FR2480943A1 - Procede de marquage fluorescent d'acides nucleiques - Google Patents
Procede de marquage fluorescent d'acides nucleiques Download PDFInfo
- Publication number
- FR2480943A1 FR2480943A1 FR8107928A FR8107928A FR2480943A1 FR 2480943 A1 FR2480943 A1 FR 2480943A1 FR 8107928 A FR8107928 A FR 8107928A FR 8107928 A FR8107928 A FR 8107928A FR 2480943 A1 FR2480943 A1 FR 2480943A1
- Authority
- FR
- France
- Prior art keywords
- iodide
- dye
- pyridine
- nucleic acids
- dimethylaminopropyl
- 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
- 238000000034 method Methods 0.000 title abstract description 13
- 108020004707 nucleic acids Proteins 0.000 title abstract description 10
- 150000007523 nucleic acids Chemical class 0.000 title abstract description 10
- 102000039446 nucleic acids Human genes 0.000 title abstract description 10
- -1 AMINO Chemical class 0.000 abstract description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 12
- 239000007850 fluorescent dye Substances 0.000 abstract description 11
- 239000012472 biological sample Substances 0.000 abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 6
- 239000001257 hydrogen Substances 0.000 abstract description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract description 5
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical compound C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 abstract description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001450 anions Chemical class 0.000 abstract description 3
- XNMYNYSCEJBRPZ-UHFFFAOYSA-N 2-[(3-butyl-1-isoquinolinyl)oxy]-N,N-dimethylethanamine Chemical compound C1=CC=C2C(OCCN(C)C)=NC(CCCC)=CC2=C1 XNMYNYSCEJBRPZ-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 229960005038 quinisocaine Drugs 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 36
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 16
- 108020004414 DNA Proteins 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000005284 excitation Effects 0.000 description 6
- 238000002372 labelling Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 210000001995 reticulocyte Anatomy 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 210000003743 erythrocyte Anatomy 0.000 description 3
- 238000000799 fluorescence microscopy Methods 0.000 description 3
- 210000000265 leukocyte Anatomy 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 210000004940 nucleus Anatomy 0.000 description 3
- 210000005259 peripheral blood Anatomy 0.000 description 3
- 239000011886 peripheral blood Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- HPSNLHKGJXFORD-UHFFFAOYSA-O 1-(2-phenylethenyl)quinolin-1-ium-2-amine Chemical compound NC1=CC=C2C=CC=CC2=[N+]1C=CC1=CC=CC=C1 HPSNLHKGJXFORD-UHFFFAOYSA-O 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 240000006240 Linum usitatissimum Species 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- DPKHZNPWBDQZCN-UHFFFAOYSA-N acridine orange free base Chemical compound C1=CC(N(C)C)=CC2=NC3=CC(N(C)C)=CC=C3C=C21 DPKHZNPWBDQZCN-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 210000003651 basophil Anatomy 0.000 description 2
- KXNQKOAQSGJCQU-UHFFFAOYSA-N benzo[e][1,3]benzothiazole Chemical compound C1=CC=C2C(N=CS3)=C3C=CC2=C1 KXNQKOAQSGJCQU-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 244000309466 calf Species 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 210000000805 cytoplasm Anatomy 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 238000001215 fluorescent labelling Methods 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 210000003000 inclusion body Anatomy 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 210000003660 reticulum Anatomy 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 210000001541 thymus gland Anatomy 0.000 description 2
- GJFCHWRCUVADJI-UHFFFAOYSA-N 2-(2-phenylethenyl)-1,3-benzothiazol-3-ium-3-amine Chemical compound S1C2=CC=CC=C2[N+](N)=C1C=CC1=CC=CC=C1 GJFCHWRCUVADJI-UHFFFAOYSA-N 0.000 description 1
- FWBHETKCLVMNFS-UHFFFAOYSA-N 4',6-Diamino-2-phenylindol Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC2=CC=C(C(N)=N)C=C2N1 FWBHETKCLVMNFS-UHFFFAOYSA-N 0.000 description 1
- 230000004568 DNA-binding Effects 0.000 description 1
- 108010034791 Heterochromatin Proteins 0.000 description 1
- 108020005196 Mitochondrial DNA Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 108091093105 Nuclear DNA Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000013614 RNA sample Substances 0.000 description 1
- 108091081062 Repeated sequence (DNA) Proteins 0.000 description 1
- 102000006382 Ribonucleases Human genes 0.000 description 1
- 108010083644 Ribonucleases Proteins 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 101100355633 Salmo salar ran gene Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 210000000349 chromosome Anatomy 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000000120 cytopathologic effect Effects 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 210000002472 endoplasmic reticulum Anatomy 0.000 description 1
- 210000003617 erythrocyte membrane Anatomy 0.000 description 1
- 238000000695 excitation spectrum Methods 0.000 description 1
- 238000005558 fluorometry Methods 0.000 description 1
- 210000004458 heterochromatin Anatomy 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 229950003937 tolonium Drugs 0.000 description 1
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
- G01N33/5094—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for blood cell populations
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Urology & Nephrology (AREA)
- Chemical & Material Sciences (AREA)
- Cell Biology (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Hematology (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Ecology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Analytical Chemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Pathology (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14232180A | 1980-04-21 | 1980-04-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2480943A1 true FR2480943A1 (fr) | 1981-10-23 |
| FR2480943B1 FR2480943B1 (enExample) | 1984-03-16 |
Family
ID=22499396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8107928A Granted FR2480943A1 (fr) | 1980-04-21 | 1981-04-21 | Procede de marquage fluorescent d'acides nucleiques |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS56158944A (enExample) |
| BE (1) | BE888509A (enExample) |
| CA (1) | CA1155041A (enExample) |
| DE (1) | DE3115278C2 (enExample) |
| FR (1) | FR2480943A1 (enExample) |
| GB (1) | GB2074340B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4500509A (en) * | 1981-03-11 | 1985-02-19 | Lawrence Kass | Metachromatic dye sorption and fluorescent light emmisive means for differential determination of developmental stages of neutrophilic granulocytic cells and other leukocytes |
| US4840784A (en) * | 1982-12-22 | 1989-06-20 | Eastman Kodak Company | Use of pyrylium and thiapyrylium compounds as biological stains |
| US4555396A (en) * | 1982-12-22 | 1985-11-26 | Eastman Kodak Company | Use of pyrylium and thiapyrylium compounds as biological stains |
| NZ207393A (en) * | 1983-08-05 | 1987-03-31 | Neal Lloyd First | Staining dna in living cells |
| JPS61280565A (ja) * | 1985-06-06 | 1986-12-11 | Toa Medical Electronics Co Ltd | フロ−サイトメトリ−用網状血球測定試薬 |
| JPH076979B2 (ja) * | 1986-09-10 | 1995-01-30 | 東亜医用電子株式会社 | フロ−サイトメトリ−による白血球分類に使用される試薬 |
| EP0613003B1 (en) * | 1993-02-22 | 2000-04-26 | Sysmex Corporation | A reagent for detecting malaria infected cells and a detecting method for malaria infected cells using the same |
| US5534416A (en) * | 1993-04-13 | 1996-07-09 | Molecular Probes, Inc. | Fluorescent viability assay using cyclic-substituted unsymmetrical cyanine dyes |
| US5445946A (en) * | 1993-04-13 | 1995-08-29 | Molecular Probes, Inc. | Intravacuolar stains for yeast and other fungi |
| US5545535A (en) * | 1993-04-13 | 1996-08-13 | Molecular Probes, Inc. | Fluorescent assay for bacterial gram reaction |
| US5436134A (en) * | 1993-04-13 | 1995-07-25 | Molecular Probes, Inc. | Cyclic-substituted unsymmetrical cyanine dyes |
| US5571727A (en) * | 1993-10-07 | 1996-11-05 | Matsushita Electric Industrial Co., Ltd. | Labelling colors for detecting cocaine or methamphetamine, method of preparing the same and detector for cocaine or methamphetamine |
| CN1036612C (zh) * | 1994-03-08 | 1997-12-03 | 中国人民解放军第304医院 | 透射电子显微镜生物样品超薄切片染色液 |
| CA2148140C (en) * | 1994-04-29 | 2010-08-10 | John W. Sutherland | Homogeneous method for assay of double-stranded nucleic acids using fluorescent dyes and kit useful therein |
| ES2156927T3 (es) * | 1994-10-20 | 2001-08-01 | Sysmex Corp | Reactivo y metodo para analizar componentes solidos en orina. |
| US7776529B2 (en) | 2003-12-05 | 2010-08-17 | Life Technologies Corporation | Methine-substituted cyanine dye compounds |
| US7598390B2 (en) | 2005-05-11 | 2009-10-06 | Life Technologies Corporation | Fluorescent chemical compounds having high selectivity for double stranded DNA, and methods for their use |
| US7781187B2 (en) * | 2005-12-30 | 2010-08-24 | Corning Incorporated | Fluorescent dyes |
| JP2013040136A (ja) * | 2011-08-17 | 2013-02-28 | Tosoh Corp | ４−アルコキシ−２−（４−アミノスチリル）ベンゾチアゾリウム塩、その製造方法およびそれを用いる核酸の検出方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2230993A1 (enExample) * | 1973-05-24 | 1974-12-20 | Gen Electric | |
| FR2307271A1 (fr) * | 1975-04-11 | 1976-11-05 | Boehringer Mannheim Gmbh | Porte-objet precolore pour l'examen du sang |
-
1981
- 1981-02-19 CA CA000371297A patent/CA1155041A/en not_active Expired
- 1981-02-20 GB GB8105360A patent/GB2074340B/en not_active Expired
- 1981-04-13 JP JP5446381A patent/JPS56158944A/ja active Granted
- 1981-04-15 DE DE19813115278 patent/DE3115278C2/de not_active Expired
- 1981-04-21 FR FR8107928A patent/FR2480943A1/fr active Granted
- 1981-04-21 BE BE0/204563A patent/BE888509A/fr not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2230993A1 (enExample) * | 1973-05-24 | 1974-12-20 | Gen Electric | |
| FR2307271A1 (fr) * | 1975-04-11 | 1976-11-05 | Boehringer Mannheim Gmbh | Porte-objet precolore pour l'examen du sang |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2480943B1 (enExample) | 1984-03-16 |
| DE3115278C2 (de) | 1983-08-18 |
| DE3115278A1 (de) | 1982-03-18 |
| CA1155041A (en) | 1983-10-11 |
| JPS56158944A (en) | 1981-12-08 |
| GB2074340B (en) | 1984-02-15 |
| JPS6361622B2 (enExample) | 1988-11-29 |
| GB2074340A (en) | 1981-10-28 |
| BE888509A (fr) | 1981-10-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2480943A1 (fr) | Procede de marquage fluorescent d'acides nucleiques | |
| Sherr et al. | Staining of heterotrophic protists for visualization via epifluorescence microscopy | |
| Determann et al. | Ultraviolet fluorescence excitation and emission spectroscopy of marine algae and bacteria | |
| JP4831914B2 (ja) | 未成熟赤血球細胞における核酸の検出用色素及び方法 | |
| Cesarone et al. | Improved microfluorometric DNA determination in biological material using 33258 Hoechst | |
| Tsien et al. | Fluorophores for confocal microscopy: photophysics and photochemistry | |
| US4544546A (en) | Fluorescent nucleic acid stains | |
| US6194213B1 (en) | Lipophilic, functionalized nanocrystals and their use for fluorescence labeling of membranes | |
| EP0603783B1 (en) | Fluorescent stain containing pyrylium salt or its similar salt, detection method of nucleic acid by use of it | |
| US5437980A (en) | Phenanthridium dye staining of nucleic acids in living cells | |
| FI72611C (fi) | Blandning som laempar sig foer testning av biologiska vaevnader och/eller vaetskor och foerfarande foer anvaendning av denna blandning. | |
| Lee et al. | Picogram per cell determination of DNA by flow cytofluorometry | |
| WO2016165487A1 (en) | Real-time monitoring mitophagy process by fluorescent photostable mitochondrial specific bioprobe with aie characteristics | |
| CA1205365A (en) | Metachromatic dye sorption and fluorescent light emissive means for determination of developmental stages of neutrophilic granulocytic cells and other leukocytes | |
| US6271035B1 (en) | Methods and compositions for rapid staining of nucleic acids in whole cells | |
| JP2006501317A (ja) | 海洋無脊椎動物から得られた天然蛍光色素、前記色素を含有する組成物及びそれらの使用 | |
| DE68912462T2 (de) | Xanthenfarbstoffe. | |
| Berglund et al. | A rapid analytical technique for flow cytometric analysis of cell viability using calcofluor white M2R | |
| CA2273959C (en) | Helium-neon excitable reticulocyte dyes derivable from halolepidines | |
| Shapiro et al. | Flow cytometry of DNA content using oxazine 750 or related laser dyes with 633 nm excitation | |
| WO2022027174A1 (zh) | 一种细胞核荧光染料及其染色方法 | |
| Yentsch et al. | Strategies for flow cytometric analysis of marine microalgae and sponge cells | |
| JP2807775B2 (ja) | 藻類のシストの定量方法 | |
| Klonis et al. | Characterization of a series of far red absorbing perylene diones: a new class of fluorescent probes for biological applications | |
| EP1509508A1 (en) | Selective chromophores |