CN115160283A - Preparation method of fluorescent reagent 5-aminofluorescein - Google Patents

Preparation method of fluorescent reagent 5-aminofluorescein Download PDF

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CN115160283A
CN115160283A CN202210860940.2A CN202210860940A CN115160283A CN 115160283 A CN115160283 A CN 115160283A CN 202210860940 A CN202210860940 A CN 202210860940A CN 115160283 A CN115160283 A CN 115160283A
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aminofluorescein
acid
preparation
producing
drying
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CN115160283B (en
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张胜海
陈思梦
邓佳旺
石亚林
路东胜
石德康
解昱辰
李润
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Ankang University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
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    • C07D311/90—Xanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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Abstract

The invention discloses a preparation method of a fluorescent reagent 5-aminofluorescein, which comprises the following steps: (1) preparation of 4-aminophthalic acid: 4-nitrophthalic acid and N 2 H 4 ·H 2 Mixing O and FeOOH, carrying out reflux reaction, filtering while hot, adjusting the pH value to 3 to 4, cooling to room temperature, refrigerating until no solid is precipitated, carrying out suction filtration, washing a filter cake to be neutral by water, and drying to obtain 4-aminophthalic acid; (2) preparing 5-aminofluorescein: sequentially adding resorcinol and methanesulfonic acid into 4-aminophthalic acid, reacting under the protection of inert gas, cooling the reaction solution to room temperature, pouring into ice water, adjusting the pH of the system to 5 to 6, standing and refrigerating until no solid is separated out, performing suction filtration, washing a filter cake to be neutral by water, and drying. The method for preparing the 5-aminofluorescein by reducing and condensing firstly has the advantages of high yield, lower reaction temperature and mild reaction condition, and avoids the use of a controlled reagent of acetic anhydrideThe application is.

Description

Preparation method of fluorescent reagent 5-aminofluorescein
Technical Field
The invention belongs to the technical field of fluorescent reagent preparation, and particularly relates to a preparation method of a fluorescent reagent 5-aminofluorescein.
Background
5-aminofluorescein (5-amino-fluorescein) with excitation wavelength of 492nm and emission wavelength of 515nm is one of the commonly used fluorescent markers. The fluorescence of the derivative is weak, the fluorescence intensity of the derivative is only about 0.67 percent of that of fluorescein, and the derivatization reaction conditions are quite harsh, so the application range of the derivative is limited. The protein can be covalently bonded with protein carboxyl by a proper condensation reagent such as 3- (3-dimethylaminopropyl) -ethyl-carbodiimide (EDC), dicyclohexylcarbodiimide (DCC) and the like, the fluorescence intensity of a bonding product is obviously enhanced, and the protein fluorescent dye is widely used in the fields of immunological research, protein tracing and the like. In order to overcome the defects of 5-aminofluorescein and harsh derivatization reaction conditions, some researchers acidify, alkylate, esterify, maleylate and azide the active amino isothiocyanate of the 5-aminofluorescein to obtain derivatives with more excellent fluorescence properties, and the derivatives can be mixed with-NH 2 The covalent bond is formed by the reaction of-SH, -COOH and the like, the marker is endowed with higher selectivity, stability and sensitivity, and the application range of the 5-aminofluorescein in the biological analysis is greatly expanded. However, due to the limitation of obtaining high purity 5-aminofluorescein, the price of 5-aminofluorescein derivatives is generally expensive, which makes low cost bioanalysis difficult.
In 2006, panhuiyin et al (applied chemistry, 2006, 23, 193) _ 197. ) Using 4-nitrophthalic acid and resorcinol as raw materials, znCl 2 Performing high-temperature melt condensation on the catalyst, and then performing Na 2 Reducing an S/NaHS mixture, recrystallizing 6% diluted hydrochloric acid, and respectively obtaining 5-aminofluorescein and 6-aminofluorescein with higher purity in the total yield of 34% and 12.75%. This synthetic process utilizes 5-amino fluorescenceThe difference of the solubility of the fluorescein and the 6-aminofluorescein in 6% dilute hydrochloric acid solves the problem of difficult separation of 5-position and 6-position isomers by adopting a recrystallization method, but the 5-aminofluorescein precursor synthesized by a high-temperature melting method has more by-products and complex products, and reduces the yield of the 5-aminofluorescein besides bringing greater pressure to subsequent separation. In 2021, liujianwu et al (chemical reagent, 2021, 43, 968) _ 972. ) Using 4-nitrophthalic acid and resorcinol as raw materials, CH 3 -SO 3 H is used as a catalyst, condensation reaction is carried out at a lower temperature to obtain a key intermediate 5 (6) -nitrofluorescein, and esterification separation and Na are carried out 2 S is reduced, and 5-aminofluorescein with higher purity is obtained with the total yield of 51.6%. The synthesis process realizes condensation of 4-nitrophthalic acid and resorcinol at a lower temperature, and improves the total yield of 5-aminofluorescein by improving the yield of a key intermediate 5 (6) -nitrofluorescein, but acetic anhydride used in an esterification separation scheme adopted for separating 5 (6) -nitrofluorescein is a tube product at present, and the source of raw materials is difficult. Therefore, it is of great importance to develop a new method for obtaining high-purity 5-aminofluorescein at a lower temperature and a lower cost.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a preparation method of a fluorescent reagent 5-aminofluorescein, which is simple and has high yield.
A preparation method of a fluorescent reagent 5-aminofluorescein comprises the following steps:
(1) Preparation of 4-aminophthalic acid: 4-nitrophthalic acid and N 2 H 4 ·H 2 Mixing O and FeOOH, carrying out reflux reaction at the temperature of 90-110 ℃ for 2-3 h, filtering while hot, adjusting the pH to 3-4, cooling to room temperature, refrigerating until no solid is precipitated, carrying out suction filtration, washing a filter cake to be neutral by water, and drying to obtain 4-aminophthalic acid;
(2) Preparation of 5-aminofluorescein: sequentially adding resorcinol and methane sulfonic acid into the 4-aminophthalic acid prepared in the step (1), reacting for 1 to 3 hours at 95 to 100 ℃ under the protection of inert gas, cooling the reaction liquid to room temperature, pouring into ice water, adjusting the pH of the system to 5 to 6, standing and refrigerating until no solid is separated out, performing suction filtration, washing a filter cake to be neutral by water, and drying to obtain the 5-aminofluorescein.
Preferably, the 4-nitrophthalic acid, N 2 H 4 ·H 2 The proportion of O and FeOOH is 1mmol, 10 to 15mmol, 0.5 to 0.8mg.
Preferably, the proportion of the 4-aminophthalic acid, the resorcinol and the methane sulfonic acid is 6mmol to 12 to 13.2 mmol.
Preferably, the volume of the ice water is 3 to 4 times of that of the methane sulfonic acid.
Preferably, the drying is vacuum drying, and the temperature of the vacuum drying is 45 to 65 ℃.
Preferably, the refrigeration temperature is 2 to 8 ℃.
Preferably, in the step (1), the pH of the filtrate is adjusted to 3 to 4 by concentrated hydrochloric acid.
Preferably, in the step (2), the pH of the system is adjusted to 5 to 6 by using a NaOH solution.
Preferably, the concentration of the NaOH solution is 4 to 6 mol.L -1 。
The ice water is ice water with the temperature of 0-5 ℃.
The reaction mechanism of the present invention is as follows:
Figure 139538DEST_PATH_IMAGE001
。
the invention has the advantages that:
(1) The reaction is carried out in two steps, the reaction temperature is relatively low, the reaction condition is mild, the use of a controlled reagent of acetic anhydride is avoided, and the experimental safety is good;
(2) The method for preparing the 5-aminofluorescein by reducing and condensing firstly has high yield and is suitable for industrial production.
Drawings
FIG. 1-mass spectrum of aminofluorescein;
FIG. 2-excitation and emission spectra of aminofluorescein.
Detailed Description
Example 1
A preparation method of a fluorescent reagent 5-aminofluorescein comprises the following steps:
(1) Preparation of 4-aminophthalic acid: 10.0 mmol (2.1 g) of 4-nitrophthalic acid, 12.5mL of 40wt% N were added in this order to a three-necked flask 2 H 4 ·H 2 O aqueous solution (containing 100 mmol of N) 2 H 4 ·H 2 O) and 5mg of FeOOH, performing reflux reaction at 100 ℃ for 3 hours, filtering while the mixture is hot to obtain a clear solution, adjusting the pH value to 3.5 by using concentrated hydrochloric acid, cooling to room temperature, refrigerating at 5 ℃ for 2 hours, performing suction filtration until dark gray solids are not separated out, washing a filter cake to be neutral by using water, and performing vacuum drying at 50 ℃ to obtain 1.45g of light gray yellow solid which is 4-aminophthalic acid, detecting that the melting point is 344.5 ℃, and obtaining the yield of 80%;
(2) Preparation of 5-aminofluorescein: adding 1.1g (6.0 mmol) of 4-aminophthalic acid prepared in the step (1) into a three-necked bottle, then sequentially adding 1.39 g (12.6 mmol) of resorcinol and 10mL of methanesulfonic acid, reacting at 97 ℃ for 3h under the protection of argon, cooling to room temperature, pouring the obtained reaction liquid into 30mL of ice water, adjusting the pH of the system to 6 by using 5 mol/L of NaOH solution, separating out a reddish brown solid, refrigerating for 2h at 5 ℃, no more solid is separated out, performing suction filtration, washing a filter cake to be neutral by using water, and performing vacuum drying at 50 ℃ to constant weight to obtain 2.03g of the brownish brown solid, namely 5-aminofluorescein with the yield of 94.5%.
Example 2
A preparation method of a fluorescent reagent 5-aminofluorescein comprises the following steps:
(1) Preparation of 4-aminophthalic acid: 10.0 mmol (2.1 g) of 4-nitrophthalic acid, 18.7mL of 40wt% N were added in this order to a three-necked flask 2 H 4 ·H 2 O aqueous solution (containing 150 mmol N) 2 H 4 ·H 2 O) and 8mg of FeOOH, performing reflux reaction at 110 ℃ for 2h, filtering while hot to obtain clear solution, adjusting pH to 3 with concentrated hydrochloric acid, cooling to room temperature, refrigerating at 2 ℃ for 1h, removing dark gray solid, performing suction filtration, washing filter cake with water to neutrality, and vacuum drying at 45 ℃ to obtain light gray yellow solid1.42g of 4-aminophthalic acid, the melting point of which is detected to be 344.4 ℃ and the yield is 78.3 percent;
(2) Preparation of 5-aminofluorescein: adding 1.1g (6.0 mmol) of 4-aminophthalic acid prepared in the step (1) into a three-necked bottle, then sequentially adding 1.32 g (12 mmol) of resorcinol and 8 mL of methanesulfonic acid, reacting at 100 ℃ for 1h under the protection of argon, cooling to room temperature, pouring the obtained reaction liquid into 20mL of ice water, adjusting the pH of the system to 5 by using 4 mol/L NaOH solution, separating out a reddish brown solid, refrigerating for 1h at 2 ℃, no solid is separated out, performing suction filtration, washing a filter cake to be neutral by using water, and performing vacuum drying at 45 ℃ to constant weight to obtain 1.96g of a brownish brown solid, namely 5-aminofluorescein with the yield of 91.2%.
Example 3
A preparation method of a fluorescent reagent 5-aminofluorescein comprises the following steps:
(1) Preparation of 4-aminophthalic acid: 10.0 mmol (2.1 g) of 4-nitrophthalic acid, 15mL of 40wt% N were added in this order to a three-necked flask 2 H 4 ·H 2 O aqueous solution (containing 120 mmol N) 2 H 4 ·H 2 O) and 5mg of FeOOH, performing reflux reaction for 3 hours at 90 ℃, filtering while hot to obtain a clear solution, adjusting the pH value to 4 by using concentrated hydrochloric acid, cooling to room temperature, refrigerating for 3 hours at 8 ℃, avoiding separation of dark gray solids, performing suction filtration, washing a filter cake to be neutral by using water, and then performing vacuum drying at 65 ℃ to obtain 1.43g of light gray yellow solid which is 4-aminophthalic acid, detecting that the melting point is 344.5 ℃, and the yield is 78.9%;
(2) Preparation of 5-aminofluorescein: adding 1.1g (6.0 mmol) of 4-aminophthalic acid prepared in the step (1) into a three-necked bottle, then sequentially adding 1.45g (13.2 mmol) of resorcinol and 12mL of methanesulfonic acid, reacting at 97 ℃ for 2h under the protection of argon, cooling to room temperature, pouring the obtained reaction liquid into 45mL of ice water, adjusting the pH of the system to 6 by using 6 mol/L of NaOH solution, separating out a red brown solid, refrigerating at 8 ℃ for 3h, no more separating out a solid, performing suction filtration, washing a filter cake to be neutral by using water, and performing vacuum drying at 65 ℃ to constant weight to obtain 1.94g of a brown solid, namely 5-aminofluorescein with the yield of 90.3%.
Mass spectrometry
The tan solid prepared in example 1 was analyzed by mass spectrometry, and the results are shown in FIG. 1.
As can be seen from FIG. 1, MS (ESI) + ) Theoretical value m/z [ C 20 H 14 NO 5 + ] + : 348.0866 [M+H] + Measured value of m/z [ C ] 20 H 14 NO 5 + ] + : 348.0869 [M+H] + 。
Second, excitation and emission spectrographic analysis of 5-aminofluorescein
The tan solid prepared in example 1 was prepared to be 1.0X 10 -6 The excitation and emission spectra of the mol/L aqueous solution are respectively scanned on a FL970 type fluorescence spectrophotometer, the maximum excitation wavelength is 492nm, the maximum emission wavelength is 517 nm, the Stokes shift is 25 nm, and the solution is consistent with the excitation and emission spectra of 5-aminofluorescein in the prior art, such as panhui-lin (the synthesis and characterization of aminofluorescein and derivatives thereof [ D ]]University of Tianjin, 2005.) study was consistent.
As can be seen from the above analysis, the preparation method provided by the present invention can prepare 5-aminofluorescein.

Claims (9)

1. A preparation method of a fluorescent reagent 5-aminofluorescein is characterized in that: the method comprises the following steps:
(1) Preparation of 4-aminophthalic acid: 4-nitrophthalic acid and N 2 H 4 ·H 2 Mixing O and FeOOH, carrying out reflux reaction at the temperature of 90-110 ℃ for 2-3 h, filtering while hot, adjusting the pH to 3-4, cooling to room temperature, refrigerating until no solid is precipitated, carrying out suction filtration, washing a filter cake to be neutral by water, and drying to obtain 4-aminophthalic acid;
(2) Preparation of 5-aminofluorescein: sequentially adding resorcinol and methane sulfonic acid into the 4-aminophthalic acid prepared in the step (1), reacting for 1 to 3 hours at 95 to 100 ℃ under the protection of inert gas, cooling the reaction liquid to room temperature, pouring into ice water, adjusting the pH of the system to 5 to 6, standing and refrigerating until no solid is separated out, performing suction filtration, washing a filter cake to be neutral by water, and drying to obtain the 5-aminofluorescein.
2. The method for producing 5-aminofluorescein as defined in claim 1, wherein: the 4-nitrophthalic acid, N 2 H 4 ·H 2 The ratio of O to FeOOH is 1mmol: 10 to 15mmol: 0.5 to 0.8mg.
3. The method for producing 5-aminofluorescein as defined in claim 2, wherein: the proportion of the 4-aminophthalic acid, the resorcinol and the methane sulfonic acid is 6mmol to 12 to 13.2 mmol.
4. The method for producing 5-aminofluorescein as defined in claim 3, wherein: the volume of the ice water is 3 to 4 times of that of the methanesulfonic acid.
5. The method for preparing 5-aminofluorescein as described in claim 1, wherein: the drying is vacuum drying, and the temperature of the vacuum drying is 45-65 ℃.
6. The method for producing 5-aminofluorescein as defined in claim 1, wherein: the refrigeration temperature is 2 to 8 ℃.
7. The method for producing 5-aminofluorescein as defined in claim 1, wherein: in the step (1), the pH of the filtrate is adjusted to 3 to 4 by concentrated hydrochloric acid.
8. The method for preparing 5-aminofluorescein as described in claim 1, wherein: and (3) regulating the pH value of the system to 5-6 by using a NaOH solution in the step (2).
9. The method for producing 5-aminofluorescein as defined in claim 8, wherein: the concentration of the NaOH solution is 4 to 6 mol.L -1 。
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2725666C1 (en) * 2019-12-17 2020-07-03 ФЕДЕРАЛЬНОЕ ГОСУДАРСТВЕННОЕ УНИТАРНОЕ ПРЕДПРИЯТИЕ "ИНСТИТУТ ХИМИЧЕСКИХ РЕАКТИВОВ И ОСОБО ЧИСТЫХ ХИМИЧЕСКИХ ВЕЩЕСТВ НАЦИОНАЛЬНОГО ИССЛЕДОВАТЕЛЬСКОГО ЦЕНТРА "КУРЧАТОВСКИЙ ИНСТИТУТ" (НИЦ "Курчатовский институт - ИРЕА) Method of producing 5-, 6-amino-fluoresceins
CN113444104A (en) * 2021-08-02 2021-09-28 苏州求索生物科技有限公司 Preparation process of 5-aminofluorescein

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Publication number Priority date Publication date Assignee Title
RU2725666C1 (en) * 2019-12-17 2020-07-03 ФЕДЕРАЛЬНОЕ ГОСУДАРСТВЕННОЕ УНИТАРНОЕ ПРЕДПРИЯТИЕ "ИНСТИТУТ ХИМИЧЕСКИХ РЕАКТИВОВ И ОСОБО ЧИСТЫХ ХИМИЧЕСКИХ ВЕЩЕСТВ НАЦИОНАЛЬНОГО ИССЛЕДОВАТЕЛЬСКОГО ЦЕНТРА "КУРЧАТОВСКИЙ ИНСТИТУТ" (НИЦ "Курчатовский институт - ИРЕА) Method of producing 5-, 6-amino-fluoresceins
CN113444104A (en) * 2021-08-02 2021-09-28 苏州求索生物科技有限公司 Preparation process of 5-aminofluorescein

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