CA2797440C - Method of analysing a cell or other biological material containing a nucleic acid - Google Patents
Method of analysing a cell or other biological material containing a nucleic acid Download PDFInfo
- Publication number
- CA2797440C CA2797440C CA2797440A CA2797440A CA2797440C CA 2797440 C CA2797440 C CA 2797440C CA 2797440 A CA2797440 A CA 2797440A CA 2797440 A CA2797440 A CA 2797440A CA 2797440 C CA2797440 C CA 2797440C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- cell
- cells
- fluorochrome
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title claims abstract description 41
- 108020004707 nucleic acids Proteins 0.000 title claims description 65
- 102000039446 nucleic acids Human genes 0.000 title claims description 65
- 150000007523 nucleic acids Chemical class 0.000 title claims description 65
- 239000012620 biological material Substances 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 278
- 150000001450 anions Chemical class 0.000 claims abstract description 11
- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical compound O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 claims description 69
- 238000001514 detection method Methods 0.000 claims description 51
- 230000030833 cell death Effects 0.000 claims description 33
- 230000027455 binding Effects 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 238000003556 assay Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- 230000005670 electromagnetic radiation Effects 0.000 claims description 21
- 238000010521 absorption reaction Methods 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- -1 amino substituted anthraquinone Chemical class 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
- 230000002596 correlated effect Effects 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 7
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 125000005122 aminoalkylamino group Chemical group 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 104
- 230000001976 improved effect Effects 0.000 abstract description 3
- 210000004027 cell Anatomy 0.000 description 388
- 238000004458 analytical method Methods 0.000 description 37
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 24
- 239000000523 sample Substances 0.000 description 24
- 230000005284 excitation Effects 0.000 description 23
- 238000010186 staining Methods 0.000 description 23
- 230000003595 spectral effect Effects 0.000 description 21
- 230000001413 cellular effect Effects 0.000 description 20
- XJMOSONTPMZWPB-UHFFFAOYSA-M propidium iodide Chemical group [I-].[I-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CCC[N+](C)(CC)CC)=C1C1=CC=CC=C1 XJMOSONTPMZWPB-UHFFFAOYSA-M 0.000 description 20
- 108020004414 DNA Proteins 0.000 description 19
- 239000012528 membrane Substances 0.000 description 17
- 239000007850 fluorescent dye Substances 0.000 description 15
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 15
- 238000000684 flow cytometry Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 12
- 230000006907 apoptotic process Effects 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 201000001441 melanoma Diseases 0.000 description 12
- 230000001640 apoptogenic effect Effects 0.000 description 11
- 230000001010 compromised effect Effects 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 108090000672 Annexin A5 Proteins 0.000 description 10
- 102000004121 Annexin A5 Human genes 0.000 description 10
- 210000001072 colon Anatomy 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 238000003384 imaging method Methods 0.000 description 10
- 210000004072 lung Anatomy 0.000 description 10
- 210000004940 nucleus Anatomy 0.000 description 10
- 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 10
- 230000035899 viability Effects 0.000 description 10
- 230000008901 benefit Effects 0.000 description 9
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 9
- 238000002189 fluorescence spectrum Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- HKSZLNNOFSGOKW-UHFFFAOYSA-N ent-staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(C)O1 HKSZLNNOFSGOKW-UHFFFAOYSA-N 0.000 description 8
- 230000003834 intracellular effect Effects 0.000 description 8
- HKSZLNNOFSGOKW-FYTWVXJKSA-N staurosporine Chemical compound C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@H]1C[C@@H](NC)[C@@H](OC)[C@]4(C)O1 HKSZLNNOFSGOKW-FYTWVXJKSA-N 0.000 description 8
- CGPUWJWCVCFERF-UHFFFAOYSA-N staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(OC)O1 CGPUWJWCVCFERF-UHFFFAOYSA-N 0.000 description 8
- 210000000481 breast Anatomy 0.000 description 7
- 210000000170 cell membrane Anatomy 0.000 description 7
- 238000010586 diagram Methods 0.000 description 7
- 229960005420 etoposide Drugs 0.000 description 7
- 238000010348 incorporation Methods 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- YXHLJMWYDTXDHS-IRFLANFNSA-N 7-aminoactinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=C(N)C=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 YXHLJMWYDTXDHS-IRFLANFNSA-N 0.000 description 6
- 108700012813 7-aminoactinomycin D Proteins 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 108010040476 FITC-annexin A5 Proteins 0.000 description 6
- 239000012491 analyte Substances 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 238000004113 cell culture Methods 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 6
- 238000002372 labelling Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 239000002159 nanocrystal Substances 0.000 description 6
- 230000002611 ovarian Effects 0.000 description 6
- 239000002096 quantum dot Substances 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 210000004881 tumor cell Anatomy 0.000 description 6
- FWBHETKCLVMNFS-UHFFFAOYSA-N 4',6-Diamino-2-phenylindol Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC2=CC=C(C(N)=N)C=C2N1 FWBHETKCLVMNFS-UHFFFAOYSA-N 0.000 description 5
- 101100278318 Dictyostelium discoideum dohh-2 gene Proteins 0.000 description 5
- 206010056740 Genital discharge Diseases 0.000 description 5
- 206010025323 Lymphomas Diseases 0.000 description 5
- 229930182555 Penicillin Natural products 0.000 description 5
- 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 5
- 230000001464 adherent effect Effects 0.000 description 5
- 238000013459 approach Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 210000003169 central nervous system Anatomy 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 238000000799 fluorescence microscopy Methods 0.000 description 5
- 230000000977 initiatory effect Effects 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229940049954 penicillin Drugs 0.000 description 5
- 229960005322 streptomycin Drugs 0.000 description 5
- 230000003442 weekly effect Effects 0.000 description 5
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 210000003483 chromatin Anatomy 0.000 description 4
- 230000001427 coherent effect Effects 0.000 description 4
- 238000004163 cytometry Methods 0.000 description 4
- 230000009977 dual effect Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000001943 fluorescence-activated cell sorting Methods 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 230000007774 longterm Effects 0.000 description 4
- 210000001700 mitochondrial membrane Anatomy 0.000 description 4
- 238000012544 monitoring process Methods 0.000 description 4
- 201000008968 osteosarcoma Diseases 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 208000003950 B-cell lymphoma Diseases 0.000 description 3
- 108010077544 Chromatin Proteins 0.000 description 3
- 230000004568 DNA-binding Effects 0.000 description 3
- 239000012980 RPMI-1640 medium Substances 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 210000003855 cell nucleus Anatomy 0.000 description 3
- 230000003833 cell viability Effects 0.000 description 3
- 238000000295 emission spectrum Methods 0.000 description 3
- 230000007717 exclusion Effects 0.000 description 3
- 230000003325 follicular Effects 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 230000004807 localization Effects 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
- 239000003550 marker Substances 0.000 description 3
- 239000003068 molecular probe Substances 0.000 description 3
- 239000002105 nanoparticle Substances 0.000 description 3
- 230000017074 necrotic cell death Effects 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 238000001429 visible spectrum Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- PRDFBSVERLRRMY-UHFFFAOYSA-N 2'-(4-ethoxyphenyl)-5-(4-methylpiperazin-1-yl)-2,5'-bibenzimidazole Chemical compound C1=CC(OCC)=CC=C1C1=NC2=CC=C(C=3NC4=CC(=CC=C4N=3)N3CCN(C)CC3)C=C2N1 PRDFBSVERLRRMY-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- 108010078791 Carrier Proteins Proteins 0.000 description 2
- 102000011727 Caspases Human genes 0.000 description 2
- 108010076667 Caspases Proteins 0.000 description 2
- 102000053602 DNA Human genes 0.000 description 2
- 241000206602 Eukaryota Species 0.000 description 2
- 101000655352 Homo sapiens Telomerase reverse transcriptase Proteins 0.000 description 2
- FGBAVQUHSKYMTC-UHFFFAOYSA-M LDS 751 dye Chemical compound [O-]Cl(=O)(=O)=O.C1=CC2=CC(N(C)C)=CC=C2[N+](CC)=C1C=CC=CC1=CC=C(N(C)C)C=C1 FGBAVQUHSKYMTC-UHFFFAOYSA-M 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
- 241001529936 Murinae Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DPXHITFUCHFTKR-UHFFFAOYSA-L To-Pro-1 Chemical compound [I-].[I-].S1C2=CC=CC=C2[N+](C)=C1C=C1C2=CC=CC=C2N(CCC[N+](C)(C)C)C=C1 DPXHITFUCHFTKR-UHFFFAOYSA-L 0.000 description 2
- ULHRKLSNHXXJLO-UHFFFAOYSA-L Yo-Pro-1 Chemical compound [I-].[I-].C1=CC=C2C(C=C3N(C4=CC=CC=C4O3)C)=CC=[N+](CCC[N+](C)(C)C)C2=C1 ULHRKLSNHXXJLO-UHFFFAOYSA-L 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- DPKHZNPWBDQZCN-UHFFFAOYSA-N acridine orange free base Chemical compound C1=CC(N(C)C)=CC2=NC3=CC(N(C)C)=CC=C3C=C21 DPKHZNPWBDQZCN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000004056 anthraquinones Chemical group 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 238000000149 argon plasma sintering Methods 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 239000012148 binding buffer Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000000423 cell based assay Methods 0.000 description 2
- 230000025084 cell cycle arrest Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000000306 component Substances 0.000 description 2
- 229960004132 diethyl ether Drugs 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 238000007877 drug screening Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 210000003527 eukaryotic cell Anatomy 0.000 description 2
- 238000000695 excitation spectrum Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 201000005202 lung cancer Diseases 0.000 description 2
- 208000020816 lung neoplasm Diseases 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 210000004962 mammalian cell Anatomy 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 230000003458 metachromatic effect Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 230000002438 mitochondrial effect Effects 0.000 description 2
- 238000012758 nuclear staining Methods 0.000 description 2
- 239000001048 orange dye Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 210000002307 prostate Anatomy 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 210000000130 stem cell Anatomy 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 239000003053 toxin Substances 0.000 description 2
- 231100000765 toxin Toxicity 0.000 description 2
- 108700012359 toxins Proteins 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CHADEQDQBURGHL-UHFFFAOYSA-N (6'-acetyloxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl) acetate Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(OC(C)=O)C=C1OC1=CC(OC(=O)C)=CC=C21 CHADEQDQBURGHL-UHFFFAOYSA-N 0.000 description 1
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
- DPKDBVSAHDKACA-UHFFFAOYSA-N 1,5-bis[2-(dimethylamino)ethylamino]anthracene-9,10-dione Chemical compound O=C1C2=C(NCCN(C)C)C=CC=C2C(=O)C2=C1C=CC=C2NCCN(C)C DPKDBVSAHDKACA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- 102000000412 Annexin Human genes 0.000 description 1
- 108050008874 Annexin Proteins 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VFJXZAPLCIZYLJ-UHFFFAOYSA-N CN(CCNC1=CC=CC=2C(C3C(C=CC(=C3C(C12)=O)O)(O)NCCN(C)C)=O)C Chemical compound CN(CCNC1=CC=CC=2C(C3C(C=CC(=C3C(C12)=O)O)(O)NCCN(C)C)=O)C VFJXZAPLCIZYLJ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 108010051152 Carboxylesterase Proteins 0.000 description 1
- 102000013392 Carboxylesterase Human genes 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 230000005778 DNA damage Effects 0.000 description 1
- 231100000277 DNA damage Toxicity 0.000 description 1
- 241000252208 Danio Species 0.000 description 1
- 241000252212 Danio rerio Species 0.000 description 1
- 206010014733 Endometrial cancer Diseases 0.000 description 1
- 206010014759 Endometrial neoplasm Diseases 0.000 description 1
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
- 101000801640 Homo sapiens Phospholipid-transporting ATPase ABCA3 Proteins 0.000 description 1
- 101000738771 Homo sapiens Receptor-type tyrosine-protein phosphatase C Proteins 0.000 description 1
- 241000575946 Ione Species 0.000 description 1
- 208000008839 Kidney Neoplasms Diseases 0.000 description 1
- 102100020870 La-related protein 6 Human genes 0.000 description 1
- 108050008265 La-related protein 6 Proteins 0.000 description 1
- 241000589242 Legionella pneumophila Species 0.000 description 1
- LTXREWYXXSTFRX-QGZVFWFLSA-N Linagliptin Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 LTXREWYXXSTFRX-QGZVFWFLSA-N 0.000 description 1
- 108091093105 Nuclear DNA Proteins 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 102100033623 Phospholipid-transporting ATPase ABCA3 Human genes 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 102100037422 Receptor-type tyrosine-protein phosphatase C Human genes 0.000 description 1
- 208000015634 Rectal Neoplasms Diseases 0.000 description 1
- 206010038389 Renal cancer Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 208000024770 Thyroid neoplasm Diseases 0.000 description 1
- MZZINWWGSYUHGU-UHFFFAOYSA-J ToTo-1 Chemical compound [I-].[I-].[I-].[I-].C12=CC=CC=C2C(C=C2N(C3=CC=CC=C3S2)C)=CC=[N+]1CCC[N+](C)(C)CCC[N+](C)(C)CCC[N+](C1=CC=CC=C11)=CC=C1C=C1N(C)C2=CC=CC=C2S1 MZZINWWGSYUHGU-UHFFFAOYSA-J 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 210000004504 adult stem cell Anatomy 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 210000004102 animal cell Anatomy 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- 210000001130 astrocyte Anatomy 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000012867 bioactive agent Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 229960000074 biopharmaceutical Drugs 0.000 description 1
- 238000001574 biopsy Methods 0.000 description 1
- 239000012503 blood component Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000000298 carbocyanine Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000006369 cell cycle progression Effects 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 239000002771 cell marker Substances 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 230000019522 cellular metabolic process Effects 0.000 description 1
- 230000033077 cellular process Effects 0.000 description 1
- 210000003850 cellular structure Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125890 compound Ia Drugs 0.000 description 1
- 238000004624 confocal microscopy Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000006059 cover glass Substances 0.000 description 1
- 230000005574 cross-species transmission Effects 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- 210000004292 cytoskeleton Anatomy 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000007876 drug discovery Methods 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 210000001671 embryonic stem cell Anatomy 0.000 description 1
- 210000002257 embryonic structure Anatomy 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000001667 episodic effect Effects 0.000 description 1
- ZMMJGEGLRURXTF-UHFFFAOYSA-N ethidium bromide Chemical compound [Br-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CC)=C1C1=CC=CC=C1 ZMMJGEGLRURXTF-UHFFFAOYSA-N 0.000 description 1
- 229960005542 ethidium bromide Drugs 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 1
- 238000002073 fluorescence micrograph Methods 0.000 description 1
- 238000012757 fluorescence staining Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 210000003494 hepatocyte Anatomy 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 210000004754 hybrid cell Anatomy 0.000 description 1
- 210000004408 hybridoma Anatomy 0.000 description 1
- 230000002895 hyperchromatic effect Effects 0.000 description 1
- 230000006882 induction of apoptosis Effects 0.000 description 1
- 230000001524 infective effect Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 201000010982 kidney cancer Diseases 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 229940115932 legionella pneumophila Drugs 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 210000005265 lung cell Anatomy 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000007102 metabolic function Effects 0.000 description 1
- 210000000274 microglia Anatomy 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 238000010235 multi-parametric assay Methods 0.000 description 1
- VMCOQLKKSNQANE-UHFFFAOYSA-N n,n-dimethyl-4-[6-[6-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]-1h-benzimidazol-2-yl]aniline Chemical compound C1=CC(N(C)C)=CC=C1C1=NC2=CC=C(C=3NC4=CC(=CC=C4N=3)N3CCN(C)CC3)C=C2N1 VMCOQLKKSNQANE-UHFFFAOYSA-N 0.000 description 1
- 230000001338 necrotic effect Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000004987 nonapoptotic effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 210000004248 oligodendroglia Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 150000004686 pentahydrates Chemical class 0.000 description 1
- 239000008191 permeabilizing agent Substances 0.000 description 1
- 230000003094 perturbing effect Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- INAAIJLSXJJHOZ-UHFFFAOYSA-N pibenzimol Chemical compound C1CN(C)CCN1C1=CC=C(N=C(N2)C=3C=C4NC(=NC4=CC=3)C=3C=CC(O)=CC=3)C2=C1 INAAIJLSXJJHOZ-UHFFFAOYSA-N 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 206010038038 rectal cancer Diseases 0.000 description 1
- 201000001275 rectum cancer Diseases 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000004116 schwann cell Anatomy 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000011218 segmentation Effects 0.000 description 1
- 238000011896 sensitive detection Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 210000001626 skin fibroblast Anatomy 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000008093 supporting effect Effects 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 238000010200 validation analysis Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002676 xenobiotic agent Substances 0.000 description 1
- 230000002034 xenobiotic effect Effects 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N1/00—Sampling; Preparing specimens for investigation
- G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
- G01N1/30—Staining; Impregnating ; Fixation; Dehydration; Multistep processes for preparing samples of tissue, cell or nucleic acid material and the like for analysis
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/207—Dyes with amino groups and with onium groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/582—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
-
- 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
- C09K2211/1011—Condensed systems
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N1/00—Sampling; Preparing specimens for investigation
- G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
- G01N1/30—Staining; Impregnating ; Fixation; Dehydration; Multistep processes for preparing samples of tissue, cell or nucleic acid material and the like for analysis
- G01N2001/302—Stain compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Materials Engineering (AREA)
- Genetics & Genomics (AREA)
- General Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Apparatus Associated With Microorganisms And Enzymes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1005939.2 | 2010-04-09 | ||
| GBGB1005939.2A GB201005939D0 (en) | 2010-04-09 | 2010-04-09 | Method of analysing a cell or other biological material containing nucleic acid |
| PCT/GB2011/050702 WO2011124927A1 (en) | 2010-04-09 | 2011-04-08 | Method of analysing a cell or other biological material containing a nucleic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2797440A1 CA2797440A1 (en) | 2011-10-13 |
| CA2797440C true CA2797440C (en) | 2020-01-28 |
Family
ID=42236073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2797440A Active CA2797440C (en) | 2010-04-09 | 2011-04-08 | Method of analysing a cell or other biological material containing a nucleic acid |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US9051467B2 (enExample) |
| EP (2) | EP3366667B1 (enExample) |
| JP (2) | JP6033767B2 (enExample) |
| KR (2) | KR101846491B1 (enExample) |
| CN (1) | CN102947266B (enExample) |
| AU (2) | AU2011236610B2 (enExample) |
| BR (1) | BR112012025820B1 (enExample) |
| CA (1) | CA2797440C (enExample) |
| DK (2) | DK2556047T3 (enExample) |
| ES (1) | ES2676351T3 (enExample) |
| GB (1) | GB201005939D0 (enExample) |
| HU (1) | HUE038706T2 (enExample) |
| NO (1) | NO2556047T3 (enExample) |
| PL (1) | PL2556047T3 (enExample) |
| PT (1) | PT2556047T (enExample) |
| WO (1) | WO2011124927A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201005939D0 (en) * | 2010-04-09 | 2010-05-26 | Biostatus Ltd | Method of analysing a cell or other biological material containing nucleic acid |
| US8790892B2 (en) | 2011-04-04 | 2014-07-29 | Biotium, Inc. | Substituted anthraquinone dyes for cellular stains and enzyme detection |
| JP2013094135A (ja) * | 2011-11-02 | 2013-05-20 | Waseda Univ | 人工ナノ材料の安全性を評価する方法 |
| US9933341B2 (en) | 2012-04-05 | 2018-04-03 | Becton, Dickinson And Company | Sample preparation for flow cytometry |
| CN104379760B (zh) * | 2012-04-05 | 2018-03-16 | Bd公司 | 用于流式细胞术的样品制备 |
| US9709500B2 (en) | 2012-05-02 | 2017-07-18 | Charles River Laboratories, Inc. | Optical method for detecting viable microorganisms in a cell sample |
| EP2769204B1 (en) | 2012-05-02 | 2016-02-17 | Charles River Laboratories, Inc. | Cell capture system and use thereof |
| US8993260B2 (en) | 2012-05-02 | 2015-03-31 | Charles River Laboratories, Inc. | Fluorescence-based viability staining method using a membrane permeable flourescent dye and membrane impermeable fluorescence quencher |
| GB201214169D0 (en) | 2012-08-08 | 2012-09-19 | Biostatus Ltd | New compounds and uses thereof |
| WO2015095152A1 (en) * | 2013-12-17 | 2015-06-25 | The Penn State Research Foundation | Manipulation of light spectral quality to reduce parasitism by cuscuta and other plant parasites |
| GB201610971D0 (en) | 2016-06-23 | 2016-08-10 | Biostatus Ltd | Compounds |
| CN113667323B (zh) * | 2019-11-21 | 2023-07-14 | 苏州优逸兰迪生物科技有限公司 | 一种染料化合物的制备方法 |
| CN112679543B (zh) * | 2020-12-29 | 2022-07-22 | 天津全和诚科技有限责任公司 | 一种亲脂性荧光素探针及其制备方法 |
| CN113072937B (zh) * | 2021-04-12 | 2022-06-07 | 郑州大学 | 一种脂滴靶向碳点、制备方法及应用 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3123605A (en) * | 1960-01-08 | 1964-03-03 | Basic anthraquinone dyestuffs | |
| FR1379649A (fr) * | 1963-06-20 | 1964-11-27 | Oreal | Nouveaux colorants anthraquinoniques et leur utilisation pour la teinture des cheveux |
| GB1053536A (enExample) * | 1962-10-29 | |||
| NL299891A (enExample) * | 1962-10-29 | |||
| JPS503337B1 (enExample) * | 1964-08-06 | 1975-02-03 | ||
| US3646072A (en) * | 1970-07-27 | 1972-02-29 | Du Pont | Turquoise biscationic anthraquinone dyes |
| JPS503337A (enExample) | 1973-05-11 | 1975-01-14 | ||
| US4123222A (en) | 1976-03-23 | 1978-10-31 | Ciba-Geigy Corporation | Process for the dyeing or printing of polyacrylonitrile material |
| FR2431128A1 (fr) * | 1978-07-13 | 1980-02-08 | Oreal | Procede d'evaluation de l'etat ionique des cheveux |
| US4353708A (en) * | 1978-07-13 | 1982-10-12 | L'oreal | Evaluation of the state of change of keratin fibers |
| US5057413A (en) | 1988-06-13 | 1991-10-15 | Becton, Dickinson And Company | Method for discriminating between intact and damaged cells in a sample |
| GB8923075D0 (en) | 1989-10-13 | 1989-11-29 | Patterson Laurence H | Anti-cancer compounds |
| JPH04136802A (ja) * | 1990-09-28 | 1992-05-11 | Nippon Kayaku Co Ltd | 着色フィルター |
| US5520707A (en) * | 1995-08-07 | 1996-05-28 | Clairol, Inc. | Methods for dyeing hair with anthraquinone hair dyes having a quaternary ammonium side chain |
| GB9813062D0 (en) * | 1998-06-18 | 1998-08-19 | Univ Wales Medicine | An anthraquinone and its derivatives |
| EP1147147A1 (en) * | 1998-12-07 | 2001-10-24 | Eastman Chemical Company | A colorant composition, a polymer nanocomposite comprising the colorant composition and articles produced therefrom |
| US6562785B1 (en) * | 1999-03-23 | 2003-05-13 | Howard M. Shapiro | Method for overcoming bacterial antibiotic resistance |
| KR20030010585A (ko) * | 2000-02-28 | 2003-02-05 | 다이이치 가가쿠 야쿠힝 가부시키가이샤 | 아연 형광탐침 |
| US6949250B2 (en) | 2002-12-16 | 2005-09-27 | The United States Of America As Represented By The Secretary Of Agriculture | Selective algaecides for control of cyanochloronta |
| US20070082377A1 (en) | 2005-10-07 | 2007-04-12 | Olin Michael R | Cytotoxicity assays |
| US9334281B2 (en) * | 2008-09-08 | 2016-05-10 | Enzo Life Sciences, Inc. | Fluorochromes for organelle tracing and multi-color imaging |
| GB201005939D0 (en) * | 2010-04-09 | 2010-05-26 | Biostatus Ltd | Method of analysing a cell or other biological material containing nucleic acid |
-
2010
- 2010-04-09 GB GBGB1005939.2A patent/GB201005939D0/en not_active Ceased
-
2011
- 2011-04-08 EP EP18167949.9A patent/EP3366667B1/en active Active
- 2011-04-08 JP JP2013503178A patent/JP6033767B2/ja active Active
- 2011-04-08 PT PT117205716T patent/PT2556047T/pt unknown
- 2011-04-08 NO NO11720571A patent/NO2556047T3/no unknown
- 2011-04-08 KR KR1020127029033A patent/KR101846491B1/ko active Active
- 2011-04-08 DK DK11720571.6T patent/DK2556047T3/en active
- 2011-04-08 KR KR1020187009266A patent/KR101957288B1/ko active Active
- 2011-04-08 DK DK18167949.9T patent/DK3366667T3/da active
- 2011-04-08 HU HUE11720571A patent/HUE038706T2/hu unknown
- 2011-04-08 BR BR112012025820-6A patent/BR112012025820B1/pt active IP Right Grant
- 2011-04-08 CN CN201180028424.3A patent/CN102947266B/zh active Active
- 2011-04-08 CA CA2797440A patent/CA2797440C/en active Active
- 2011-04-08 US US13/639,872 patent/US9051467B2/en active Active
- 2011-04-08 PL PL11720571T patent/PL2556047T3/pl unknown
- 2011-04-08 AU AU2011236610A patent/AU2011236610B2/en active Active
- 2011-04-08 EP EP11720571.6A patent/EP2556047B1/en active Active
- 2011-04-08 ES ES11720571.6T patent/ES2676351T3/es active Active
- 2011-04-08 WO PCT/GB2011/050702 patent/WO2011124927A1/en not_active Ceased
-
2015
- 2015-06-05 US US14/731,647 patent/US11255761B2/en active Active
-
2016
- 2016-10-26 JP JP2016209377A patent/JP6586070B2/ja active Active
- 2016-10-26 AU AU2016250384A patent/AU2016250384B2/en active Active
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2797440C (en) | Method of analysing a cell or other biological material containing a nucleic acid | |
| AU2011236610A1 (en) | Method of analysing a cell or other biological material containing a nucleic acid | |
| Feng et al. | Dual-functional colorimetric fluorescent probe for sequential Cu2+ and S2− detection in bio-imaging | |
| US5314805A (en) | Dual-fluorescence cell viability assay using ethidium homodimer and calcein AM | |
| Shivalingam et al. | The interactions between a small molecule and G-quadruplexes are visualized by fluorescence lifetime imaging microscopy | |
| WO2012083064A1 (en) | Silaanthracene as a red and near infrared sensor and a method to manufacture such a sensor | |
| Li et al. | A novel 3-Hydroxychromone fluorescence sensor for intracellular Zn2+ and its application in the recognition of prostate cancer cells | |
| Erdemir et al. | Monitoring Hg2+ ions in food and environmental matrices using a novel ratiometric NIR fluorescent sensor via carbonothioate-deprotection reaction | |
| CN108358814A (zh) | 一种基于水杨酰腙衍生物的aie荧光探针及其制备方法、应用 | |
| KR20050120668A (ko) | 형광성을 향상시키는 방법 | |
| Jensen et al. | Strategies for choosing a deoxyribonucleic acid stain for flow cytometry of metaphase chromosomes. | |
| Liu et al. | Piperazine multi-substituted triarylboron compound as an aqueous soluble fluorescent probe for imaging nucleoli, nuclear matrix and nuclear membrane | |
| Class et al. | Patent application title: Method of Analysing a Cell or Other Biological Material Containing a Nucleic Acid Inventors: Paul James Smith (Vale Of Glamorgan, GB) Rachel J. Errington (Vale Of Glamorgan, GB) Laurence Hylton Patterson (North Yorkshire, GB) Assignees: BIOSTATUS LIMITED | |
| Kolińska et al. | Dyes based on the 2 (1H)‐quinolone skeleton as potential colorimetric and fluorescent sensors for cyanide anions | |
| Ren et al. | Constructing ratiometric enhanced probes via regulating recognition moiety, for bacteriostasis, nanofibrous film detection, and Hg2+ imaging in living systems | |
| McGowan et al. | Equilibrium binding of Hoechst 33258 and Hoechst 33342 fluorochromes with rat colorectal cells. | |
| CN109369565A (zh) | 一种苯并噻唑衍生物及其制备方法和应用 | |
| Adair et al. | Correlative multimodal optical and X-ray fluorescence imaging of brominated fluorophores | |
| Sargenti et al. | Fluorescence lifetime imaging of intracellular magnesium content in live cells | |
| Gasser M et al. | Sensitive ratiometric sensor for Al (III) detection in water samples using luminescence or eye-vision | |
| Ortolani | Fluorochromes That Bind Nucleic Acids | |
| Weiss et al. | Single-Cell Analysis of Perturbations in the Bacterial Cell Envelope Enabled by Monitoring Generalized Polarization of a Nile Red-Based Solvatochromic Peptide UNR-1 | |
| Shapiro | Fluorescent probes | |
| Chen | T Luminescence Imaging and Biosensing in Cells and Tissues | |
| Papkovsky et al. | Luminescent Probes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20160401 |