CN103804370A - Fluorescent dye compound and preparation method and application thereof - Google Patents
Fluorescent dye compound and preparation method and application thereof Download PDFInfo
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- CN103804370A CN103804370A CN201410045536.5A CN201410045536A CN103804370A CN 103804370 A CN103804370 A CN 103804370A CN 201410045536 A CN201410045536 A CN 201410045536A CN 103804370 A CN103804370 A CN 103804370A
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- 0 C*(C)N(C1C2=CC=CC1)C=CC2=CC Chemical compound C*(C)N(C1C2=CC=CC1)C=CC2=CC 0.000 description 1
- DXYYSGDWQCSKKO-UHFFFAOYSA-N Cc1nc(cccc2)c2[s]1 Chemical compound Cc1nc(cccc2)c2[s]1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
Abstract
The invention discloses a fluorescent dye compound, the structural formula of which is shown as the formula I described in the specification, wherein X is C(CH3)2, S or O; n is 3 or 4; m is 2 or 3. The invention further discloses a method of preparing the fluorescent dye compound. The invention further discloses an application of the fluorescent dye compound. Aiming at the deficiencies in the prior art, by improvement on the basis, the invention provides novel compounds which are simple in structure, high in sensitivity and long in wavelength and have good membrane permeability. The fluorescent dye compound disclosed by the invention mainly reflects very good water solubility, and is simple in structure, easy to get raw materials and low in toxicity. A target molecule can be synthesized by 4-5 steps ordinarily, so that the fluorescent dye compound is easy to industrialize.
Description
Technical field
The invention belongs to fine chemical technology field, be specifically related to a kind of fluorescent dye compound and its preparation method and application.Be mainly preparation and the application of nitrogenous cyanine fluorochrome and utilize this fluorescence dye or the application of its composition aspect biological stain.
Background technology
Fluorescence dye is used widely in every field of science and technology as functional pigmented, especially in life science, and clinical medicine diagnosis, the research of the aspects such as cotton dress analyzing and testing attracts attention greatly in the whole world.At present, the commercialization fluorescence dye such as phenanthridines class (EP, PI), acridine (AO), imidazoles (Hoechst, DAPI) and Jing Jia same clan (Cy, TOTO, SYTO) all plays an important role in the fields such as genomics technology, nucleic acid quantification detection, blood cell analysis.But these dyestuffs all exist the limitation of application separately.One shows as most fluorescence dye and is limited to fixed cell sample.Such as TOPRO, TOTO family dyestuff, ethidium bromide (EB), propidium iodide (PI) etc. need to could carry out effective fluorescent mark to biological sample by the permeability or the similar method that makes film disintegration that increase cytolemma.But this fixing means often has negative impact (Kozubek S, Lukasova E, Amrichova J, Kozubek M, Liskova A, Slotva J.Anal Biochem2000 to the observation of nucleus biological tissue true form; 282:2938).The acridines such as while ethidium bromide, phenanthridines class dyestuff has very large toxicity and carinogenicity.They are two years old, there is the exciting light of quite a few fluorescence dye to be in ultraviolet region, if the fluorescence dye 4 of single-minded identification thymus nucleic acid (DNA), 6-diamino-2-phenylindone quinoline compound (DAPI), Hoechst33258, Hoechst34580 etc., after being combined with DNA, under burst of ultraviolel radiation, produce blue-fluorescence.Because UV-light is to intracellular nucleic acid, the components such as albumen can cause serious damage, and therefore this class fluorescence use in fluorescence microscopy is subject to optical excitation time limitation (Davis SK, Bardeen CJ.Photochem Photobiol2003; 77:675-679), in addition, while carrying out fluoroscopic examination in ultraviolet region, biological sample makes light enter biological tissue inside in the absorption in this interval and becomes difficulty, and in biological sample, the autofluorescence of some composition forms very strong background interference simultaneously, and detection efficiency is reduced greatly, therefore, research and develop and have good fluorescence spectrum property, toxicity is little, and the novel fluorescence dyestuff of viable cell permeability remains the key and the core that promote fluorescence analysis and life science development.
In the fluorescence dye of numerous kinds, cyanine fluorochrome is wide with its wavelength region, the advantages such as molar extinction coefficient is large, and fluorescence quantum yield is moderate, are widely used as biomolecules fluorescent probe, CD and VCD recording materials, sensitive materials photosensitizers, photoelectric conversion material etc.Wherein quinoline asymmetric cyanine fluorochrome and nucleic acid have high affinity, and with the substantially uncombined specificity of other biological macromole, it are shown one's talent in the application in the fields such as genomics technology, nucleic acid quantification detection, blood cell analysis.The combination of this compounds and nucleic acid comprises that electrostatic attraction, base pair embed and groove contact.Concrete combination and binding ability depend on the structure of this marker and the ratio with nucleic acid concentration thereof.Most typical in asymmetric cyanine compounds is TOTO and analogue YOYO and derivative TOPRPO.TOTO(thiazole orange dimer), the yellow dimer of YOYO(oxazole) be the class developed by Glazer study group the has high affinity asymmetric cyanine type dye of many positive charges to nucleic acid, can obtain the derivative of different heterodimer analogues by changing the structure of the length of many subunits chain and the fragrant parent nucleus at two ends (thiazole, oxazole, quinoline, pyridine and indoline).This class dyestuff almost without fluorescence, has reduced the fluorescence background in testing process and has disturbed in solution, and the rear fluorescence of being combined with nucleic acid strengthens.The use determination of solution viscosity methods such as Jason and atomic force microscope have been explained the dual damascene effect (J.A.Bordelon, K.J.Feierabend, S.A.Siddiqui, L.Wright.J.Phys.Chem.B.2002,106,4838-3843) of TOTO and YOYO and DNA.Furstenberg etc. utilize supper-fast fluorescence conversion and Single Photon Counting method further to state the kinetics mechanism that fluorescence strengthens.[A.Furstenberg, M.D.Julliard, T.G.Deligeorgiec, N.I.Gadjev.J.AM.CHEM.SOC., 2006,128,7661-7669] commercialization of some kind in this type of dyestuff, as: SYTOXBlue, TOTO, POPO, BOBO, YO-PRO etc., but the most of molecule of these commercial dyestuffs is larger, complex structure, belongs to the non-permeability of viable cell, can only be applied in vitro identification and the detection of nucleic acid.
Summary of the invention
Goal of the invention: the problem and shortage existing for above-mentioned existing scheme, first object of the present invention has been to provide a kind of fluorescent dye compound.Second object of the present invention is to provide the preparation method of above-mentioned fluorescent dye compound.The 3rd object of the present invention has been to provide the application of above-mentioned fluorescent dye compound.
Technical scheme: for achieving the above object, technical scheme of the present invention is as follows: a kind of fluorescent dye compound, its structural formula is following general structure I:
In formula, X is S; N is 3 or 4; M is 2 or 3.
Above-mentioned fluorescent dye compound, described compound is selected from:
In the time that X is O and C (CH3) 2, fluorescent chemicals structural formula is respectively:
Wherein, the method for above-mentioned fluorescent dye compound, comprises the following steps:
1) formula II compound benzothiazole heteroaromatic compound and propane sultone or butyl sultone reaction are made to the ammonium salt intermediate III first season;
2) by the first season ammonium salt intermediate III and N, N, the condensation of-diphenyl methylether, obtains formula IV compound;
3) IV compound is reacted and obtains formula VI compound with formula V compound:
Wherein, above-mentioned steps 1) temperature of reaction be 10-200 ℃, reaction times is 1-48 hour, and reaction solvent is selected from: methylene dichloride, chloroform, ethanol, acetonitrile, ethyl acetate, toluene, dimethylbenzene, the molar ratio of formula II compound and propane sultone or butyl sultone is 1:1-1:5.
Wherein, above-mentioned steps 2) temperature of reaction be 10-200 ℃, the reaction times is 1-48 hour, reaction solvent is aceticanhydride, acetic acid is bronsted acid catalyst, the first season, the mol ratio of ammonium salt intermediate III and diphenyl methylether was 3:1-1:3.
Wherein, above-mentioned steps 3) temperature of reaction is 10-200 ℃, the reaction times is 1-48 hour, reaction solvent is aceticanhydride, and acetic acid is bronsted acid catalyst, or reaction solvent is ethanol, triethylamine is alkaline catalysts, and the mol ratio of formula IV compound and formula V compound is 3:1-1:3.
The application of above-mentioned fluorescent dye compound aspect preparation and the biological stain of nitrogenous cyanine fluorochrome.
Beneficial effect: compared with prior art, fluorescent dye compound of the present invention has lower fluorescence background in the time not there is not nucleic acid, after being combined with nucleic acid, there is higher fluorescent quantum output capacity, and the biomolecules beyond nucleic acid is had good water-soluble without avidity, there is good permeability of cell membrane simultaneously; The spectral range of spectral range and biological sample has larger difference.The present invention is directed to the deficiencies in the prior art, on basis, improve, provide a class formation simple, highly sensitive, long wavelength, and there is the new compound of good permeability of cell membrane.Fluorescent dye compound major embodiment of the present invention is extraordinary water-soluble in having, and simple in structure, and raw material is easy to get, and toxicity is little, generally can synthesize target molecule, easily industrialization by 4 to 5 step reactions.
Embodiment
Can explain in more detail the present invention by the following examples, disclose object of the present invention and be intended to protect all changes and improvements in the scope of the invention, the present invention is not limited to the following examples.
Embodiment 1:
1) formula II compound benzothiazole heteroaromatic compound and propane sultone reaction are made to the ammonium salt intermediate III(n=3 first season); Temperature of reaction is 150 ℃, and the reaction times is 20 hours, and reaction solvent is selected from: methylene dichloride, chloroform, and the molar ratio of formula II compound and propane sultone or butyl sultone is 1:1;
2) by the first season ammonium salt intermediate III and N, N, the condensation of-diphenyl methylether, obtains formula IV compound; Temperature of reaction is 150 ℃, and the reaction times is 24 hours, and reaction solvent is aceticanhydride, and acetic acid is bronsted acid catalyst, and the first season, the mol ratio of ammonium salt and diphenyl methylether was 1:3;
3) IV compound is reacted and obtains formula VI compound with formula V compound (m=2): temperature of reaction is 150 ℃, reaction times is 24 hours, reaction solvent is aceticanhydride, acetic acid is bronsted acid catalyst, or reaction solvent is ethanol, triethylamine is alkaline catalysts, and the mol ratio of IV compound and V compound is 1:1.
Embodiment 2:
1) formula II compound benzothiazole heteroaromatic compound and butyl sultone reaction are made to the ammonium salt intermediate III(n=4 first season); Temperature of reaction is 200 ℃, and the reaction times is 10 hours, and reaction solvent is selected from: ethanol, acetonitrile, and the molar ratio of formula II compound and propane sultone or butyl sultone is 1:3;
2) by the first season ammonium salt intermediate III and N, N, the condensation of-diphenyl methylether, obtains formula IV compound; Temperature of reaction is 50 ℃, and the reaction times is 20 hours, and reaction solvent is aceticanhydride, and acetic acid is bronsted acid catalyst, and the first season, the mol ratio of ammonium salt and diphenyl methylether was 1:2;
3) by IV compound and formula V(m=2) compound reacts and obtains formula VI compound: temperature of reaction is 10 ℃, reaction times is 48 hours, reaction solvent is aceticanhydride, acetic acid is bronsted acid catalyst, or reaction solvent is ethanol, triethylamine is alkaline catalysts, and the mol ratio of IV compound and V compound is 1:3.
Embodiment 3
1) formula II compound benzothiazole heteroaromatic compound and propane sultone reaction are made to the ammonium salt intermediate III(n=3 first season); Temperature of reaction is 10 ℃, and the reaction times is 48 hours, and reaction solvent is selected from: ethyl acetate, toluene, and the molar ratio of formula II compound and propane sultone or butyl sultone is 1:5;
2) by the first season ammonium salt intermediate III and N, N, the condensation of-diphenyl methylether, obtains formula IV compound; Temperature of reaction is 100 ℃, and the reaction times is 10 hours, and reaction solvent is aceticanhydride, and acetic acid is bronsted acid catalyst, and the first season, the mol ratio of ammonium salt and diphenyl methylether was 1:1;
3) by IV compound and formula V(m=3) compound reacts and obtains formula VI compound: temperature of reaction is 85 ℃, reaction times is 24 hours, reaction solvent is aceticanhydride, acetic acid is bronsted acid catalyst, or reaction solvent is ethanol, triethylamine is alkaline catalysts, and the mol ratio of IV compound and V compound is 1:1.
Embodiment 4
1) formula II compound benzothiazole heteroaromatic compound and butyl sultone reaction are made to the ammonium salt intermediate III(n=4 first season); Temperature of reaction is 50 ℃, and the reaction times is 30 hours, and reaction solvent is selected from: ethyl acetate, toluene, dimethylbenzene, and the molar ratio of formula II compound and propane sultone or butyl sultone is 1:4;
2) by the first season ammonium salt intermediate III and N, N, the condensation of-diphenyl methylether, obtains formula IV compound; Temperature of reaction is 10 ℃, and the reaction times is 48 hours, and reaction solvent is aceticanhydride, and acetic acid is bronsted acid catalyst, and the first season, the mol ratio of ammonium salt and diphenyl methylether was 3:1;
3) by IV compound and formula V(m=3) compound reacts and obtains formula VI compound: temperature of reaction is 85 ℃, reaction times is 24 hours, reaction solvent is aceticanhydride, acetic acid is bronsted acid catalyst, or reaction solvent is ethanol, triethylamine is alkaline catalysts, and the mol ratio of IV compound and V compound is 3:1.
Embodiment 5
In the time that X is O, preparation method is identical with the condition of embodiment 1.
Embodiment 6
In the time that X is C (CH3) 2, preparation method is identical with the condition of embodiment 2.
Above content is the further description of the present invention being done in conjunction with concrete preferred implementation, can not assert that specific embodiment of the invention is confined to these explanations.
Claims (7)
1. a fluorescent dye compound, its structural formula is following general structure I:
In formula, X is C (CH
3)
2, S or O; N is 3 or 4; M is 2 or 3.
2. fluorescent dye compound according to claim 1, is characterized in that: described compound is selected from:
3. a preparation method for the fluorescent dye compound described in claim 1 or 2 any one, is characterized in that, comprises the following steps:
1) formula II compound benzothiazole heteroaromatic compound and propane sultone or butyl sultone reaction are made to the ammonium salt intermediate III first season;
2), by the first season ammonium salt intermediate III and N, the condensation of N-diphenyl methylether, obtains formula IV compound;
3) formula IV compound is reacted and obtains formula VI compound with formula V compound;
Each structural formula of compound is as follows:
4. the preparation method of fluorescent dye compound according to claim 3, it is characterized in that, the temperature of reaction of described step 1) is 10-200 ℃, reaction times is 1-48 hour, reaction solvent is selected from: methylene dichloride, chloroform, ethanol, acetonitrile, ethyl acetate, toluene, dimethylbenzene, the mol ratio of formula II compound and propane sultone or butyl sultone is 1:1-1:5.
5. the preparation method of fluorescent dye compound according to claim 3, it is characterized in that, described step 2) temperature of reaction be 10-200 ℃, reaction times is 1-48 hour, reaction solvent is aceticanhydride, acetic acid is bronsted acid catalyst, the first season ammonium salt intermediate III and N, the mol ratio of N-diphenyl methylether is 3:1-1:3.
6. the preparation method of fluorescent dye compound according to claim 3, it is characterized in that, described step 3) temperature of reaction is 10-200 ℃, reaction times is 1-48 hour, reaction solvent is aceticanhydride, and acetic acid is bronsted acid catalyst, or reaction solvent is ethanol, triethylamine is alkaline catalysts, and the mol ratio of formula IV compound and formula V compound is 3:1-1:3.
7. the application of the fluorescent dye compound described in claim 1 or 2 any one aspect preparation and the biological stain of nitrogenous cyanine fluorochrome.
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| CN201410045536.5A CN103804370A (en) | 2014-02-08 | 2014-02-08 | Fluorescent dye compound and preparation method and application thereof |
| CN201510031821.6A CN104610773A (en) | 2014-02-08 | 2015-01-21 | Fluorochrome compound as well as preparation method and application thereof |
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| WO2022100717A1 (en) * | 2020-11-13 | 2022-05-19 | 大连理工大学 | Leukocyte classification reagent, erythrocyte analysis reagent, kits, and analysis method |
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| US4108668A (en) * | 1973-09-13 | 1978-08-22 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide photographic materials |
| JPS53294B2 (en) * | 1973-09-13 | 1978-01-07 | ||
| JP3430386B2 (en) * | 1996-08-19 | 2003-07-28 | コニカ株式会社 | Silver halide photographic materials |
| EP1325084A2 (en) * | 1998-12-05 | 2003-07-09 | Otto Samuel Wolfbeis | Pyridine dyes and quinoline dyes used as markers for biomolecules, polymers, medicaments, and particles |
| JP2003501540A (en) * | 1999-06-09 | 2003-01-14 | カーネギー メロン ユニヴァーシティ | PH-functional cyanine dyes as reactive fluorescent reagents |
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| WO2022100717A1 (en) * | 2020-11-13 | 2022-05-19 | 大连理工大学 | Leukocyte classification reagent, erythrocyte analysis reagent, kits, and analysis method |
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Application publication date: 20140521 |