Source: http://www.google.fr/patents/US5571388
Timestamp: 2013-05-22 04:34:30
Document Index: 696959429

Matched Legal Cases: ['art 1', 'art 1', 'art 2', 'art 3', 'art 4', 'art 5', 'art 6', 'art 7']

Brevet US5571388 - Sequencing near infrared and infrared fluorescense labeled DNA for detecting ... - Google�BrevetsRecherche Images Maps Play YouTube Actualit�s Gmail Drive Plus » Recherche avanc�e dans les brevets | Historique Web | Connexion Recherche avanc�e dans les brevets BrevetsTo sequence DNA automatically, DNA marked with far infrared, near infrared, or infrared fluorescent dyes are electrophoresed in a plurality of channels through a gel electrophoresis slab or capillary tubes wherein the DNA samples are resolved in accordance with the size of DNA fragments in the gel electrophoresis...http://www.google.fr/patents/US5571388?utm_source=gb-gplus-shareBrevet US5571388 - Sequencing near infrared and infrared fluorescense labeled DNA for detecting using laser diodes and suitable labels thereof Num�ro de publicationUS5571388 AType de publicationOctroi Num�ro de demande08/204,627 Date de publication5 nov. 1996 Date de d�p�t1 mars 1994 Date de priorit�29 mars 1984Autre r�f�rence de publicationEP0670374A1EP0670374B1US5800995 InventeursMalgorzata LipowskaLyle R. MiddendorfNarasimhachari NarayananGabor PatonayLucjan Strekowski Cessionnaire d'origineLi-Cor, Inc. Classification aux �tats-Unis204/461204/616204/466435/968204/612436/800435/6.13 Classification internationaleG01N33/58C09B23/00C12N15/09C07D209/12G01N21/64C12Q1/68C07D209/60C09B23/01G01N27/447 Classification coop�rativeC12Q1/6816C12Q1/6869G01N21/6458G01N27/44726G01N27/44721G01N27/447C07D209/60G01N21/6428C09B23/0066 Classification europ�enneG01N21/64P4CC12Q1/68EG01N27/447B3AG01N27/447B3A2G01N21/64HC12Q1/68B2C07D209/60C09B23/00DG01N27/447R�f�rencesCitations de brevets (11)Citations hors brevets (8) R�f�renc� par (39)Liens externesUSPTO Cession USPTO EspacenetSequencing near infrared and infrared fluorescense labeled DNA for detecting using laser diodes and suitable labels thereofUS 5571388 A R�sum� To sequence DNA automatically, DNA marked with far infrared, near infrared, or infrared fluorescent dyes are electrophoresed in a plurality of channels through a gel electrophoresis slab or capillary tubes wherein the DNA samples are resolved in accordance with the size of DNA fragments in the gel electrophoresis slab or capillary tubes into fluorescently marked DNA bands. The separated samples are scanned photoelectrically with a laser diode and a sensor, wherein the laser scans with scanning light at a wavelength within the absorbance spectrum of said fluorescently marked DNA samples and light is sensed at the emission wavelength of the marked DNA.
What is claimed is: 1. A method of identifying strands of DNA comprising the steps of: marking the strands with fluorescent labels that emit light in a region of wavelengths including at least one wavelength within the infrared and near infrared region wherein the fluorescent label includes a chromophore having the formula: ##STR7## where X is (CH.sub.2).sub.n ; n=4-10 or X is --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --CH.sub.2 --O--CH.sub.2 --CH.sub.2 --; irradiating the strands with light having a wavelength within one of the infrared and near infrared regions; and detecting the light emitted from the fluorescent labels.
4. A method according to claims 3 further comprising: applying DNA samples marked with fluorescent dye having absorbance and fluorescense maxima at near infrared or infrared wavelengths when combined with the DNA at a plurality of locations in a gel electrophoresis slab for electrophoresing in a plurality of channels through a gel electrophoresis slab; establishing electrical potential across said gel electrophoresis slab wherein DNA samples are resolved in accordance with the size of DNA fragments in said gel electrophoresis slab into fluorescently marked DNA bands; and irradiating the separated samples photoelectrically while they are in the slab with a laser diode and a sensor wherein the laser scans with near infrared or infrared scanning light at a wavelength within the absorbance spectrum of said fluorescently marked DNA samples and sensing light at the emission wavelength of the marked DNA.
REFERENCE TO RELATED APPLICATIONS This application is a continuation-in-part of U.S. Ser. No. application 07/860,140, filed Mar. 30, 1992, now U.S. Pat. No. 5,366,603 which is a division of U.S. application Ser. No. 07/763,230 filed Sep. 20, 1991, now U.S. Pat. No. 5,230,781, which is a continuation-in-part of application Ser. No. 07/570,503 filed Aug. 21, 1990, now U.S. Pat. No. 5,207,880, which is a continuation-in-part application of Ser. No. 07/078,279 filed Jul. 27, 1987, now abandoned which is a division of U.S. application Ser. No. 594,676 for DNA SEQUENCING filed by Middendorf et al. on Mar. 29, 1984, and assigned to the same assignee as this application, now U.S. Pat. No. 4,729,947.
Formula 1 shows synthesized cyanine dyes having NCS as a reactive group for attachment of a biomolecule. In this embodiment, when X is H, the maximum absorbance wavelength is between 787 and 801 nm, depending on the solvent and the maximum emission wavelength is between 807 and 818 depending on the solvent. When X is --OCH.sub.3, the maximum absorbance wavelength is 786 nm and the maximum emission wavelength is 806 nm. The quantum yield is high.
In the synthesized dyes represented by formula 3, when R is SO.sub.3 Na, the maximum absorbance wavelength is between 773 and 778 nm and the maximum emission wavelength is between 789 and 806 nm.
A proposed series of molecules represented by formula 6 is expected to have increased solubility to permit its use in an aqueous medium through the use of an amino group or ether group attached to the benzene ring. In this series, X may be oxygen or NH, Y may be NCS or H, and R may be H, NCS, CH.sub.2 OH, CH.sub.2 NCS or COOH according to tables 1 or 2.
In formula 7: R may be ethyl, 4-sulfonatobutyl, 3-amino propyl, phthalimidobutyl hexyl and pentyl carboxylates; Z may be S, O, CMe.sub.2, Y may be H, SO.sub.3 Na, SO.sub.3 Et.sub.3 NH, OCH.sub.3, NO.sub.2 CO.sub.2 Na or CO.sub.2 Et.sub.3 NH and X may be H, N(CH.sub.2 CO.sub.2 CH.sub.3).sub.2, CH.sub.2 CH.sub.2 OH, CHS, CH.sub.2 CH.sub.2 CH.sub.2 OH or --(CH.sub.2).sub.n -OH where the number n=any number between and including 8-12. ##STR1##
(6) When X is C.sub.3 H.sub.6 OH and R is hydrogen, the maximum absorbance wavelength is between 766 and 768 nm and the maximum emission wavelength is between 788 and 790 nm.
(7) When X is NCS and R is SO.sub.5 Na, the maximum absorbance wavelength is between 773 and 778 nm and the maximum emission wavelength is between 789 and 806 nm. ##STR2##
(2) When X is CH.sub.2 CH.sub.2 CH.sub.2 OH the absorbance wavelength is between 762 and 770 nanometers and the emission wavelength is between 782 to 790 nanometers.
The series of molecules represented by formula 11 have been synthesized and are effective as IR labels when R.sub.1 and X are as shown in table 4.
The series of molecules represented by formula 12 have been synthesized and are effective as IR labels when R.sub.1, R.sub.2 and X are as shown in table 5.
The series of molecules represented by formula 13 have been synthesized and are effective as IR labels when R.sub.1, R.sub.3 and R.sub.2 are as shown in table 6.
In the one embodiment, the dye has the formula shown in formula 17, with R being --CH.sub.2 --CH.sub.3. This dye is close to having the desired wavelength of maximum fluorescence and the wavelength of maximum absorbance may be modified by changing the functional group R. The unmodified dye may be obtained from Laboratory and Research Products Division, Eastman Kodak Company, Rochester, N.Y. 14650. It is advertised in the Kodak laser dyes, Kodak publication JJ-169.
The modifications with 1,3-propanediol can be made in a manner known in the art as illustrated by equation 1. For example, changes occur when different esters are formed replacing the ethyl alcohol in the original dye molecule (R equal --CH.sub.2 CH.sub.3 of formula 17). If different glycol esters are formed, absorption maxima of these new near infrared dyes shift to the longer wavelengths. Moreover, new dyes may be synthesized rather than modifying existing dyes in a manner known in the art.
The absorption maximum is dependent on the distance of the 0 atoms in the glycol functional group. However, the fluorescence maxima of these new near infrared dyes are practically at same wavelength of the dye of formula 17, i.e. 819 nm. This indicates that only the excitation process has changed, i.e. to what energy level the transition occurs. The lowest vibronic level of first excited state remains unchanged. The absorption maxima of several such esters are: (1) ethylene glycol 796 nm (nanometers); (2) 1,3-Propanediol 780 nm; (3) 1,4-Butanediol 754 nm; (4) 1,6-Hexanediol 744 nm; (5) Triethylene glycol (#4) 790 nm; and (6) IR-144 (R═CH.sub.2 --CH.sub.3) 742 nm.
(5) --CH.sub.2 --CH.sub.2 --SH for an emission wavelength of 810 nanometers.
Dye synthesis is illustrated by chart 1, which shows the synthesis of formulas 7, 8, 9, and 10. In the chloro intermediate in chart 1, R and R.sub.1 may have the values shown in table 9. Chart 2 shows the synthesis of formula 11. Chart 3 shows the synthesis of formulas 1 and 12. Chart 4 shows the synthesis of formula 13. Chart 5 shows the synthesis of formula 14. Chart 6 shows the synthesis of formula 15. Chart 7 shows the
Citations de brevets Brevet cit� Date de d�p�t Date de publication D�posant TitreUS526848615 mai 19927 d�c. 1993Carnegie-Mellon UnversityMethod for labeling and detecting materials employing arylsulfonate cyanine dyesUS531292114 mai 199317 mai 1994Regents Of The University Of CaliforniaDyes designed for high sensitivity detection of double-stranded DNAUS532113010 f�vr. 199214 juin 1994Molecular Probes, Inc.Unsymmetrical cyanine dyes with a cationic side chainUS537560628 f�vr. 199027 d�c. 1994Zynaxis, Inc.Bio-analytical separation methodUS54100305 avr. 199325 avr. 1995Molecular Probes, Inc.Dimers of unsymmetrical cyanine dyes containing pyridinium moietiesDE3912046A1 Titre non disponibleEP0519474A119 juin 199223 d�c. 1992Canon Kabushiki KaishaLabeled complexEP0533302A17 sept. 199224 mars 1993Li-Cor, Inc.Sequencing near infrared and infrared fluorescence labeled DNA for detecting using laser diodesEP0609894A24 f�vr. 199410 ao�t 1994Canon Kabushiki KaishaLabeled complex and method of analysis therewithWO1993006482A116 sept. 19921 avr. 1993Molecular Probes, Inc.Dimers of unsymmetrical cyanine dyesWO1994024213A113 avr. 199427 oct. 1994Molecular Probes, Inc.Cyclic-substituted unsymmetrical cyanine dyesCitations hors brevetsR�f�rence1Bruno Becker et al "In Situ Screening Assay for Cell Viability Using a Dimeric Cyanine Nucleic Acid Stain" Analytical Biochemistry, vol. 221, No. 1 (Aug. 1994) 78-84.2Bruno Becker et al In Situ Screening Assay for Cell Viability Using a Dimeric Cyanine Nucleic Acid Stain Analytical Biochemistry, vol. 221, No. 1 (Aug. 1994) 78 84.3Fu Tai A. Chen et al Semiconductor laser induced Fluorescence detection in capillary electrophoresis using a cyanine dye Journal of Chromatography vol. 652, No. 2 (Oct. 1993) 355 360.4Fu-Tai A. Chen et al "Semiconductor laser-induced Fluorescence detection in capillary electrophoresis using a cyanine dye" Journal of Chromatography vol. 652, No. 2 (Oct. 1993) 355-360.5Lipowska, M., et al., 1993, "New Near-Infrared Cyanine Dyes for Labeling of Proteins", Synthetic Communications, 23(21):3087-3094.6Lipowska, M., et al., 1993, New Near Infrared Cyanine Dyes for Labeling of Proteins , Synthetic Communications, 23(21):3087 3094.7Strekowski, L., et al., 1992, "Substitution Reactions of a Nucleofugal Group in Heptamethine Cyanine Dyes. Synthesis of an Isothiocyanato Derivative for Labeling of Proteins with a Near-Infrared Chomophore", J. Organ. Chem., 57:4578-4580.8Strekowski, L., et al., 1992, Substitution Reactions of a Nucleofugal Group in Heptamethine Cyanine Dyes. Synthesis of an Isothiocyanato Derivative for Labeling of Proteins with a Near Infrared Chomophore , J. Organ. Chem., 57:4578 4580. R�f�renc� par Brevet citant Date de d�p�t Date de publication D�posant TitreUS631290614 janv. 20006 nov. 2001Imperial College Innovations, Ltd.Immobilized nucleic acid hybridization reagent and methodUS63316329 nov. 200018 d�c. 2001Beckman Coulter, Inc.Cyanine dye phosphoramiditesUS63354509 nov. 20001 janv. 2002Beckman Coulter, Inc.Efficient cyclic-bridged cyanine dyesUS64038076 juil. 200011 juin 2002Surromed, Inc.Bridged fluorescent dyes, their preparation and their use in assaysUS653104425 oct. 199911 mars 2003Hitachi, Ltd.Capillary array electrophoresis apparatusUS65931487 mars 200015 juil. 2003Li-Cor, Inc.Cyanine dye compounds and labeling methodsUS66283856 janv. 200030 sept. 2003Axon Instruments, Inc.High efficiency, large field scanning microscopeUS670687928 f�vr. 200216 mars 2004StratageneFluorescent dyeUS68339164 sept. 200321 d�c. 2004Axon Instruments, Inc.High efficiency, large field scanning microscopeUS683828914 nov. 20014 janv. 2005Beckman Coulter, Inc.Analyte detection systemUS696282012 f�vr. 20048 nov. 2005Beckman Coulter, Inc.Analyte detection systemUS699527428 janv. 20037 f�vr. 2006Li-Cor, Inc.Cyanine dyesUS702956214 janv. 200318 avr. 2006Hitachi, Ltd.Capillary array electrophoresis apparatusUS70913481 juil. 200315 ao�t 2006Guava Technologies, Inc.Fluorescent dyes, energy transfer couples and methodsUS712564411 ao�t 200324 oct. 2006Hewlett-Packard Development Company, L.P.Systems and methods for storing data on an optical diskUS718936625 mai 200113 mars 2007The United States Of America As Represented By The Secretary Of The InteriorMolecular tag readerUS719883422 mars 20053 avr. 2007Hewlett-Packard Development Company, L.P.Imaging media including interference layer for generating human-readable marking on optical mediaUS723011712 juil. 200412 juin 2007Beckman Coulter, Inc.Stable cyanine dye phosphoramiditesUS725051728 nov. 200331 juil. 2007Ewald A. TerpetschnigLuminescent compoundsUS730080013 mai 200527 nov. 2007Beckman Coulter, Inc.Analyte detection systemUS73123269 avr. 200425 d�c. 2007Beckman Coulter, Inc.Fluorescent labeled nucleotide derivativesUS741106810 nov. 200412 ao�t 2008Terpetschnig Ewald ALuminescent compoundsUS75040894 nov. 200517 mars 2009Li-Cor, Inc.Cyanine dyesUS759787819 mai 20066 oct. 2009Li-Cor, Inc.Optical fluorescent imagingUS762918121 f�vr. 20078 d�c. 2009The United States Of America, As Represented By The Secretary Of The InteriorMolecular tag readerUS76686976 f�vr. 200723 f�vr. 2010Life Technologies CorporationMethod for analyzing dynamic detectable events at the single molecule levelUS793933025 oct. 201010 mai 2011Tetsuo NaganoFluorescent probeUS816838010 mai 20011 mai 2012Life Technologies CorporationMethods and products for analyzing polymersUS822762112 juin 200624 juil. 2012Li-Cor, Inc.Cyanine dyes and methods of useUS830393615 juin 20126 nov. 2012Li-Cor, Inc.Optical fluorescent imagingUS831421629 d�c. 200620 nov. 2012Life Technologies CorporationEnzymatic nucleic acid synthesis: compositions and methods for inhibiting pyrophosphorolysisUS201002155853 ao�t 200726 ao�t 2010Beth Israel Deaconess Medical Center, Inc.Dyes and precursors and conjugates thereofWO2002024815A118 sept. 200128 mars 2002Draney, Daniel, R.Cyanine dyesWO2003087052A210 avr. 200323 oct. 2003Borovoy, IgorDyes and fluorescent compoundsWO2005103162A122 mars 20053 nov. 2005Beckman Coulter, Inc.Fluorescent labeled nucleotide derivativesWO2007114398A130 mars 200711 oct. 2007Date, MutsuhiroPyrazole-type cyanine dyeWO2010126045A127 avr. 20104 nov. 2010Wako Pure Chemical Industries, Ltd.Pyrazole-based cyanine dye containing quaternary ammonium cationWO2012054749A120 oct. 201126 avr. 2012Li-Cor, Inc.Cyanine dyes and their conjugatesWO2012054784A120 oct. 201126 avr. 2012Li-Cor, Inc.Fluorescent imaging with substituted cyanine dyesFaire pivoterImage d'origineAccueil Google - Plan du site - T�l�chargements par lot sur l'USPTO - R�gles de confidentialit� - Conditions d'utilisation - � propos de Google�Brevets - Envoyer des commentairesDonn�es fournies par IFI CLAIMS Patent Services©2012 Google