WO2015064786A1 - Colorant de cyanine pour le marquage de biomolécules et son procédé de préparation - Google Patents
Colorant de cyanine pour le marquage de biomolécules et son procédé de préparation Download PDFInfo
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- WO2015064786A1 WO2015064786A1 PCT/KR2013/009789 KR2013009789W WO2015064786A1 WO 2015064786 A1 WO2015064786 A1 WO 2015064786A1 KR 2013009789 W KR2013009789 W KR 2013009789W WO 2015064786 A1 WO2015064786 A1 WO 2015064786A1
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- DJQYYYCQOZMCRC-UHFFFAOYSA-N 2-aminopropane-1,3-dithiol Chemical group SCC(N)CS DJQYYYCQOZMCRC-UHFFFAOYSA-N 0.000 description 1
- OALHHIHQOFIMEF-UHFFFAOYSA-N 3',6'-dihydroxy-2',4',5',7'-tetraiodo-3h-spiro[2-benzofuran-1,9'-xanthene]-3-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 OALHHIHQOFIMEF-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- QVWAEZJXDYOKEH-UHFFFAOYSA-N 3-(3-hydroxyphenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=CC(O)=C1 QVWAEZJXDYOKEH-UHFFFAOYSA-N 0.000 description 1
- YQWPHBFLHAJVCG-UHFFFAOYSA-N 3-(4-sulfanylphenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(S)C=C1 YQWPHBFLHAJVCG-UHFFFAOYSA-N 0.000 description 1
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical compound ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 description 1
- IOMZCWUHFGMSEJ-UHFFFAOYSA-N 4-(azaniumylamino)benzenesulfonate Chemical compound NNC1=CC=C(S(O)(=O)=O)C=C1 IOMZCWUHFGMSEJ-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 238000011729 BALB/c nude mouse Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- SARCVPDCROTUOX-UHFFFAOYSA-O CC1(C)c(cc(cc2)[S](C)(O)(=O)=O)c2[N+](CCCCS(O)(=O)=O)=C1/C=C/C(CCC/C1=C\C=C(/C2(C)C)\N(CCCCS(O)(=O)=O)c(cc3)c2cc3S(O)(=O)=O)=C1Oc1ccc(CCC(NNc2nc(Cl)nc(Cl)n2)=O)cc1 Chemical compound CC1(C)c(cc(cc2)[S](C)(O)(=O)=O)c2[N+](CCCCS(O)(=O)=O)=C1/C=C/C(CCC/C1=C\C=C(/C2(C)C)\N(CCCCS(O)(=O)=O)c(cc3)c2cc3S(O)(=O)=O)=C1Oc1ccc(CCC(NNc2nc(Cl)nc(Cl)n2)=O)cc1 SARCVPDCROTUOX-UHFFFAOYSA-O 0.000 description 1
- FGQYETUNXAMWII-UHFFFAOYSA-O CC1(C)c(cccc2)c2[N+](CCCC[S](C)(O)(=O)=O)=C1/C=C/C(CCC/C1=C\C=C(/C2(C)C)\N(CCCCS(O)(=O)=O)c3c2cccc3)=C1Oc1ccc(CCC(NN)=O)cc1 Chemical compound CC1(C)c(cccc2)c2[N+](CCCC[S](C)(O)(=O)=O)=C1/C=C/C(CCC/C1=C\C=C(/C2(C)C)\N(CCCCS(O)(=O)=O)c3c2cccc3)=C1Oc1ccc(CCC(NN)=O)cc1 FGQYETUNXAMWII-UHFFFAOYSA-O 0.000 description 1
- CPRZSGPMXJEEHF-UHFFFAOYSA-O CCCN(/C(/C1(C)C)=C/C=C(\CCC2)/C(Sc3ccc(CCC(NN)=O)cc3)=C2/C=C/C(C2(C)C)=[N+](CCC)c3c2cccc3)c2c1cccc2 Chemical compound CCCN(/C(/C1(C)C)=C/C=C(\CCC2)/C(Sc3ccc(CCC(NN)=O)cc3)=C2/C=C/C(C2(C)C)=[N+](CCC)c3c2cccc3)c2c1cccc2 CPRZSGPMXJEEHF-UHFFFAOYSA-O 0.000 description 1
- 238000000018 DNA microarray Methods 0.000 description 1
- 101000760085 Daucus carota 21 kDa protein Proteins 0.000 description 1
- 238000009007 Diagnostic Kit Methods 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001251 acridines Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
- 229920000249 biocompatible polymer Polymers 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012888 bovine serum Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 150000001846 chrysenes Chemical class 0.000 description 1
- 238000010835 comparative analysis Methods 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 150000004775 coumarins Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical group C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 238000002675 image-guided surgery Methods 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229960002725 isoflurane Drugs 0.000 description 1
- 150000002518 isoindoles Chemical class 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000002493 microarray Methods 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000012474 protein marker Substances 0.000 description 1
- 239000012460 protein solution Substances 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000003753 real-time PCR Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
- A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
- A61K49/0032—Methine dyes, e.g. cyanine dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/08—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0066—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
- C09B23/086—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines more than five >CH- groups
Definitions
- cyanine dyes include indole structures as hetero rings and succinimidyl ester groups as reactors, but in recent years maleimide, amine, hydrazide ( Many substituents and reactors such as hydrazide) are used alone or in combination.
- An object of the present invention can be widely used in observing biomolecules in the fields of proteomics, optical molecular imaging, etc., and a novel near-infrared fluorescent cyanine compound which is easy to label biomolecules and a method of preparing the same. To provide.
- the present invention also provides a near-infrared fluorescent contrast agent composition
- a near-infrared fluorescent contrast agent composition comprising the cyanine compound represented by Formula 1 as an active ingredient.
- X is a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine,
- Absorption values at the absorption wavelength and the maximum wavelength of the synthesized dye were measured by Lambda 45 from Perkin Elmer, and emission values at the emission wavelength and the maximum emission wavelength were obtained using LS 55 from Perkin Elmer.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
La présente invention concerne un colorant de cyanine permettant de marquer par fluorescence diverses biomolécules, puisque le colorant de cyanine présente une intensité de fluorescence élevée dans une région de longueurs d'onde du proche infrarouge, présente une stabilité élevée dans des conditions aqueuses, reste stable pendant de longues périodes de coloration des biomolécules, et présente une excellente réactivité de liaison avec les biomolécules. Une composition de milieu de contraste, comprenant le colorant de cyanine selon la présente invention utilisé comme principe actif, peut être appliquée de manière plus efficace pour modifier le contraste et obtenir des images optiques de régions malades en étant administrée dans le corps.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/KR2013/009789 WO2015064786A1 (fr) | 2013-10-31 | 2013-10-31 | Colorant de cyanine pour le marquage de biomolécules et son procédé de préparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/KR2013/009789 WO2015064786A1 (fr) | 2013-10-31 | 2013-10-31 | Colorant de cyanine pour le marquage de biomolécules et son procédé de préparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2015064786A1 true WO2015064786A1 (fr) | 2015-05-07 |
Family
ID=53004374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2013/009789 WO2015064786A1 (fr) | 2013-10-31 | 2013-10-31 | Colorant de cyanine pour le marquage de biomolécules et son procédé de préparation |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2015064786A1 (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107266929A (zh) * | 2017-06-21 | 2017-10-20 | 四川大学 | 一类以菁染料荧光基团为母体骨架结构的近红外荧光染料及其制备方法与应用 |
| US20210347766A1 (en) * | 2020-05-08 | 2021-11-11 | On Target Laboratories, LLC | Methods of manufacture and synthesis of fluorescent dye compounds and uses thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004006963A1 (fr) * | 2002-07-12 | 2004-01-22 | Beth Israel Deaconess Medical Center | Substances fluorescentes infrarouges conjuguees permettant de detecter la mort cellulaire |
| US6828116B1 (en) * | 1998-06-11 | 2004-12-07 | Amersham Biosciences Uk Limited | Energy transfer assay method and reagent |
| WO2010091243A1 (fr) * | 2009-02-06 | 2010-08-12 | Beth Israel Deaconess Medical Center, Inc. | Agents d'imagerie équilibrés en charge |
-
2013
- 2013-10-31 WO PCT/KR2013/009789 patent/WO2015064786A1/fr active Application Filing
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6828116B1 (en) * | 1998-06-11 | 2004-12-07 | Amersham Biosciences Uk Limited | Energy transfer assay method and reagent |
| WO2004006963A1 (fr) * | 2002-07-12 | 2004-01-22 | Beth Israel Deaconess Medical Center | Substances fluorescentes infrarouges conjuguees permettant de detecter la mort cellulaire |
| WO2010091243A1 (fr) * | 2009-02-06 | 2010-08-12 | Beth Israel Deaconess Medical Center, Inc. | Agents d'imagerie équilibrés en charge |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107266929A (zh) * | 2017-06-21 | 2017-10-20 | 四川大学 | 一类以菁染料荧光基团为母体骨架结构的近红外荧光染料及其制备方法与应用 |
| CN107266929B (zh) * | 2017-06-21 | 2019-10-29 | 四川大学 | 一类以菁染料荧光基团为母体骨架结构的近红外荧光染料及其制备方法与应用 |
| US20210347766A1 (en) * | 2020-05-08 | 2021-11-11 | On Target Laboratories, LLC | Methods of manufacture and synthesis of fluorescent dye compounds and uses thereof |
| US11964965B2 (en) * | 2020-05-08 | 2024-04-23 | On Target Laboratories, LLC | Methods of manufacture and synthesis of fluorescent dye compounds and uses thereof |
| EP4146741A4 (fr) * | 2020-05-08 | 2024-08-14 | On Target Laboratories Llc | Procédés de fabrication et de synthèse de composés colorants fluorescents et leurs utilisations |
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