FR2868071A1 - Reactifs de marquage, procedes de synthese de tels reactifs et procedes de detection de molecules biologiques - Google Patents
Reactifs de marquage, procedes de synthese de tels reactifs et procedes de detection de molecules biologiquesInfo
- Publication number
- FR2868071A1 FR2868071A1 FR0450600A FR0450600A FR2868071A1 FR 2868071 A1 FR2868071 A1 FR 2868071A1 FR 0450600 A FR0450600 A FR 0450600A FR 0450600 A FR0450600 A FR 0450600A FR 2868071 A1 FR2868071 A1 FR 2868071A1
- Authority
- FR
- France
- Prior art keywords
- integer
- methods
- reagents
- biological molecules
- nhco
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003153 chemical reaction reagent Substances 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 230000002194 synthesizing effect Effects 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 238000002372 labelling Methods 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000021615 conjugation Effects 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- -1 diazomethyl function Chemical group 0.000 abstract 1
- 150000007523 nucleic acids Chemical class 0.000 abstract 1
- 102000039446 nucleic acids Human genes 0.000 abstract 1
- 108020004707 nucleic acids Proteins 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/13—Tracers or tags
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/142222—Hetero-O [e.g., ascorbic acid, etc.]
- Y10T436/143333—Saccharide [e.g., DNA, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
La présente invention concerne un réactif de marquage stable à la température de formule (0) :dans laquelle :• R1 représente H ou un groupe alkyle, aryle ou aryle substitué,• R2 représente un marqueur détectable ou au moins deux marqueurs détectables reliés entre eux par au moins une structure multimérique,• L est un bras de liaison comportant un enchaînement linéaire d'au moins deux liaisons covalentes et n un nombre entier égal à 0 ou 1,• R3 et R4 représentent indépendamment l'un de l'autre : H, NO2, Cl, Br, F, I, R2 -(L)n-Y-X-, OR, SR, NR2, R, NHCOR, CONHR, COOR, -CO-NH-(CH2)3-(O-CH2-CH2)3-CH2-NH-R2, - CO-NH-(CH2)3-(O-CH2-CH2)4-CH2-NH-R2 avec R = alkyle ou aryle,• A est un bras de liaison comportant au moins une double liaison covalente permettant la conjugaison de la fonction diazo avec le cycle aromatique et u est un nombre entier compris entre 0 et 2, préférentiellement de 0 ou 1,• -Y-X- représente -CONH-, -NHCO-, -CH2O-, -CH2S-,• -Z- représente -NH-, -NHCO-, -CONH- ou -O-,• m est un nombre entier compris entre 1 et 10, préférentiellement entre 1 et 3, et• p est un nombre entier compris entre 1 et 10, préférentiellement entre 1 et 3.La présente invention décrit aussi un procédé de synthèse desdits marqueurs ainsi que des applications pour le marquage de molécules biologiques, en particulier des acides nucléiques, avec un réactif de marquage portant la fonction diazométhyle.L'invention trouve une application préférentielle dans le domaine du diagnostic.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0450600A FR2868071B1 (fr) | 2004-03-26 | 2004-03-26 | Reactifs de marquage, procedes de synthese de tels reactifs et procedes de detection de molecules biologiques |
| PCT/FR2005/050192 WO2005092910A1 (fr) | 2004-03-26 | 2005-03-24 | Réactifs de marquage, procédés de synthèse de tels réactifs et procédés de détection de molécules biologiques |
| CA002558357A CA2558357A1 (fr) | 2004-03-26 | 2005-03-24 | Reactifs de marquage, procedes de synthese de tels reactifs et procedes de detection de molecules biologiques |
| EP05739660A EP1727825A1 (fr) | 2004-03-26 | 2005-03-24 | Reactifs de marquage, procedes de synthese de tels reactifs et procedes de detection de mol cules biologiques |
| CNA2005800097858A CN1938329A (zh) | 2004-03-26 | 2005-03-24 | 标记试剂、合成这样的试剂的方法和检测生物分子的方法 |
| US10/590,973 US7691635B2 (en) | 2004-03-26 | 2005-03-24 | Labeling reagents, methods for the synthesis of such reagents and methods for the detection of biological molecules |
| AU2005225589A AU2005225589A1 (en) | 2004-03-26 | 2005-03-24 | Labelling reagents, methods for the synthesis of such reagents and methods for the detection of biological molecules |
| JP2007504455A JP4745331B2 (ja) | 2004-03-26 | 2005-03-24 | 標識用試薬、その試薬の合成方法、及び、生体分子の検出法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0450600A FR2868071B1 (fr) | 2004-03-26 | 2004-03-26 | Reactifs de marquage, procedes de synthese de tels reactifs et procedes de detection de molecules biologiques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2868071A1 true FR2868071A1 (fr) | 2005-09-30 |
| FR2868071B1 FR2868071B1 (fr) | 2006-06-09 |
Family
ID=34945038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR0450600A Expired - Fee Related FR2868071B1 (fr) | 2004-03-26 | 2004-03-26 | Reactifs de marquage, procedes de synthese de tels reactifs et procedes de detection de molecules biologiques |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7691635B2 (fr) |
| EP (1) | EP1727825A1 (fr) |
| JP (1) | JP4745331B2 (fr) |
| CN (1) | CN1938329A (fr) |
| AU (1) | AU2005225589A1 (fr) |
| CA (1) | CA2558357A1 (fr) |
| FR (1) | FR2868071B1 (fr) |
| WO (1) | WO2005092910A1 (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1886141B1 (fr) * | 2005-06-01 | 2011-06-01 | bioMérieux S.A. | Procédé de marquage ou de traitement d'un échantillon biologique contenant des acides nucléiques |
| WO2022191725A1 (fr) * | 2021-03-10 | 2022-09-15 | Uniwersytet Warszawski | Analogues d'arn à base de n-(2-aminoéthyl)morpholine, leur procédé de préparation et leur utilisation |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2868071B1 (fr) | 2004-03-26 | 2006-06-09 | Biomerieux Sa | Reactifs de marquage, procedes de synthese de tels reactifs et procedes de detection de molecules biologiques |
| US8299015B2 (en) * | 2006-07-25 | 2012-10-30 | Lipoxen Technologies Limited | Derivatisation of granulocyte colony-stimulating factor |
| FR2917090B1 (fr) * | 2007-06-11 | 2012-06-15 | Biomerieux Sa | Reactifs de marquage portant des fonctions diazo et nitro, procedes de synthese de tels reactifs et procedes de detection de molecules biologiques |
| FR2934595B1 (fr) * | 2008-07-29 | 2013-04-05 | Biomerieux Sa | Reactifs de marquage ayant un noyau pyridine portant une fonction diazomethyle, procedes de synthese de tels reactifs et procedes de detection de molecules biologiques |
| FR2994184B1 (fr) | 2012-08-02 | 2017-12-08 | Biomerieux Sa | Procedes de fonctionalisation et reactifs utilises dans de tels procedes utilisant un anhydride aza-isatoique ou un de ses derives, molecules biologiques ainsi traitees et kits |
| AU2015240088B2 (en) | 2014-03-31 | 2021-07-22 | Merck Patent Gmbh | Method for detecting protein modifications using specific antibodies |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988004289A1 (fr) * | 1986-12-08 | 1988-06-16 | National Distillers And Chemical Corporation | Sondes d'acides nucleiques non-radioactives |
| WO2002090584A2 (fr) * | 2001-05-04 | 2002-11-14 | Bio Merieux | Procédé de marquage et de fragmentation d'adn |
| WO2002090319A1 (fr) * | 2001-05-04 | 2002-11-14 | Bio Merieux | Reactifs de marquage, procedes de synthese de tels reactifs et procedes de detection de molecules biologiques |
Family Cites Families (50)
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| US4711955A (en) * | 1981-04-17 | 1987-12-08 | Yale University | Modified nucleotides and methods of preparing and using same |
| CA1219824A (fr) | 1981-04-17 | 1987-03-31 | David C. Ward | Nucleotides modifies, leur preparation et leur emploi |
| ATE48140T1 (de) | 1981-04-17 | 1989-12-15 | Univ Yale | Modifizierte nukleotide und verfahren zu ihrer herstellung und anwendung. |
| CA1223831A (fr) | 1982-06-23 | 1987-07-07 | Dean Engelhardt | Nucleotides modifies, methodes de preparation et d'utilisation et composes les contenant |
| US4568737A (en) * | 1983-01-07 | 1986-02-04 | The Dow Chemical Company | Dense star polymers and dendrimers |
| US4507466A (en) * | 1983-01-07 | 1985-03-26 | The Dow Chemical Corporation | Dense star polymers having core, core branches, terminal groups |
| US4672040A (en) * | 1983-05-12 | 1987-06-09 | Advanced Magnetics, Inc. | Magnetic particles for use in separations |
| US4683202A (en) * | 1985-03-28 | 1987-07-28 | Cetus Corporation | Process for amplifying nucleic acid sequences |
| US4683195A (en) * | 1986-01-30 | 1987-07-28 | Cetus Corporation | Process for amplifying, detecting, and/or-cloning nucleic acid sequences |
| US4800159A (en) * | 1986-02-07 | 1989-01-24 | Cetus Corporation | Process for amplifying, detecting, and/or cloning nucleic acid sequences |
| US5750338A (en) * | 1986-10-23 | 1998-05-12 | Amoco Corporation | Target and background capture methods with amplification for affinity assays |
| FR2607507B1 (fr) | 1986-12-02 | 1990-04-13 | Centre Nat Rech Scient | Nouveaux derives a-d-oligonucleotides, leur preparation et leur emploi |
| US5130238A (en) | 1988-06-24 | 1992-07-14 | Cangene Corporation | Enhanced nucleic acid amplification process |
| FR2634023B1 (fr) | 1988-07-08 | 1994-03-25 | Bio Merieux | Reactif sous forme de support solide permettant de fixer par covalence un ligand biologique amine, sa preparation et son utilisation |
| ATE138106T1 (de) | 1988-07-20 | 1996-06-15 | David Segev | Verfahren zur amplifizierung und zum nachweis von nukleinsäuresequenzen |
| CA2005589C (fr) | 1988-12-16 | 2001-02-06 | Akzo Nobel Nv | Systeme de replication de sequences auto-entretenu |
| CA2007431A1 (fr) | 1989-01-10 | 1990-07-10 | Larry W. Mclauglin | Etiquetage d'acides nucleiques au moyen de traceurs fluorescents |
| US5234809A (en) * | 1989-03-23 | 1993-08-10 | Akzo N.V. | Process for isolating nucleic acid |
| DE3910151A1 (de) | 1989-03-29 | 1990-10-04 | Toni Dr Lindl | 5'-bromo-2'-desoxyuridinmarkierte dna- oder rna- sonden |
| CA2020958C (fr) * | 1989-07-11 | 2005-01-11 | Daniel L. Kacian | Methodes d'amplification de sequences d'acide nucleique |
| EP0628051B1 (fr) | 1992-02-12 | 2003-07-02 | Chromagen, Inc. | Utilisation de n-nucleosides fluorescents et de leurs analogues structurels fluorescents |
| FR2688788B1 (fr) | 1992-03-17 | 1994-05-13 | Bio Merieux | Composes hydrosolubles derives d'un homopolymere ou copolymere de l'anhydride maleique, et applications desdits composes au support de molecules biologiques. |
| DE4213703A1 (de) | 1992-04-25 | 1993-10-28 | Merck Patent Gmbh | Fluoreszenzmarkierte Verbindungen, ihre Herstellung und Verwendung |
| FR2690691B1 (fr) | 1992-04-29 | 1999-02-12 | Bio Merieux | Procede d'amplification d'arn necessitant une seule etape de manipulation. |
| FR2710075B1 (fr) * | 1993-09-15 | 1995-10-27 | Bio Merieux | Réactif et procédé pour la détection d'une séquence nucléotidique avec amplification de signal. |
| US5807522A (en) * | 1994-06-17 | 1998-09-15 | The Board Of Trustees Of The Leland Stanford Junior University | Methods for fabricating microarrays of biological samples |
| US6083708A (en) * | 1995-08-11 | 2000-07-04 | Dade Behring Inc. | Polypeptide: dendrimer complexes |
| FR2746413B1 (fr) | 1996-03-19 | 1998-04-24 | Bio Merieux | Detection d'une sequence nucleotidique avec amplification de signal |
| FR2749082B1 (fr) * | 1996-05-24 | 1998-06-26 | Bio Merieux | Particules superparamagnetiques et monodispersees |
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| US6537783B1 (en) * | 1996-08-02 | 2003-03-25 | Bio Merieux | Prefunctionalized nucleotide and process for amplifying a sequence using a prefunctionalized nucleotide |
| CA2276462C (fr) * | 1996-12-31 | 2007-06-12 | High Throughput Genomics, Inc. | Procede et dispositif d'analyse moleculaire multiplexee |
| FR2768743B1 (fr) * | 1997-09-23 | 2001-09-14 | Bio Merieux | Procede de lyse de micro-organisme |
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| FR2777293B1 (fr) | 1998-04-10 | 2000-05-19 | Bio Merieux | Procede d'electro-separation d'un echantillon biologique et dispositif de mise en oeuvre |
| FR2780059B1 (fr) * | 1998-06-17 | 2002-10-11 | Bio Merieux | Procede de marquage d'un acide ribonucleique et fragments d'arn marques ainsi obtenus |
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| JP2000048880A (ja) * | 1998-07-30 | 2000-02-18 | Nippon Amp Kk | カード用コネクタ組立体 |
| FR2781802B1 (fr) | 1998-07-31 | 2001-05-11 | Bio Merieux | Derives satures ou insatures de l'abietane, conjugues derives et utilisations dans une composition diagnostique, un reactif et un dispositif |
| US6235502B1 (en) * | 1998-09-18 | 2001-05-22 | Molecular Staging Inc. | Methods for selectively isolating DNA using rolling circle amplification |
| ATE277065T1 (de) * | 1999-01-05 | 2004-10-15 | Bio Merieux | Funktionalisierte verbindung, gegebenenfalls markierte polynukleotide und verfahren zur detektion einer ziel-nukleinsäure |
| FR2791697B1 (fr) * | 1999-04-01 | 2003-02-28 | Biomerieux Sa | Appareil et procede de lyse par ultrasons de cellules biologiques |
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| US6489114B2 (en) * | 1999-12-17 | 2002-12-03 | Bio Merieux | Process for labeling a ribonucleic acid, and labeled RNA fragments which are obtained thereby |
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| US7338805B2 (en) * | 2001-05-04 | 2008-03-04 | Bio Merieux | Labeling reagents, methods for synthesizing such reagents and methods for detecting biological molecules |
| AU2003279697A1 (en) * | 2002-05-17 | 2004-02-16 | Nugen Technologies, Inc. | Methods for fragmentation, labeling and immobilizaton of nucleic acids |
| FR2868071B1 (fr) | 2004-03-26 | 2006-06-09 | Biomerieux Sa | Reactifs de marquage, procedes de synthese de tels reactifs et procedes de detection de molecules biologiques |
-
2004
- 2004-03-26 FR FR0450600A patent/FR2868071B1/fr not_active Expired - Fee Related
-
2005
- 2005-03-24 CA CA002558357A patent/CA2558357A1/fr not_active Abandoned
- 2005-03-24 US US10/590,973 patent/US7691635B2/en not_active Expired - Fee Related
- 2005-03-24 EP EP05739660A patent/EP1727825A1/fr not_active Withdrawn
- 2005-03-24 WO PCT/FR2005/050192 patent/WO2005092910A1/fr not_active Ceased
- 2005-03-24 AU AU2005225589A patent/AU2005225589A1/en not_active Abandoned
- 2005-03-24 CN CNA2005800097858A patent/CN1938329A/zh active Pending
- 2005-03-24 JP JP2007504455A patent/JP4745331B2/ja not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988004289A1 (fr) * | 1986-12-08 | 1988-06-16 | National Distillers And Chemical Corporation | Sondes d'acides nucleiques non-radioactives |
| WO2002090584A2 (fr) * | 2001-05-04 | 2002-11-14 | Bio Merieux | Procédé de marquage et de fragmentation d'adn |
| WO2002090319A1 (fr) * | 2001-05-04 | 2002-11-14 | Bio Merieux | Reactifs de marquage, procedes de synthese de tels reactifs et procedes de detection de molecules biologiques |
Non-Patent Citations (5)
| Title |
|---|
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| LANGER P R ET AL: "ENZYMATIC SYNTHESIS OF BIOTIN-LABELED POLYNUCLEOTIDES: NOVEL NUCLEID ACID AFFINITY PROBES", PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES, NATIONAL ACADEMY OF SCIENCE, WASHINGTON, DC, US, vol. 78, no. 11, November 1981 (1981-11-01), pages 6633 - 6637, XP000892770, ISSN: 0027-8424 * |
| SHIGA M ET AL: "FLUORESCENCE DETECTION OF DNA USING A NOVEL PEROXIDASE SUBSTRATE, 4-(4-HYDROXYPHENYLCARBAMOYL)BUTANOIC ACID", ANALYTICAL SCIENCES, JAPAN SOCIETY FOR ANALYTICAL CHEMISTRY, TOKYO,, JP, vol. 11, no. 4, August 1995 (1995-08-01), pages 591 - 595, XP008005960, ISSN: 0910-6340 * |
| SHIGA M ET AL: "SYNTHESIS OF A NOVEL BIOTIN DERIVATIVE THAT BEARS A DIAZO GROUP AS THE REACTIVE SITE", ANALYTICAL SCIENCES, JAPAN SOCIETY FOR ANALYTICAL CHEMISTRY, TOKYO,, JP, vol. 9, no. 4, August 1993 (1993-08-01), pages 553 - 556, XP008005959, ISSN: 0910-6340 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1886141B1 (fr) * | 2005-06-01 | 2011-06-01 | bioMérieux S.A. | Procédé de marquage ou de traitement d'un échantillon biologique contenant des acides nucléiques |
| US8637322B2 (en) | 2005-06-01 | 2014-01-28 | Biomerieux | Method for labeling or treating a biological sample containing biological molecules of interest, in particular nucleic acids |
| WO2022191725A1 (fr) * | 2021-03-10 | 2022-09-15 | Uniwersytet Warszawski | Analogues d'arn à base de n-(2-aminoéthyl)morpholine, leur procédé de préparation et leur utilisation |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1938329A (zh) | 2007-03-28 |
| JP2007530024A (ja) | 2007-11-01 |
| US20080032288A1 (en) | 2008-02-07 |
| EP1727825A1 (fr) | 2006-12-06 |
| FR2868071B1 (fr) | 2006-06-09 |
| AU2005225589A1 (en) | 2005-10-06 |
| CA2558357A1 (fr) | 2005-10-06 |
| JP4745331B2 (ja) | 2011-08-10 |
| WO2005092910A1 (fr) | 2005-10-06 |
| US7691635B2 (en) | 2010-04-06 |
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