CN108640874A - A kind of molecular probe and the preparation method and application thereof - Google Patents
A kind of molecular probe and the preparation method and application thereof Download PDFInfo
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- CN108640874A CN108640874A CN201810287737.4A CN201810287737A CN108640874A CN 108640874 A CN108640874 A CN 108640874A CN 201810287737 A CN201810287737 A CN 201810287737A CN 108640874 A CN108640874 A CN 108640874A
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- 239000003068 molecular probe Substances 0.000 title claims abstract description 121
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims abstract description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- JAMNSIXSLVPNLC-UHFFFAOYSA-N (4-ethenylphenyl) acetate Chemical class CC(=O)OC1=CC=C(C=C)C=C1 JAMNSIXSLVPNLC-UHFFFAOYSA-N 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical class CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 6
- 238000012545 processing Methods 0.000 claims description 6
- 229910000077 silane Inorganic materials 0.000 claims description 6
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical group CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 claims description 6
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical group CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 5
- 238000002444 silanisation Methods 0.000 claims description 4
- 238000006884 silylation reaction Methods 0.000 claims description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
- 238000001514 detection method Methods 0.000 abstract description 23
- 238000003384 imaging method Methods 0.000 abstract description 13
- 229940034610 toothpaste Drugs 0.000 abstract description 10
- 239000000606 toothpaste Substances 0.000 abstract description 10
- 238000000799 fluorescence microscopy Methods 0.000 abstract description 8
- 150000002500 ions Chemical class 0.000 abstract description 8
- 238000004737 colorimetric analysis Methods 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 230000035945 sensitivity Effects 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 238000010189 synthetic method Methods 0.000 abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 20
- 239000000523 sample Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 9
- 150000001450 anions Chemical class 0.000 description 7
- 230000004044 response Effects 0.000 description 7
- 210000001519 tissue Anatomy 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 238000002189 fluorescence spectrum Methods 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- -1 isoquinolin -2 (3H)-yl Chemical group 0.000 description 2
- BYVCTYDTPSKPRM-UHFFFAOYSA-N naphthalene-1-carbonyl naphthalene-1-carboxylate Chemical class C1=CC=C2C(C(OC(=O)C=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 BYVCTYDTPSKPRM-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- KYLUAQBYONVMCP-UHFFFAOYSA-N (2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P KYLUAQBYONVMCP-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- 206010007027 Calculus urinary Diseases 0.000 description 1
- 206010016818 Fluorosis Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229940008309 acetone / ethanol Drugs 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000006854 communication Effects 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 208000004042 dental fluorosis Diseases 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- UNWUYTNKSRTDDC-UHFFFAOYSA-N tert-butylsilane Chemical group CC(C)(C)[SiH3] UNWUYTNKSRTDDC-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 208000008281 urolithiasis Diseases 0.000 description 1
- 229910001868 water Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O 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
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
-
- 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
- G01N21/645—Specially adapted constructive features of fluorimeters
- G01N21/6456—Spatial resolved fluorescence measurements; Imaging
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N29/00—Investigating or analysing materials by the use of ultrasonic, sonic or infrasonic waves; Visualisation of the interior of objects by transmitting ultrasonic or sonic waves through the object
- G01N29/22—Details, e.g. general constructional or apparatus details
- G01N29/24—Probes
- G01N29/2418—Probes using optoacoustic interaction with the material, e.g. laser radiation, photoacoustics
-
- 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
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
Abstract
The present invention discloses a kind of molecular probe and the preparation method and application thereof, and the structural formula of molecular probe is as follows：Wherein,R=CH3Or CH2‑CH3.The molecular probe of the present invention can realize that ultraviolet colorimetric method, fluorescence imaging and photoacoustic imaging accurately detect fluorine ion, high sensitivity；The content that Fluoride in Toothpaste ion can also be detected has a good application prospect in fluorine ion context of detection；In addition, the synthetic method of molecular probe of the present invention is simple, synthesis condition is not harsh, easy to operate.
Description
Technical field
The present invention relates to molecular probe identification field more particularly to a kind of molecular probes and its system of fluorine ion photo-acoustic detection
Preparation Method and application.
Background technology
Fluorine ion (F-) it is a kind of important anion, there is important role in Human physiology, about F-Detection
Cause extensive concern.Fluorine is the indispensable trace element of human body, contains about 2 grams~3 grams of fluorine element in normal adult human body,
It is mainly distributed in tooth and bone, but the daily intake of fluorine is more than that 4mg will result in poisoning, can cause seriously to endanger to human body
Evil leads to the generation of many diseases, such as fluorosis of bone, urolithiasis, renal failure even cancer etc..In addition, with F-
Industrial extensive use, irreversible pollution and injury are also increasingly apparent caused by environment.Therefore, highly sensitive height is developed
Specificity has both the F of certain tissue penetration-Detection method, for F-Detection in vivo and in vitro it is particularly important.
In present analysis detection method, the method for ion detection includes mainly fluorescence detection and colorimetric method.However, this
Two methods have specific requirement for the state of sample and operating condition etc..Meanwhile the exciting light of most of fluorescence probes
It, can not be into for deep tissues and position since the tissue penetration depths of visible light are limited with transmitting light all in visible light region
Row detection, even if near-infrared fluorescence imaging has certain tissue penetration depths, but since light has scattering in communication process,
So that the depth capacity of fluorescence imaging detection is about 1mm, the detection and imaging of deeper tissue cannot be met.For example, excessive F-
It may lead to Acute gastric injury, since spatial resolution difference and imaging depth are limited, be difficult to detect F by fluorescence imaging-.Cause
This realizes the F of highly sensitive high specific in deep tissues-Detection is a huge challenge.
Currently, the molecular detection technology based on photoacoustic imaging (Photoacoustic Imaging, PAI) becomes a kind of new
The detection method of type.PAI is a kind of Noninvasive, without ionising radiation, combine the imaging side of photothermal conversion and sonic detection
Method.Under light illumination, PAI contrast agent converts light into as heat, and simultaneous thermally expands, and generates ultrasonic signal, is popped one's head in by optoacoustic
Capture.Since sound wave scatters less in transmittance process, PAI can reach the imaging depth of about 60mm.Therefore, PAI can be provided
The high-resolution image information of some special objectives of deep tissues.For example, oxygen concentration, ion concentration, tumour growth etc..From
Molecular Detection is related generally to these fields to fields, PAI such as disease trackings.But there is presently no examined based on PAI technologies
Survey the molecular probe of fluorine ion.
Therefore, the technology highly development and application of F- is detected based on PAI.
Invention content
In view of above-mentioned deficiencies of the prior art, the purpose of the present invention is to provide a kind of molecular probe and preparation method thereof with
Using, it is intended to solve that existing Fluoride Analysis sensitivity is low, poor specificity, it is difficult to realize to the fluorine ion in deep tissues
The problem of being detected.
Technical scheme is as follows：
A kind of molecular probe, structural formula are as follows：
Wherein,R=-CH3Or-CH2-CH3
A kind of preparation method of molecular probe as described above, wherein work as R1When=- H, including step：
A, by 4- bromo- 1,8- naphthalic anhydrides dissolve in organic solvent with ethylenediamine, and stir 12- at 25-50 DEG C
It 24 hours, is cooled to room temperature, obtains molecular probe intermediate 1；
B, in the anhydrous acetonitrile existing for acid chloride (II) and tri-o-tolyl phosphine, using 4- acetoxy-styrenes
Processing is alkylated to the molecular probe intermediate 1, obtains molecular probe intermediate 2；
C, the molecular probe intermediate 2 is hydrolyzed in basic solvent, obtains molecular probe.
A kind of preparation method of molecular probe as described above, wherein whenWhen, packet
Include step：
A, by 4- bromo- 1,8- naphthalic anhydrides dissolve in organic solvent with ethylenediamine, and stir 12- at 25-50 DEG C
It 24 hours, is cooled to room temperature, obtains molecular probe intermediate 1；
B, in the anhydrous acetonitrile existing for acid chloride (II) and tri-o-tolyl phosphine, using 4- acetoxy-styrenes
Processing is alkylated to the molecular probe intermediate 1, obtains molecular probe intermediate 2；
C, the molecular probe intermediate 2 is hydrolyzed in basic solvent, obtains molecular probe；
D, silanization treatment is carried out to the molecular probe in strong basicity solvent, obtains silylation molecular probe.
The preparation method of the molecular probe, wherein in step A, the ethylenediamine be N, N- dimethyl-ethylenediamines or
N, N- diethyl ethylenediamine, the organic solvent are ethyl alcohol.
The preparation method of the molecular probe, wherein in step A, stirred 12 hours at 40 DEG C.
The preparation method of the molecular probe, wherein in step C, the basic solvent is that the tetrahydrofuran of alkalinity is molten
Liquid.
The preparation method of the molecular probe, wherein in step D, the strong basicity solvent is the four of sodium hydride alkalization
Hydrogen tetrahydrofuran solution；The silane is tertiary butyl chloride diphenyl silane or tertiary butyl chloride dimethylsilane.
A kind of application of molecular probe as described above in detecting fluorine ion.
The application, wherein the method for the detection is ultraviolet colorimetric method.
The application, wherein the method for the detection is fluorescence imaging method.
The application, wherein the method for the detection is photoacoustic imaging method.
Advantageous effect：The above-mentioned molecular probe of the present invention can realize that ultraviolet colorimetric method, fluorescence imaging and photoacoustic imaging are accurate
Detect fluorine ion, high sensitivity；The content that Fluoride in Toothpaste ion can also be detected has good answer in fluorine ion context of detection
Use foreground.Meanwhile the synthetic method of the above-mentioned molecular probe of the present invention is simple, synthesis condition is not harsh, easy to operate.
Description of the drawings
Fig. 1 (a) is the synthetic route chart of molecular probe in the embodiment of the present invention 1；(b) it is the UV absorption light of molecular probe
Spectrogram；(c) it is the fluorescence spectra of molecular probe；(d) it is the hydrogen nuclear magnetic spectrogram of molecular probe.
Fig. 2 (a) is response of the ultra-violet absorption spectrum of molecular probe in the embodiment of the present invention 2 to various concentration fluorine ion
Figure；(b) response diagram of the fluorescence spectrum of molecular probe to various concentration fluorine ion.
Fig. 3 (a) is response of UV absorption of the molecular probe at 645nm to different anions in the embodiment of the present invention 3
Figure；(b) it is response diagram of fluorescent emission of the molecular probe at 600nm to different anions.
Fig. 4 (a, b) is photoacoustic signal of the molecular probe at 680nm in the embodiment of the present invention 4 to the sound of different anions
Ying Tu；(c, b) is response diagram of photoacoustic signal of the molecular probe at 680nm to various concentration fluorine ion.
Fig. 5 is photoacoustic signal of the molecular probe at 680nm in the embodiment of the present invention 5 to containing various concentration fluorine ion
The response diagram of toothpaste sample.
Specific implementation mode
The present invention provides a kind of molecular probe and the preparation method and application thereof, for make the purpose of the present invention, technical solution and
Effect is clearer, clear, and the present invention is described in more detail below.It should be appreciated that specific embodiment described herein,
It is only used to explain the present invention, be not intended to limit the present invention.
The present invention provides a kind of molecular probe preferred embodiments, wherein the structural formula of the molecular probe is as follows：
Wherein,R=-CH3Or-CH2-CH3
WhenWhen, the molecular probe of above structure of the present invention is with naphthalimide
Precursor structure, the precursor structure are fluorescent chromophore, have strong electron-withdrawing ability；Its 4 are the phenol hydroxyl protected containing silylation
The electron-donating group of base, the molecular probe are broken silicon oxygen bond in the presence of fluorine ion, slough t-butylsilane group so that
The fluorescence of the molecular probe declines, and ultraviolet absorption peak red shift occurs new absorption near infrared region, new photoacoustic signal occurs；
And as fluorinion concentration increases, newly generated absorption also gradually increases.
Preferably, the structural formula of the molecular probe is as follows：
The molecular probe of above structure of the present invention, using naphthalimide as precursor structure, which sends out for fluorescence
Color group has strong electron-withdrawing ability；Its 4 is, containing the electron-donating group with phenol, the phenolic hydroxyl group of the molecular probe are in fluorine
Deprotonation occurs in the presence of ion and sloughs phenolic hydroxyl group hydrogen so that the fluorescence of the molecular probe declines, ultraviolet absorption peak red shift,
Occur new absorption near infrared region, new photoacoustic signal occurs；And as fluorinion concentration increases, it is newly generated absorption also by
It is cumulative strong.
The present invention also provides a kind of preparation methods of molecular probe as described above, wherein works as R1When=- H, including step
Suddenly：
A, by 4- bromo- 1,8- naphthalic anhydrides and ethylenediamine (such as N, N- dimethyl-ethylenediamine or N, N- diethyl ethylenediamines)
It is dissolved in organic solvent (such as ethyl alcohol), and is stirred 12-24 hours at 25-50 DEG C and (it is small preferably, to stir 12 at 40 DEG C
When), it is cooled to room temperature, obtains molecular probe intermediate 1 (white crystal)；
B, in the anhydrous acetonitrile existing for acid chloride (II) and tri-o-tolyl phosphine, using 4- acetoxy-styrenes
Processing is alkylated to the molecular probe intermediate 1, obtains molecular probe intermediate 2 (dark yellow solid)；
C, place is hydrolyzed in basic solvent (such as the tetrahydrofuran solution of alkalinity) in the molecular probe intermediate 2
Reason, obtains molecular probe (orange/yellow solid).
The present invention, for raw material, successively passes through acylation reaction, alkylated reaction, hydrolysis with bromo- 1, the 8- naphthalic anhydrides of 4-
Molecular probe is finally made in reaction.The present invention synthetic method is simple, and synthesis condition is not harsh, easy to operate.
The present invention also provides a kind of preparation methods of molecular probe as described above, wherein when
When, including step：
A, by 4- bromo- 1,8- naphthalic anhydrides and ethylenediamine (such as N, N- dimethyl-ethylenediamine or N, N- diethyl ethylenediamines)
It is dissolved in organic solvent (such as ethyl alcohol), and is stirred 12-24 hours at 25-50 DEG C and (it is small preferably, to stir 12 at 40 DEG C
When), it is cooled to room temperature, obtains molecular probe intermediate 1 (white crystal)；
B, in the anhydrous acetonitrile existing for acid chloride (II) and tri-o-tolyl phosphine, using 4- acetoxy-styrenes
Processing is alkylated to the molecular probe intermediate 1, obtains molecular probe intermediate 2 (dark yellow solid)；
C, by the molecular probe intermediate 2 in basic solvent (such as the tetrahydrofuran solution of alkalinity)
It is hydrolyzed, obtains molecular probe (orange/yellow solid)；
D, the molecular probe is carried out at silanization in strong basicity solvent (tetrahydrofuran solution of such as sodium hydroxide)
Reason, obtains silylation molecular probe.The wherein described silane is tertiary butyl chloride diphenyl silane or tertiary butyl chloride dimethylsilane.
The present invention, for raw material, successively passes through acylation reaction, alkylated reaction, hydrolysis with bromo- 1, the 8- naphthalic anhydrides of 4-
Molecular probe is finally made in reaction, silanization treatment.The present invention synthetic method is simple, and synthesis condition is not harsh, operation side
Just.
The present invention also provides a kind of application of molecular probe as described above in detecting fluorine ion；Specifically, described
The method of detection can be one kind in ultraviolet colorimetric method, fluorescence imaging method, photoacoustic imaging method.Molecular probe of the present invention can be real
Existing ultraviolet colorimetric method, fluorescence imaging and photoacoustic imaging accurately detect fluorine ion, high sensitivity；Fluoride in Toothpaste ion can also be detected
Content, have a good application prospect in fluorine ion context of detection.
Below by embodiment, the present invention is described in detail.
Embodiment 1
Molecular probe 2- (6- (4-Vinyl phenol base) -1,3- dioxo -1H- benzos [de] isoquinolin -2 (3H)-yl) -
The synthetic route chart of the preparation of N, N- diethyl ethanamine, the molecular probe is as shown in Figure 1a, wherein EtOH is ethyl alcohol, Pd
(OAc)2For acid chloride (II), (o-tol)3P is tri-o-tolyl phosphine, Et3N is triethylamine, and MeCN is acetonitrile, and NaOH is hydrogen-oxygen
Change sodium, HCl is hydrochloric acid, and THF is tetrahydrofuran.The preparation process of the molecular probe is as follows：
A, bromo- 1, the 8- naphthalenedicarboxylic acids (1.0g) of 4- and N, N- diethyl ethylenediamine (1.0mL) are dissolved in ethyl alcohol (15mL)
And it is stirred 12 hours at 40 DEG C.Precipitation is collected by filtration, with acetone/ethanol (volume ratio 9:1) it recrystallizes, obtains white crystal,
As molecular probe intermediate 1 (yield 82.1%).
B, above-mentioned white crystal (500mg) is added in round-bottomed flask, and acid chloride (II) (20mg) and three neighbours is added
Mixed solvent (triethylamine 5mL/ acetonitrile 15mL) is then added in the mixture of tolylphosphine (1.0mL).Under nitrogen atmosphere, to
4- acetoxy-styrenes (2.0mL) are added in the reaction system, and reaction temperature is maintained at 105 DEG C, and reaction stops reaction two days later.
It is cooled to room temperature, uses CH2Cl2/H2O is extracted twice, and organic layer saturated brine is stripped and is evaporated in vacuo.Using silica gel post separation
Purification, eluant, eluent are acetone/petroleum ether (1/4, Rf=0.4), obtain dark yellow solid, as 2 (yield of molecular probe intermediate
For 68.0%).
C, above-mentioned dark yellow solid (100mg) and THF (3.0mL) are dissolved in round-bottomed flask, are placed in ice bath and stir.It is accurate
This NaOH solution, is then added drop-wise in reaction solution by the methanol solution (0.5mol/L, 3mL) of standby NaOH in 5 minutes；Reaction 4
After hour, the HCl solution (3mL, 0.5mol/L) of precooling is added drop-wise to above-mentioned reaction solution, is kept for 20 minutes, is collected by filtration orange
Color precipitates, as molecular probe (yield 40.0%).Hydrogen spectrum is carried out to the molecular probe to measure, obtain by nuclear magnetic resonance apparatus
It is as shown in Figure 1 d to its hydrogen nuclear magnetic resonance spectrogram；The uv absorption spectra of the molecular probe is as shown in Figure 1 b, wherein 430nm
For its maximum absorption wavelength；The fluorescence spectra of the molecular probe is as illustrated in figure 1 c, wherein 625nm is its maximum fluorescence emission
Wavelength.
Embodiment 2
Measure response of the molecular probe to fluorine ion
Prepare the DMSO solution of 3mL molecular probes (0.01mM).The fluoride solution of various concentration is added drop-wise to probe solution
In, while measuring probe A625nm/A430nmRatio, characterized by ultraviolet-uisible spectrophotometer and fluorescence spectrum.Such as figure
Shown in 2a, in molecular probe solution be added fluorine ion after, absorbance of the molecular probe at 430nm with fluorinion concentration increasing
It is big gradually to weaken；Occur a new absorption peak at 500~750nm simultaneously, and occurs maximum absorption band at 630nm, and
The absorbance of the position is gradually increased with the increase of fluorinion concentration；The A of molecular probe625nm/A430nmRatio and fluorine ion it is dense
Spend it is in a linear relationship, slope be 0.0114 (R2=0.9866).As shown in Figure 2 b, in fluorescence titration experiment, can be observed point
The fluorescence intensity of sub- probe increases with fluorinion concentration and is declined.
Embodiment 3
Measure selectivity of the molecular probe to fluorine ion
Prepare the DMSO solution of 3mL molecular probes (0.01mM).By (being respectively KI, NaH by corresponding salt2PO4,
NaHCO3, NaAcO, NaCl, NaNO2, MeCN, Na2SO4And KF) be dissolved in deionized water and prepare various anion solutions (I-,
H2PO4 -, HCO3 -, AcO-, Cl-, NO2 -, CN-, SO4 2-And F-, 1.0mM).Then, the anion solutions of 40 equivalents (equiv) are added
Enter into probe solution, is detected by UV absorption and fluorescence spectrum.As shown in Fig. 3 (a, b), 1-11 points in abscissa
Blank, I are not represented-, H2PO4 -, HCO3 -, AcO-, Cl-, NO2 -, CN-, SO4 2-, tetrabutyl ammonium fluoride (TBAF) and F-.Such as Fig. 3 a institutes
Show, only in F-Addition under, the absorption intensity of molecular probe is significantly increased at 645nm, and is visually observed probe
Apparent color change occurs for solution：Become blue from yellow.As shown in Figure 3b, F-It is capable of the fluorescence of apparent quencher molecule probe
Intensity.It is highly selective to show that the molecular probe has the detection of fluorine ion.
Embodiment 4
Molecular probe detects the application of anion in photoacoustic imaging method
Under the same conditions, control group is set up：Molecular probe adds fluorine ion group and molecular probe to add other ions (F-,
I-, H2PO4 -, HCO3 -, AcO-, Cl-, NO2 -, CN-, SO4 2-) group；Photoacoustic signal is detected at 680nm, and by changing fluorine ion
Concentration (0-1.4mM) detects probe photoacoustic signal situation of change at 680nm.As shown in Fig. 4 (a, b), in the feelings of not fluorine ion
Under condition, molecular probe is at 680nm almost without photoacoustic signal (PA680nm)；As shown in Fig. 4 (c, d), photoacoustic signal is with fluorine ion
The increase of concentration and enhance；As shown in figure 4d, PA680 is linear related within the scope of 0-1.4mM to fluorinion concentration.
Embodiment 5
The practical application of molecular probe
Establish toothpaste model：Fluoride solution is added in no fluorine toothpaste, and obtains and contains different F-The toothpaste of concentration
Sample；Then molecular probe is added in above-mentioned toothpaste sample, it is to be detected.The toothpaste sample of probe will have been added to be placed directly within optoacoustic
In Image-forming instrument, the photoacoustic signal at 680nm is detected.As shown in figure 5, photoacoustce signal intensity with the increase of fluorinion concentration and
Enhancing.
In conclusion a kind of molecular probe of present invention offer and the preparation method and application thereof, molecular probe energy of the invention
Enough realize that ultraviolet colorimetric method, fluorescence imaging and photoacoustic imaging accurately detect fluorine ion, high sensitivity；Fluoride in Toothpaste can also be detected
The content of ion has a good application prospect in fluorine ion context of detection；In addition, the synthetic method letter of molecular probe of the present invention
Single, synthesis condition is not harsh, easy to operate.
It should be understood that the application of the present invention is not limited to the above for those of ordinary skills can
With improvement or transformation based on the above description, all these modifications and variations should all belong to the guarantor of appended claims of the present invention
Protect range.
Claims (10)
1. a kind of molecular probe, which is characterized in that the structural formula of the molecular probe is as follows：Its
In,R=-CH3Or-CH2-CH3。
2. a kind of preparation method of molecular probe as described in claim 1, which is characterized in that work as R1When=- H, including step：
A, by 4- bromo- 1,8- naphthalic anhydrides dissolve in organic solvent with ethylenediamine, and stirring 12-24 is small at 25-50 DEG C
When, it is cooled to room temperature, obtains molecular probe intermediate 1；
B, in the anhydrous acetonitrile existing for acid chloride (II) and tri-o-tolyl phosphine, using 4- acetoxy-styrenes to institute
It states molecular probe intermediate 1 and is alkylated processing, obtain molecular probe intermediate 2；
C, the molecular probe intermediate 2 is hydrolyzed in basic solvent, obtains molecular probe.
3. the preparation method of molecular probe according to claim 2, which is characterized in that in step A, the ethylenediamine is N,
N- dimethyl-ethylenediamines or N, N- diethyl ethylenediamines.
4. the preparation method of molecular probe according to claim 2, which is characterized in that in step C, the basic solvent is
The tetrahydrofuran solution of alkalinity.
5. a kind of preparation method of molecular probe as described in claim 1, which is characterized in that when
When, including step：
A, by 4- bromo- 1,8- naphthalic anhydrides dissolve in organic solvent with ethylenediamine, and stirring 12-24 is small at 25-50 DEG C
When, it is cooled to room temperature, obtains molecular probe intermediate 1；
B, in the anhydrous acetonitrile existing for acid chloride (II) and tri-o-tolyl phosphine, using 4- acetoxy-styrenes to institute
It states molecular probe intermediate 1 and is alkylated processing, obtain molecular probe intermediate 2；
C, the molecular probe intermediate 2 is hydrolyzed in basic solvent, obtains molecular probe；
D, silanization treatment is carried out to the molecular probe in strong basicity solvent, obtains silylation molecular probe.
6. the preparation method of molecular probe according to claim 5, which is characterized in that in step A, the ethylenediamine is N,
N- dimethyl-ethylenediamines or N, N- diethyl ethylenediamines.
7. the preparation method of molecular probe according to claim 5, which is characterized in that in step C, the basic solvent is
The tetrahydrofuran solution of alkalinity.
8. the preparation method of molecular probe according to claim 5, which is characterized in that in step D, the strong basicity solvent
For the tetrahydrofuran solution of sodium hydroxide.
9. the preparation method of molecular probe according to claim 5, which is characterized in that in step D, silane is tertiary butyl chloride
Diphenyl silane or tertiary butyl chloride dimethylsilane.
10. a kind of application of molecular probe as described in claim 1 in detecting fluorine ion.
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