CN115677592B - Amino coordination type high-selectivity mercury ion fluorescent probe, preparation method and application - Google Patents
Amino coordination type high-selectivity mercury ion fluorescent probe, preparation method and application Download PDFInfo
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- CN115677592B CN115677592B CN202211379660.6A CN202211379660A CN115677592B CN 115677592 B CN115677592 B CN 115677592B CN 202211379660 A CN202211379660 A CN 202211379660A CN 115677592 B CN115677592 B CN 115677592B
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- compound
- mercury
- fluorescent probe
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- probe
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- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 45
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title abstract description 5
- 238000002360 preparation method Methods 0.000 title description 4
- -1 mercury ions Chemical class 0.000 claims abstract description 64
- 229910052753 mercury Inorganic materials 0.000 claims abstract description 63
- 239000000523 sample Substances 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 9
- 238000012216 screening Methods 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000012043 crude product Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000012535 impurity Substances 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 239000012472 biological sample Substances 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- 238000000799 fluorescence microscopy Methods 0.000 claims description 3
- 238000003828 vacuum filtration Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000007853 buffer solution Substances 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims 3
- DPZSNGJNFHWQDC-ARJAWSKDSA-N (z)-2,3-diaminobut-2-enedinitrile Chemical compound N#CC(/N)=C(/N)C#N DPZSNGJNFHWQDC-ARJAWSKDSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 241000252212 Danio rerio Species 0.000 abstract description 9
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 abstract description 4
- 238000012632 fluorescent imaging Methods 0.000 abstract description 3
- 125000003277 amino group Chemical group 0.000 abstract 1
- 238000012921 fluorescence analysis Methods 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 23
- 210000004027 cell Anatomy 0.000 description 14
- 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 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 239000007995 HEPES buffer Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 7
- 230000008859 change Effects 0.000 description 6
- 238000001514 detection method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 5
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 5
- 239000005695 Ammonium acetate Substances 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 229940043376 ammonium acetate Drugs 0.000 description 5
- 235000019257 ammonium acetate Nutrition 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 238000002189 fluorescence spectrum Methods 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000003384 imaging method Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 3
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 3
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 3
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 3
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 229910001424 calcium ion Inorganic materials 0.000 description 3
- 229910001430 chromium ion Inorganic materials 0.000 description 3
- 229910001431 copper ion Inorganic materials 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229910001447 ferric ion Inorganic materials 0.000 description 3
- 229910001448 ferrous ion Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910001425 magnesium ion Inorganic materials 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 229910001453 nickel ion Inorganic materials 0.000 description 3
- 229910001414 potassium ion Inorganic materials 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 229910001415 sodium ion Inorganic materials 0.000 description 3
- JJWSNOOGIUMOEE-UHFFFAOYSA-N Monomethylmercury Chemical compound [Hg]C JJWSNOOGIUMOEE-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 2
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 2
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000004624 confocal microscopy Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000002073 fluorescence micrograph Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- RVPVRDXYQKGNMQ-UHFFFAOYSA-N lead(2+) Chemical compound [Pb+2] RVPVRDXYQKGNMQ-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 208000008763 Mercury poisoning Diseases 0.000 description 1
- 206010027439 Metal poisoning Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 210000004102 animal cell Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 231100000693 bioaccumulation Toxicity 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 238000004993 emission spectroscopy Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011896 sensitive detection Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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CN202211379660.6A CN115677592B (en) | 2022-11-04 | 2022-11-04 | Amino coordination type high-selectivity mercury ion fluorescent probe, preparation method and application |
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CN202211379660.6A CN115677592B (en) | 2022-11-04 | 2022-11-04 | Amino coordination type high-selectivity mercury ion fluorescent probe, preparation method and application |
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CN115677592A CN115677592A (en) | 2023-02-03 |
CN115677592B true CN115677592B (en) | 2023-05-02 |
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Publication number | Priority date | Publication date | Assignee | Title |
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CN107056651B (en) * | 2017-02-24 | 2018-10-30 | 广东工业大学 | A kind of tetraphenyl ethylene-diaminomaleonitrile derivative and preparation method thereof, application |
CN114249740B (en) * | 2021-11-23 | 2023-04-14 | 南京林业大学 | Tanshinone benzimidazole type fluorescent probe and preparation method and application thereof |
CN115181068B (en) * | 2022-07-18 | 2023-10-27 | 南京师范大学 | TPI derivative fluorescent probe and application thereof in preparation of copper ion detection reagent |
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Application publication date: 20230203 Assignee: Shandong Zhimeifeng Technology Co.,Ltd. Assignor: BIOLOGY INSTITUTE OF SHANDONG ACADEMY OF SCIENCES Contract record no.: X2024980013565 Denomination of invention: A highly selective mercury ion fluorescent probe with amino coordination, preparation method and application Granted publication date: 20230502 License type: Open License Record date: 20240906 Application publication date: 20230203 Assignee: Shandong Huize Biopharmaceutical Co.,Ltd. Assignor: BIOLOGY INSTITUTE OF SHANDONG ACADEMY OF SCIENCES Contract record no.: X2024980013519 Denomination of invention: A highly selective mercury ion fluorescent probe with amino coordination, preparation method and application Granted publication date: 20230502 License type: Open License Record date: 20240906 |
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