CN107383077A - A kind of organic compound for detecting formaldehyde and its application - Google Patents
A kind of organic compound for detecting formaldehyde and its application Download PDFInfo
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- CN107383077A CN107383077A CN201710623853.4A CN201710623853A CN107383077A CN 107383077 A CN107383077 A CN 107383077A CN 201710623853 A CN201710623853 A CN 201710623853A CN 107383077 A CN107383077 A CN 107383077A
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims abstract description 191
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 12
- 239000000523 sample Substances 0.000 claims abstract description 48
- 238000001514 detection method Methods 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 14
- 210000000056 organ Anatomy 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 7
- 238000001727 in vivo Methods 0.000 abstract description 4
- 230000003834 intracellular effect Effects 0.000 abstract description 4
- 230000008569 process Effects 0.000 abstract description 4
- 230000035508 accumulation Effects 0.000 abstract description 3
- 238000009825 accumulation Methods 0.000 abstract description 3
- 230000007246 mechanism Effects 0.000 abstract description 3
- 230000009471 action Effects 0.000 abstract description 2
- 238000011835 investigation Methods 0.000 abstract description 2
- 210000003470 mitochondria Anatomy 0.000 abstract description 2
- 210000004027 cell Anatomy 0.000 description 15
- 230000008859 change Effects 0.000 description 13
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 8
- 239000007995 HEPES buffer Substances 0.000 description 8
- 229930040373 Paraformaldehyde Natural products 0.000 description 5
- 238000002189 fluorescence spectrum Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 description 5
- 229920002866 paraformaldehyde Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- -1 aldehyde compound Chemical class 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000012224 working solution Substances 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 241000165940 Houjia Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 2
- RADKZDMFGJYCBB-UHFFFAOYSA-N Pyridoxal Chemical compound CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000004962 physiological condition Effects 0.000 description 2
- 230000035479 physiological effects, processes and functions Effects 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
- 230000003313 weakening effect Effects 0.000 description 2
- DWNBOPVKNPVNQG-LURJTMIESA-N (2s)-4-hydroxy-2-(propylamino)butanoic acid Chemical compound CCCN[C@H](C(O)=O)CCO DWNBOPVKNPVNQG-LURJTMIESA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000208340 Araliaceae Species 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229960003581 pyridoxal Drugs 0.000 description 1
- 235000008164 pyridoxal Nutrition 0.000 description 1
- 239000011674 pyridoxal Substances 0.000 description 1
- 239000003642 reactive oxygen metabolite Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- 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
-
- 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
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
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- Biomedical Technology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The present invention relates to the fluorescence probe of detection formaldehyde (HCHO), is a kind of organic compound for detecting formaldehyde and its application specifically.Compound is used as the fluorescence probe of formaldehyde using the compound as shown in structural formula I.The invention provides a kind of fluorescence probe available for the intracellular formaldehyde of selective enumeration method, and fluorescence intensity generation is obvious in the presence of formaldehyde reduces, and available for the detection of formaldehyde, and can substantially reduce the interference of external detection condition, improve accuracy of detection.This kind of compound can be used for the detection of intraor extracellular levels of formaldehyde as fluorescence probe, this kinetics mechanism to processes such as further investigation formaldehyde generation, conveying and accumulations in vivo, especially studying formaldehyde has important biomedical meaning in mitochondria physiological action.
Description
Technical field
The present invention relates to the fluorescence probe of detection formaldehyde (HCHO), is a kind of organic compound for detecting formaldehyde specifically
Thing and its application.
Background technology
For formaldehyde as a kind of simple aldehyde compound, chemical property is active, is widely used in every field, as material,
The industries such as coating, agricultural chemicals, cosmetics, medicine, it is also possible to sterilize, fixed and anti-corrosion.Formaldehyde one side source in environment
In nature, such as biomass combustion, the discharge of vegetation and microorganism；On the other hand derive from artificially, as the manufacture of formaldehyde, vapour
Tail gas discharge etc..Formaldehyde is present in each position of human body simultaneously, and important work is served in biological methylation process
With.The generation of human endogenous's property formaldehyde is the physiology course intervened by enzyme system.Normal concentration of formaldehyde is able to maintain that body generation
Thank to balance, and formaldehyde and the rise of related active carbonyl group material can cause many diseases, including cancer, diabetes, chronic liver disease,
Neurodegenerative disease and cardiovascular disease etc..
Fluorescence probe is one of means of active material in effective detection life entity.One fluorescence with application prospect is visited
Pin should have the advantages that change in fluorescence is obvious before and after acting on, fast, selectivity is responded to target molecule and can be used for In vivo detection well.
Jefferson Chan etc. disclose one kind, and to detect the fluorescence probe FP1 of formaldehyde, (structure is shown in Fig. 1, Jefferson Chan
Et.al, J.Am.Chem.Soc.2015,137,10890) Fluorescence Increasing of probe is so as to detecting formaldehyde after, being acted on formaldehyde
In the presence of.Christopher J.Chang etc. disclose it is a kind of detect formaldehyde fluorescence probe FA-1 (structure is shown in Fig. 1,
Christopher J.Chang et.al,J.Am.Chem.Soc,2015,137,10886).But above-mentioned probe synthesis
Complexity, low yield, take time and effort.And this kind of fluorescence probe PARA FORMALDEHYDE PRILLS(91,95) low-response, detect limit for height, it is impossible to be used in rapidly detect
Formaldehyde.Therefore, exploitation is readily synthesized, has good selectivity, can be used for quickly detecting the fluorescence probe of formaldehyde in biosystem
It is significant.
The content of the invention
Present invention aims at provide a kind of organic compound for detecting formaldehyde and its application.
To achieve the above object, the present invention use technical scheme for：
A kind of organic compound for detecting formaldehyde, compound is the organic compound based on BODIPY, the structural formula such as institute of formula I
Show,
A kind of organic compound application for detecting formaldehyde, application of the compound in formaldehyde is detected shown in the formula I.
Compound shown in the formula I is as the application in detection formaldehyde fluorescence probe.
A kind of fluorescence probe for detecting formaldehyde, the fluorescence probe for detecting formaldehyde is compound shown in formula I,
Probe shown in the formula I is used to detect the formaldehyde under physiological environment, in cell and isolated organ.
The fluorescence probe qualitative/quantitative detects formaldehyde：
When formula I is applied into detection OCHO, it is compound of the generation with Formula II structure after being acted on survey OCHO, from
And cause the change of fluorescence intensity；
The formalin that concentration in gradient changes is separately added into the HEPES cushioning liquid of formula I, measure adds respectively
The fluorescence intensity of formaldehyde fore-and-aft architecture, then using the fluorescence intensity level at the concentration of formalin and maximum emission wavelength as horizontal seat
Mark, ordinate mapping, according to fluorescence intensity level, you can read the content of formaldehyde in solution from figure.
Beneficial effects of the present invention：
The compounds of this invention, as fluorescent parent, is used as the work reacted with formaldehyde using BODIPY dyestuffs by introducing amino
Property center, reaction center is amino, its activated centre with formaldehyde selectively acting, after amino and formaldehyde react, on probe
The carbon-to-nitrogen double bon of formation, there occurs decaying phenomenon under excited state, causes the consume of energy, caused there occurs structure alienation
Fluorescence signal weakens or quenching, and formaldehyde is optionally detected to realize；Occurred using carbon-to-nitrogen double bon front and rear to whole compound
Detection signal of the influence of fluorescence intensity as identification, cause the change of compound photoluminescent property, and compound is used to detect
The fluorescence imaging of intracellular formaldehyde.
The compounds of this invention can be as the fluorescence probe for the intracellular formaldehyde of selective enumeration method, and this probe can be selective
Ground acts on formaldehyde, and the obvious detection for changing, PARA FORMALDEHYDE PRILLS(91,95) can be achieved occurs for fluorescence intensity after effect.
The compounds of this invention is used as formaldehyde fluorescence probe, and fluorescence intensity changes in the presence of formaldehyde, available for formaldehyde
Qualitative and quantitative detection, improve detection sensitivity.Especially, this kind of compound is used as fluorescence probe, available for cell, tissue with
And in live body formaldehyde detection, this dynamics to processes such as further investigation formaldehyde generation, conveying and accumulations in vivo
Mechanism, further appreciated that the physiology of formaldehyde and toxicological effect were significant.
Brief description of the drawings
Fig. 1 is by the published formaldehyde fluorescence probe structural representation lifted in background technology；
Fig. 2 is probe in detecting principle schematic of the present invention；
Fig. 3 is synthesising probing needle BoN provided in an embodiment of the present invention synthetic route；
Fig. 4 is the fluorescence intensity change curve of fluorescence probe under different pH provided in an embodiment of the present invention；
Fig. 5 is the selective schematic diagram of fluorescence probe PARA FORMALDEHYDE PRILLS(91,95) provided in an embodiment of the present invention；
Fig. 6 is uv absorption spectra of the probe provided in an embodiment of the present invention before and after formaldehyde is added；
Fig. 7 is fluorescence probe BoN fluorescence intensities provided in an embodiment of the present invention with the schematic diagram of OCHO change in concentration, illustration
Represent 515nm change in fluorescence figures；
Fig. 8 is that fluorescence probe BoN provided in an embodiment of the present invention is used to detect being total to for the exogenous OCHO of SMMC-7721 cells
Focusing microscope photo.
Embodiment
Below in conjunction with the accompanying drawings and embodiment is used to further illustrate the present invention, but the invention is not restricted to embodiment.
The compounds of this invention is used as the fluorescence probe of formaldehyde using the compound as shown in structural formula I.The invention provides
A kind of fluorescence probe available for the intracellular formaldehyde of selective enumeration method, fluorescence intensity generation is obvious in the presence of formaldehyde reduces, can
For the detection of formaldehyde, and the interference of external detection condition can be substantially reduced, improve accuracy of detection.This kind of compound is as fluorescence
Probe can be used for the detection of intraor extracellular levels of formaldehyde, and this is to furtheing investigate generation, conveying and the accumulation of formaldehyde in vivo
Etc. the kinetics mechanism of process, especially studying formaldehyde has important biomedical meaning in mitochondria physiological action.
Embodiment 1 (probe BoN synthesis)：
Probe BoN synthesis：As shown in figure 3, taking 250mL round-bottomed flasks, tetrahydrofuran (40mL) and ammonia are added thereto
Mixture, is stirred by water (80mL, 29.3%) at 25 DEG C.The BODIPY dyestuffs (1.48g, 5mmol) of commerce-change are dissolved in
In 80mL tetrahydrofurans, it is added dropwise in mixture dropwise with constant pressure funnel, it is dripped off within 4 hours.Then proceed to anti-
Answer 4 hours, liquid stands liquid separation, and compound (BoN) 1.135g shown in bronzing formula I is obtained after organic phase is evaporated.Production
Rate is 82%.
1H NMR(DMSO-d6,500MHz)δ(ppm)：8.79(s,1H),5.65(s,1H),5.17(s,1H),3.32(s,
2H), 2.12 (s, 9H), 0.87 (s, 1H) (d, J=0.89Hz, 1H)13C NMR(DMSO-d6,125MHz)δ(ppm):152.8,
147.6,145.7,144.1,137.3,132.2,123.4,114.8,111.8,42.1,18.3,15.7,14.4,13.8.LC-
MS(ESI+):m/z C14H16BClF2N2calcd.277.1678,found[M-H]–276.1678.
Embodiment 2
Type I compound obtained by preparing in aqueous systems, simulation physiological environment and is carried out to sulphur into the cell as probe application
The detection of alkane sulphur, simulates physiological condition, and the following experiment carries out (HEPES cushioning liquid, concentration under the conditions of pH=7.4
For 10mM), concentration and probe concentration uses 1.0mM.
The pH effects of probe PARA FORMALDEHYDE PRILLS(91,95) response obtained by above-mentioned preparation：
PH gradient is controlled using HEPES cushioning liquid.10.0 μM of BoN are added in each 10ml colorimetric cylinders, are added not
With pH 10mM HEPES, ultra-pure water constant volume to 10ml, solution is shaken up, after balancing 10min, above-mentioned working solution is added into fluorescence ware
Middle measure fluorescence spectrum.Ratio fluorescent is as shown in Figure 4 with pH change.PH value is in the range of 4.0-9.2, the fluorescence intensity of probe
Do not change, illustrate that probe BoN has preferably detection potentiality in physiological conditions.
Embodiment 3 (selectivity of the BoN to OCHO)：
10.0 μM of BoN are added in 10ml colorimetric cylinders, 10mM HEPES pH 7.4 is added and arrives 5ml, shake up, Ran Houjia
Enter various determinands, finally with pH 7.4 HEPES constant volumes to 10mL.Solution is shaken up, 10min is balanced, above-mentioned solution is poured into
Fluorescence ware determines fluorescence spectrum.BoN is as shown in Figure 5 to OCHO selectivity, and determinand working solution is followed successively by：Blank, formaldehyde (50
μM), acetaldehyde (50 μM), pyroracemic aldehyde (50 μM), glyoxal (50 μM), benzaldehyde (50 μM), pyridoxal (50 μM), 4- nitrobenzoyls
Aldehyde (50 μM), Sodium Pyruvate (5mM), alanine (400 μM), glycine (5mM), serine (5mM), arginine (5mM), half Guang
Propylhomoserin (5mM), glutathione (5mM), glucose (1mM), hydrogen peroxide (100 μM), hydrogen sulfide (100 μM), formic acid (100 μ
M), hydroascorbic acid (100 μM).
Measure fluorescence spectrum condition be：
BoN has selectivity well to OCHO as seen from Figure 5, and after being acted on OCHO, 515nm fluorescence corresponding to BoN drops
It is low.All kinds of amino acid and activity of reactive oxygen species sulfur material have little to no effect to the fluorescence intensity of probe under condition determination, and
Aldoketones material generates influence on fluorescence intensity, and the wherein influence of pyroracemic aldehyde is maximum, but it influences far on Quenching of fluorescence
Less than quenching effect of the formaldehyde to probe.So BoN PARA FORMALDEHYDE PRILLS(91,95)s have good selectivity, it is suitable for cell and organism
Research.
Embodiment 4 (quantitative detections of the BoN to OCHO)：
10.0 μM of BoN are added in 10ml colorimetric cylinders, 10mM HEPES pH 7.4 is added and arrives 5ml, shake up, Ran Houjia
Enter various concentrations formaldehyde, finally with pH 7.4 HEPES constant volumes to 10mL.Solution is shaken up, 10min is balanced, working solution is poured into
Fluorescence ware measure fluorescence spectrum (referring to Fig. 6 and 7).
Concentration of formaldehyde after constant volume：0,10,20,40,60,80,100,200,300,400,500.0 μM.
Measure fluorescence spectrum condition be：
OCHO addition causes system UV absorption intensity and the situation of change of displacement as seen from Figure 6, shows CHO concentration
Increase, the UV absorption of probe is without significant change.
Fig. 7 represents the change of the change system fluorescence intensity with OCHO concentration, shows the increase with OCHO concentration, system
515nm fluorescence intensities reduce, and illustration represents the linear fit curve with OCHO change in concentration of the fluorescence intensity at 515nm,
The linear regression constant of linear fit curve is 0.9946, shows the concentration for the measure OCHO that probe can quantify.
Embodiment 5 (BoN is used for the exogenous OCHO detections of cell)：
A groups are incubated SMMC-7721 cells 15min as a control group with 5 μM of BoN；
B groups, SMMC-7721 cells are chosen, add 100 μM of formaldehyde, 1h is incubated in incubator, is cleaned 3 times with DMEM,
5 μM of BoN are then added, then 15min is incubated in incubator, then are cleaned 3 times with DMEM, carry out co-focusing imaging.
C group cells, SMMC-7721 cells are chosen, add 200 μM of formaldehyde, 1h is incubated in incubator, is cleaned with DMEM
3 times, 5 μM of BoN are then added, then 15min is incubated in incubator, then are cleaned 3 times with DMEM, carry out co-focusing imaging.(ginseng
See Fig. 8).
As shown in Fig. 8 A, cell shows very strong fluorescence；Shown in B, fluorescent weakening；Shown in C, fluorescent weakening is more bright
It is aobvious.It can be seen that BoN can be used in detecting the formaldehyde of cell exogenous.
It is respectively from left to right in Fig. 8：Cell fluorescence figure；Cell light field figure；The stacking chart of cell fluorescence and light field.
Above content is to combine specific preferred embodiment further description made for the present invention, it is impossible to is assert
The specific implementation of the present invention is confined to these explanations.For general technical staff of the technical field of the invention,
On the premise of not departing from present inventive concept, some simple deduction or replace can also be made, should all be considered as belonging to the present invention's
Protection domain.It is a kind of purposes of noval chemical compound of the present invention as fluorescent dye, it is impossible to assert that the compound of the present invention is only used for
Fluorescent dye, for general technical staff of the technical field of the invention, fluorescence is being used as based on the compounds of this invention
Under the consideration of the identical mechanism of action of dyestuff, some simple inferences can also be made, draw the present invention compound other should
With purposes, protection scope of the present invention should be all considered as belonging to.
Claims (5)
- A kind of 1. organic compound for detecting formaldehyde, it is characterised in that：Compound is the organic compound based on BODIPY, structure Formula as shown in formula I,
- A kind of 2. organic compound application of the detection formaldehyde described in claim 1, it is characterised in that：Chemical combination shown in the formula I Application of the thing in formaldehyde is detected.
- 3. the organic compound application of the detection formaldehyde as described in claim 1, it is characterised in that：Compound shown in the formula I As the application in detection formaldehyde fluorescence probe.
- A kind of 4. fluorescence probe for detecting formaldehyde, it is characterised in that：The fluorescence probe for detecting formaldehyde is compound shown in formula I,
- 5. the fluorescence probe of the detection formaldehyde as described in claim 4, it is characterised in that：Probe shown in the formula I is used to detect Formaldehyde under physiological environment, in cell and isolated organ.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111196821A (en) * | 2018-11-16 | 2020-05-26 | 中国科学院上海药物研究所 | Compounds, preparation method thereof and application thereof as near-infrared two-region fluorescent probe for detecting methylglyoxal |
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| CN105542752A (en) * | 2015-12-14 | 2016-05-04 | 济南大学 | Formaldehyde fluorescence probe and preparation method and application thereof |
| CN105542756A (en) * | 2016-02-03 | 2016-05-04 | 浙江理工大学 | Fluorescent probe for detecting formaldehyde as well as preparation method and application of fluorescent probe |
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| CN105542752A (en) * | 2015-12-14 | 2016-05-04 | 济南大学 | Formaldehyde fluorescence probe and preparation method and application thereof |
| CN105542756A (en) * | 2016-02-03 | 2016-05-04 | 浙江理工大学 | Fluorescent probe for detecting formaldehyde as well as preparation method and application of fluorescent probe |
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| HYESUN SONG等: "A tailor designed fluorescent ‘turn-on’ sensor of formaldehyde based on the BODIPY motif", 《TETRAHEDRON LETTERS》 * |
| WAN ZHOU等: "HCHO-reactive molecule with dual-emission-enhancement property for quantitatively detecting HCHO in near 100% water solution", 《SENSORS AND ACTUATORS B》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111196821A (en) * | 2018-11-16 | 2020-05-26 | 中国科学院上海药物研究所 | Compounds, preparation method thereof and application thereof as near-infrared two-region fluorescent probe for detecting methylglyoxal |
| CN111196821B (en) * | 2018-11-16 | 2022-11-29 | 中国科学院上海药物研究所 | Compounds, preparation method thereof and application thereof as near-infrared two-region fluorescent probe for detecting methylglyoxal |
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