
20. A nucleotide analog labelled with a dye of the general formula:
Figure imgf000009_0002
FORMULA 1
wherein R is -OH, -C02H, NH2 or -NCS, and x and y, independently, are integers between 1 and about 10.
21. A DNA chain terminator labelled with a dye of the general formula: 36
Figure imgf000010_0001
FORMULA 1
wherein R is -OH, -C02H, -NH2 or -NCS and x and y, independently, are integers between 1 and about 10 22. A dye phosphoramidite having the formula
Figure imgf000010_0002
23. An oligonucleotide labeled with a dye phosphoramidite of claim 19.
24. An oligonucleotide labeled with a dye phosphoramidite of claim 22.
PCT/US1998/000475 1997-01-10 1998-01-08 Fluorescent cyanine dyes Ceased WO1998030992A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
DE69812982T DE69812982T2 (en) 1997-01-10 1998-01-08 FLUORESCENT CYANINE DYES
AU60206/98A AU739930B2 (en) 1997-01-10 1998-01-08 Fluorescent cyanine dyes
AT98903434T ATE236442T1 (en) 1997-01-10 1998-01-08 FLUORESCENT CYANINE DYES
EP98903434A EP1019887B1 (en) 1997-01-10 1998-01-08 Fluorescent cyanine dyes
JP53116298A JP4361138B2 (en) 1997-01-10 1998-01-08 Fluorescent cyanine dye
CA002278313A CA2278313C (en) 1997-01-10 1998-01-08 Fluorescent cyanine dyes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/781,326 1997-01-10
US08/781,326 US6027709A (en) 1997-01-10 1997-01-10 Fluorescent cyanine dyes

Publications (3)

Publication Number Publication Date
WO1998030992A2 WO1998030992A2 (en) 1998-07-16
WO1998030992A3 WO1998030992A3 (en) 1998-11-12
WO1998030992B1 true WO1998030992B1 (en) 1998-12-17

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1998/000475 Ceased WO1998030992A2 (en) 1997-01-10 1998-01-08 Fluorescent cyanine dyes

Country Status (8)

Country Link
US (1) US6027709A (en)
EP (1) EP1019887B1 (en)
JP (1) JP4361138B2 (en)
AT (1) ATE236442T1 (en)
AU (1) AU739930B2 (en)
CA (1) CA2278313C (en)
DE (1) DE69812982T2 (en)
WO (1) WO1998030992A2 (en)

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