Aza-benzazolium containing cyanine dyes

Chemistry: molecular biology and microbiology – Measuring or testing process involving enzymes or... – Involving nucleic acid

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C435S004000, C435S029000, C435S034000, C435S091200, C436S800000, C546S016000, C546S165000, C546S270100, C546S271100

Reexamination Certificate

active

07871773

ABSTRACT:
Unsymmetrical cyanine dyes that incorporate an aza-benzazolium ring moiety are described, including cyanine dyes substituted by a cationic side chain, monomeric and dimeric cyanine dyes, chemically reactive cyanine dyes, and conjugates of cyanine dyes. The subject dyes are virtually non-fluorescent when diluted in aqueous solution, but exhibit bright fluorescence when associated with nucleic acid polymers such as DNA or RNA, or when associated with detergent-complexed proteins. A variety of applications are described for detection and quantitation of nucleic acids and detergent-complexed proteins in a variety of samples, including solutions, electrophoretic gels, cells, and microorganisms.

REFERENCES:
patent: 2269234 (1942-01-01), Sprague
patent: 3326688 (1967-06-01), Brooker et al.
patent: 4003750 (1977-01-01), Heseltine et al.
patent: 4665024 (1987-05-01), Mansour et al.
patent: 4711955 (1987-12-01), Ward et al.
patent: 4883867 (1989-11-01), Lee et al.
patent: 4937198 (1990-06-01), Lee et al.
patent: 4997928 (1991-03-01), Hobbs
patent: 5047519 (1991-09-01), Hobbs et al.
patent: 5171534 (1992-12-01), Smith et al.
patent: 5221518 (1993-06-01), Mills
patent: 5321130 (1994-06-01), Yue et al.
patent: 5332666 (1994-07-01), Prober
patent: 5401847 (1995-03-01), Glazer
patent: 5410030 (1995-04-01), Yue et al.
patent: 5436134 (1995-07-01), Haugland et al.
patent: 5445946 (1995-08-01), Roth et al.
patent: 5459268 (1995-10-01), Haugland et al.
patent: 5534416 (1996-07-01), Millard et al.
patent: 5564554 (1996-10-01), Lawrence
patent: 5565554 (1996-10-01), Glazer
patent: 5582977 (1996-12-01), Yue et al.
patent: 5616502 (1997-04-01), Haugland et al.
patent: 5656449 (1997-08-01), Yue
patent: 5658751 (1997-08-01), Yue et al.
patent: 5714327 (1998-02-01), Houthoff et al.
patent: 5760201 (1998-06-01), Glazer
patent: 5863753 (1999-01-01), Haugland et al.
patent: 5869689 (1999-02-01), Zhang et al.
patent: 6083699 (2000-07-01), Leushner et al.
patent: 7226740 (2007-06-01), Haugland et al.
patent: 870753 (1958-07-01), None
patent: 05-287209 (1992-04-01), None
patent: WO-94/05688 (1994-03-01), None
patent: WO-96/13552 (1996-05-01), None
U.S. Appl. No. 09/557,275, Notice of Allowance mailed Jun. 4, 2003.
U.S. Appl. No. 09/557,275, Office Action mailed Nov. 20, 2002.
U.S. Appl. No. 09/557,275, Response to Nov. 20, 2002 Office Action Filed Mar. 13, 2003.
U.S. Appl. No. 09/557,275, Response to Rest. Req. Filed Aug. 21, 2002.
U.S. Appl. No. 09/557,275, Restriction Req. mailed Jul. 22, 2000.
U.S. Appl. No. 09/557,275, Supp. Resp. to Rest. Req. Filed Oct. 16, 2002.
U.S. Appl. No. 10/683,753, Notice of Allowance mailed Jan. 29, 2007.
U.S. Appl. No. 10/683,753, Office Action mailed Jun. 9, 2006.
U.S. Appl. No. 10/683,753, Office Action mailed Oct. 2, 2006.
U.S. Appl. No. 10/683,753, Response to Jun. 9, 2006 Office Action, Filed Sep. 11, 2006.
U.S. Appl. No. 10/683,753, Response to Oct. 2, 2006 Office Action, Filed Jan. 3, 2007.
U.S. Appl. No. 10/683,753, Response to Rest. Req. Filed Apr. 27, 2006.
U.S. Appl. No. 10/683,753, Restriction Req. mailed Mar. 29, 2006.
Barlin, Gordon B. et al., “Purine Analogues as Amplifiers of Phleomycin. IX* Some 2- and 6-Substituted Thiazolo [4,5,-b] Pyrazines, 2-Substituted Thiazolo[4,5,-c]- and Thiazolo[5,4,-b]-Pyridines and Related Compunds”,Aust. J. Chem. vol. 37 1984, 1729-1737.
Barlin, Gordon B. et al., “Purine Analogues as Amplifiers of Phleomyein. Some Thiazolo[4,5-g] pyrazines and Related Compounds”,Aust. J. Chem. vol. 36 1983, 983-985.
Brinkley, Michael, “A Brief Survey of Methods for Preparing Protein Conjugates with Dyes, Haptens, and Cross-Linking Reagents”,Bioconjugate Chem. vol. 3, No. 1 1992, 2-13.
Brooker, L G. et al., “Color and consitution. V. The absorption of unsymmetrical cyanines. Resonance as a basis for a classification of dyes”,Journal of the American Chemical Societyvol. 64, Communication No. 833 From the Kodak Research Laboratories Feb. 1942, 199-210.
Chu-Moyer, Margaret Y. et al., “Preparation of the Four Regioisomeric 2-(Methylthio)oxazolopyridines: Useful Synthons for Elaboration to 2-(Amino substituted)oxazolopyridines”,Journal of Organic Chemistryvol. 60, No. 17 1995, 5721-5725.
Couture, Axel et al., “2-ARYL-OXazolo- and Thiazolopyrdines. Synthesis via Cyclization of N-(2 Chloro-3-Pyridinyl) Arylamides and Thiomides”,Heterocyclesvol. 22, No. 6 1984, 1383-1385.
Couture, Axel et al., “Nouvelle Methode De Synthese De Thiazolopyridines”, (French Version)J. Heterocyclin Chem. vol. 24 1987, 1765-1769.
Ficken, et al., “Diazaines and Their Quarternary Salts Part 2”,CA 55:70677, abstract only of J of Chem Soc1961, 584-588.
Ficken, G E. et al., “Diazaindenes and Their Quaternary Salts Part 1: The preparation of 2,3,3-Trimethyl-3H-1,7-diazaindene, and its Methiodides and Derived Cyanine Dyes”,Journal of Chemical Society1959, 3202-3212.
Foye, William O. et al., “Antiradiation compounds XV: Condensations of carbon disulfide with amino, chloro, cyanomethyl, and sulfonamido heterocycles”,Journal of Pharmaceutical Sciencevol. 64, No. 8 Aug. 1975, 1371-1374.
Haugland, Richard P.,Molecular Probes Handbook of Fluorescent Probes and Research Products(Table of Contents) 9th edition, CD ROM, Molecular Probes, Inc/Invitrogen 2002, 1-6.
Haugland, Richard P., “Chapters 1-3”,Molecular Probes Handbook of Fluorescent Probes and Research ChemicalsMolecular Probes, Inc/Invitrogen 1996.
Haugland, Richard P., “Handbook of Flourescent Probes and Research Chemicals”, 9th Edition CD-ROM, Molecular Probes, Inc/Invitrogen Sep. 2002.
Haugland, Richard P., “Molecular Probes Handbook of Fluorescent Probes and Research Chemicals”, 6th Edition (Subsequent 7th and 8th edition updates issued on CD Rom. 1996, 1-421.
Haugland, Rosaria P., “Ch 22: Coupling of monoclonal antibodies with fluorophores”,Methods in Molecular Biologyvol. 45: Monoclonal Antibody Protocols 1995, 205-221.
Haugland, Rosaria P., et al., “Coupling of Antibodies with Biotin”,The Protein Protocols HandbookHumana Press 1996, 293.
Haugland, Rosaria P., et al., “Coupling of Antibodies with Biotin”,Humana Pressvol. 418 1996, 13-23.
Haugland, Rosaria P., et al., “Coupling of monoclonal antibodies with biotin”,Methods in Molecular Biologyvol. 45 1995, 223-233.
Heravi, M M. et al., “Heterocyclic monoazo dyes derived from 2-(p-aminophenyl)oxazolo-[4,5-b]pyridine and 7-(p-aminophenyl)-4H-[1,3,4]thiadiazolo-[2,3-c][1,2,4]triazin-4-one”,Indian J. Chem. 36B 1997, 1025-1029.
Khanna, Ish K. et al., “Facile, Regioselective Synthesis of N-Alkylated 2,3-Diaminopyridines and Imidazo[4,5-b]pyridines”,J. Org. Chem. vol. 60 1995, 960-965.
PCT International Search Report, WO/2000/66664, dated Sep. 7, 2000.
Petric, A et al., “Azido-Tetrazolo Isomerizations of Some Thiazolopyridines (1)”,J. Heterocyclin Chem. vol. 14 Oct. 1977, 1045-1047.
Saikachi, Haruo et al., “Studies on Compounds Related to Pyrazine. III. Synthesis of 2-Substituted Thiazolo[b]quinozaline.”,Chem.&Pharm. Bull. vol. 9, No. 12 Dec. 1961, 941-944.
Smith, Keith et al., “A Convenient Synthesis of 2-Substituted Thiazolo [4,5-b]pyridines via Directed Metalation”,Sulfur Lettersvol. 18, No. 2 (not available online- BJC) 1995, 79-95.
Smith, Keith et al., “Convenient synthesis of 4-aminopyridine-3-thiol and several thiazolo[5,4-c]pyridines via direct ligation”,Chemistry and Industryvol. 9 May 2, 1988, 302-303.
Smith, Keith et al., “The synthesis of 2-substituted thiazolo[5,4-c]pyridines via directed methalation”,Sulfur Lettersvol. 17, No. 4 1994, 197-216.
Turner, James A., “Regiospecific electrophilic substitution of aminopyridines: ortho lithiation of 2-, 3-, and 4-(pivaloylamino)pyridines”,Journal of Organic Chemistryvol. 48 1983, 3401-3408.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Aza-benzazolium containing cyanine 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 Aza-benzazolium containing cyanine dyes, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Aza-benzazolium containing cyanine dyes will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-2694041

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.