CA2429816A1 - Sulfonated diarylrhodamine dyes as fluorescent labels - Google Patents
Sulfonated diarylrhodamine dyes as fluorescent labels Download PDFInfo
- Publication number
- CA2429816A1 CA2429816A1 CA002429816A CA2429816A CA2429816A1 CA 2429816 A1 CA2429816 A1 CA 2429816A1 CA 002429816 A CA002429816 A CA 002429816A CA 2429816 A CA2429816 A CA 2429816A CA 2429816 A1 CA2429816 A1 CA 2429816A1
- Authority
- CA
- Canada
- Prior art keywords
- dye
- compound
- labelled
- polynucleotide
- energy
- 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.)
- Abandoned
Links
- 239000000975 dye Substances 0.000 title claims description 363
- 150000001875 compounds Chemical class 0.000 claims abstract description 198
- 125000003729 nucleotide group Chemical group 0.000 claims abstract description 103
- 239000002157 polynucleotide Substances 0.000 claims abstract description 98
- 239000002773 nucleotide Substances 0.000 claims abstract description 97
- 108091033319 polynucleotide Proteins 0.000 claims abstract description 96
- 102000040430 polynucleotide Human genes 0.000 claims abstract description 96
- 239000000523 sample Substances 0.000 claims abstract description 50
- 239000002777 nucleoside Substances 0.000 claims abstract description 32
- 239000012634 fragment Substances 0.000 claims abstract description 21
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 19
- 238000009396 hybridization Methods 0.000 claims abstract description 16
- 150000007523 nucleic acids Chemical class 0.000 claims abstract description 16
- 229920001184 polypeptide Polymers 0.000 claims abstract description 16
- 102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 16
- 102000039446 nucleic acids Human genes 0.000 claims abstract description 14
- 108020004707 nucleic acids Proteins 0.000 claims abstract description 14
- 238000003199 nucleic acid amplification method Methods 0.000 claims abstract description 12
- 230000003321 amplification Effects 0.000 claims abstract description 11
- 238000004458 analytical method Methods 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 138
- -1 C1-C12 alkyldiyl Chemical group 0.000 claims description 123
- 230000015572 biosynthetic process Effects 0.000 claims description 96
- 238000003786 synthesis reaction Methods 0.000 claims description 93
- 125000005647 linker group Chemical group 0.000 claims description 91
- 238000012546 transfer Methods 0.000 claims description 65
- 108091034117 Oligonucleotide Proteins 0.000 claims description 56
- 239000003153 chemical reaction reagent Substances 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 49
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 239000000758 substrate Substances 0.000 claims description 36
- 238000002372 labelling Methods 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 239000007787 solid Substances 0.000 claims description 26
- 150000008300 phosphoramidites Chemical class 0.000 claims description 23
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 22
- 230000005284 excitation Effects 0.000 claims description 21
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 20
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- PEHVGBZKEYRQSX-UHFFFAOYSA-N 7-deaza-adenine Chemical compound NC1=NC=NC2=C1C=CN2 PEHVGBZKEYRQSX-UHFFFAOYSA-N 0.000 claims description 16
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical group ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 16
- 229910019142 PO4 Inorganic materials 0.000 claims description 16
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 16
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 16
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 239000010452 phosphate Substances 0.000 claims description 16
- 238000000926 separation method Methods 0.000 claims description 16
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 16
- 238000005859 coupling reaction Methods 0.000 claims description 15
- 238000001962 electrophoresis Methods 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000001226 triphosphate Substances 0.000 claims description 15
- 150000008064 anhydrides Chemical class 0.000 claims description 14
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- 125000003277 amino group Chemical group 0.000 claims description 13
- 230000008878 coupling Effects 0.000 claims description 13
- 238000010168 coupling process Methods 0.000 claims description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 13
- 238000012163 sequencing technique Methods 0.000 claims description 13
- 150000001412 amines Chemical group 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 239000004305 biphenyl Substances 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical class [H]O* 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- 229930024421 Adenine Natural products 0.000 claims description 8
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 8
- 229960000643 adenine Drugs 0.000 claims description 8
- 229940104302 cytosine Drugs 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 8
- 229940113082 thymine Drugs 0.000 claims description 8
- 229940035893 uracil Drugs 0.000 claims description 8
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
- 238000000137 annealing Methods 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 150000001721 carbon Chemical class 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 229940124530 sulfonamide Drugs 0.000 claims description 7
- 235000011178 triphosphate Nutrition 0.000 claims description 7
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 6
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001624 naphthyl group Chemical class 0.000 claims description 6
- 150000004713 phosphodiesters Chemical class 0.000 claims description 6
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- 150000003456 sulfonamides Chemical class 0.000 claims description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 5
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 150000001540 azides Chemical class 0.000 claims description 5
- 238000002189 fluorescence spectrum Methods 0.000 claims description 5
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 230000002194 synthesizing effect Effects 0.000 claims description 5
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 230000001419 dependent effect Effects 0.000 claims description 4
- 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 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
- 239000001022 rhodamine dye Substances 0.000 claims description 4
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical class C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 claims description 3
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 3
- 150000001720 carbohydrates Chemical class 0.000 claims description 3
- 239000001177 diphosphate Substances 0.000 claims description 3
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 3
- 235000011180 diphosphates Nutrition 0.000 claims description 3
- 238000001917 fluorescence detection Methods 0.000 claims description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims description 3
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- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 2
- YOSZEPWSVKKQOV-UHFFFAOYSA-N 12h-benzo[a]phenoxazine Chemical compound C1=CC=CC2=C3NC4=CC=CC=C4OC3=CC=C21 YOSZEPWSVKKQOV-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
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- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
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- JRYMOPZHXMVHTA-DAGMQNCNSA-N 2-amino-7-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1h-pyrrolo[2,3-d]pyrimidin-4-one Chemical compound C1=CC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O JRYMOPZHXMVHTA-DAGMQNCNSA-N 0.000 claims 5
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- 238000006243 chemical reaction Methods 0.000 description 83
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- 239000000243 solution Substances 0.000 description 36
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 34
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- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 24
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- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 235000019419 proteases Nutrition 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- PTJWIQPHWPFNBW-GBNDHIKLSA-N pseudouridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1C1=CNC(=O)NC1=O PTJWIQPHWPFNBW-GBNDHIKLSA-N 0.000 description 1
- 125000004219 purine nucleobase group Chemical group 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000002342 ribonucleoside Substances 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000010187 selection method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 108010068698 spleen exonuclease Proteins 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 239000005451 thionucleotide Substances 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229960003087 tioguanine Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- AVBGNFCMKJOFIN-UHFFFAOYSA-N triethylammonium acetate Chemical compound CC(O)=O.CCN(CC)CC AVBGNFCMKJOFIN-UHFFFAOYSA-N 0.000 description 1
- 125000002264 triphosphate group Chemical class [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
-
- 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/02—Diaryl- or thriarylmethane dyes derived from diarylmethanes
-
- 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
- Peptides Or Proteins (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/724,855 US6583168B1 (en) | 1997-11-25 | 2000-11-28 | Sulfonated diarylrhodamine dyes |
| US09/724,855 | 2000-11-28 | ||
| PCT/US2001/044475 WO2002044416A2 (en) | 2000-11-28 | 2001-11-27 | Sulfonated diarylrhodamine dyes as fluorescent labels |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2429816A1 true CA2429816A1 (en) | 2002-06-06 |
Family
ID=24912198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002429816A Abandoned CA2429816A1 (en) | 2000-11-28 | 2001-11-27 | Sulfonated diarylrhodamine dyes as fluorescent labels |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US6583168B1 (enExample) |
| EP (3) | EP1339798A2 (enExample) |
| JP (4) | JP4486781B2 (enExample) |
| AU (1) | AU2002219896A1 (enExample) |
| CA (1) | CA2429816A1 (enExample) |
| WO (1) | WO2002044416A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7833756B2 (en) | 1997-11-25 | 2010-11-16 | Applied Biosystems, Llc | Methods of labelling polynucleotides with dibenzorhodamine dyes |
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| WO2000071559A1 (en) * | 1999-05-24 | 2000-11-30 | Invitrogen Corporation | Method for deblocking of labeled oligonucleotides |
| US6979530B2 (en) * | 2001-05-21 | 2005-12-27 | Applera Corporation | Peptide conjugates and fluorescence detection methods for intracellular caspase assay |
| CA2490961A1 (en) * | 2002-07-01 | 2004-01-08 | Guava Technologies, Inc. | Fluorescent dyes, energy transfer couples and methods |
| US20050186606A1 (en) * | 2004-02-11 | 2005-08-25 | Schroeder Benjamin G. | Methods and compositions for detecting nucleic acids |
| US7767834B2 (en) * | 2004-08-13 | 2010-08-03 | Elitech Holding B.V. | Phosphonylated fluorescent dyes and conjugates |
| ES2461858T3 (es) * | 2004-08-13 | 2014-05-21 | Epoch Biosciences, Inc. | Colorantes fluorescentes de fosfonato y conjugados |
| CA2581174A1 (en) * | 2004-09-16 | 2006-03-30 | Applera Corporation | Fluorescent dye compounds, conjugates and uses thereof |
| EP2001871B1 (en) * | 2006-03-31 | 2014-07-16 | Applied Biosystems, LLC | Rhodamine-labeled oligonucleotides |
| US8178360B2 (en) * | 2006-05-18 | 2012-05-15 | Illumina Cambridge Limited | Dye compounds and the use of their labelled conjugates |
| GB0611405D0 (en) | 2006-06-09 | 2006-07-19 | Univ Belfast | FKBP-L: A novel inhibitor of angiogenesis |
| KR101117722B1 (ko) * | 2009-08-28 | 2012-03-07 | 삼성모바일디스플레이주식회사 | 유기 발광 소자 |
| KR101193182B1 (ko) * | 2009-09-02 | 2012-10-19 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| DE102010042634A1 (de) | 2010-10-19 | 2012-04-19 | Atto-Tec Gmbh | Neue Amin-substituierte tricyclische Fluoreszenzfarbstoffe |
| EP2782916B1 (en) | 2011-11-21 | 2018-02-28 | Promega Corporation | Carboxy x rhodamine analogs |
| JP5729491B2 (ja) * | 2012-01-24 | 2015-06-03 | 株式会社島津製作所 | 有機系太陽電池用色素材料の分析方法及び精製方法 |
| EP2942352A4 (en) * | 2013-01-07 | 2016-09-07 | Univ Tokyo | ASYMMETRIC SI-RHODAMINE AND RHODOL SYNTHESIS |
| JP6815603B2 (ja) * | 2016-11-22 | 2021-01-20 | スガイ化学工業株式会社 | ジナフトチオフェン誘導体及びその製造方法 |
| JP2018090535A (ja) * | 2016-12-02 | 2018-06-14 | 国立大学法人 東京大学 | 近赤外蛍光カルシウムプローブ |
| JP2018090536A (ja) * | 2016-12-02 | 2018-06-14 | 国立大学法人 東京大学 | 近赤外蛍光レシオ型プローブ |
| CN109111421B (zh) * | 2018-10-12 | 2022-04-22 | 湖南科技大学 | 一种氧杂蒽类荧光探针及其制备方法和应用 |
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-
2000
- 2000-11-28 US US09/724,855 patent/US6583168B1/en not_active Expired - Lifetime
-
2001
- 2001-11-27 JP JP2002546764A patent/JP4486781B2/ja not_active Expired - Fee Related
- 2001-11-27 EP EP01998658A patent/EP1339798A2/en not_active Ceased
- 2001-11-27 WO PCT/US2001/044475 patent/WO2002044416A2/en not_active Ceased
- 2001-11-27 CA CA002429816A patent/CA2429816A1/en not_active Abandoned
- 2001-11-27 AU AU2002219896A patent/AU2002219896A1/en not_active Abandoned
- 2001-11-27 EP EP09016130A patent/EP2221347A1/en not_active Withdrawn
- 2001-11-27 EP EP09016135A patent/EP2179996A1/en not_active Withdrawn
-
2003
- 2003-06-24 US US10/602,974 patent/US7018431B2/en not_active Expired - Lifetime
-
2008
- 2008-12-29 JP JP2008335693A patent/JP2009108098A/ja not_active Withdrawn
-
2009
- 2009-11-30 JP JP2009272932A patent/JP2010053137A/ja not_active Withdrawn
-
2010
- 2010-07-15 JP JP2010161112A patent/JP2010285625A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7833756B2 (en) | 1997-11-25 | 2010-11-16 | Applied Biosystems, Llc | Methods of labelling polynucleotides with dibenzorhodamine dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002044416A2 (en) | 2002-06-06 |
| US20040096397A1 (en) | 2004-05-20 |
| AU2002219896A1 (en) | 2002-06-11 |
| JP2009108098A (ja) | 2009-05-21 |
| EP1339798A2 (en) | 2003-09-03 |
| JP2010053137A (ja) | 2010-03-11 |
| WO2002044416A3 (en) | 2002-10-31 |
| JP2010285625A (ja) | 2010-12-24 |
| EP2179996A1 (en) | 2010-04-28 |
| JP4486781B2 (ja) | 2010-06-23 |
| EP2221347A1 (en) | 2010-08-25 |
| US7018431B2 (en) | 2006-03-28 |
| US6583168B1 (en) | 2003-06-24 |
| JP2004514727A (ja) | 2004-05-20 |
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