CN114478308A - Camphor-based ketoxime fluorescent probe for detecting hypochlorous acid and preparation method and application thereof - Google Patents
Camphor-based ketoxime fluorescent probe for detecting hypochlorous acid and preparation method and application thereof Download PDFInfo
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- ketoxime
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- trimethylbicyclo
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- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 title claims abstract description 9
- 241000723346 Cinnamomum camphora Species 0.000 title claims abstract description 9
- 229960000846 camphor Drugs 0.000 title claims abstract description 9
- 229930008380 camphor Natural products 0.000 title claims abstract description 9
- 238000001514 detection method Methods 0.000 claims abstract description 12
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000523 sample Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000001686 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one Substances 0.000 claims description 5
- 239000012043 crude product Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000012295 chemical reaction liquid Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000006482 condensation reaction Methods 0.000 abstract description 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 8
- 238000002189 fluorescence spectrum Methods 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- -1 9-Anthranylmethylene Chemical group 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 206010069351 acute lung injury Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
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- 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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Abstract
The invention discloses a camphor ketoxime fluorescent probe for detecting hypochlorous acid and a preparation method and application thereof. The fluorescent probe is 3- (9-anthracene methylene) -1, 7, 7-trimethyl bicyclo [2.2.1]]Hepta-2-ketoxime. The invention utilizes 3- (9-anthracene methylene) -1, 7, 7-trimethyl bicyclo [2.2.1]]The heptan-2-ketone is taken as a raw material and is subjected to condensation reaction with hydroxylamine hydrochloride to obtain 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1]]Hepta-2-ketoxime. The compound can selectively react with hypochlorous acid, and the fluorescent color of the probe solution changes from colorless to bright blue under 365nm ultraviolet irradiation, so the compound can be used as a reagent for selectively detecting hypochlorous acidThe fluorescent probe can rapidly and sensitively detect the hypochlorous acid content in the solution, the detection range is 0-180 mu M, and the detection limit is as low as 1.18 multiplied by 10‑7M, the detection time is less than 5s, and the method has good application prospect.
Description
Technical Field
The invention belongs to the technical field of fine organic synthesis, and relates to a camphor-based ketoxime fluorescent probe for detecting hypochlorous acid, and a preparation method and application thereof.
Background
Hypochlorous acid is one of important active oxygen in organisms and plays a crucial role in maintaining the redox balance in cells. In addition, hypochlorous acid plays a role in the immune system of the organism to resist invasion of bacteria, viruses, pathogenic microorganisms and the like. However, excessive hypochlorous acid causes oxidative stress, resulting in various diseases such as rheumatoid arthritis, atherosclerosis, cardiovascular diseases, renal diseases, acute lung injury, and cancer. Therefore, it is very important to develop an analysis method capable of identifying and accurately detecting hypochlorous acid.
The current methods for detecting hypochlorous acid mainly comprise: colorimetry, iodometry, electrochemistry, chemiluminescence, and the like. Compared with the detection methods, the fluorescent probe has the advantages of good selectivity, high sensitivity, simple operation, high detection speed and the like, and is widely applied to the fields of life science, environmental science, food science and the like. A novel fluorescent probe for detecting hypochlorous acid is synthesized by using 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-one as a raw material, and related reports are not provided for a while.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a camphor-based ketoxime fluorescent probe for detecting hypochlorous acid, which can meet the use requirement. The invention aims to solve another technical problem of providing a preparation method of 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-ketoxime. The invention also aims to solve the technical problem of providing the application of the 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-one oxime.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
the camphorketoxime fluorescent probe is 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-ketoxime, and has the structural formula:
the preparation method of the camphorketoxime fluorescent probe for detecting hypochlorous acid comprises the step of carrying out condensation reaction on 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-one serving as a raw material and hydroxylamine hydrochloride to obtain 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-ketoxime. The preparation method comprises the following specific steps:
(1) sequentially adding 0.15mol of 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-one, 0.45-0.75 mol of camphor, 0.55-0.85 mol of sodium hydroxide and 4.30-4.70L of absolute ethyl alcohol into a three-neck flask with a stirrer, and carrying out reflux reaction at 78-83 ℃ for 45-50 h;
(2) distilling the reaction liquid to recover the solvent to obtain a crude product of 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-ketoxime;
(3) and (3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-ketoxime crude product is subjected to column chromatography and methanol recrystallization to obtain yellow powder 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-ketoxime.
3- (9-Anthranylmethylene) -1, 7, 7-trimethylbicyclo [2.2.1]The hepta-2-ketoxime can selectively react with hypochlorous acid, the fluorescence color of the probe solution is changed from colorless to bright blue under the irradiation of 365nm ultraviolet light, the content of the hypochlorous acid in the solution can be rapidly and sensitively detected, the detection range is 0-180 mu M, and the detection limit is as low as 1.18 multiplied by 10-7And M, the detection time is less than 5 s.
Has the advantages that: compared with the prior art, the invention utilizes 3- (9-anthracene methylene) -1, 7, 7-trimethyl bicyclo [2.2.1] heptan-2-ketone as a raw material to perform condensation reaction with hydroxylamine hydrochloride to prepare the 3- (9-anthracene methylene) -1, 7, 7-trimethyl bicyclo [2.2.1] heptan-2-ketoxime, can selectively identify hypochlorous acid and accurately detect the content of the hypochlorous acid in a solution, and has the advantages of simple synthesis, quick response, good selectivity, high sensitivity and the like as a fluorescent probe for detecting the hypochlorous acid, thereby having good application value.
Drawings
FIG. 1 is a fluorescence spectrum of 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-one oxime reacted with hypochlorous acid of various concentrations;
FIG. 2 is a fluorescence spectrum of 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-one oxime reacting with different metal ions, anions and active oxygen.
Detailed Description
The present invention will be further described with reference to the following specific examples.
Example 1
Preparation of 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-one oxime, reaction formula is as follows:
the method comprises the following specific steps:
preparation of 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-one oxime:
1.5mmol of 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [ 2.2.1%]Heptan-2-one, 6.0mmol of hydroxylamine hydrochloride, 7.5mmol of sodium hydroxide and 30mL of absolute ethanol are put into a three-neck flask which is sequentially provided with a stirrer to carry out reflux reaction for 48 hours at 80 ℃. Distilling the reaction liquid to recover the solvent to obtain 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1]Subjecting the crude product of hept-2-ketoxime to silica gel chromatography (petroleum ether: ethyl acetate: 4: 1) and methanol recrystallization to obtain yellow powder of 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2 ] oxime.2.1]The yield of the hepta-2-ketoxime is 41.3 percent.1H NMR(600MHz，DMSO-d6)δ：0.54(s，3H)，0.82(s，3H)，0.96(s，3H)，1.06-1.14(m，1H)，1.34-1.43(m，2H)，1.53-1.61(m，2H)，7.46(s，4H)，8.01(s，4H)，8.35(s，1H)，8.45(s，1H)，11.26(s，1H)；13C NMR(150MHz，DMSO-d6)δ：11.90，17.93，20.34，25.72，33.04，47.64，50.62，52.87，125.51，125.83，125.97，126.10，126.38，126.89，128.34，128.52，128.84，129.01，129.17，131.14，131.25，131.32，132.12，143.43，159.70；HRMS(m/z)：[M+H]+calcd for C25H25NO+H+，356.2014；found，356.2015。
Example 2
Mixing 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [ 2.2.1%]Preparation of heptan-2-ketoxime to 1.5X 10-6M PBS buffer solution, dissolving cysteine in PBS buffer solution to make concentration of 0, 1.0 × 10-5、2.0×10-5、4.0×10-5、6.0×10-5、8.0×10-5、10.0×10-5、12.0×10-5、14.0×10-5、16.0×10-5、18.0×10-5A solution of M. Measuring 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] under the action of hypochlorous acid with different concentrations on a fluorescence spectrophotometer by adopting a fluorescence spectrum titration method]Fluorescence emission spectrum of hepta-2-ketoxime, as shown in FIG. 1. The results show that the fluorescence emission intensity of the probe at 453nm is gradually enhanced along with the gradual increase of the concentration of hypochlorous acid in the solution, thereby indicating that the compound can be used as a fluorescence probe for sensitively detecting the content of hypochlorous acid in the solution.
Example 3
Mixing 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [ 2.2.1%]Preparation of heptan-2-ketoxime to 1.5X 10-6M PBS buffer solution, and dissolving different metal ions, anions and active oxygen in the PBS buffer solution to prepare the solution with the concentration of 1.8 multiplied by 10- 4A solution of M. Measuring 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] under the action of different metal ions, anions and active oxygen on a fluorescence spectrophotometer by adopting a fluorescence spectrum titration method]G-2-Fluorescence emission spectrum of ketoxime, as shown in FIG. 2. The results show that the addition of hypochlorous acid can obviously increase the fluorescence emission intensity of the probe at 453nm, and other metal ions (Na) are added+，Cu2+，Zn2+，Mg2+，Al3+，Cd2+) An anion (F)-，SO3 2-，CO3 2-，AcO-，NO2 -) And active oxygen (b)1O2，H2O2，ONOO-) The fluorescence spectrum of the probe is not obviously changed when the probe is observed by iso-reference contrast. This demonstrates that this compound can be used as a fluorescent probe for selective recognition of hypochlorous acid.
Claims (6)
1. A camphor-based ketoxime fluorescent probe for detecting hypochlorous acid is characterized in that the structural formula is as follows:
2. the method of claim 1, wherein 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-one is condensed with hydroxylamine hydrochloride to obtain 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-one oxime.
3. The method for preparing camphor-ketoxime fluorescent probe for detecting hypochlorous acid as claimed in claim 2, wherein the specific preparation method comprises:
(1) sequentially adding 0.15mol of 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-one, 0.45-0.75 mol of 1 camphor, 0.55-0.85 mol of sodium hydroxide and 4.30-4.70L of absolute ethyl alcohol into a three-neck flask with a stirrer, and carrying out reflux reaction at 78-83 ℃ for 45-50 h;
(2) distilling the reaction liquid to recover the solvent to obtain a crude product of 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-ketoxime;
(3) and (3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-ketoxime crude product is subjected to column chromatography and methanol recrystallization to obtain yellow powder 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-ketoxime.
4. Use of the camphor-based ketoxime-based fluorescent probe for detecting hypochlorous acid as claimed in claim 1 for detecting hypochlorous acid.
5. The use of claim 4, wherein the 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1] heptan-2-one oxime is capable of reacting selectively with hypochlorous acid, and the fluorescent color of the probe solution changes from colorless to bright blue under 365nm ultraviolet light.
6. Use according to claim 4, characterized in that 3- (9-anthracenemethylene) -1, 7, 7-trimethylbicyclo [2.2.1]The content of hypochlorous acid in the detection solution of the hepta-2-ketoxime is detected, the concentration range of the detection range is below 180 mu M, and the detection limit is as low as 1.18 multiplied by 10-7And M, the detection time is less than 5 s.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110357913A (en) * | 2019-08-16 | 2019-10-22 | 南京林业大学 | A kind of fluorescence probe and its preparation method and application for detecting hypochlorite ion |
| CN112500386A (en) * | 2020-11-27 | 2021-03-16 | 山西大学 | Near-infrared HClO fluorescent probe based on pyrrazone oxime, and preparation and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110357913A (en) * | 2019-08-16 | 2019-10-22 | 南京林业大学 | A kind of fluorescence probe and its preparation method and application for detecting hypochlorite ion |
| CN112500386A (en) * | 2020-11-27 | 2021-03-16 | 山西大学 | Near-infrared HClO fluorescent probe based on pyrrazone oxime, and preparation and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| ZHONGLONG WANG等: "Rational design of a facile camphor-based fluorescence turn-on probe for real-time tracking of hypochlorous acid in vivo and in vitro", ANALYST, vol. 147, 15 April 2022 (2022-04-15), pages 2080 - 2088 * |
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