Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Reexamination Certificate
2001-08-04
2004-04-06
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
C546S028000, C546S036000, C435S006120, C435S040500, C436S172000, C436S800000
Reexamination Certificate
active
06716979
ABSTRACT:
FIELD OF THE INVENTION
The invention relates to colored and fluorescent dyes, including reactive dye derivatives, and dye-conjugates; and to their use in staining samples and detecting ligands or other analytes.
BACKGROUND OF THE INVENTION
Fluorescent dyes are known to be particularly suitable for applications in which a highly sensitive detection reagent is desirable. Fluorescent dyes are used to impart both visible color and fluorescence to other materials. As researchers increasingly utilize fluorescent probes as research tools, the ability to select the wavelength of fluorescence becomes more important, particularly asmore multiple-color applications are developed.
A variety of fluorescent dyes have been previously and extensively described, including coumarins, fluoresceins, rhodamines, rhodols, oxazines, carbocyanines, and derivatives thereof. The selection of certain substituents has been shown to be useful in adjusting the spectral properties of such dyes but there have remained regions of the visible spectrum where suitable fluorescent dyes either did not exist, or did not possess particularly favorable properties.
The dyes of the invention incorporate additional fused aromatic or heteroaromatic rings, and exhibit a shift of fluorescence emission to longer wavelength that is typically greater than 20 nm, relative to otherwise structurally similar dyes known in the art. This bathochromic spectral shift yields dyes that are particularly useful for excitation in the wavelength ranges between 400 nm and 600 nm and in particular at greater than 630 nm. Of particular importance are the dyes of the invention that exhibit absorbance maxima between 530 nm and 650 nm, as they match the principal emission lines of the mercury arc lamp (546 nm), frequency-doubled Nd-Yag laser (532 nm), Kr-ion laser (568 nm, and 647 nm) and HeNe laser (543 nm, 594 nm, and 633 nm).
Fluorescent dyes of the invention with longer wavelength absorption and emission are particularly useful in conjunction with materials of biological origin such as blood, urine, fecal matter, cells and tissues, because background or inherent fluorescence or absorption is less likely to interfere with dye detection. Furthermore, infrared dyes of the invention have enhanced utility in biological systems that are transparent at infrared wavelengths. The long wavelength dyes of the invention also have advantages in use as laser dyes, or in electronics as optical memory elements using relatively low cost illumination sources such as laser diodes.
REFERENCES:
patent: 4544546 (1985-10-01), Wang et al.
patent: 4711955 (1987-12-01), Ward et al.
patent: 4945171 (1990-07-01), Haugland et al.
patent: 4997928 (1991-03-01), Hobbs
patent: 5047519 (1991-09-01), Hobbs et al.
patent: 5049673 (1991-09-01), Tsien et al.
patent: 5137810 (1992-08-01), Sizemore et al.
patent: 5171534 (1992-12-01), Smith et al.
patent: 5208148 (1993-05-01), Haugland et al.
patent: 5227487 (1993-07-01), Haugland et al.
patent: 5290706 (1994-03-01), Camiener
patent: 5332666 (1994-07-01), Prober et al.
patent: 5405975 (1995-04-01), Kuhn et al.
patent: 5453517 (1995-09-01), Kuhn et al.
patent: 5516911 (1996-05-01), London et al.
patent: 5567588 (1996-10-01), Gold et al.
patent: 5648270 (1997-07-01), Kuhn et al.
patent: 5696157 (1997-12-01), Wang et al.
patent: 5714327 (1998-02-01), Houthoff et al.
patent: 5750409 (1998-05-01), Hermann et al.
patent: 5936087 (1999-08-01), Benson et al.
patent: 6080852 (2000-06-01), Lee et al.
patent: 6130101 (2000-10-01), Mao et al.
patent: 6140500 (2000-10-01), Yan et al.
patent: 0 330 444 (1989-08-01), None
patent: WO 94/05688 (1994-03-01), None
Gee, et al. Tet. Lett. 37, 7905 (1996).
Raju et al., Am. J. Physiol. 256, C540 (1989).
R., Haugland, Molecular Probes Handbook of Fluorescent Probes and Research Chemicals, Chapters 1-3 (1996).
Brinkley, Bioconjugate Chem., 3, 2 (1992).
Tsien et al. Meth. Enzym. 172, 230 (1989).
Amlaiky et al., FEBS Lett 176, 436 (1984).
Haugland et al. Meth. Mol. Biol. 45, 205 (1995).
Haugland. Meth. Mol. Biol. 45, 223 (1995).
Haugland. Meth. Mol. Biol. 45, 235 (1995).
Kendall et al, J. Biol. Chem. 257,13892 (1982).
Szoka, Jr. et al., Proc. Natl. Acad. Sci. USA 75, 4194 (1978).
Szoka, Jr. et al. (Ann. Rev. Biophys. Bioeng. 9, 467 (1980).
Blankenfeld et al. J. Neurosci. Meth. 36, 309 (1991).
Sauer, et al. J. Fluorescence 5, 247 (1995).
Kano, et al. Heterocycles 15 (2), 1011 (1981).
Temciuc, et al. Tetrahedron 51 (48), 13185 (1995).
Diwu Zhenjun
Gee Kyle R.
Haugland Richard P.
Liu Jiaxing
Molecular Probes, Inc.
Powers Fiona T.
Skaugret Anton
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