JP2019527289A5 - - Google Patents

Info

Publication number

JP2019527289A5

JP2019527289A5 JP2019526198A JP2019526198A JP2019527289A5 JP 2019527289 A5 JP2019527289 A5 JP 2019527289A5 JP 2019526198 A JP2019526198 A JP 2019526198A JP 2019526198 A JP2019526198 A JP 2019526198A JP 2019527289 A5 JP2019527289 A5 JP 2019527289A5

Authority

JP

Japan

Prior art keywords

independently

functional group

appearance

covalent bond

alkyl

Prior art date

2017-07-27

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.)

Granted

Links

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• 150000001875 compounds Chemical class 0.000 claims description 285
• 125000000524 functional group Chemical group 0.000 claims description 253
• 125000005647 linker group Chemical group 0.000 claims description 248
• 238000000034 method Methods 0.000 claims description 198
• -1 alkoxyalkyl ethers Chemical class 0.000 claims description 141
• 239000000975 dye Substances 0.000 claims description 117
• 125000000217 alkyl group Chemical group 0.000 claims description 107
• 125000003545 alkoxy group Chemical group 0.000 claims description 91
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 90
• 230000000295 complement effect Effects 0.000 claims description 84
• 239000012491 analyte Substances 0.000 claims description 83
• 239000007787 solid Substances 0.000 claims description 79
• 150000005215 alkyl ethers Chemical class 0.000 claims description 66
• 238000006243 chemical reaction Methods 0.000 claims description 60
• 229920000642 polymer Polymers 0.000 claims description 48
• 229910019142 PO4 Inorganic materials 0.000 claims description 44
• 235000021317 phosphate Nutrition 0.000 claims description 43
• 230000008685 targeting Effects 0.000 claims description 42
• 229910052760 oxygen Inorganic materials 0.000 claims description 40
• 229910052717 sulfur Inorganic materials 0.000 claims description 39
• 230000009257 reactivity Effects 0.000 claims description 37
• 150000001336 alkenes Chemical class 0.000 claims description 36
• 125000003118 aryl group Chemical group 0.000 claims description 35
• 239000000539 dimer Substances 0.000 claims description 34
• 125000002947 alkylene group Chemical group 0.000 claims description 32
• 125000004414 alkyl thio group Chemical group 0.000 claims description 28
• 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 27
• 239000002253 acid Substances 0.000 claims description 25
• 150000001412 amines Chemical class 0.000 claims description 25
• 150000001502 aryl halides Chemical class 0.000 claims description 25
• 150000001345 alkine derivatives Chemical class 0.000 claims description 24
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 24
• RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims description 23
• 238000004458 analytical method Methods 0.000 claims description 22
• 150000001350 alkyl halides Chemical group 0.000 claims description 21
• 239000000203 mixture Substances 0.000 claims description 21
• 150000007523 nucleic acids Chemical group 0.000 claims description 21
• 125000004405 heteroalkoxy group Chemical group 0.000 claims description 20
• 150000003852 triazoles Chemical class 0.000 claims description 20
• CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Chemical group C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 19
• 125000004474 heteroalkylene group Chemical group 0.000 claims description 18
• 239000002777 nucleoside Substances 0.000 claims description 18
• 150000003833 nucleoside derivatives Chemical class 0.000 claims description 18
• 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 230000000269 nucleophilic effect Effects 0.000 claims description 17
• 239000010452 phosphate Substances 0.000 claims description 17
• 150000004820 halides Chemical class 0.000 claims description 16
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 16
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 16
• 230000000007 visual effect Effects 0.000 claims description 16
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 15
• 125000004419 alkynylene group Chemical group 0.000 claims description 15
• 150000001540 azides Chemical class 0.000 claims description 15
• BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 15
• 125000004450 alkenylene group Chemical group 0.000 claims description 14
• 125000002837 carbocyclic group Chemical group 0.000 claims description 14
• 238000006352 cycloaddition reaction Methods 0.000 claims description 14
• 150000002170 ethers Chemical class 0.000 claims description 14
• 108020004707 nucleic acids Proteins 0.000 claims description 14
• 102000039446 nucleic acids Human genes 0.000 claims description 14
• 239000000049 pigment Substances 0.000 claims description 14
• 150000001413 amino acids Chemical group 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 125000003282 alkyl amino group Chemical group 0.000 claims description 12
• 230000003287 optical effect Effects 0.000 claims description 12
• 108090000765 processed proteins & peptides Chemical group 0.000 claims description 12
• RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 12
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 11
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 11
• 150000002500 ions Chemical class 0.000 claims description 11
• 230000004044 response Effects 0.000 claims description 11
• POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 10
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 10
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 10
• GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims description 10
• WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical group C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 10
• GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 10
• 150000007970 thio esters Chemical class 0.000 claims description 10
• 150000003568 thioethers Chemical class 0.000 claims description 10
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
• 239000004202 carbamide Substances 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical group C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 8
• 150000001408 amides Chemical class 0.000 claims description 8
• VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical group C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 claims description 8
• ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 8
• 238000001514 detection method Methods 0.000 claims description 8
• 150000002540 isothiocyanates Chemical class 0.000 claims description 8
• NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 claims description 8
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 8
• QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical group [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 claims description 7
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 7
• 125000000464 thioxo group Chemical group S=* 0.000 claims description 7
• PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 6
• 239000012948 isocyanate Substances 0.000 claims description 6
• 150000002513 isocyanates Chemical class 0.000 claims description 6
• 238000002156 mixing Methods 0.000 claims description 6
• 238000007363 ring formation reaction Methods 0.000 claims description 6
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 6
• NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims description 5
• 150000004713 phosphodiesters Chemical class 0.000 claims description 5
• 238000012546 transfer Methods 0.000 claims description 5
• XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 claims description 4
• VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical group OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims description 4
• BZTDTCNHAFUJOG-UHFFFAOYSA-N 6-carboxyfluorescein Chemical compound C12=CC=C(O)C=C2OC2=CC(O)=CC=C2C11OC(=O)C2=CC=C(C(=O)O)C=C21 BZTDTCNHAFUJOG-UHFFFAOYSA-N 0.000 claims description 4
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
• 229920004933 Terylene® Polymers 0.000 claims description 4
• DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 4
• NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
• DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical group C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 claims description 4
• 235000001671 coumarin Nutrition 0.000 claims description 4
• 229960000956 coumarin Drugs 0.000 claims description 4
• WZYNTGFFWDNWGG-UHFFFAOYSA-N n,n-dimethyl-2-(2-phenylethenyl)aniline Chemical compound CN(C)C1=CC=CC=C1C=CC1=CC=CC=C1 WZYNTGFFWDNWGG-UHFFFAOYSA-N 0.000 claims description 4
• 239000001048 orange dye Substances 0.000 claims description 4
• 229930184652 p-Terphenyl Natural products 0.000 claims description 4
• 239000005020 polyethylene terephthalate Substances 0.000 claims description 4
• 150000004032 porphyrins Chemical class 0.000 claims description 4
• YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical group C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 claims description 4
• 229910052707 ruthenium Inorganic materials 0.000 claims description 4
• 238000010186 staining Methods 0.000 claims description 4
• ACOJCCLIDPZYJC-UHFFFAOYSA-M thiazole orange Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC=C2C(C=C3N(C4=CC=CC=C4S3)C)=CC=[N+](C)C2=C1 ACOJCCLIDPZYJC-UHFFFAOYSA-M 0.000 claims description 4
• PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical group C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 claims description 3
• FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 claims description 3
• XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 claims description 3
• 238000000684 flow cytometry Methods 0.000 claims description 3
• 229940031826 phenolate Drugs 0.000 claims description 3
• 150000002118 epoxides Chemical class 0.000 claims 2
• 150000003923 2,5-pyrrolediones Chemical class 0.000 claims 1
• NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical class ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims 1
• 125000005490 tosylate group Chemical group 0.000 claims 1
• 0 CC(C)(*)*C(*)(*)IN Chemical compound CC(C)(*)*C(*)(*)IN 0.000 description 38
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
• 229910052757 nitrogen Inorganic materials 0.000 description 23
• 125000005842 heteroatom Chemical group 0.000 description 20
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
• 239000000243 solution Substances 0.000 description 17
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• 230000015572 biosynthetic process Effects 0.000 description 15
• 239000000126 substance Substances 0.000 description 15
• 229910052799 carbon Inorganic materials 0.000 description 14
• 125000004432 carbon atom Chemical group C* 0.000 description 14
• 125000004122 cyclic group Chemical group 0.000 description 14
• 150000003839 salts Chemical class 0.000 description 14
• 238000012360 testing method Methods 0.000 description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
• 125000000623 heterocyclic group Chemical group 0.000 description 13
• 239000000523 sample Substances 0.000 description 13
• 210000004027 cell Anatomy 0.000 description 12
• 125000001072 heteroaryl group Chemical group 0.000 description 12
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
• 239000002585 base Substances 0.000 description 11
• 239000000460 chlorine Substances 0.000 description 11
• 125000006239 protecting group Chemical group 0.000 description 11
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
• 229940024606 amino acid Drugs 0.000 description 10
• 235000001014 amino acid Nutrition 0.000 description 10
• 229940125904 compound 1 Drugs 0.000 description 10
• 150000008300 phosphoramidites Chemical class 0.000 description 10
• 238000002360 preparation method Methods 0.000 description 10
• 239000011734 sodium Substances 0.000 description 10
• 238000003786 synthesis reaction Methods 0.000 description 10
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
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• 239000001257 hydrogen Substances 0.000 description 7
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• 125000001424 substituent group Chemical group 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
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• 125000000753 cycloalkyl group Chemical group 0.000 description 6
• JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 6
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• 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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• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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