JP2018513836A - フェニルエチニルナフタレン染料およびそれらの使用方法 - Google Patents
フェニルエチニルナフタレン染料およびそれらの使用方法 Download PDFInfo
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- JP2018513836A JP2018513836A JP2017544935A JP2017544935A JP2018513836A JP 2018513836 A JP2018513836 A JP 2018513836A JP 2017544935 A JP2017544935 A JP 2017544935A JP 2017544935 A JP2017544935 A JP 2017544935A JP 2018513836 A JP2018513836 A JP 2018513836A
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- compound
- compound according
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- alkyl
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- 238000000034 method Methods 0.000 title claims abstract description 72
- 239000000975 dye Substances 0.000 title abstract description 34
- RJTQETWCPOVCSR-UHFFFAOYSA-N 1-(2-phenylethynyl)naphthalene Chemical compound C1=CC=CC=C1C#CC1=CC=CC2=CC=CC=C12 RJTQETWCPOVCSR-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 204
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 238000004458 analytical method Methods 0.000 claims abstract description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 115
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 79
- 239000012491 analyte Substances 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 125000003282 alkyl amino group Chemical group 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000001769 aryl amino group Chemical group 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 24
- 125000004104 aryloxy group Chemical group 0.000 claims description 24
- 150000008300 phosphoramidites Chemical class 0.000 claims description 23
- 239000007787 solid Substances 0.000 claims description 22
- 125000005647 linker group Chemical group 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 229920001281 polyalkylene Polymers 0.000 claims description 16
- 230000000007 visual effect Effects 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 13
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 13
- 229910019142 PO4 Inorganic materials 0.000 claims description 12
- 235000021317 phosphate Nutrition 0.000 claims description 12
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 11
- 108020004707 nucleic acids Proteins 0.000 claims description 11
- 150000007523 nucleic acids Chemical class 0.000 claims description 11
- 102000039446 nucleic acids Human genes 0.000 claims description 11
- 230000004044 response Effects 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 10
- 239000010452 phosphate Substances 0.000 claims description 10
- 238000001514 detection method Methods 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 9
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 8
- 108090000790 Enzymes Proteins 0.000 claims description 8
- 102000004190 Enzymes Human genes 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 239000003446 ligand Substances 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- 108090000288 Glycoproteins Proteins 0.000 claims description 6
- 102000003886 Glycoproteins Human genes 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 150000001720 carbohydrates Chemical class 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 108091023037 Aptamer Proteins 0.000 claims description 5
- 102000029797 Prion Human genes 0.000 claims description 5
- 108091000054 Prion Proteins 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000006294 amino alkylene group Chemical group 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- 150000001345 alkine derivatives Chemical class 0.000 claims description 4
- 125000002431 aminoalkoxy group Chemical group 0.000 claims description 4
- 239000000427 antigen Substances 0.000 claims description 4
- 108091007433 antigens Proteins 0.000 claims description 4
- 102000036639 antigens Human genes 0.000 claims description 4
- 238000000684 flow cytometry Methods 0.000 claims description 4
- 150000002632 lipids Chemical class 0.000 claims description 4
- 150000003017 phosphorus Chemical class 0.000 claims description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 150000003384 small molecules Chemical class 0.000 claims description 3
- 238000010186 staining Methods 0.000 claims description 3
- 239000011782 vitamin Substances 0.000 claims description 3
- 235000013343 vitamin Nutrition 0.000 claims description 3
- 229940088594 vitamin Drugs 0.000 claims description 3
- 229930003231 vitamin Natural products 0.000 claims description 3
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 229960002685 biotin Drugs 0.000 claims description 2
- 235000020958 biotin Nutrition 0.000 claims description 2
- 239000011616 biotin Substances 0.000 claims description 2
- 238000006352 cycloaddition reaction Methods 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 229960002317 succinimide Drugs 0.000 claims description 2
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 2
- 150000003722 vitamin derivatives Chemical class 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 10
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 8
- 239000007850 fluorescent dye Substances 0.000 abstract description 6
- 239000000126 substance Substances 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 20
- 125000002947 alkylene group Chemical group 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 125000005843 halogen group Chemical group 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 150000005215 alkyl ethers Chemical class 0.000 description 13
- 150000002500 ions Chemical class 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 125000003710 aryl alkyl group Chemical group 0.000 description 10
- 125000004429 atom Chemical group 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- 230000005284 excitation Effects 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- 0 C*(C*(OP(O)(OCC*OCCOP(O)(OCCOCCCOP(O)(OCN)=O)=O)=O)=C)c1cc(C#Cc(cc2)ccc2N(C)C)c(cccc2)c2c1C#Cc(cc1)ccc1N(C)C Chemical compound C*(C*(OP(O)(OCC*OCCOP(O)(OCCOCCCOP(O)(OCN)=O)=O)=O)=C)c1cc(C#Cc(cc2)ccc2N(C)C)c(cccc2)c2c1C#Cc(cc1)ccc1N(C)C 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 102000004196 processed proteins & peptides Human genes 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 8
- 235000001014 amino acid Nutrition 0.000 description 7
- 239000011324 bead Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000000539 dimer Substances 0.000 description 6
- 125000001033 ether group Chemical group 0.000 description 6
- 238000002376 fluorescence recovery after photobleaching Methods 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 239000012453 solvate Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 108091034117 Oligonucleotide Proteins 0.000 description 5
- 150000001412 amines Chemical group 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 238000003384 imaging method Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
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- 239000002904 solvent Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
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- 230000006820 DNA synthesis Effects 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
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- 125000004474 heteroalkylene group Chemical group 0.000 description 4
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
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- 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 3
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/68—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2429—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of arylalkanols
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
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Abstract
Description
(分野)
本発明は、フェニルエチニルナフタレン部分を含む新規な蛍光染料または有色染料、ならびにそれらの調製法および種々の分析法における使用に関する。
研究および診断の混合物中の分析物として化学的物質、生化学的物質、および生物学的物質を検出および定量するための迅速で特異性の高い方法には、継続してかつ拡大しつつある必要性が存在する。少量の核酸、ペプチド、サッカリド、医薬、代謝産物、微生物、イオン、および診断価値のある他の物質を測定するための方法は、特に価値がある。このような物質の例としては、麻薬および毒、治療目的で投与される薬物、ホルモン、病原性微生物およびウイルス、ペプチド(例えば、抗体および酵素)、ならびに核酸(特に、疾患状態に関わるもの)が挙げられる。
簡潔には、本発明は一般に、生体分子および他の分析物の視覚的検出を可能にする水溶性の蛍光または有色の染料およびプローブとして有用な化合物、ならびにそれらの調製のための試薬に関する。生体分子を視覚的に検出するため、および生体分子のサイズを決定するための方法もまた、記載される。本発明の水溶性の蛍光染料または有色染料は、強く有色および/または蛍光性であり、目視または他の手段によって容易に観察され得る。いくつかの実施形態において、上記化合物は、事前の照射または化学的もしくは酵素的活性化なしに観察され得る。有利なことには、上記染料の実施形態は、約400nm〜約420nmの範囲に及ぶ極大励起波長および約520nm〜約540nmの範囲に及ぶ極大発光波長を有する。例えば、ある種の実施形態において、上記染料は、約410nmの極大励起波長および約533nmの極大発光波長を有する。上記染料は、従って、種々の分析法における使用に理想的である。本明細書で記載されるように、上記染料の適切な選択によって、種々の色の視覚的に検出可能な生体分子が、得られ得る。
(a)本明細書で記載される代表的化合物を提供する工程;および
(b)上記化合物をその視覚的特性によって検出する工程
を包含する。
(a)開示される化合物のうちのいずれかと1もしくはこれより多くの生体分子とを混合する工程;および
(b)上記化合物をその視覚的特性によって検出する工程
を包含する。
以下の説明において、ある種の具体的詳細が、本発明の種々の実施形態の完全な理解を提供するために示される。しかし、当業者は、これら詳細なしに本発明が実施され得ることを理解する。
R1a、R1b、R1c、R1d、R1eおよびR1fは、各々独立して、非存在、H、ハロ、ニトロ、C1−C6アルキル、−SO3 −、−SO3アルキル、C1−C6アルコキシ、アリール、アリールオキシ、C1−C6アルキルカルボニル、C1−C6アルキルカルボニルオキシ、アリールカルボニル、アリールカルボニルオキシ、アミノ、アルキルアミノ、アリールアミノ、アラルキルアミノ(aralklyamino)、−L1−(R3)z−L2−Mまたは−L1−(R3)z−L2−S−S−L2−(R3)z−L1−Iであり、ここでIは、独立して、構造(I)のさらなる化合物を表すか;あるいはR1a、R1b、R1c、R1d、R1eまたはR1fのうちの1つは、R1a、R1b、R1c、R1d、R1eまたはR1fのうちの別の1つと結合して炭素環式環もしく複素環式環を形成し、そして残りのR1a、R1b、R1c、R1d、R1eおよびR1fは、各々独立して、非存在、H、ハロ、ニトロ、C1−C6アルキル、−OSO2 −、−OSO2アルキル、C1−C6アルコキシ、アリール、アリールオキシ、C1−C6アルキルカルボニル、C1−C6アルキルカルボニルオキシ、アリールカルボニル、アリールカルボニルオキシ、アミノ、アルキルアミノ、アリールアミノ、アリールアルキルアミノ、−L1−(R3)z−L2−Mまたは−L1−(R3)z−L2−S−S−L2−(R3)z−L1−Iであり、ここでIは、独立して、構造(I)のさらなる化合物を表し;
R2a、R2b、R2c、R2d、R2e、R2f、R2g、R2h、R2iおよびR2jは、各々独立して、H、ハロ、C1−C6アルコキシ、アリールオキシ、アミノ、アルキルアミノ、アリールアミノ、アラルキルアミノ、ヘテロシクリル、−L1−(R3)z−L2−Mまたは−L1−(R3)z−L2−S−S−L2−(R3)z−L1−Iであり、ここでIは、独立して、構造(I)のさらなる化合物を表すか;あるいはR2a、R2b、R2c、R2d、R2e、R2f、R2g、R2h、R2iまたはR2jのうちの1つもしくはこれより多くは、同じ環の上のR2a、R2b、R2c、R2d、R2e、R2f、R2g、R2h、R2iまたはR2jのうちの別の1つもしくはこれより多く(例えば、1つもしくは2つ)と結合して、単環式または縮合二環式の炭素環式環もしく複素環式環を形成し、そして残りのR2a、R2b、R2c、R2d、R2e、R2f、R2g、R2h、R2iおよびR2jは、各々独立して、H、ハロ、C1−C6アルコキシ、アリールオキシ、アミノ、アルキルアミノ、アリールアミノ、アラルキルアミノ、ヘテロシクリル、−L1−(R3)z−L2−Mまたは−L1−(R3)z−L2−S−S−L2−(R3)z−L1−Iであり、ここでIは、独立して、構造(I)のさらなる化合物を表し;
R3は、各存在において、独立して、ポリアルキルエーテル(polyalkyether)、ポリアルキレンエーテル、ヒドロキシルアルコキシ、ヒドロキシルアルキル、ヒドロキシルアルキレン、アミノアルキレン、アミノアルコキシ、ヒドロキシルポリアルキルエーテル、ヒドロキシルポリアルキレンエーテル、アミノポリアルキルエーテル、アミノポリアルキレンエーテル、ホスフェート、チオホスフェート、ホスホ、チオホスホ、ホスホアルキル、ホスホアルキレン、ホスホアルキルエーテル、チオホスホアルキル、チオホスホアルキレン、チオホスホアルキルエーテル、ホスホロアミダイトおよび活性化リンからなる群より選択される一価もしくは二価の官能基であり;
Mは、非存在、Hまたは分析物分子もしくは固体支持体と結合できる部分であるか;あるいはMは、分析物分子もしくは固体支持体であり;
L1およびL2は、各存在において、独立して、選択肢的リンカーであり;
xおよびyは、各々独立して、0〜4の整数であり、そしてxおよびyの合計は、2またはこれより大きく;
zは、1〜10の整数であり;そして
ただしR1a、R1b、R1c、R1d、R1e、R1f、R2a、R2b、R2c、R2d、R2e、R2f、R2g、R2h、R2iまたはR2jのうちの少なくとも1つは、−L1−(R3)z−L2−Mまたは−L1−(R3)z−L2−S−S−L2−(R3)z−L1−Iであり、ここでIは、独立して、構造(I)のさらなる化合物を表す。
(a)Mが分析物分子である構造(I)の化合物を提供する工程;および
(b)上記化合物をその視覚的特性によって検出する工程
を包含する。
(a)上述の化合物のうちのいずれかと1個もしくはこれより多くの生体分子とを混合する工程;および
(b)上記化合物をその視覚的特性によって検出する工程
を包含する。
1H NMRスペクトルを、JEOL 400MHz分光計で得た。1Hスペクトルは、TMSを基準とした。逆相HPLC染料分析を、45℃で保持した2.1mm×50mm Acquity BEH−C18カラム付きのWaters Acquity UHPLCシステムを使用して行った。質量分析を、Waters/Micromass QuattroマイクロMS/MSシステムで(MSのみモードで)、MassLynx 4.1獲得ソフトウェアを使用して行った。染料に関してLC/MSに使用した移動相は、100mM 1,1,1,3,3,3−ヘキサフルオロ−2−プロパノール(HFIP)、8.6mM トリエチルアミン(TEA)、pH8であった。ホスホロアミダイトおよび前駆体分子を、ダイオードアレイ検出器および高速オートサンプラーのAgilent Infinity 1260 UHPLCシステムを使用して、Aapptec(C) SpiritTM Peptide C18カラム(4.6mm×100mm、5μm粒度)を使用して分析した。モノマー中間体の分子量を、トロピリウムカチオン注入増強イオン化(tropylium cation infusion enhanced ionization)を使用して得た1。励起および発光プロフィール実験を、Cary Eclipse分光光度計で記録した。
Claims (65)
- 以下の構造(I):
R1a、R1b、R1c、R1d、R1eおよびR1fは、各々独立して、非存在、H、ハロ、ニトロ、C1−C6アルキル、−SO3 −、−SO3アルキル、C1−C6アルコキシ、アリール、アリールオキシ、C1−C6アルキルカルボニル、C1−C6アルキルカルボニルオキシ、アリールカルボニル、アリールカルボニルオキシ、アミノ、アルキルアミノ、アリールアミノ、アラルキルアミノ、−L1−(R3)z−L2−Mまたは−L1−(R3)z−L2−S−S−L2−(R3)z−L1−Iであり、ここでIは、独立して、構造(I)のさらなる化合物を表すか;あるいはR1a、R1b、R1c、R1d、R1eまたはR1fのうちの1つは、R1a、R1b、R1c、R1d、R1eまたはR1fのうちの別の1つと結合して、炭素環式環もしく複素環式環を形成し、残りのR1a、R1b、R1c、R1d、R1eおよびR1fは、各々独立して、非存在、H、ハロ、ニトロ、C1−C6アルキル、−OSO2 −、−OSO2アルキル、C1−C6アルコキシ、アリール、アリールオキシ、C1−C6アルキルカルボニル、C1−C6アルキルカルボニルオキシ、アリールカルボニル、アリールカルボニルオキシ、アミノ、アルキルアミノ、アリールアミノ、アラルキルアミノ、−L1−(R3)z−L2−Mまたは−L1−(R3)z−L2−S−S−L2−(R3)z−L1−Iであり、ここでIは、独立して、構造(I)のさらなる化合物を表し;
R2a、R2b、R2c、R2d、R2e、R2f、R2g、R2h、R2iおよびR2jは、各々独立して、H、ハロ、C1−C6アルコキシ、アリールオキシ、アミノ、アルキルアミノ、アリールアミノ、アラルキルアミノ、ヘテロシクリル、−L1−(R3)z−L2−Mまたは−L1−(R3)z−L2−S−S−L2−(R3)z−L1−Iであり、ここでIは、独立して、構造(I)のさらなる化合物を表すか;あるいはR2a、R2b、R2c、R2d、R2e、R2f、R2g、R2h、R2iまたはR2jのうちの1つもしくはこれより多くは、同じ環上のR2a、R2b、R2c、R2d、R2e、R2f、R2g、R2h、R2iまたはR2jのうちの別の1つもしくはこれより多くと結合して、単環式もしくは縮合二環式の炭素環式環もしく複素環式環を形成し、残りのR2a、R2b、R2c、R2d、R2e、R2f、R2g、R2h、R2iおよびR2jは、各々独立して、H、ハロ、C1−C6アルコキシ、アリールオキシ、アミノ、アルキルアミノ、アリールアミノ、アラルキルアミノ、ヘテロシクリル、−L1−(R3)z−L2−Mまたは−L1−(R3)z−L2−S−S−L2−(R3)z−L1−Iであり、ここでIは、独立して、構造(I)のさらなる化合物を表し;
R3は、各存在において、独立して、ポリアルキルエーテル、ポリアルキレンエーテル、ヒドロキシルアルコキシ、ヒドロキシルアルキル、ヒドロキシルアルキレン、アミノアルキレン、アミノアルコキシ、ヒドロキシルポリアルキルエーテル、ヒドロキシルポリアルキレンエーテル、アミノポリアルキルエーテル、アミノポリアルキレンエーテル、ホスフェート、チオホスフェート、ホスホ、チオホスホ、ホスホアルキル、ホスホアルキレン、ホスホアルキルエーテル、チオホスホアルキル、チオホスホアルキレン、チオホスホアルキルエーテル、ホスホロアミダイトおよび活性化リンからなる群より選択される一価もしくは二価の官能基であり;
Mは、非存在、Hまたは分析物分子もしくは固体支持体と結合できる部分であるか;またはMは、分析物分子もしくは固体支持体であり;そして
L1およびL2は、各存在において、独立して、選択肢的リンカーであり;
xおよびyは、各々独立して、0〜4の整数であり、そしてxおよびyの合計は、2もしくはこれより大きく;
zは、1〜10の整数であり;そして
ただしR1a、R1b、R1c、R1d、R1e、R1f、R2a、R2b、R2c、R2d、R2e、R2f、R2g、R2h、R2iまたはR2jのうちの少なくとも1つは、−L1−(R3)z−L2−Mまたは−L1−(R3)z−L2−S−S−L2−(R3)z−L1−Iであり、ここでIは、独立して、構造(I)のさらなる化合物を表す、
化合物またはその塩。 - xおよびyの合計は、2である、請求項1に記載の化合物。
- xは、0であり、yは、2である、請求項1に記載の化合物。
- R1aは、−L1−(R3)z−L2−Mである、請求項1〜5のいずれか1項に記載の化合物。
- R1d、R1eまたはR1fのうちの1つは、−L1−(R3)z−L2−Mである、請求項1〜5のいずれか1項に記載の化合物。
- R2a、R2b、R2c、R2d、R2e、R2f、R2g、R2h、R2iまたはR2jのうちの1つは、−L1−(R3)z−L2−Mである、請求項1〜5のいずれか1項に記載の化合物。
- R2a、R2b、R2c、R2d、R2e、R2f、R2g、R2h、R2iまたはR2jのうちの2つは、−L1−(R3)z−L2−Mである、請求項1〜5のいずれか1項に記載の化合物。
- R1aおよびR1bは、両方が−L1−(R3)z−L2−Mである、請求項1〜5のいずれか1項に記載の化合物。
- R1aまたはR1bのうちの一方は、−L1−(R3)z−L2−Mであり、R2a、R2b、R2c、R2d、R2e、R2f、R2g、R2h、R2iまたはR2jのうちの1つは、−L1−(R3)z−L2−Mである、請求項1〜5のいずれか1項に記載の化合物。
- R1aまたはR1bのうちの一方は、−L1−(R3)z−L2−Mであり、R1d、R1eまたはR1fのうちの1つは、−L1−(R3)z−L2−Mである、請求項1〜5のいずれか1項に記載の化合物。
- R2a、R2b、R2c、R2d、R2e、R2f、R2g、R2h、R2iまたはR2jのうちの少なくとも1つは、アミノ、アルキルアミノ、アリールアミノ、アラルキルアミノまたはヘテロシクリルである、請求項1〜12のいずれか1項に記載の化合物。
- R2cもしくはR2h、またはその両方は、アミノ、アルキルアミノ、アリールアミノ、アラルキルアミノまたはヘテロシクリルである、請求項13に記載の化合物。
- アルキルアミノは、ジメチルアミノ、ジエチルアミノ、ジイソプロピルアミノまたはエチルイソプロピルアミノである、請求項13〜14のいずれか1項に記載の化合物。
- アリールアミノは、ジフェニルアミノである、請求項13〜14のいずれか1項に記載の化合物。
- ヘテロシクリルは、N−ピロリジニルまたはN−ピロリルである、請求項13〜14のいずれか1項に記載の化合物。
- R2a、R2b、R2c、R2d、R2e、R2f、R2g、R2h、R2iまたはR2jのうちの1つもしくはこれより多くは、同じ環上のR2a、R2b、R2c、R2d、R2e、R2f、R2g、R2h、R2iまたはR2jのうちの別の1つもしくはこれより多くと結合して、単環式または縮合二環式の炭素環式環もしく複素環式環を形成し、残りのR2a、R2b、R2c、R2d、R2e、R2f、R2g、R2h、R2iおよびR2jは、各々独立して、H、ハロ、C1−C6アルコキシ、アリールオキシ、アミノ、アルキルアミノ、アリールアミノ、アラルキルアミノ、ヘテロシクリル、−L1−(R3)z−L2−Mまたは−L1−(R3)z−L2−S−S−L2−(R3)z−L1−Iであり、ここでIは、独立して、構造(I)のさらなる化合物を表す、請求項1〜12のいずれか1項に記載の化合物。
- R2a、R2b、R2d、R2e、R2f、R2g、R2iまたはR2jのうちの少なくとも1つは、ハロ、アルコキシまたはアリールオキシである、請求項1〜19のいずれか1項に記載の化合物。
- R2a、R2b、R2d、R2e、R2f、R2g、R2iまたはR2jのうちの少なくとも1つは、ハロである、請求項1〜20のいずれか1項に記載の化合物。
- R2a、R2b、R2d、R2e、R2f、R2g、R2iまたはR2jのうちの少なくとも1つは、アルコキシである、請求項1〜20のいずれか1項に記載の化合物。
- R2a、R2b、R2d、R2e、R2f、R2g、R2iまたはR2jのうちの少なくとも1つは、アリールオキシである、請求項1〜20のいずれか1項に記載の化合物。
- R2a、R2b、R2d、R2e、R2f、R2g、R2iまたはR2jのうちの少なくとも1つは、Hである、請求項1〜23のいずれか1項に記載の化合物。
- R2a、R2b、R2d、R2e、R2f、R2g、R2iおよびR2jの各々は、Hである、請求項1〜19のいずれか1項に記載の化合物。
- R1a、R1b、R1c、R1d、R1eおよびR1fは、各々独立して、非存在、H、ハロ、ニトロ、C1−C6アルキル、−SO3 −、−SO3アルキル、C1−C6アルコキシ、アリール、アリールオキシ、C1−C6アルキルカルボニル、C1−C6アルキルカルボニルオキシ、アリールカルボニル、アリールカルボニルオキシ、アミノ、アルキルアミノ、アリールアミノ、アラルキルアミノ、−L1−(R3)z−L2−Mまたは−L1−(R3)z−L2−S−S−L2−(R3)z−L1−Iであり、ここでIは、独立して、構造(I)のさらなる化合物を表す、請求項1〜25のいずれか1項に記載の化合物。
- R1a、R1b、R1c、R1d、R1eまたはR1fのうちの少なくとも1つは、C1−C6アルコキシ、アリールオキシまたはC1−C6アルキルカルボニルオキシである、請求項26に記載の化合物。
- C1−C6アルコキシは、メトキシである、請求項27に記載の化合物。
- R1a、R1b、R1c、R1d、R1eまたはR1fのうちの少なくとも1つは、アミノ、アルキルアミノ、アリールアミノまたはアラルキルアミノである、請求項26に記載の化合物。
- アルキルアミノは、ジメチルアミノである、請求項29に記載の化合物。
- R1a、R1b、R1c、R1d、R1eまたはR1fのうちの少なくとも1つは,ハロまたはニトロである、請求項26に記載の化合物。
- R1a、R1b、R1c、R1d、R1eまたはR1fのうちの少なくとも1つは、−SO3 −または−SO3アルキルである、請求項26に記載の化合物。
- R1a、R1b、R1c、R1d、R1eまたはR1fのうちの少なくとも1つは、C1−C6アルキルまたはアリールである、請求項26に記載の化合物。
- C1−C6アルキルは、メチルまたはエチルである、請求項33に記載の化合物。
- R1a、R1b、R1c、R1dまたはR1eのうちの少なくとも1つは、アルキルカルボニルまたはアリールカルボニルである、請求項26に記載の化合物。
- R1a、R1b、R1c、R1d、R1eまたはR1fのうちの1つは、R1a、R1b、R1c、R1d、R1eまたはR1fのうちの別の1つと結合して、炭素環式環もしく複素環式環を形成し、残りのR1a、R1b、R1c、R1d、R1eおよびR1fは、各々独立して、非存在、H、ハロ、ニトロ、C1−C6アルキル、−OSO2 −、−OSO2アルキル、C1−C6アルコキシ、アリール、アリールオキシ、C1−C6アルキルカルボニル、C1−C6アルキルカルボニルオキシ、アリールカルボニル、アリールカルボニルオキシ、アミノ、アルキルアミノ、アリールアミノ、アラルキルアミノ、−L1−(R3)z−L2−Mまたは−L1−(R3)z−L2−S−S−L2−(R3)z−L1−Iであり、ここでIは、独立して、構造(I)のさらなる化合物を表す、請求項1〜25のいずれか1項に記載の化合物。
- L1は、存在する、請求項1〜37のいずれか1項に記載の化合物。
- L1は、C1−C6アルキレンである、請求項38に記載の化合物。
- R3は、ポリアルキレンエーテル、ホスフェート、ホスホおよびホスホアルキレンからなる群より選択される、請求項1〜39のいずれか1項に記載の化合物。
- R3は、ホスホロアミダイトであり、Mは、非存在である、請求項1〜39のいずれか1項に記載の化合物。
- Mは、非存在またはHである、請求項1〜43のいずれか1項に記載の化合物。
- Mは、分析物分子もしくは固体支持体と結合できる部分である、請求項1〜42のいずれか1項に記載の化合物。
- Mは、求核性反応性基、求電子性反応性基または環化付加反応性基を含む、請求項45項に記載の化合物。
- Mは、スルフヒドリル、ジスルフィド、活性化エステル、イソチオシアネート、アジド、アルキン、アルケン、ジエン、ジエノフィル、酸ハライド、スルホニルハライド、ホスフィン、α−ハロアミド、ビオチン、アミノまたはマレイミドを含む、請求項46に記載の化合物。
- 前記活性化エステルは、N−スクシンイミドエステル、イミドエステルまたはポリフルオロフェニルエステルである、請求項47に記載の化合物。
- 前記アルキンは、アルキルアジドまたはアシルアジドである、請求項47に記載の化合物。
- Mは、分析物分子もしくは固体支持体である、請求項1〜42のいずれか1項に記載の化合物。
- 前記分析物分子は、生体分子である、請求項50に記載の化合物。
- 前記生体分子は、核酸、アミノ酸またはこれらのポリマーである、請求項51に記載の化合物。
- 前記生体分子は、核酸、ペプチド、炭水化物、脂質、酵素、レセプター、レセプターリガンド、抗体、糖タンパク質、アプタマー、抗原またはプリオンである、請求項51に記載の化合物。
- 前記分析物分子は、薬物、ビタミンまたは低分子である、請求項51に記載の化合物。
- Mは、−SHである、請求項55に記載の化合物。
- サンプルを染色するための方法であって、該方法は、該サンプルに、請求項1〜56のいずれか1項に記載の化合物を、該サンプルが適切な波長で照射される場合に光学的応答を生じるために十分な量で添加する工程を包含する方法。
- 前記光学的応答は、蛍光応答である、請求項57に記載の方法。
- 前記サンプルは、細胞を含む、請求項57〜58のいずれか1項に記載の方法。
- 前記細胞をフローサイトメトリーによって観察する工程をさらに包含する、請求項59に記載の方法。
- 前記蛍光応答を、検出可能に異なる光学的特性を有する第2の発蛍光団の蛍光応答から区別する工程をさらに包含する、請求項60に記載の方法。
- 分析物分子を視覚的に検出するための方法であって、該方法は、
(a)Mが分析物分子である請求項1〜56のいずれか1項に記載のいずれかの化合物を提供する工程;および
(b)該化合物をその視覚的特性によって検出する工程、
を包含する方法。 - 生体分子を視覚的に検出するための方法であって、該方法は、
(a)請求項1〜56のいずれかに記載の化合物と1個もしくはこれより多くの生体分子とを混合する工程;および
(b)該化合物をその視覚的特性によって検出する工程、
を包含する方法。 - 請求項1〜56のいずれか1項に記載の化合物および1もしくはこれより多くの生体分子を含む、組成物。
- 前記1もしくはこれより多くの生体分子の検出のための分析方法における請求項64に記載の組成物の使用。
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