Non-sulfonated cyanine dyes for labeling nucleosides and nucleot

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

536 253, 536 2531, 536 2532, 536 267, 548416, 548455, 435 6, C07H 1904

Patent

active

059860863

ABSTRACT:
A chemical compound of the following formula: ##STR1## wherein R.sup.1 is selected from the group consisting of alkyl, aralkyl, and substituted alkyl groups; R.sup.3 is selected from the group consisting of H, PO.sub.3.sup.-2, P.sub.2 O.sub.6.sup.-3 ; P.sub.3 O.sub.9.sup.-4, and .alpha.-thio phoshates (PSO.sub.2.sup.-2 ; P.sub.2 SO.sub.5.sup.-3 ; P.sub.3 O.sub.8.sup.-4); and .alpha.BH.sub.3.sup.- phosphates (P(BH.sub.3)O.sub.2.sup.-2, P.sub.2 (BH.sub.3)O.sub.5.sup.-3, P.sub.3 (BH.sub.3)O.sub.8.sup.-4); R.sup.4 is selected from the group consisting of H, lower alkyl, acyl, (CH.sub.2).sub.p COO(CH.sub.2).sub.q CH.sub.3 wherein p is an integer from 0 to 4 and q is an integer from 0 to 4, and 5,6; 6,7; or 7,8-butadienyl; R.sup.5 is selected from the group consisting of H lower alkyl, acyl, (CH.sub.2).sub.p COO(CH.sub.2).sub.q CH.sub.3 wherein p is an integer from 0 to 4 and q is an integer from 0 to 4 and 5,6; 6,7; or 7,8- butadienyl; r is 1, 2, or 3 to form a second fused aromatic; X or Y are selected from the group consisting of O, S, C(R.sup.6).sub.2, or N(R.sub.6), wherein R.sup.6 is preferably CH.sub.3 or a lower alkyl; and R.sup.3 --O-Sugar-Base is a nucleoside or nucleotide is disclosed.

REFERENCES:
patent: 4981977 (1991-01-01), Southwick et al.
patent: 5268486 (1993-12-01), Waggoner et al.
patent: 5556959 (1996-09-01), Brush et al.
patent: 5569587 (1996-10-01), Waggoner
patent: 5627027 (1997-05-01), Waggoner
J.B. Randolph and A.S. Waggoner, "Stability, Specificity and Fluorescence Brightness of Multiply-labeled Fluorescent DNA Probes," Nuc. Acids Res. 25(14):2923-2929, 1997.
Z. Zhu, et al., "Directly Labeled DNA Probes Using Fluorescent Nucleotides with Different Length Linkers," Nuc. Acids Res. 22(16):3418-3422, 1994.
E. Anderson, et al., "Synthesis of a Carbocyanine Phsophoramidite and its use in Oligonucleotide Labeling," International Conference on Nucleic Acid Medical Applications, Jan. 15, 1993.
D. Andrews-Wilberforce and G. Patonay, "Fluorescence Quenching Studies of Near-Infrared Fluorophores," App. Spectro. 43(8):1450-1455, 1989.
Collaborative Research, Semiannual Progress Report No. 2, 1978.
B.H. Dahl, et al., "Mechanistic Studies on the Phosphoramidite Coupling Reaction in Oligonucleotide Synthesis. I. Evidence for Nucleophilic Catalysis by Tetrazole and Rate Variations with the Phosphorus Substituents," Nucl. Acids Res. 15(4):1729-1743, 1987.
J.H. Kenton, et al., "Improved Electrochemiluminescent Label for DNA Probe Assays: Rapid Quantitative Assays of HIV-1 Polymerase Chain Reaction Products," Clin. Chem. 38(6):873-879, 1992.
M. Mag and J.W. Engels, "Synthesis and Selective Cleavage of Oligodeoxyribonucleotides Containing Non-chiral Internucleotide Phosphoramidate Linkages," 17(15):5973-5988.
R.B. Mujumdar, et al., "Cyanine Dye Labeling Reagents Containing Isothiocyanate Groups," Cytometry 10:11-19, 1989.
Nippon Zeon, JP 62070391, 1987 (Abstract).
K.K. Ogilvie, et al., "Total Chemical Synthesis of a 77-nucleotide-long RNA Sequence having Methionine-acceptance Activity," Proc. Natl. Acad. Sci. USA 85:5764-5768, 1988.
G. Patonay and M.D. Antoine, "Near-infrared Fluorogenic Labels: New Approach to an Old Problem," Analy. Chem. 63(6):321-326, 1991.
J.C. Schulhof, et al., "The Final Deprotection Step in Oligonucleotide Synthesis is Reduced to a Mild and Rapid Ammonia Treatment by using Labile Base-protecting Groups," Nucl. Acids Res. 15(2):397-416, 1987.
Sekine, et al., J. Am. Chem. Soc. 108:4581-4586, 1986.
H. Seliger and H.-H. Gortz, "Kenetik der Schutzgruppenabspaltung bei Derivaten des 2'-Desoxycytiden-5'-phosphats," Chem. Ber. 111:3732-3739, 1978.
P.L. Southwick, et al., "Cyanine Dye Labeling Reagents--Carboxymethylindocyanine Succinimidyl Esters," Cytometry 11:418-430, 1990.
H. Yu, et al., "Cyanine Dye dUTP Analogs for Enzymatic Labeling of DNA Probes," Nucl. Acids Res. 22(15):3226-3232, 1994.
H. Yu, et al., "Sensitive Detection of RNAs in Single Cells by Flow Cytometry," Nucl. Acids Res. 20(1):83-88, 1991.

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

Non-sulfonated cyanine dyes for labeling nucleosides and nucleot does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Non-sulfonated cyanine dyes for labeling nucleosides and nucleot, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Non-sulfonated cyanine dyes for labeling nucleosides and nucleot will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1326421

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