CN106280533B - A kind of near infrared fluorescent dye and its synthetic method and for parasite fluorescence labeling - Google Patents
A kind of near infrared fluorescent dye and its synthetic method and for parasite fluorescence labeling Download PDFInfo
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- CN106280533B CN106280533B CN201610675071.0A CN201610675071A CN106280533B CN 106280533 B CN106280533 B CN 106280533B CN 201610675071 A CN201610675071 A CN 201610675071A CN 106280533 B CN106280533 B CN 106280533B
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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
- C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
- C09B23/083—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines five >CH- groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
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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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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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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
Abstract
The invention belongs to the Photobiology marker field of parasitic disease, predominantly a kind of synthesis of near infrared fluorescent dye, and it is applied to imago of blood fluke fluorescence labeling.A kind of near infrared fluorescent dye, there is conjugated diene bond structure, more particularly molecular structure is linked by three ethylene linkages, and hydrophilic radical has sulfonic group (SO3) and carboxyl (COOH) H；And this near infrared fluorescent dye can be used for the imaging of imago of blood fluke fluorescence labeling.Realize the design, synthesis and fluorescence labeling imago of blood fluke of near infrared fluorescent dye.Near infrared fluorescent dye makes fluorescent dye launch light and is located near infrared region by conjugated system, carried out in conjunction with hydrophilic sulfonic group and carboxyl water-soluble modified, such near infrared fluorescent dye is used for fluorescence labeling imago of blood fluke, efficiently solves that fluorescent staining effect in imago of blood fluke fluorescence imaging is poor, background fluorescence interference and the problem of light peneration difference.
Description
Technical field
The invention belongs to the Photobiology marker field of preventing and treating verminosis, in particular it relates to a kind of near red
The synthesis of outer organic fluorescent dye and its fluorescence labeling applied to imago of blood fluke, the present invention is imago of blood fluke fluorescence labeling
A kind of novel method is provided, the near infrared fluorescent dye has excellent fluorescence labeling effect to imago of blood fluke.
Technical background
Snail fever be it is a kind of it is prevailing in subtropical and tropical zones, have on people's health and seriously endanger and influence society
The infectious disease of meeting economic development, the reproduction infectious disease easily reappeared is classified as by the World Health Organization (WHO).Schistosomiasis endemic in
74 countries and regions, it is compromised that the whole world there are about 6.52 hundred million populations at present, has 1.93 hundred million the infecteds, there is symptom case about 1.2
Hundred million, wherein 20,000,000 be several cases, China is the Major Epidemic area of snail fever.Snail fever is one kind typically through water source
The parasitic zoonoses of propagation, its history of life can be divided into ovum, miracidium, mother sporocyst, daughter sporocyst, cercaria, virgin worm and adult etc. 7
Individual Main Stage.Blood fluke cercaria enters after human body, develops for the virgin worm stage, then grows into adult by 30 days or so, into
Worm causes greatly to injure to human body, triggers hepatosplenomegaly, hepatic sclerosis etc., late period severe patient can be with causing death.Grind at present
Made the medicine (such as praziquantel) for having good killing effect to fluke adult, but due to antischistosomal drug it is long-term extensively
A large amount of to use, blood fluke produces drug resistance to it.Such medicine is killed the practical function mechanism of adult and is still not clear simultaneously,
So also need to carry out in-depth study to antischistosomal drug.But traditional research method is (predominantly to dead polypide
Detection) the possibility mechanism of action of the medicine to adult is studied, it can not accurately and directly reflect effect of the medicine on live body
Mode and site, influence the accuracy and confidence level of result of study, it is therefore desirable to seek new research method to explore its effect
Mechanism.At present, fluorescence imaging is sensitive, non-intrusion type, a low-cost Visual retrieval technology, and its resolution ratio is reachable
Hundred nanometers, the living imaging from cell to organism can be achieved.Imaging-PAM have sensitive monitoring, imaging it is rapid, can be same
When the advantages that observing polymolecular event, therefore be with a wide range of applications in terms of antischistosomal drug Study on mechanism.
In terms of fluorescence imaging is used for blood fluke research, Andrea B.Kohn etc. use 4,5-diaminoXuorescein-2
Nitric oxide production content in fluorescence probe detection blood fluke body, result of study find that the nitric oxide production release of polypide depends on an oxygen
Change nitrogen synthase (NOS), show that Nitric oxide syntheses physiologically play an important role bilharzial.SATO H. etc. apply fluorescence
The excretory system of the method observation Schistosoma mansoni adult of imaging.Polypide is observed using fluorescence probe resorufin (resorufin)
The binding mode of excretory system, its result of study will be helpful to understand the physiological function of Schistosoma mansoni protonephridial system.
It is above-mentioned to use traditional organic fluorescent dye to be studied as fluorescence probe imago of blood fluke, following lack be present
Point：(1) short wavelength excites has the interference of archebiosis background fluorescence with transmitting.(2) most fluorescence probe photostability is poor,
Causing can not long-time Fluirescence observation.(3) most of organic molecule fluorescent dye hydrophily is poor, limits its biologic applications.
Meanwhile imago of blood fluke structure has following characteristics：(1) imago of blood fluke body wall is made up of body quilt, basement membrane and body by lower floor, and
It is connected by kytoplasm tubule with body, body is covered by lower floor by the body of the seedless acellular separation in top layer.(2) blood fluke into
Worm is parasitized in mammal blood vessel, and body surface directly contacts with host blood, and in order to escape the autoimmune attack of host, body is coated to
A kind of and host's red blood cell ab antigen identical specific carbohydrates are covered, stronger hydrophily is presented in adult body surface.(3) blood fluke
Adult individual is larger, requires higher to the penetrability of fluorescence.In view of the deficiency of current fluorescent dye and the physiology of imago of blood fluke
Contradiction between architectural feature, so it is one to develop the fluorescent dye that there is good fluorescence to mark effect to imago of blood fluke
Challenge.
The present invention combines the advantage of near infrared fluorescent dye, as organism seldom has autofluorescence near infrared spectrum,
So that near infrared fluorescent dye imaging is disturbed very little by background fluorescence；Secondly, because the biquadratic of scattered light intensity and wavelength is into anti-
Than the near infrared fluorescent dye that transmitting light is located at long-wavelength region is small by its interference, and damage strong to biological tissue's penetration capacity is small.Cause
This, inventor considered fluorescent dye excite with the factor such as transmitting boundary, water solubility, blood fluke physiological characteristic, by
Near infrared fluorescent dye is applied to the fluorescence labeling of imago of blood fluke as fluorescence probe, and it is glimmering to successfully solve imago of blood fluke
The problem of fluorescent staining effect is poor in photoimaging process, background fluorescence disturbs big and fluorescence penetrability difference.
The content of the invention
The invention provides a kind of near infrared fluorescent dye, makes it have the property that fluorescence labeling is carried out to imago of blood fluke
Can, imago of blood fluke fluorescent labeling reagent can be used as.
The specific structure of near infrared fluorescent dye of the present invention is as follows：
The compounds of this invention can be prepared according to following synthetic route：
It is known compound to prepare the raw material of the compounds of this invention and agents useful for same, can commercially be obtained, or can
Prepared with methods known in the art.
Compound 1,1,2- trimethyl -1H- benzindoles (1.0-2.0mmol) exist with 3- bromo-propionic acids (1.2-2.4mmol)
110 DEG C of heating can obtain product M-1 in 24 hours in toluene.Gained intermediate product M-1 (1.0-2.0mmol) and MDA diphenylamines
(1.0-2.0mmol) 110 DEG C of heating in the solution of acetic anhydride obtain product M-2 in 2 hours.Product M-2 (1.0-2.0mmol) with
Mixing of 3- (3- sulfonic groups-the propyl group) -1,1,2- trimethyl -1H- benzindoles (1.0-2.0mmol) in potassium acetate and acetic anhydride
70 DEG C of heating responses 2 hours in solution, synthesis target fluorescent dyestuff NIR-COOH-SO3H。
Above-mentioned fluorescent dye comprises the following steps as imago of blood fluke fluorescence labeling probe, fluorescence labeling method：
(1) blood fluke cercaria is obtained：The positive oncomelania of cercaria from infection miracidium obtains, and takes positive spiral shell to be put into clear water,
2 hours or so the fresh cercarias of effusion of illumination under incandescent lamp.
(2) mouse infection：Six week old female mices are cut off into mouse web portion chaeta, take warm water to moisten mouse part skin,
And the cover glass containing 50 or so cercarias is affixed on the plucked skin of abdomen of mouse, keep making cercaria penetrate mouse in 20 minutes
Skin is infected.
(3) imago of blood fluke is obtained：After metainfective Mouse feeder 6 weeks, make its cervical dislocation lethal, in strict accordance with nothing
Bacterium operation requires, splits skin of abdomen, peritonaeum successively, takes perfusion to collect adult in liver portal-mesentcric vein.It will collect
To adult rinse 3 times in physiological saline after be assigned in culture dish, add RPMI-1640 (Roswell Park
Memorial Institute) after cell culture fluid culture 2 hours, the good polypide of microscopy screening activity is used for fluorescence imaging.
(4) imago of blood fluke fluorescence imaging：Fluorescent dye dimethyl sulfoxide (DMSO) (DMSO) dissolving is accurately configured to 1mmol's
Mother liquor, 5 μM of dilution is then diluted to PBS again.Pipette 200 μ L dilutions to be added in culture dish, use tweezers
Picking adult is added in fluorescent dye dilution, and after incubation at room temperature 5 minutes to 6 hours, adult is transferred into fluorescence imaging
Vessel, the fluorescence labeling situation of the micro- sem observation adult of lower confocal fluorescent is excited in 635nm, gathers 650-750nm fluorescence
Signal carries out fluorescence imaging.
Near-infrared organic fluorescent dye is used for grinding for imago of blood fluke fluorescence labeling by inventor by design and synthesis
Study carefully, can successfully solve that fluorescence labeling effect during adult fluorescence imaging is poor, background fluorescence interference is big and light peneration is poor
Deficiency.
Brief description of the drawings
Fig. 1 fluorescent dyes NIR-COOH-SO3H absorption spectrum and fluorescence emission spectrum
Fig. 2 fluorescent dyes NIR-COOH-SO3H cell laser co-focusing fluorescence imaging figures
Fig. 3 fluorescent dyes NIR-COOH-SO3H marks the laser co-focusing fluorescence imaging figure of Schistosoma japonicum adult
Fig. 4 fluorescent dyes NIR-COOH-SO3H marks the laser co-focusing fluorescence imaging figure of Schistosoma japonicum adult head device
Fig. 5 fluorescent dyes NIR-COOH-SO3H marks the signal to noise ratio figure of Schistosoma japonicum fluorescence imaging
Embodiment
Set forth below is the specific embodiment of the compounds of this invention, and they are of the invention with example in detail, but to this hair
It is bright to be not limited in any way.Raw material used is known compound in the present embodiment, can be obtained by commercial sources, or can press
Pertinent literature design method synthesizes.
In the following embodiments, involved physical and chemical parameter is by following Instrument measurings：1H H NMR spectroscopies are in Bruker
Determined on Mercuryplus using 400MHz, be internal standard with TMS；Mass spectrometric data MALDI-TOF-MS is in the types of AB SCIEX 5800
Obtained on mass spectrograph；Ultraviolet-visible absorption spectroscopy is completed on Shimadzu UV-2700 uv-visible absorption spectra instrument；Fluorescence
Emission spectrum on PerkinElmer LS-55 XRFs by determining；Imago of blood fluke fluorescence imaging is in OLYMPUS
It is acquired on FV1000 type laser confocal fluorescence microscopes, laser provides 635nm excitation source, collects 650nm-
Transmitting fluorescence signal in the range of 750nm.
Embodiment 1
Fluorescent dye NIR-COOH-SO3H synthesis：
(1) M-1 synthesis：By the 1 of 1mmol, 1,2- trimethyl -1H- benzindoles, 1.2mmol 3- bromo-propionic acids, add
Into three-neck flask, then add 30mL toluene and make solvent.Under the protection of nitrogen, reaction system is reacted 24 hours at 110 DEG C.
Room temperature is cooled to, reaction solution is extracted (10mL × 3) with dichloromethane, merges organic layer, with anhydrous sodium sulfate drying, column chromatography point
From obtaining M-1.Nuclear-magnetism characterize data：1H NMR(400MHz,CDCl3) δ 8.07 (dd, J=13.6,8.3Hz, 5H), 7.80-
7.54 (m, 2H), 4.05 (d, J=7.0Hz, 2H), 3.26 (s, 5H), 1.87 (s, 6H), 1.19 (t, J=6.9Hz, 3H).
(2) M-2 synthesis：1mmol M-1 and 1mmol MDA diphenylamines, are dissolved in 25mL acetic anhydride, 110 DEG C
Reaction 2 hours.Room temperature is cooled to, sodium bicarbonate aqueous solution is added and neutralizes, reaction solution is extracted (10mL × 3) with dichloromethane, is closed
And organic layer, with anhydrous sodium sulfate drying, column chromatography for separation obtains M-2.High resolution mass spectrum characterize data：MALDI-TOF-MS:
m/z 453.2175。
(3)NIR-COOH-SO3H synthesis：By 1.0mmol M-2 compounds, 1.0mmol 3- (3- sulfonic groups-the third
Base) -1,1,2- trimethyl -1H- benzindoles and 1.0mmol potassium acetate added in round-bottomed flask, then add 30mL acetic acid
Acid anhydride.Under the protection of nitrogen, reaction system is reacted 2 hours at 70 DEG C.Room temperature is cooled to, sodium bicarbonate aqueous solution is added and neutralizes,
Reaction solution extracts (10mL × 3) with dichloromethane, and column chromatography for separation obtains NIR-COOH-SO3H.Nuclear-magnetism characterize data：1H NMR
(400MHz, MeOD) δ 8.38 (s, 2H), 8.22 (s, 2H), 7.98 (d, J=8.1Hz, 4H), 7.71 (d, J=8.8Hz, 1H),
7.62 (d, J=8.6Hz, 3H), 7.46 (s, 2H), 6.71 (t, J=12.3Hz, 1H), 6.49 (d, J=13.5Hz, 1H), 6.35
(d, J=11.1Hz, 1H), 4.50 (s, 4H), 3.05 (t, J=6.6Hz, 2H), 2.84 (t, J=6.9Hz, 2H), 2.40-2.22
(m,2H),1.99(s,12H).High resolution mass spectrum characterize data：MALDI-TOF-MS:m/z 649.2711.
Embodiment 2
Fluorescent dye NIR-COOH-SO3H Absorption and fluorescence spectrum test：
Fluorescent dye NIR-COOH-SO3H is made into 1mmolL-1Ethanol mother liquor, then dilute for testing.Ultraviolet light
Spectrum measure：Scanning range 500nm-850nm, record its ultra-violet absorption spectrum feature.The solution of said determination is used further to determine glimmering
Light spectrum.Fluorescence spectrometry：Excitation wavelength 620nm, emission spectrum scope 640nm-850nm.Absorption and fluorescence spectrum
As shown in figure 1, test result shows that the emission peak of the fluorescent dye is located at 650-850nm near infrared region.
Embodiment 3
Fluorescent dye NIR-COOH-SO3H cell fluorescence imaging：
(1) reagent and material
Dimethyl sulfoxide (DMSO) (AR) is purchased from Aladdin chemical reagent Co., Ltd, and RPMI 1640 culture mediums are purchased from the silent winged generation of match
That scientific ＆ technical corporation, human cervix cancer cells HeLa are purchased from Chinese Academy of Sciences's Shanghai biochemistry and Institute of Cell Biology.
(2) cell fluorescence is imaged
Human cervix cancer cells HeLa is incubated in the RPMI 1640 culture mediums containing 10% fetal bovine serum, 37 DEG C,
5%CO2With adherent growth in 95% air atmosphere.Fluorescent dye NIR-COOH-SO3H cell fluorescence is imaged on OLYMPUS
Tested on FV1000 type laser confocal fluorescence microscopes, excitation wavelength 635nm, receive 650-750nm fluorescence signal.
Cell fluorescence imaging results are as shown in Fig. 2 test result indicates that dyestuff NIR-COOH-SO3H can carry out glimmering to cell well
Signal.
Embodiment 4
Fluorescent dye NIR-COOH-SO3H is imaged to the fluorescence labeling of imago of blood fluke：
(1) reagent and material
Reagent：Dimethyl sulfoxide (DMSO) (AR) is purchased from Aladdin chemical reagent Co., Ltd, and RPMI 1640 culture mediums are purchased from Sai Mo
Fly generation that scientific ＆ technical corporation, phosphate buffer (PBS, pH=7.4) self-control.
Cercaria：Obtained by Snails, Snails are provided by Jiangsu Prov. Bilharziasis Prevention and Control Inst..
(2) blood fluke cercaria is obtained
The positive oncomelania of cercaria from infection miracidium obtains, and takes positive spiral shell to be put into clear water, illumination 2 hours under incandescent lamp
Left and right escapes fresh cercaria.
(3) mouse infection
Six week old female mices are cut off into mouse web portion chaeta, take warm water to moisten mouse part skin, and 50 will be contained
The cover glass of left and right cercaria is affixed on the plucked skin of abdomen of mouse, and keeping, which makes cercaria penetrate mouse skin in 20 minutes, is felt
Dye.
(4) imago of blood fluke is obtained
After metainfective Mouse feeder 6 weeks, make its cervical dislocation lethal, split skin of abdomen, peritonaeum successively, take filling
Note method collects adult in liver portal-mesentcric vein.Culture is assigned to after the adult being collected into is rinsed into 3 times in physiological saline
In ware, after adding the culture of RPMI-1640 cell culture fluids 2 hours, the good polypide of microscopy screening activity is used for fluorescence imaging.
(5) imago of blood fluke fluorescence labeling imaging method
Fluorescent dye NIR-COOH-SO3The accurate mother liquor for being configured to 1mmol of H dimethyl sulfoxide (DMSO)s (DMSO) dissolving, then
5 μM of dilution is diluted to PBS.Pipette 200 μ L dilutions to be added in culture dish, added with tweezers picking adult
Into organic fluorescent dye dilution, after being incubated 5 minutes to 6 hours at room temperature, adult is transferred to fluorescence imaging special-purpose device
Ware, the lower fluorescence labeling situation using laser confocal fluorescence microscope observation adult is excited in 635nm, and gather 650-
750nm fluorescence signal carries out fluorescence imaging.
(6) fluorescence labeling result
Specific mark result can be drawn referring to Fig. 3, Fig. 4 and Fig. 5 from fluorescence imaging figure：Fluorescence probe NIR-COOH-
SO3H can carry out fluorescence labeling imaging to imago of blood fluke.Meanwhile we are quantified to imago of blood fluke fluorescence intensity
Analysis, as shown in figure 5, background area 1 (reference) and the fluorescence signal signal to noise ratio S/N in polypide region 2 on figure cathetus>10, table
Understand that the fluorescence imaging that the near infrared fluorescent dye is used for imago of blood fluke has high s/n ratio.
Claims (1)
- A kind of 1. application of the near infrared fluorescent dye with formula, it is characterised in that：The near infrared fluorescent dye can be with It is imaged for imago of blood fluke fluorescence labeling；Fluorescence labeling method comprises the following steps：(1) blood fluke cercaria is obtained：The positive oncomelania of cercaria from infection miracidium obtains, and takes positive spiral shell to be put into clear water, white Illumination escapes fresh cercaria in 2 hours under vehement lamp；(2) mouse infection：Six week old female mices are cut off into mouse web portion chaeta, take warm water to moisten mouse part skin, and will Cover glass containing 50 cercarias is affixed on the plucked skin of abdomen of mouse, keeps making within 20 minutes cercaria penetrate mouse skin progress Infection；(3) imago of blood fluke is obtained：After metainfective Mouse feeder 6 weeks, make its cervical dislocation lethal, in strict accordance with sterile behaviour It is required, splits skin of abdomen, peritonaeum successively, takes perfusion to collect adult in liver portal-mesentcric vein；By what is be collected into Adult is assigned in culture dish after rinsing 3 times in physiological saline, after adding the culture of RPMI-1640 cell culture fluids 2 hours, mirror The good polypide of inspection screening activity is used for fluorescence imaging；(4) imago of blood fluke fluorescence imaging：Fluorescent dye is accurately configured to 1mmol mother liquor with dmso solution, then 5 μM of dilution is diluted to PBS again；Pipette 200 μ L dilutions to be added in culture dish, added with tweezers picking adult Enter into fluorescent dye dilution, after incubation at room temperature 5 minutes to 6 hours, adult is transferred to fluorescence imaging vessel, 635nm excites the fluorescence labeling situation of the micro- sem observation adult of lower confocal fluorescent, and the fluorescence signal for gathering 650-750nm is carried out Fluorescence imaging.
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| US6027709A (en) * | 1997-01-10 | 2000-02-22 | Li-Cor Inc. | Fluorescent cyanine dyes |
| US6083486A (en) * | 1998-05-14 | 2000-07-04 | The General Hospital Corporation | Intramolecularly-quenched near infrared fluorescent probes |
| DE19921234B4 (en) * | 1999-05-07 | 2005-07-28 | Few Chemicals Gmbh | Cyanine dyes |
| WO2006047452A2 (en) * | 2004-10-25 | 2006-05-04 | Anaspec, Inc. | Reactive 1,3’-crosslinked carbocyanines and their bioconjugates |
| CN101131347B (en) * | 2007-09-04 | 2010-05-19 | 武汉大学 | Fluorescent quantitative PCR reagent kit for fast detecting Japanese blood fluke |
| US8669374B2 (en) * | 2010-08-25 | 2014-03-11 | Gene Shen | Functionalized cyanine dyes (PEG) |
| NL2008241C2 (en) * | 2012-02-06 | 2013-08-08 | Hq Medical Netherlands B V | Cell death probe. |
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| CN104962560B (en) * | 2015-06-16 | 2017-07-21 | 湖南大学 | A kind of aptamer for detecting SCHISTOSOMA JAPONICUM and its application in detection preparation is prepared |
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