CN106967302A - A kind of synthetic method of blood cell analysis dyestuff - Google Patents
A kind of synthetic method of blood cell analysis dyestuff Download PDFInfo
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- CN106967302A CN106967302A CN201710196223.3A CN201710196223A CN106967302A CN 106967302 A CN106967302 A CN 106967302A CN 201710196223 A CN201710196223 A CN 201710196223A CN 106967302 A CN106967302 A CN 106967302A
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- 239000000975 dye Substances 0.000 title claims abstract description 25
- 238000010189 synthetic method Methods 0.000 title claims abstract description 18
- 238000004458 analytical method Methods 0.000 title claims abstract description 16
- 210000000601 blood cell Anatomy 0.000 title claims abstract description 15
- 239000013067 intermediate product Substances 0.000 claims abstract description 35
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 31
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 31
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000012467 final product Substances 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 230000035484 reaction time Effects 0.000 claims description 8
- 150000000215 1-octanols Chemical class 0.000 claims description 4
- MUDSDYNRBDKLGK-UHFFFAOYSA-N 4-methylquinoline Chemical class C1=CC=C2C(C)=CC=NC2=C1 MUDSDYNRBDKLGK-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 15
- 239000002994 raw material Substances 0.000 abstract description 5
- 208000027418 Wounds and injury Diseases 0.000 abstract description 4
- 238000010276 construction Methods 0.000 abstract description 4
- 230000006378 damage Effects 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 4
- 208000014674 injury Diseases 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 230000001737 promoting effect Effects 0.000 abstract description 3
- 231100000331 toxic Toxicity 0.000 abstract description 3
- 230000002588 toxic effect Effects 0.000 abstract description 3
- -1 dimethyl-benzothiazole Methylsulfates Chemical class 0.000 abstract description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 abstract 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical class C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000005292 vacuum distillation Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 210000000265 leukocyte Anatomy 0.000 description 2
- 239000006166 lysate Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000007523 nucleic acids Chemical class 0.000 description 2
- 102000039446 nucleic acids Human genes 0.000 description 2
- 108020004707 nucleic acids Proteins 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- QGZCUOLOTMJILH-UHFFFAOYSA-N 2h-tetrazol-2-ium;bromide Chemical compound [Br-].C1=N[NH+]=NN1 QGZCUOLOTMJILH-UHFFFAOYSA-N 0.000 description 1
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 1
- 241001062009 Indigofera Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 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 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- ZMMJGEGLRURXTF-UHFFFAOYSA-N ethidium bromide Chemical compound [Br-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CC)=C1C1=CC=CC=C1 ZMMJGEGLRURXTF-UHFFFAOYSA-N 0.000 description 1
- 229960005542 ethidium bromide Drugs 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- 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
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N1/00—Sampling; Preparing specimens for investigation
- G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
- G01N1/30—Staining; Impregnating ; Fixation; Dehydration; Multistep processes for preparing samples of tissue, cell or nucleic acid material and the like for analysis
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N1/00—Sampling; Preparing specimens for investigation
- G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
- G01N1/30—Staining; Impregnating ; Fixation; Dehydration; Multistep processes for preparing samples of tissue, cell or nucleic acid material and the like for analysis
- G01N2001/302—Stain compositions
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Organic Chemistry (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
Have the invention discloses a kind of synthetic method of blood cell analysis dyestuff, including step：2,3 dimethyl-benzothiazole Methylsulfates and N, N ' dimethyl carbonamidine synthesis obtain the first intermediate product；1 octanol and Trifluoromethanesulfonic anhydride synthesis obtain the second intermediate product；Second intermediate product and the synthesis of 4 methylquinolines obtain the 3rd intermediate product；First intermediate product and the synthesis of the 3rd intermediate product obtain final product.By the above-mentioned means, the synthetic method of the blood cell analysis dyestuff of the present invention, the synthetic method toxic side effect is small, raw material is easy to get, simple in construction, and the injury of pairing into personnel are smaller, production cost is low, and synthetic route is short, and target molecule can be synthesized by the reaction of 4 steps, yield is higher, synthesis is quick, and purity is excellent, cost-effective, easy industrialization, with actual promotional value.
Description
Technical field
The present invention relates to a class cell dyeing dyestuff in in-vitro diagnosis field, more particularly to a kind of blood cell analysis is used
The synthetic method of dyestuff.
Background technology
Cell dyeing is dyed by various acid-base property dyestuffs in early days, and this colouring method degree of accuracy is not good enough, and right
Leukocyte differential count needs to show very fine internal structure difference in haemocyte, and then by using red laser diode
Carry out captured information for the detecting instrument of light source, so this colouring method is slightly inadequate.Now, led in leukocyte differential count
Domain, widely used is fluorescent dyeing.
In the early stage of development, the dyestuff of application has methylene blue, bright benzene indigo plant, Pai Nuoning, Ethidium Bromide etc..They are by insertion
Or electrostatic attraction nucleic acid molecules are to form compound, by means of the enhanced fluorescence of micro- sem observation.Due to these dyestuffs in itself
Also compound is easily formed, very strong fluorescence background interference can be caused, while the fluorescent quantum produced is relatively low, the standard of detection is influenceed
True property；Recently it has been proposed that carry out nucleus dyeing with acridine orange or tetrazolium bromide, they or led in energy transfer process
Optical quenching is caused, the fluorescence reduction for sending dye nucleotide compound so as to influence the degree of accuracy, or requires expensive laser
Light source is excited in 488nm, or needs to specify higher temperature（35℃）The lower reaction long period could be used to detect, and be brought to clinic
Inconvenience.In this case, polymethine class dyestuff solves this problem well.Because its launch wavelength is long, can have
Effect eliminate background fluorescence interference, 10 DEG C or so just can penetration cell film, with nucleic acid molecules strength be firmly combined with dyeing, sensitivity
Height, photostability is good, is especially adapted for use in the light source with red laser diode, can be used as preferable fluorescent dye.
Due to the premium properties and unique advantage of polymethine class dyestuff, the synthesis technique on such dyestuff is also a variety of
Various but mostly more numerous and diverse, the prices of raw materials are higher, and synthesis cycle is long, and the material that pilot process is produced has to human body
Certain injury, it is difficult to remove thoroughly, the purity of target product is not high.In general, the synthesis work of this kind of dyestuff how is optimized
Skill, improves dye characteristic and reduces the production cost of such dyestuff and have become the emphasis of current research.
The content of the invention
The present invention solves the technical problem of provide a kind of synthetic method of blood cell analysis dyestuff, the technique mistake
Journey toxic side effect is small, and raw material is easy to get, simple in construction, and synthetic route is short, and target molecule, easy industry can be synthesized by the reaction of 4 steps
Change, with actual promotional value.
In order to solve the above technical problems, one aspect of the present invention is：A kind of blood cell analysis dye is provided
The synthetic method of material, including step have：
（1）2,3- dimethyl-benzothiazoles Methylsulfate and N, N '-dimethyl carbonamidine synthesis obtain the first intermediate product
；
（2）1- octanols and Trifluoromethanesulfonic anhydride synthesis obtain the second intermediate product
；
（3）Second intermediate product and the synthesis of 4- methylquinolines obtain the 3rd intermediate product
；
（4）First intermediate product and the synthesis of the 3rd intermediate product obtain final product
。
In a preferred embodiment of the present invention, step（1）The reaction time of the first intermediate product of middle synthesis for 1.5~
2.5h。
In a preferred embodiment of the present invention, step（2）The reaction time of the second intermediate product of middle synthesis for 0.75~
1.5h。
In a preferred embodiment of the present invention, step（3）The reaction time of the 3rd intermediate product of middle synthesis for 1.0~
1.5h。
In a preferred embodiment of the present invention, step（4）The reaction time of middle synthesis final product is 3.0~4.0h.
In a preferred embodiment of the present invention, step is completed（1）, step（2）, step（3）And step（4）Need altogether
Time is 7.0~9.0h.
The beneficial effects of the invention are as follows：The synthetic method of the blood cell analysis dyestuff of the present invention, synthetic method poison is secondary
Effect is small, and raw material is easy to get, simple in construction, and the injury of pairing into personnel are smaller, and production cost is low, and synthetic route is short, anti-by 4 steps
Target molecule should can be synthesized, yield is higher, synthesis is quick, and purity is excellent, cost-effective, easy industrialization, be promoted with actual
Value.
Embodiment
The technical scheme in the embodiment of the present invention will be clearly and completely described below, it is clear that described implementation
Example is only a part of embodiment of the present invention, rather than whole embodiments.Based on the embodiment in the present invention, this area is common
All other embodiment that technical staff is obtained under the premise of creative work is not made, belongs to the model that the present invention is protected
Enclose.
A kind of synthetic method of blood cell analysis dyestuff is provided, specific steps are seen below：
Embodiment one：The synthesis of first intermediate product
3mmol N are taken, N '-dimethyl carbonamidine is put into a test tube, then add 0.2 ml acetic anhydride, in stirring under 85 DEG C of oil baths
Dissolving（B liquid）.Then 1mmol 2 is taken, 3- dimethyl-benzothiazole Methylsulfates are put into another test tube, adds 1.5 ml vinegar
Acid is after stirring and dissolving under 85 DEG C of oil baths（A liquid）.
In under 85 DEG C of oil baths, A liquid is added dropwise in B liquid, centre is stirred continuously.Mixed solution can be gradually during dropwise addition
Redden, this explanation A and B has begun to reaction.
After completion of dropping, mixed liquor is in continuing the h of stirring reaction 1.5 under 85 DEG C of oil baths, it should be deep that reaction, which terminates rear mixed liquor,
Red liquid.
After liquid cooling to be mixed, the acetic acid in mixed liquor and acetic anhydride are removed using vacuum distillation method, then added
About 20 ml methanol dissolving mixt again.
First intermediate product is separated using thin-layer chromatography method.Specific practice：By the uniform place of lysate on silica gel plate,
Dried up with hair-dryer, solvent is then made with ethyl acetate, separate each product.A yellow expansion occurs during expansion
Band, it is to be deployed completely after, carefully scrape yellow expansion band, after smashing to pieces add proper amount of methanol dissolving yellow product, be filtrated to get
Yellow solution.The methanol in yellow solution is removed using vacuum distillation method, yellow solid powder is obtained, the solid is the
One intermediate product.
Embodiment two：The synthesis of second intermediate product
By 5mmol 1- octanols and 0.435 g pyridines and about 2 ml CH2Cl2（Dichloromethane）Mixing.
By 0.91 ml Trifluoromethanesulfonic anhydrides and 5 ml CH2Cl2It is well mixed, then at -5 DEG C ~ 0 DEG C and N2（Nitrogen）
Under protection, 1- octanols, pyridine and CH are added dropwise to2Cl2Mixed liquor in.The min of dropwise addition process about 20, dropwise addition is too fast to be caused
Temperature rises rapidly, is unfavorable for the progress of reaction.
After completion of dropping, in the min of stirring reaction 45 at -10 DEG C.Occur that pink product and white are solid in course of reaction
Body（Trifluoromethanesulfonic anhydride and the product of pyridine reaction）.
Reaction adds appropriate CH after terminating2Cl2And water, water can dissolve white solid, and the aqueous solution is removed after layering.It is many
It is secondary that product is washed with water to remove unnecessary pyridine.
Anhydrous sodium sulfate drying water suction is added, CH is then removed by vacuum distillation2Cl2, it is to obtain light brown liquid
Two intermediate products.
Embodiment three：The synthesis of 3rd intermediate product
Take 3.34mmol intermediate products 2 and about 5 ml CH2Cl2（Dichloromethane）Mixing.
3.34mmol 4- methylquinolines are added in above-mentioned mixed liquor, N2About 1 h is heated to reflux under protection.
Vacuum distillation removes CH2Cl2, then finally obtained a kind of shallow with the multiple washed product of absolute ether with removing impurity
Brown oil, the grease is the 3rd intermediate product.
Example IV：The synthesis of final product
First intermediate product is mixed with the 3rd intermediate product with equimolar ratio, and using pyridine as reaction dissolvent, at 90 DEG C
3 h are reacted under oil bath.After completion of the reaction, pyridine is removed using distillation under vacuum, is subsequently added into appropriate methanol and dissolves again
Reaction product.Finally use thin-layer chromatography method purification reaction product.Specific practice：By the uniform place of lysate in silica gel plate
On, dried up with hair-dryer, solvent is then made with ethyl acetate, separate each product.A navy blue occurs during expansion
Deploy band, it is to be deployed completely after, carefully scrape navy blue expansion band, after smashing to pieces add proper amount of methanol dissolving blue product, mistake
Filter obtains blue solution, then removes the methanol in blue solution using vacuum distillation method, obtains blue solid, the solid
As final product.
The target product yield synthesized using process above reaches 75%；Mass Spectrometric Identification only has a target molecular weight peak, nothing
The miscellaneous peak of other intermediate products is present, and purity illustrates that the polymethine class dyestuffs purity of such a technique synthesis is non-up to more than 99.7%
Chang Gao；The technical process toxic side effect is small, and the injury of pairing into personnel are smaller, and raw material is easy to get, simple in construction, and synthetic route is short,
Target molecule can be synthesized by the reaction of 4 steps, synthesis cycle is substantially reduced.To sum up, a kind of haemocyte of the present invention point
The synthetic method of analysis dyestuff, can be achieved it is many, fast, good, four advantages are saved, with actual promotional value.
Embodiments of the invention are the foregoing is only, are not intended to limit the scope of the invention, it is every to utilize this hair
Equivalent structure or equivalent flow conversion that bright description is made, or directly or indirectly it is used in other related technology necks
Domain, is included within the scope of the present invention.
Claims (6)
1. a kind of synthetic method of blood cell analysis dyestuff, it is characterised in that have including step：
（1）2,3- dimethyl-benzothiazoles Methylsulfate and N, N '-dimethyl carbonamidine synthesis obtain the first intermediate product
；
（2）1- octanols and Trifluoromethanesulfonic anhydride synthesis obtain the second intermediate product
；
（3）Second intermediate product and the synthesis of 4- methylquinolines obtain the 3rd intermediate product
；
（4）First intermediate product and the synthesis of the 3rd intermediate product obtain final product
。
2. the synthetic method of blood cell analysis dyestuff according to claim 1, it is characterised in that step（1）Middle synthesis
The reaction time of first intermediate product is 1.5~2.5h.
3. the synthetic method of blood cell analysis dyestuff according to claim 1, it is characterised in that step（2）Middle synthesis
The reaction time of second intermediate product is 0.75~1.5h.
4. the synthetic method of blood cell analysis dyestuff according to claim 1, it is characterised in that step（3）Middle synthesis
The reaction time of 3rd intermediate product is 1.0~1.5h.
5. the synthetic method of blood cell analysis dyestuff according to claim 1, it is characterised in that step（4）Middle synthesis
The reaction time of final product is 3.0~4.0h.
6. the synthetic method of blood cell analysis dyestuff according to claim 1, it is characterised in that complete step（1）, step
Suddenly（2）, step（3）And step（4）The time needed altogether is 7.0~9.0h.
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| CN201710196223.3A CN106967302B (en) | 2017-03-29 | 2017-03-29 | A kind of synthetic method of blood cell analysis dyestuff |
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|---|---|---|---|
| CN201710196223.3A CN106967302B (en) | 2017-03-29 | 2017-03-29 | A kind of synthetic method of blood cell analysis dyestuff |
Publications (2)
| Publication Number | Publication Date |
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| CN106967302A true CN106967302A (en) | 2017-07-21 |
| CN106967302B CN106967302B (en) | 2019-04-12 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111004178A (en) * | 2019-12-27 | 2020-04-14 | 苏州康铭诚业医用科技有限公司 | Rapid synthesis method of dye intermediate for blood leukocyte analysis |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6004816A (en) * | 1997-05-19 | 1999-12-21 | Sysmex Corporation | Reagent and method for classification and counting of leukocytes |
| CN104048932A (en) * | 2014-06-13 | 2014-09-17 | 苏州康铭诚业医用科技有限公司 | Method for testing content of glycol phenylate |
| CN104198471A (en) * | 2014-08-14 | 2014-12-10 | 苏州康铭诚业医用科技有限公司 | Surface active agent for determination of human serum albumin |
-
2017
- 2017-03-29 CN CN201710196223.3A patent/CN106967302B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6004816A (en) * | 1997-05-19 | 1999-12-21 | Sysmex Corporation | Reagent and method for classification and counting of leukocytes |
| CN104048932A (en) * | 2014-06-13 | 2014-09-17 | 苏州康铭诚业医用科技有限公司 | Method for testing content of glycol phenylate |
| CN104198471A (en) * | 2014-08-14 | 2014-12-10 | 苏州康铭诚业医用科技有限公司 | Surface active agent for determination of human serum albumin |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111004178A (en) * | 2019-12-27 | 2020-04-14 | 苏州康铭诚业医用科技有限公司 | Rapid synthesis method of dye intermediate for blood leukocyte analysis |
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