CN104610773A - Fluorochrome compound as well as preparation method and application thereof - Google Patents
Fluorochrome compound as well as preparation method and application thereof Download PDFInfo
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- CN104610773A CN104610773A CN201510031821.6A CN201510031821A CN104610773A CN 104610773 A CN104610773 A CN 104610773A CN 201510031821 A CN201510031821 A CN 201510031821A CN 104610773 A CN104610773 A CN 104610773A
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- LLNJHIATPXUOII-SKOGUXMJSA-N C/C=C\C(\C1=CC=CCC1)=C/C=C/c([o]c1ccccc11)c1SC Chemical compound C/C=C\C(\C1=CC=CCC1)=C/C=C/c([o]c1ccccc11)c1SC LLNJHIATPXUOII-SKOGUXMJSA-N 0.000 description 1
- 0 CC(C)C1c(cccc2)c2*(*)=C1C=CC=C1C2=CC=CCC2*(*=C)C=C1 Chemical compound CC(C)C1c(cccc2)c2*(*)=C1C=CC=C1C2=CC=CCC2*(*=C)C=C1 0.000 description 1
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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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- 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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- 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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- 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
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention discloses a fluorochrome compound. The structural formula of the fluorochrome compound is shown in the structural general formula I (refer to the Specification), wherein in the general formula I, X is C(CH3)2, S or O, n is 3 or 4, and m is 2 or 3. The invention further discloses a preparation method of the fluorochrome compound. The invention also discloses application of the fluorochrome compound. Aiming at the defects in the prior art, improvement is performed on the base, and a novel compound with simple structure, high sensitivity, long wavelength and good cell membrane permeability is provided; the fluorochrome compound disclosed by the invention mainly has a great water solubility and a simple structure, raw materials are easy to obtain, the toxicity is low, an objective molecule can be synthetized through a reaction in 4 to 5 steps, and the fluorochrome compound is easy to industrialize.
Description
Technical field
The invention belongs to technical field of fine, be specifically related to a kind of fluorescent dye compound and its preparation method and application.The Synthesis and applications of mainly nitrogenous cyanine fluorochrome and utilize this fluorescence dye or the application of its composition in biological stain.
Background technology
Fluorescence dye is used widely in every field of science and technology as functional pigmented, and especially in life science, clinical medicine is diagnosed, and the research of the aspects such as cotton dress analyzing and testing attracts attention greatly in the whole world.At present, the commercial fluorescence dyestuff 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 technologies, nucleic acid quantification detection, blood cell analysis.But these dyestuffs also exist the limitation of application all 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 carry out effective fluorescent mark to biological sample by increase membrane passage or the similar method of film disintegration that makes.But this fixing means often organizes the observation of true form to have negative impact (Kozubek S, Lukasova E, Amrichova J, Kozubek M, LiskovaA, Slotva J.Anal Biochem 2000 to nuclear; 282:2938).The simultaneously acridine such as ethidium bromide, phenanthridines class dyestuff has very large toxicity and carinogenicity.They are two years old, the exciting light of quite a few fluorescence dye is had 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 the use of this kind of fluorescence in fluorescence microscopy is subject to optical excitation time limitation (Davis SK, BardeenCJ.Photochem Photobiol 2003; 77:675-679), in addition, when 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 core that promote fluorescence analysis and life science development.
In the fluorescence dye of numerous kinds, cyanine fluorochrome is wide with its wavelength region, molar extinction coefficient is large, and the advantages such as 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 make to show one's talent in the application in the fields such as it detects at genomics technologies, nucleic acid quantification, blood cell analysis with the substantially uncombined specificity of other biological macromole.The combination of this compounds and nucleic acid comprises electrostatic attraction, base pair embeds 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 thereof and derivative TOPRPO.TOTO (thiazole orange dimer), YOYO (oxazole yellow dimer) are the class developed by Glazer study group the has high affinity asymmetric cyanine type dyes of many positive charges to nucleic acid, can be obtained the derivative of different heterodimer analogues by the structure of the fragrant parent nucleus (thiazole, oxazole, quinoline, pyridine and indoline) of the length and two ends that change many subunits chain.This kind of dyestuff almost unstressed configuration in the solution, reduces the fluorescence background interference in testing process, is combined Fluorescence Increasing afterwards with nucleic acid.The determination of solution viscosity method and atomic force microscope such as Jason explain the dual damascene effect (J.A.Bordelon of TOTO and YOYO and DNA, K.J.Feierabend, S.A.Siddiqui, L.Wright.J.Phys.Chem.B.2002,106,4838-3843).Furstenberg etc. utilize supper-fast fluorescence to change and Single Photon Counting method has stated the kinetics mechanism of Fluorescence Increasing further.[A.Furstenberg, M.D.Julliard, T.G.Deligeorgiec, N.I.Gadjev.J.AM.CHEM.SOC., 2006,128,7661-7669] some kind commercialization in this type of dyestuff, as: SYTOXBlue, TOTO, POPO, BOBO, YO-PRO etc., but these commercial dyestuff major part molecules are larger, complex structure, belongs to viable cell non-permeable, can only be applied to identification and the detection of in vitro nucleic acid.
Summary of the invention
Goal of the invention: for above-mentioned existing scheme Problems existing and deficiency, first object of the present invention there is provided a kind of fluorescent dye compound.Second object of the present invention is to provide the preparation method of above-mentioned fluorescent dye compound.3rd object of the present invention there is provided 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, and 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:
When 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) by formula II compound benzothiazole heteroaromatic compound and propane sultone or the butyl sultone reaction ammonium salt intermediate III obtained first season;
2) by ammonium salt intermediate III and the N first season, N, the condensation of-diphenyl methylether, obtains formula IV compound;
3) IV compound and formula V compound are obtained by reacting formula VI compound:
Wherein, above-mentioned steps 1) temperature of reaction be 10-200 DEG C, reaction times is 1-48 hour, reaction solvent is selected from: methylene dichloride, chloroform, ethanol, acetonitrile, ethyl acetate, toluene, dimethylbenzene, and 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 DEG C, the reaction times is 1-48 hour, and reaction solvent is aceticanhydride, and acetic acid is bronsted acid catalyst, the first season ammonium salt intermediate III and the mol ratio of diphenyl methylether be 3:1-1:3.
Wherein, above-mentioned steps 3) temperature of reaction is 10-200 DEG C, 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 in the preparation and biological stain of nitrogenous cyanine fluorochrome.
Beneficial effect: compared with prior art, fluorescent dye compound of the present invention has lower fluorescence background when there is not nucleic acid, higher fluorescent quantum output capacity is had after being combined with nucleic acid, and have good water-soluble without avidity to the biomolecules beyond nucleic acid, 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, basis is improved, provide a class formation simple, highly sensitive, long wavelength, and the new compound with good permeability of cell membrane.Fluorescent dye compound major embodiment of the present invention is extraordinary water-soluble in having, and structure is simple, and raw material is easy to get, and toxicity is little, generally can synthesize target molecule, easy industrialization by 4 to 5 step reactions.
Accompanying drawing explanation
Fluorescent dye compound infrared spectrogram prepared by Fig. 1 embodiment of the present invention 1.
Embodiment
Can explain the present invention in more detail 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:
preparation
1) formula II compound benzothiazole heteroaromatic compound and propane sultone reaction are obtained the ammonium salt intermediate III first season (n=3); Temperature of reaction is 150 DEG C, 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 ammonium salt intermediate III and the N first season, N, the condensation of-diphenyl methylether, obtains formula IV compound; Temperature of reaction is 150 DEG C, and the reaction times is 24 hours, and reaction solvent is aceticanhydride, and acetic acid is bronsted acid catalyst, the first season ammonium salt and the mol ratio of diphenyl methylether be 1:3;
3) IV compound and formula V compound (m=2) are obtained by reacting formula VI compound: temperature of reaction is 150 DEG C, 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.
As Fig. 1, by infrared spectra map analysis, contrast structure formula, hydroxyl (-OH) in the representative structure formula of wave number 3426 position, wave number 1045 position is the addition peak of the carbon-oxygen bond (C-O) representing sulphur oxygen key (S-O) and primary alconol in fact, and wave number 1204 represents sulphur oxygen key (wave number 1045 and 1204 altogether just representative-SO3-), wave number 1520 and 1549 represent C-H bond (C-H), and wave number 1463 and 1416 represents phenyl ring
wave number 1742 represents carbon-carbon double bond (C=C), wave number 751 represents carbon-sulfur bond (C-S), wave number 612 represents carbonnitrogen bond (C-N), in structural formula, main functional group can spectrally find corresponding wave number, so infrared spectrogram can illustrate the basic chemical structure formula of this compound;
The compound VI of nmr analysis gained:
1HNMR(400MHz，DMSO)：δ9.39(t，J
1＝4Hz，J
2＝4Hz，1H)，8.66-7.70(m，4H)，7.51～7.18(m，4H)，6.66(d，J＝8,1H)，5.31(d，J＝8.0Hz，1H)，4.78(d，J＝8.0Hz，1H)，4.56(t，J
1＝4.0Hz，J
2＝4.0Hz，1H)，4.27(d，J＝8，1H)，3.33(t，J
1＝4.0Hz，J
2＝8Hz，4H)，3.01(t，J
1＝4.0Hz，J
2＝4.0Hz，1H)，2.10-2.01(m，2H)，1.91～1.60(m，4H)，1.23(t，J
1＝4.0Hz，J
2＝4.0，2H).
Embodiment 2:
preparation
1) formula II compound benzothiazole heteroaromatic compound and butyl sultone reaction are obtained the ammonium salt intermediate III first season (n=4); Temperature of reaction is 200 DEG C, 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 ammonium salt intermediate III and the N first season, N, the condensation of-diphenyl methylether, obtains formula IV compound; Temperature of reaction is 50 DEG C, and the reaction times is 20 hours, and reaction solvent is aceticanhydride, and acetic acid is bronsted acid catalyst, the first season ammonium salt and the mol ratio of diphenyl methylether be 1:2;
3) IV compound and formula V (m=2) compound are obtained by reacting formula VI compound: temperature of reaction is 10 DEG C, 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
preparation
1) formula II compound benzothiazole heteroaromatic compound and propane sultone reaction are obtained the ammonium salt intermediate III first season (n=3); Temperature of reaction is 10 DEG C, 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 ammonium salt intermediate III and the N first season, N, the condensation of-diphenyl methylether, obtains formula IV compound; Temperature of reaction is 100 DEG C, and the reaction times is 10 hours, and reaction solvent is aceticanhydride, and acetic acid is bronsted acid catalyst, the first season ammonium salt and the mol ratio of diphenyl methylether be 1:1;
3) IV compound and formula V (m=3) compound are obtained by reacting formula VI compound: temperature of reaction is 85 DEG C, 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
preparation
1) formula II compound benzothiazole heteroaromatic compound and butyl sultone reaction are obtained the ammonium salt intermediate III first season (n=4); Temperature of reaction is 50 DEG C, 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 ammonium salt intermediate III and the N first season, N, the condensation of-diphenyl methylether, obtains formula IV compound; Temperature of reaction is 10 DEG C, and the reaction times is 48 hours, and reaction solvent is aceticanhydride, and acetic acid is bronsted acid catalyst, the first season ammonium salt and the mol ratio of diphenyl methylether be 3:1;
3) IV compound and formula V (m=3) compound are obtained by reacting formula VI compound: temperature of reaction is 85 DEG C, 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
preparation
When X is O, preparation method is identical with the condition of embodiment 1.
Embodiment 6
preparation
When X is C (CH3) 2, preparation method is identical with the condition of embodiment 2.
Above content is the further description done the present invention 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 any one of claim 1 or 2, is characterized in that, comprise the following steps:
1) by formula II compound benzothiazole heteroaromatic compound and propane sultone or the butyl sultone reaction ammonium salt intermediate III obtained first season;
2) by ammonium salt intermediate III and the N first season, the condensation of N-diphenyl methylether, obtains formula IV compound;
3) formula IV compound and formula V compound are obtained by reacting formula VI 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, described step 1) temperature of reaction be 10-200 DEG C, reaction times is 1-48 hour, reaction solvent is selected from: methylene dichloride, chloroform, ethanol, acetonitrile, ethyl acetate, toluene, dimethylbenzene, and 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 DEG C, 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 DEG C, 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 fluorescent dye compound in the preparation and biological stain of nitrogenous cyanine fluorochrome described in any one of claim 1 or 2.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022099659A1 (en) * | 2020-11-13 | 2022-05-19 | 大连理工大学 | Leukocyte classification reagent, erythrocyte analysis reagent, reagent kit, and analysis method |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1445777A (en) * | 1973-09-13 | 1976-08-11 | Konishiroku Photo Ind | Light-sensitive silver halide photographic materials |
| US4108668A (en) * | 1973-09-13 | 1978-08-22 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide photographic materials |
| JPH1062889A (en) * | 1996-08-19 | 1998-03-06 | Konica Corp | Silver halide photographic sensitive material |
| WO2000034394A2 (en) * | 1998-12-05 | 2000-06-15 | Otto Samuel Wolfbeis | Pyridine dyes and quinoline dyes used as markers for biomolecules, polymers, medicaments, and particles |
| WO2000075237A2 (en) * | 1999-06-09 | 2000-12-14 | Carnegie Mellon University | pH SENSITIVE CYANINE DYES AS REACTIVE FLUORESCENT REAGENTS |
-
2014
- 2014-02-08 CN CN201410045536.5A patent/CN103804370A/en active Pending
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- 2015-01-21 CN CN201510031821.6A patent/CN104610773A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1445777A (en) * | 1973-09-13 | 1976-08-11 | Konishiroku Photo Ind | Light-sensitive silver halide photographic materials |
| US4108668A (en) * | 1973-09-13 | 1978-08-22 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide photographic materials |
| JPH1062889A (en) * | 1996-08-19 | 1998-03-06 | Konica Corp | Silver halide photographic sensitive material |
| WO2000034394A2 (en) * | 1998-12-05 | 2000-06-15 | Otto Samuel Wolfbeis | Pyridine dyes and quinoline dyes used as markers for biomolecules, polymers, medicaments, and particles |
| WO2000075237A2 (en) * | 1999-06-09 | 2000-12-14 | Carnegie Mellon University | pH SENSITIVE CYANINE DYES AS REACTIVE FLUORESCENT REAGENTS |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022099659A1 (en) * | 2020-11-13 | 2022-05-19 | 大连理工大学 | Leukocyte classification reagent, erythrocyte analysis reagent, reagent kit, and analysis method |
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Application publication date: 20150513 |