Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...
Patent
1995-06-05
1997-02-04
Ivy, C. Warren
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitrogen attached directly or indirectly to the purine ring...
546108, 546109, C07D40106
Patent
active
055999328
ABSTRACT:
Intercalator compounds are provided which are comprised of intercalator moieties, or substituted intercalator moieties, having one or more functionalized chains, or moieties, and which compounds provide a high affinity for binding to the DNA molecule and show reduced self-quenching, while providing superior transport kinetics. The compounds have been found to provide enhanced fluorescence when bound to a DNA molecule within a fluorescent flow cytometry environment which is about eight to ten times brighter in fluorescence than "bis" structure conventional intercalating agents and other known intercalating agents utilized in flow cytometry environment.
REFERENCES:
patent: 4119521 (1978-10-01), Chirikjian
patent: 4665184 (1987-05-01), Dervan et al.
patent: 4921805 (1990-05-01), Gebeyehu et al.
patent: 4981977 (1991-01-01), Southwick et al.
patent: 5312921 (1994-05-01), Glazer
Glazer, Alexander N., et al., "Stable Dye-DNA Intercalation Complexes As Reagents For High-Sensitivity Fluorescence Detection", Nature, 359, pp. 859-861 (Oct. 29, 1992).
Quesada, M. A., et al., "High-Sensitivity DNA Detection With A Laser-Excited Confocal Fluorescence Gel Scanner", BioTechniques, 10 (5), pp. 616-625 (1991).
Glazer, Alexander N., et al., "A Stable Double-Stranded DNA-Ethidium Homodimer Complex: Application To Picogram Fluorescence Detection Of DNA In Agarose Gels," Proc. Natl. Acad. Sci. USA, 87, pp. 3851-3855 (May 1990).
Rye, Hays S., et al., "Stable Fluorescent Complexes Of Double-Stranded DNA With Bis-Intercalating Asymmetric Cyanine Dyes: Properties And Applications", Nucleic Acids Research, 20 (11), pp. 2803-2812 (1990).
Rye, Hays S., et al., "High-Sensitivity Two-Color Detection Of Double-Stranded DNA With A Confocal Fluorescence Gel Scanner Using Ethidium Homodimer and Thiazole Orange", Nucleic Acids Research, 19 (2), pp. 327-333 (1990).
Mathies, Richard A., et al., "Capillary Array Electrophoresis: An Approach To High-Speed, High-Throughput DNA Sequencing", Nature, 359, pp. 167-169 (Sep. 10, 1992).
Gao, Qi, et al., "Drug-Induced DNA Repair: X-Ray Structure Of A DNA-Ditercalinium Complex", Proc. Natl. Acad. Sci. USA, 88, pp. 2422-2426 (Mar. 1991).
Mathies, Richard A., et al., "Optimization Of High-Sensitivity Fluorescence Detection", Anal. Chem., 62 (17), pp. 1786-1791 (Sep. 1, 1990).
Peck, Konan, et al., "Single-Molecule Fluorescence Detection: Autocorrelation Criterion And Experimental Realization With Phycoerythrin", Proc. Natl. Acad. Sci. USA, 86, pp. 4087-4091 (Jun. 1989).
Severini, Alberto, et al., "An Assay For Proteinases And Their Inhibitors Based On DNA/Ethidium Bromide Fluorescence", Anal. Biochem., 193, pp. 83-89 (1991).
Gaugain, Bernard, et al., "DNA Bifunctional Intercalators. I. Synthesis And Conformational Properties Of An Ethidium Homodimer And Of An Acridine Ethidium Heterodimer", Biochemistry, 17 (24), pp. 5071-5078 (Nov. 28, 1978).
Dervan, Peter B., et al., "Molecular Recognition Of DNA By Small Molecules, Synthesis Of Bis(methidium)spermine, A DNA Polyintercalating Molecule", J. Chem. Soc., 100 (6), pp. 1968-1970 (Mar. 15, 1978).
Gaugain, Bernard, et al., "DNA Bifunctional Intercalators. 2. Fluorescence Properties And DNA Binding Interaction Of An Ethidium Homodimer And An Acridine Ethidium Heterodimer", Biochemistry, 17 (24), pp. 5078-5088 (1978).
Markovits, Judith, et al., "Ethidium Dimer: A New Reagent For The Fluorimetric Determination Of Nucleic Acids", Anal. Biochem., 94, pp. 259-264 (1979).
Benson, Scott C., et al., "Heterodimeric DNA-Binding Dyes Designed For Energy Transfer: Stability And Applications Of The DNA Complexes", Nucleic Acids Research, 21 (24), pp. 5720-5726 (1993).
Petersen, S. E., "Accuracy And Reliability Of Flow Cytometric DNA Analysis Using A Simple, One-Step Ethidium Bromide Staining Protocol", Cytometry, 7 (4), pp. 301-306 (Jul., 1986).
Riboldi, et al., "Ethidium Bromide In The Detection Of Antibodies To DNA And Of Circulating DNA By Two-Stage Counterimmunoelectrophoresis", J. Immunol. Methods, 85 (1), pp. 217-220 (Dec. 17, 1985).
Denny, W. A., "DNA-Intercalating Ligands As Anti-Cancer Drugs: Prospects for Future Design", Anticancer Drug Design, 4, pp. 241-263 (Dec., 1989).
Benson, Scott C., et al., "Heterodimeric DNA-Binding Dyes Designed For Energy Transfer: Synthesis And Spectroscopic Properties", 21 (24), pp. 5727-5735 (1993).
Sasaki, et al., "Discrimination Of Viable and Non-Viable Cells Using Propidium Iodide In Two Color Immunofluorescence", Cytometry, 8, pp. 413-420 (1987).
Mishell, et al., "Selected Methods In Immunology", pp. 10-17 (1980).
Ernst, et al., "Cyanine Dye Labeling Reagents For Sulfhydryl Groups", Cytometry, 10, pp. 3-10 (1989).
Hamer, Frances M., "The Cyanine Dyes And Related Compounds", John Wiley & Sons, pp. 34-39 (1964).
Wiberg, Kenneth B., et al., "Solvolysis of cis- and trans-Fused Bicyclo[4.2.0]octyl 7-Tosylates", J. Am. Chem. Soc., 92:3, pp. 553-564 (Feb. 11, 1970).
Wilt, James W., "Reaction of 2-(.DELTA..sup.3 -Cyclopentenyl)ethyl Bromide with Tri-n-butyltin Hydride. Cyclization to Norbornane", J. Org. Chem., 35:8, pp. 2803-2806 (1970).
Hooz, J., et al., "A Rapid, Mild Procedure for the Preparation of Alkyl Chlorides and Bromides", Can. J. Chem., 46:86, pp. 86-87 (1968).
Lee, et al., "Preparation of Acyl Halides Under Very Mild Conditions", J. Am. Chem. Soc., 88:14, pp. 3440-3441 (Jul. 20, 1966).
Christen, et al., "An Ethidium Bromide-Agarose Plate Assay for the Nonradioactive Detection of cDNA Synthesis", Anal. Biohem., 178:2, pp. 269-272 (1989).
Jaycox, Gary D., et al., "Potential DNA bis-Intercalating Agents: Synthesis and Antitumor Activity of Novel, Conformationally Restricted bis(9-Aminoacridines)", J. Heterocyclic Chem., 24, pp. 1405-1408 (Sep.-Oct. 1987).
Orchin, Milton, et al., The Vocabulary of Organic Chemistry, Wiley, p. 94 (1980).
Morrison, Robert Thornton, et al., Organic Chemistry, Allyn and Bacon, Inc., p. 1002 (1973).
Reques, Bernard P, et al., "Pharmacologie Moleculaire", C. R. Acad. S. Paris, 283, pp. 1365-1367 (Nov. 1976).
Bieniarz Christopher
Henrard Denis R.
Huff Jeffrey B.
Abbott Laboratories
Huang Evelyn
Ivy C. Warren
Weinstein David L.
LandOfFree
Intercalators having affinity for DNA and methods of use does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Intercalators having affinity for DNA and methods of use, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Intercalators having affinity for DNA and methods of use will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-679922