JP2004107331A5 - - Google Patents
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- JP2004107331A5 JP2004107331A5 JP2003300011A JP2003300011A JP2004107331A5 JP 2004107331 A5 JP2004107331 A5 JP 2004107331A5 JP 2003300011 A JP2003300011 A JP 2003300011A JP 2003300011 A JP2003300011 A JP 2003300011A JP 2004107331 A5 JP2004107331 A5 JP 2004107331A5
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- JP
- Japan
- Prior art keywords
- compound
- group
- substituent
- carbons
- nitrogen
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims 99
- 125000001424 substituent group Chemical group 0.000 claims 33
- 125000005647 linker group Chemical group 0.000 claims 32
- 239000000975 dye Substances 0.000 claims 29
- 125000000217 alkyl group Chemical group 0.000 claims 24
- 230000003381 solubilizing effect Effects 0.000 claims 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 21
- 125000003118 aryl group Chemical group 0.000 claims 20
- -1 cyano, phenyl Chemical group 0.000 claims 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 19
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 19
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 102000040430 polynucleotide Human genes 0.000 claims 13
- 108091033319 polynucleotide Proteins 0.000 claims 13
- 239000002157 polynucleotide Substances 0.000 claims 13
- 150000001336 alkenes Chemical class 0.000 claims 12
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 12
- YYYFRRSYTVJIOE-WWAIPBPMSA-N (2S,4R)-4-[[2-[(1R,3R)-1-acetyloxy-3-[[(2S,3S)-2-[[(2R)-1,2-dimethylpyrrolidine-2-carbonyl]amino]-3-methylpentanoyl]-methylamino]-4-methylpentyl]-1,3-thiazole-4-carbonyl]amino]-5-(4-aminophenyl)-2-methylpentanoic acid Chemical compound CC[C@H](C)[C@H](NC(=O)[C@@]1(C)CCCN1C)C(=O)N(C)[C@H](C[C@@H](OC(C)=O)c1nc(cs1)C(=O)N[C@H](C[C@H](C)C(O)=O)Cc1ccc(N)cc1)C(C)C YYYFRRSYTVJIOE-WWAIPBPMSA-N 0.000 claims 11
- 150000001345 alkine derivatives Chemical class 0.000 claims 11
- 239000000460 chlorine Substances 0.000 claims 11
- 229910052801 chlorine Inorganic materials 0.000 claims 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 10
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 229910019142 PO4 Inorganic materials 0.000 claims 9
- 150000001412 amines Chemical group 0.000 claims 9
- 235000021317 phosphate Nutrition 0.000 claims 9
- 229920003169 water-soluble polymer Polymers 0.000 claims 9
- 150000002148 esters Chemical class 0.000 claims 8
- 150000003871 sulfonates Chemical class 0.000 claims 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 150000007942 carboxylates Chemical class 0.000 claims 7
- 239000011737 fluorine Substances 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 239000002777 nucleoside Substances 0.000 claims 6
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 6
- XSQUKJJJFZCRTK-OUBTZVSYSA-N Urea-13C Chemical compound N[13C](N)=O XSQUKJJJFZCRTK-OUBTZVSYSA-N 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 239000012634 fragment Substances 0.000 claims 5
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 5
- 150000003467 sulfuric acid derivatives Chemical group 0.000 claims 5
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical class O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims 4
- 125000005179 haloacetyl group Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical class NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 claims 4
- 150000002540 isothiocyanates Chemical class 0.000 claims 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 4
- 239000010452 phosphate Substances 0.000 claims 4
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 241000255930 Chironomidae Species 0.000 claims 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 150000001721 carbon Chemical class 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 150000002825 nitriles Chemical class 0.000 claims 3
- 238000000926 separation method Methods 0.000 claims 3
- 229940124530 sulfonamide Drugs 0.000 claims 3
- 150000003456 sulfonamides Chemical class 0.000 claims 3
- 150000003457 sulfones Chemical class 0.000 claims 3
- 150000003462 sulfoxides Chemical class 0.000 claims 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims 2
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 150000001993 dienes Chemical class 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 230000005284 excitation Effects 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000003367 polycyclic group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- WVXRAFOPTSTNLL-NKWVEPMBSA-N 2',3'-dideoxyadenosine Chemical group C1=NC=2C(N)=NC=NC=2N1[C@H]1CC[C@@H](CO)O1 WVXRAFOPTSTNLL-NKWVEPMBSA-N 0.000 claims 1
- OCLZPNCLRLDXJC-NTSWFWBYSA-N 2-amino-9-[(2r,5s)-5-(hydroxymethyl)oxolan-2-yl]-3h-purin-6-one Chemical group C1=2NC(N)=NC(=O)C=2N=CN1[C@H]1CC[C@@H](CO)O1 OCLZPNCLRLDXJC-NTSWFWBYSA-N 0.000 claims 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims 1
- JZIBVTUXIVIFGC-UHFFFAOYSA-N 2H-pyrrole Chemical compound C1C=CC=N1 JZIBVTUXIVIFGC-UHFFFAOYSA-N 0.000 claims 1
- YWXUDGDVUBAALQ-UHFFFAOYSA-N 2h-oxazine;pyrazine Chemical compound C1=CN=CC=N1.N1OC=CC=C1 YWXUDGDVUBAALQ-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical group O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 238000004458 analytical method Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229910021386 carbon form Inorganic materials 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 229940104302 cytosine Drugs 0.000 claims 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims 1
- 238000001962 electrophoresis Methods 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 238000002189 fluorescence spectrum Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000005286 illumination Methods 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical group C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 230000001678 irradiating effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 238000012163 sequencing technique Methods 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 125000001806 thionaphthenyl group Chemical group 0.000 claims 1
- 229940035893 uracil Drugs 0.000 claims 1
- 229960000523 zalcitabine Drugs 0.000 claims 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/978,775 US5936087A (en) | 1997-11-25 | 1997-11-25 | Dibenzorhodamine dyes |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000522168A Division JP4038017B2 (ja) | 1997-11-25 | 1998-11-17 | 蛍光標識試薬として有用なジベンゾローダミン色素 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010025761A Division JP5303486B2 (ja) | 1997-11-25 | 2010-02-08 | 蛍光標識試薬として有用なジベンゾローダミン色素 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004107331A JP2004107331A (ja) | 2004-04-08 |
| JP2004107331A5 true JP2004107331A5 (enExample) | 2006-01-12 |
Family
ID=25526378
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000522168A Expired - Fee Related JP4038017B2 (ja) | 1997-11-25 | 1998-11-17 | 蛍光標識試薬として有用なジベンゾローダミン色素 |
| JP2003300011A Withdrawn JP2004107331A (ja) | 1997-11-25 | 2003-08-25 | 蛍光標識試薬として有用なジベンゾローダミン色素 |
| JP2010025761A Expired - Fee Related JP5303486B2 (ja) | 1997-11-25 | 2010-02-08 | 蛍光標識試薬として有用なジベンゾローダミン色素 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000522168A Expired - Fee Related JP4038017B2 (ja) | 1997-11-25 | 1998-11-17 | 蛍光標識試薬として有用なジベンゾローダミン色素 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010025761A Expired - Fee Related JP5303486B2 (ja) | 1997-11-25 | 2010-02-08 | 蛍光標識試薬として有用なジベンゾローダミン色素 |
Country Status (6)
| Country | Link |
|---|---|
| US (11) | US5936087A (enExample) |
| EP (4) | EP2295503A1 (enExample) |
| JP (3) | JP4038017B2 (enExample) |
| AU (1) | AU742571B2 (enExample) |
| CA (1) | CA2311476C (enExample) |
| WO (1) | WO1999027020A1 (enExample) |
Families Citing this family (147)
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|---|---|---|---|---|
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| US5936087A (en) * | 1997-11-25 | 1999-08-10 | The Perkin-Elmer Corporation | Dibenzorhodamine dyes |
| US6583168B1 (en) * | 1997-11-25 | 2003-06-24 | Applera Corporation | Sulfonated diarylrhodamine dyes |
| EP1141404A1 (en) * | 1998-12-24 | 2001-10-10 | Aclara BioSciences, Inc. | Individually addressable solid surfaces for multiplexed operations |
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| US6248884B1 (en) | 1999-06-03 | 2001-06-19 | The Perkin-Elmer Corporation | Extended rhodamine compounds useful as fluorescent labels |
| US6191278B1 (en) | 1999-11-03 | 2001-02-20 | Pe Corporation | Water-soluble rhodamine dyes and conjugates thereof |
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| US7432298B2 (en) * | 2003-05-09 | 2008-10-07 | Applied Biosystems Inc. | Fluorescent polymeric materials containing lipid soluble rhodamine dyes |
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