CN117865884A - Quinoline fluorescent compound and preparation method and application thereof - Google Patents
Quinoline fluorescent compound and preparation method and application thereof Download PDFInfo
- Publication number
- CN117865884A CN117865884A CN202311697026.1A CN202311697026A CN117865884A CN 117865884 A CN117865884 A CN 117865884A CN 202311697026 A CN202311697026 A CN 202311697026A CN 117865884 A CN117865884 A CN 117865884A
- Authority
- CN
- China
- Prior art keywords
- fluorescent compound
- quinoline
- pharmaceutically acceptable
- acceptable salt
- cooh
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title claims abstract description 61
- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 238000012984 biological imaging Methods 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical group [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229940072107 ascorbate Drugs 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
- 239000011668 ascorbic acid Substances 0.000 claims description 2
- 229940077388 benzenesulfonate Drugs 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 2
- 229940001468 citrate Drugs 0.000 claims description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 2
- 229940001447 lactate Drugs 0.000 claims description 2
- 229940049920 malate Drugs 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 2
- 229960001860 salicylate Drugs 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- 239000012216 imaging agent Substances 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract 1
- 231100000053 low toxicity Toxicity 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 35
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 15
- 238000012544 monitoring process Methods 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 238000001291 vacuum drying Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229960001701 chloroform Drugs 0.000 description 6
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 6
- 238000003384 imaging method Methods 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 6
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 230000001376 precipitating effect Effects 0.000 description 4
- 230000003013 cytotoxicity Effects 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000003745 diagnosis Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000000799 fluorescence microscopy Methods 0.000 description 3
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000012632 fluorescent imaging Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- AKYHKWQPZHDOBW-UHFFFAOYSA-N (5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl)-(6-methoxyquinolin-4-yl)methanol Chemical compound OS(O)(=O)=O.C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 AKYHKWQPZHDOBW-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 239000001576 FEMA 2977 Substances 0.000 description 1
- 102000006833 Multifunctional Enzymes Human genes 0.000 description 1
- 108010047290 Multifunctional Enzymes Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 238000005415 bioluminescence Methods 0.000 description 1
- 230000029918 bioluminescence Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 238000004624 confocal microscopy Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- REIZEQZILPXYKS-UHFFFAOYSA-N methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1B1OC(C)(C)C(C)(C)O1 REIZEQZILPXYKS-UHFFFAOYSA-N 0.000 description 1
- MSLICLMCQYQNPK-UHFFFAOYSA-N n-(4-bromophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(Br)C=C1 MSLICLMCQYQNPK-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 229960003110 quinine sulfate Drugs 0.000 description 1
- -1 quinoline compound Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000011897 real-time detection Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- 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
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
-
- 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
- G01N21/6458—Fluorescence microscopy
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Immunology (AREA)
- General Physics & Mathematics (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pathology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
The invention discloses a quinoline fluorescent compound, a preparation method and application thereof, and belongs to the field of biological medicines. The invention provides a novel quinoline fluorescent compound with a structure shown in a general formula I or pharmaceutically acceptable salt thereof, which has low toxicity and longer emission wavelength and has important significance in the field of biological imaging.
Description
Technical Field
The invention relates to a quinoline fluorescent compound, a preparation method and application thereof, belonging to the field of biological medicine.
Background
Imaging is an indispensable tool in the diagnosis, treatment and research of diseases. Fluorescent imaging technology has also received extensive attention from researchers with the development of modern medicine, and it is desirable to develop an imaging molecular tool that can help doctors visualize the expression of specific molecules, cells and biological processes. The bio-fluorescence imaging has the characteristics of high sensitivity, simple implementation, real-time detection, good compatibility with biological samples and the like, and has become one of the most novel and powerful biochemical technologies for monitoring and tracking targets in biological systems.
Quinoline is a double-ring heterocyclic ring system formed by fusing six-membered benzene rings and pyridine, is a multifunctional pharmacophore, and has wide biological activity such as Alzheimer disease resistance, diabetes resistance, antibiosis, anti-inflammatory, anticancer, antimalarial and the like. In addition, quinoline has a larger conjugated system, shows pi-pi electron transition characteristics, is a potential fluorophore with good fluorescence performance, and partial derivative thereof has been used in the aspects of metal ion detection, biosensor and the like.
Therefore, it is of great importance to explore design strategies for optimizing the fluorescence properties of quinoline frameworks and to obtain novel fluorescent molecules capable of visualizing disease development and treatment processes.
Disclosure of Invention
The invention provides a novel quinoline compound fluorescent molecule and application thereof in development of fluorescent probes and biological fluorescent imaging technology.
The invention mainly solves the technical problems through the following technical scheme.
[ Compound ]
Novel quinoline fluorescent compounds with a structure shown in general formula I or pharmaceutically acceptable salts thereof:
wherein,
R 1 selected from halogen (F, cl, br, I), C1-4 alkoxy, aryl
R 2 Selected from-CN, -COOR 4 ；
R 3 Selected from H, -OR ', -COOR', R 4 R ', R' are each independently selected from H, C1-4 alkyl.
In one embodiment of the invention, R 1 Specifically selected from-Br, -OCH 3 ，R 2 Specifically selected from-CN-COOH。
In one embodiment of the invention, the novel quinoline fluorescent compound has a structure shown in a formula II:
wherein R is 3 Independently selected from-COOMe, -COOH, -H, -OH, R 2 Independently selected from-CN, -COOH.
In one embodiment of the invention, the novel quinoline fluorescent compound has a structure shown in a formula II:
wherein R is 3 Independently selected from-COOMe, -COOH, -H, -OH, R 2 Independently selected from-CN, -COOH.
In one embodiment of the present invention, most preferably, the specific structure of a novel class of quinoline fluorescent compounds is:
in one embodiment of the invention, the pharmaceutically acceptable salt comprises an inorganic or organic salt; wherein the inorganic salt comprises hydrochloride, hydrobromide, hydroiodide, perchlorate, sulfate, bisulfate, nitrate, phosphate, and acid phosphate; the organic salt is selected from formate, acetate, trifluoroacetate, propionate, pyruvate, glycolate, oxalate, malonate, succinate, glutarate, fumarate, maleate, lactate, malate, citrate, tartrate, methanesulfonate, ethanesulfonate, benzenesulfonate, salicylate, p-toluenesulfonate, ascorbate.
[ Synthesis method ]
The invention also provides a preparation method of the novel quinoline fluorescent compound shown in the general formulas I and II (the preparation method of the quinoline fluorescent compound shown in the general formula III is the same as the general formula II), and the method is implemented by the following reaction scheme:
synthesis scheme 1
Reagents and conditions: a) Phosphorus oxychloride, N, N-dimethylformamide, at 90 ℃ for 16h; b) 70% acetic acid, 90 ℃ for 12h; c) Absolute ethanol, pyridine, 75 ℃ for 4h
Dropping phosphorus oxychloride into DMF under ice bath condition, stirring for 30 min at room temperature, adding 1-1 into the mixed solution, refluxing in an oil bath at 90 ℃ for 16h, after monitoring reaction, dropping the reaction liquid into ice water, precipitating solid, suction-filtering, washing the solid with water, collecting the solid, vacuum drying to obtain compound 1-2, dissolving 1-2 into 70% acetic acid solution, placing the reaction liquid into an oil bath at 90 ℃ for heating and refluxing for 14h, after monitoring reaction, suction-filtering the solid, washing with water, collecting the solid, vacuum drying to obtain compound 1-3, taking 1-3 to dissolve into absolute ethyl alcohol, dropping 3 drops of pyridine, then adding malononitrile, placing the solution into an oil bath at 75 ℃ for refluxing for 4h, after monitoring reaction, suction-filtering the solid, washing with absolute ethyl alcohol, collecting the solid, and vacuum drying to obtain compound I-4.
Synthesis scheme 2
Reagents and conditions: a) Trichloromethane, pyridine, 60 ℃ for 48h;
dissolving 1-3 in chloroform, dripping 3 drops of pyridine, adding cyanoacetic acid, placing the solution in an oil bath at 60 ℃ for reflux for 48 hours, monitoring the reaction completion, filtering the solid, washing the solid with absolute ethyl alcohol, collecting the solid, and drying in vacuum to obtain the compound 2-1.
Synthesis scheme 3
Reagents and conditions: a) 1,1' -Didiphenylphosphino ferrocene palladium dichloride, potassium carbonate, N, N-Dimethylformamide (DMF), H 2 O,80 ℃ for 4 hours; b) Phosphorus oxychloride, N-Dimethylformamide (DMF), 8h; c) Acetic acid at 90 ℃ for 16h; d) Lithium hydroxide, tetrahydrofuran (THF), H 2 O，24h；
Dissolving 3-1, 3-2, potassium carbonate, 1' -bis-diphenylphosphino ferrocene palladium dichloride in DMF and H 2 Substitution of N in the O mixed solution (20:1) 2 Reflux the solution in an oil bath at 80 ℃ for 4 hours, monitoring the reaction completion, adding ethyl acetate and saturated saline water for extraction, collecting an organic phase, drying anhydrous sodium sulfate, concentrating the organic phase to obtain a crude product, purifying by column chromatography to obtain a compound 3-3, dripping phosphorus oxychloride into DMF under ice bath conditions, stirring for 30 minutes at room temperature, adding 3-3 into a mixed solution, placing the solution in an oil bath at 90 ℃ for reflux for 8 hours, monitoring the reaction completion, dripping the reaction liquid into ice water, precipitating solids, suction-filtering, washing with water, collecting solids, purifying by column chromatography to obtain a compound 3-4, dissolving the 3-4 in acetic acid solution, placing the solution in an oil bath at 90 ℃ for reflux for 16 hours, monitoring the reaction completion, suction-filtering solids, washing with water, collecting solids, vacuum-drying to obtain a compound 3-5, dissolving the compound 3-5 in THF, adding a lithium hydroxide aqueous solution under ice bath conditions, stirring for 24 hours at room temperature, monitoring the reaction completion, vacuum-drying to remove the solvent, dissolving, adding water for suction-filtering, adjusting the pH to 1M to 2, freezing the solution to obtain a solid, and drying the compound to obtain a hydrochloric acid solution.
Synthesis scheme 4
As in step c of scheme 1.
Synthesis scheme 5
As in step a of FIG. 2.
[ use ]
The invention also provides application of the novel quinoline fluorescent compound or the pharmaceutically acceptable salt thereof in the field of fluorescent probe preparation.
The invention also provides application of the quinoline fluorescent compound or the pharmaceutically acceptable salt thereof in the field of biological imaging.
The invention also provides a biological imaging reagent which contains the fluorescent compound or pharmaceutically acceptable salt thereof and pharmaceutic adjuvant.
The effective effects are as follows:
the novel quinoline fluorescent compound has the maximum excitation wavelength of 350-450nm and the maximum emission wavelength of 550-630nm, has good fluorescence performance, and is successfully applied to tumor cell fluorescence imaging. In addition, the result of the cytotoxicity experiment shows that the kit has lower cytotoxicity, can provide a new molecular tool for integration of bioluminescence imaging and diagnosis and treatment, and has important significance for diagnosis, treatment and research processes of related tumor diseases.
Drawings
FIG. 1 is a graph showing the results of the test for inhibition of human Peripheral Blood Mononuclear Cell (PBMC) activity by the compounds of example 3.
FIG. 2 is a graph showing the results of a cell imaging test of the compound of example 4 on U2OS cells
Detailed Description
The synthesis process according to the present application comprises the steps of:
unless specifically indicated, methods and apparatus employed in the present invention are well known in the art.
Example 1
Reagents and conditions: a) Phosphorus oxychloride, N-Dimethylformamide (DMF), 90 ℃ for 16h; b) 70% acetic acid, 90 ℃ for 12h; c) Absolute ethyl alcohol, pyridine, 75 ℃ for 4 hours;
dropping phosphorus oxychloride (32 g,0.210 mol) into DMF (4.3 g,0.058 mol) under ice bath condition, stirring at room temperature for 30 min, then adding 3-bromo-N-acetanilide 1-1 (5 g,0.023 mol) into the mixed solution, refluxing in an oil bath pot at 90 ℃ for 16h, monitoring that the reaction is complete, dropping the reaction liquid into ice water, precipitating solid, suction filtering, washing the solid with water, collecting the solid, vacuum drying to obtain the compound 1-2 (2.2 g, yield 35%)
1-2 (2.0 g, 0.007mol) was weighed and dissolved in 20ml of 70% acetic acid solution, the reaction solution was placed in an oil bath at 90 ℃ and heated under reflux for 14h, after the reaction was monitored to be complete, the solid was suction filtered, washed with water, the solid was collected and dried under vacuum to give compound 1-3 (1.3 g, yield 68%).
1-3 (1.0 g,0.004 mol) was dissolved in 10mL of absolute ethanol, 3 drops of pyridine were added dropwise, then malononitrile (0.5 g,0.008 mol) was added, the solution was put into an oil bath at 75℃for 4 hours under reflux, after the reaction was monitored to completion, the solid was suction filtered, washed with absolute ethanol, the solid was collected and dried under vacuum to give yellow solid I-2 (0.9 g, yield 73%).
1 H NMR(400MHz,DMSO-d 6 )δ12.43(s,1H),8.71(s,1H),8.34(s,1H),7.80(d,J＝8.4Hz,1H),7.52(d,J＝1.6Hz,1H),7.44(dd,J＝8.4,1.6Hz,1H).MS(ESI):m/z calcd for C 13 H 7 BrN 3 O[M+H] + 299.97,found 299.85.
Example 2
Reagents and conditions: a) Trichloromethane, pyridine, 60 ℃ for 48h;
1-3 (1.0 g,0.004 mol) was dissolved in 10mL of chloroform, 3 drops of pyridine were added dropwise, then cyanoacetic acid (0.7 g,0.008 mol) was added, the solution was put into an oil bath at 60℃for reflux for 48 hours, after the reaction was monitored to be complete, the solid was suction-filtered, washed with absolute ethanol, the solid was collected and dried under vacuum to obtain Compound I-4 (0.773 g, yield 62%).
1 H NMR(600MHz,DMSO-d 6 )δ12.34(s,1H),8.79(s,1H),8.41(s,1H),7.78(d,J＝8.4Hz,1H),7.52(d,J＝1.8Hz,1H),7.42(dd,J＝8.4,1.8Hz,1H).MS(ESI):m/z calcd for C 13 H 8 BrN 2 O 3 [M+H] + 318.96,found 319.00.
Example 3
Reagents and conditions: a) 1,1' -Didiphenylphosphino ferrocene palladium dichloride, potassium carbonate, N, N-Dimethylformamide (DMF), H 2 O,80 ℃ for 4 hours; b) Phosphorus oxychloride, N-Dimethylformamide (DMF), 8h; c) Acetic acid at 90 ℃ for 16h; d) Lithium hydroxide, tetrahydrofuran (THF), H 2 O，24h；
4-Methoxyformylphenylboronic acid pinacol ester 3-1 (3.0 g, 0.01102 mol), p-bromoacetanilide 3-2 (2.0 g, 0.09 mol), potassium carbonate (2.6 g, 0.0111 mol), 1' -bis-diphenylphosphino ferrocene palladium dichloride (0.7 g,0.0009 mol) were dissolved in 20mL DMF and 1mL H 2 Substitution of N in the mixed solution of O 2 Reflux the solution in 80 deg.c oil bath for 4 hr, monitoring the reaction, extracting with ethyl acetate and saturated salt water, collecting organic phase, drying over anhydrous sodium sulfate, concentrating the organic phase to obtain crude product, and purifying by column chromatography to obtain compound 3-3 (1.96 g, 77% yield)
Dropping phosphorus oxychloride (10.3 g,0.067 mol) into DMF (1.4 g,0.017 mol) under ice bath condition, stirring at room temperature for 30 min, adding 3-3 (2.0 g, 0.0070 mol) into the mixed solution, placing the solution into an oil bath pot at 90 ℃ for refluxing for 8h, monitoring that the reaction is complete, dropping the reaction solution into ice water, precipitating solid, suction filtering, washing with water, collecting solid, purifying by column chromatography to obtain the compound 3-4 (0.489 g, yield 20%)
Dissolving 3-4 (1.0 g, 0.003mol) in 10mL of acetic acid solution, placing the solution in an oil bath at 90 ℃ for heating reflux for 16h, monitoring the complete reaction, filtering the solid, washing with water, collecting the solid, and drying in vacuum to obtain the compound 3-5 (0.831 g, yield 88%)
3-5 (1.0 g, 0.003mol) was dissolved in 5mL of tetrahydrofuran, 5mL of lithium hydroxide aqueous solution (2M) was added under ice bath conditions, stirred at room temperature for 24 hours, after monitoring the reaction completion, the solvent was removed by vacuum drying to give a solid, which was dissolved in water, pH was adjusted to 1 to 2 with dilute hydrochloric acid, the solid was suction filtered, and freeze-dried to give compound 3-6 (8.9 g, yield 93%).
Example 4
Reagents and conditions: a) Absolute ethyl alcohol, pyridine, 75 ℃ for 4 hours;
3-5 (0.500 g, 0.002mol) was dissolved in 5mL of absolute ethanol, 3 drops of pyridine were added dropwise, then malononitrile (0.213 g, 0.003mol) was added, the solution was put into an oil bath at 75℃under reflux for 4 hours, after the reaction was monitored to completion, the solid was suction filtered, washed with absolute ethanol, the solid was collected and dried under vacuum to give Compound II-1 (0.399 g, yield 69%).
1 H NMR(600MHz,DMSO-d 6 )δ12.53(s,1H),8.82(s,1H),8.39(s,1H),8.31(d,J＝1.8Hz,1H),8.11(dd,J＝8.4,1.8Hz,2H),8.05(d,J＝8.4Hz,2H),7.93(d,J＝8.4Hz,2H),7.46(d,J＝8.4Hz,1H),3.88(s,3H).MS(ESI):m/z calcd for C 21 H 12 N 3 O 3 [M-H] - 355.10,found 354.05.
Example 5
Reagents and conditions: a) Trichloromethane, pyridine, 60 ℃ for 48h;
3-5 (0.500 g, 0.002mol) was dissolved in 5mL of chloroform, 3 drops of pyridine were added dropwise, then cyanoacetic acid (0.265 g, 0.003mol) was added, the solution was put into an oil bath at 60℃for reflux for 48 hours, after the reaction was monitored to completion, the solid was suction filtered, washed with absolute ethanol, the solid was collected and dried under vacuum to give Compound II-4 (0, 387g, 67% yield).
1 H NMR(600MHz,DMSO-d 6 )δ12.42(s,1H),8.90(s,1H),8.47-8.44(m,1H),8.25(d,J＝1.8Hz,1H),8.07-8.04(m,4H),7.93-7.91(m,2H),7.45(d,J＝9.0Hz,1H),3.88(s,3H).MS(ESI):m/z calcd for C 21 H 13 N 2 O 5 [M-H] - 373.09,found 373.00.
The following compounds were prepared by referring to the above-prepared methods except that the corresponding reaction compounds were appropriately replaced, to obtain different compounds, and the results are shown in table 1.
TABLE 1 characterization data results for different quinoline fluorescent compounds
Example 6: quinoline fluorescent compound spectral experimental test
1) Ultraviolet absorption spectrum experiment
1mg of the compound is weighed, 1M mother liquor is prepared by DMSO, 20 mu L of mother liquor is sucked by a pipette and placed in a cuvette, 180 mu LDMSO is added, and the mixture is uniformly mixed, and the ultraviolet absorption spectrum is measured.
2) Fluorescence emission spectrum
1mg of the compound was weighed, 1M mother liquor was prepared by DMSO, 20. Mu.L of mother liquor was removed by a pipette and placed in a cuvette, 180. Mu.L of LDMSO was added thereto, and the mixture was homogenized, and fluorescence emission spectra were measured using an ultraviolet absorption characteristic peak as an excitation wavelength.
The test results obtained in example 2 are shown in Table 2.
TABLE 2 spectral data of novel quinoline fluorescent compounds
Measurement of fluorescence Quantum yield Using quinine sulfate as Standard Compound
Example 7: compound inhibition human Peripheral Blood Mononuclear Cell (PBMC) Activity assay
1) Materials:
cell lines: PBMC (PBMCs)
Reagent: 1640 medium containing 10% fetal bovine serum and 1% penicillin/streptomycin, 96-well white bottom plate;
2) The process comprises the following steps: inoculating cells into transparent 96-well cell culture plate at 10000 cells/well density, wherein the volume of cell suspension in each well is 80 μL, and culturing at 37deg.C for 2 hr under 37+5% CO 2 . Then adding compound II-3 and compound II-4 with gradient concentration respectively. After three days, 20. Mu.L of CTG solution was added, and after 20 minutes at room temperature, the data were recorded using an Envision multifunctional enzyme-labeled instrument (Perkin Elmer) to calculate the relative viability of the cells.
3) Sample treatment: the samples were dissolved in DMSO and stored at-20 ℃, the concentration of DMSO in the final system being controlled within a range that does not affect the assay activity.
The test results obtained are shown in FIG. 1. From the graph, the compounds II-3 and II-4 show lower cytotoxicity and have potential application value in the aspect of cell imaging.
Example 8: cell imaging test of compounds in U2OS cells
Confocal microscopy.
U2OS cells: u2OS cells were cultured on glass dishes for 24 hours prior to treatment. The cells were incubated with 20. Mu.M of compounds II-3 and II-4, respectively, for 16 hours with U2OS, washed 3 times with PBS, fixed in 4% paraformaldehyde solution for 15 minutes, and washed with PBS. Cell images were obtained using a Nikon Ti2-E+A1 confocal microscope. As shown in fig. 2.
Analysis of results shows that: in U2OS cell fluorescence imaging, compound II-3 emits more intense blue light than II-4.
Claims (10)
1. Quinoline fluorescent compounds with a structure shown in a general formula I or pharmaceutically acceptable salts thereof,
wherein,
R 1 selected from halogen (F, cl, br, I), C1-4 alkoxy, aryl
R 2 Selected from-CN, -COOR 4 ；
R 3 Selected from H, -OR ', -COOR', R 4 R ', R' are each independently selected from H, C1-4 alkyl.
2. The quinoline fluorescent compound according to claim 1, wherein R 1 Specifically selected from-Br, -OCH 3 ，R 2 Specifically selected from-CN and-COOH.
3. The quinoline fluorescent compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein the novel quinoline fluorescent compound has a structure represented by formula ii:
wherein R is 3 Independently selected from-COOMe, -COOH, -H, -OH, R 2 Independently selected from-CN, -COOH.
4. The quinoline fluorescent compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein the novel quinoline fluorescent compound has a structure represented by formula ii:
wherein R is 3 Independently selected from-COOMe, -COOH, -H, -OH, R 2 Independently selected from-CN, -COOH.
5. The quinoline fluorescent compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein the novel quinoline fluorescent compound has the structure shown below:
6. the quinoline fluorescent compound according to any one of claims 1-5, wherein the pharmaceutically acceptable salt comprises an inorganic or organic salt; wherein the inorganic salt comprises hydrochloride, hydrobromide, hydroiodide, perchlorate, sulfate, bisulfate, nitrate, phosphate, and acid phosphate; the organic salt is selected from formate, acetate, trifluoroacetate, propionate, pyruvate, glycolate, oxalate, malonate, succinate, glutarate, fumarate, maleate, lactate, malate, citrate, tartrate, methanesulfonate, ethanesulfonate, benzenesulfonate, salicylate, p-toluenesulfonate, ascorbate.
7. The quinoline fluorescent compound according to any one of claims 1-6, wherein the quinoline fluorescent compound is excited at a wavelength of 200-800nm and emits fluorescent light at a wavelength of 400-800 nm.
8. Use of a fluorescent compound according to any one of claims 1 to 7 or a pharmaceutically acceptable salt thereof in the field of fluorescent probe preparation.
9. Use of a fluorescent compound according to any one of claims 1 to 7 or a pharmaceutically acceptable salt thereof in the field of preparation of a biological imaging agent.
10. A biological imaging agent comprising the fluorescent compound of any one of claims 1-7 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable adjuvant.
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