Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1989-09-22
1992-07-21
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
548528, 548543, 552 6, 562 45, 562 46, 562 47, 562 55, 8648, 436172, C07C24724, C07C30938, C01D20736, G01N 2200
Patent
active
051324326
ABSTRACT:
The invention relates to novel fluorescent dyes based on the following pyrenyloxy sulfonic acid structure: ##STR1## wherein at least one of R.sub.1, R.sub.2, R.sub.3, and R.sub.4 is --OCH.sub.2 C(O)OCH.sub.3, --OCH.sub.2 CON(O)H, --OCH.sub.2 CON.sub.3, --OCH.sub.2 CONHNH.sub.2, ##STR2## or --CH.sub.2 CONH(CH.sub.2).sub.n NH.sub.2 where n is an integer from 1 to 10; at least one of R.sub.1, R.sub.2, R.sub.3, and R.sub.4 is sulfonic acid or alkali salts of sulfonic acid; and all other of R.sub.1, R.sub.2, R.sub.3, and R.sub.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.
REFERENCES:
patent: 2122828 (1938-07-01), Wiegand et al.
patent: 3996345 (1976-12-01), Ullman et al.
patent: 4213904 (1980-07-01), Haugland
patent: 4520110 (1985-05-01), Stryer et al.
patent: 4542104 (1985-09-01), Stryon et al.
patent: 4844841 (1989-07-01), Koller et al.
Baker and Collis, "Fluorescent Acylating Agents Derived From 7-Hydroxycoumarin," J. Chem. Soc. (1949) S12-S15.
Barzilay et al., "Anion Transport in Red Blood Cells I. Chemical Properties of Anion Recognition Sites as Revealed by Structure-Activity Relationships of Aromatic Sulfonic Acids," Membr. Biochem. 2:227-254 (1979).
Braunitzer et al., "Zur Vollstandigen Automatischen Sequenzanalyse von Peptiden mit Quadrol," Hoppe-Seyler's Z. Physiol. Chem. 352:1730-1732 (1971).
Coons and Kaplan, "Localization of Antigen in Tissue Cells II. Improvements in a Method for the Detection of Antigen by Means of Fluorescent Antibody," J. Exp. Med. 91:1 (1950).
Cornelisse and Ploem, "A New Type of Two-Color Fluorescence Staining for Cytology Specimens," J. Histochem. and Cytochem. 24:72-81 (1976).
Khalfan et al., "Fluorigenic Method for the Assay of Proteinase Activity With the Use of 4-Methylumbelliferyl-casein," Biochem. J. 209:265-267 (1983).
Khalfan et al., "Aminomethyl Coumarin Acetic Acid: A New Fluorescent Labelling Agent for Proteins," Histochem. J. 18:497-499 (1986).
Lutty, "The Acute Intravenous Toxicity of Biological Stains, Dyes, and Other Fluorescent Substances," Toxicol. and Appl. Pharmacol. 44:225-249 (1978).
Riggs et al., "Isothiocyanate Compounds as Fluorescent Labeling Agents for Immune Serum," Amer. J. Path. 34:1081-1092 (1958).
Smith et al., "The Synthesis of Oligonucleotides Containing an Aliphatic Amino Group at the 5' Terminus: Synthesis of Fluorescent DNA Primers for Use in DNA Sequence Analysis," Nucl. Acids Res. 13:2399-2412 (1985).
Smith et al., "Fluorescence Detection in Automated DNA Sequence Analysis," Nature 321:674-679 (1986).
Speth and Schulze, "On the Nature of the Interaction Between 4,4'-Diisothiocyanostilbene 2,2'-Disulfonic Acid and Microsomal Glucose-6-Phosphatase," Eur. J. Biochem. 174:111-117 (1988).
Staines et al., "Three-Color Immunofluorescence Histochemistry Allowing Triple Labeling Within a Single Section," J. Histochem. and Cytochem. 36:145-151 (1988).
Cooper, Spectroscopic Techniques for Organic Chemists [New York, J. Wiley, 1980,] pp. 240 to 243.
Titus, et al. J. Immunological Methods 50 (1982) 193-204.
Lanier, et al. J. of Immunology 132(1) 1984 pp. 151 to 156.
Kanaoka Angew. Chem. 16 137-147 1977 Weber Biochem. J. 51, 145 (1952).
Bassi, et al. Expermentia vol. XVI 430, 1960 Rinderknecht, Expermentia 16, 430, 1960.
Jolley, et al. Clinical Chemistry, 27/7, 1981 pp. 1190-1197.
Hemmila, Clinical Chemistry 31/3, 1985 359-370.
Braunitzer et al., Hoppe-Seyler's Z. Physiologik Chemie. Dec. 1973, pp. 1563-1566.
Malencik et al. Biochemistry, vol. 11,(16) 1972 pp.3022-3027.
Wolfbeis, Fresenius Z Anal. Chemie, 320 (271-273) 1985.
Khalaf et al. Hoppe-Seyler's, Physiol. Chemie 358, 1977, pp. 505-511.
Haugland Richard P.
Whitaker James E.
Molecular Probes, Inc.
Shah Mukund J.
Ward Edward C.
LandOfFree
Chemically reactive pyrenyloxy sulfonic acid dyes does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Chemically reactive pyrenyloxy sulfonic acid dyes, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Chemically reactive pyrenyloxy sulfonic acid dyes will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-844557