CA2949447C - Compositions and methods for stabilizing luminogenic substrates - Google Patents
Compositions and methods for stabilizing luminogenic substrates Download PDFInfo
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- CA2949447C CA2949447C CA2949447A CA2949447A CA2949447C CA 2949447 C CA2949447 C CA 2949447C CA 2949447 A CA2949447 A CA 2949447A CA 2949447 A CA2949447 A CA 2949447A CA 2949447 C CA2949447 C CA 2949447C
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- triazin
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- 239000000758 substrate Substances 0.000 title claims abstract description 116
- 239000000203 mixture Substances 0.000 title claims abstract description 115
- 238000000034 method Methods 0.000 title claims abstract description 53
- 230000000087 stabilizing effect Effects 0.000 title claims abstract description 17
- HTBLMRUZSCCOLL-UHFFFAOYSA-N 8-benzyl-2-(furan-2-ylmethyl)-6-phenylimidazo[1,2-a]pyrazin-3-ol Chemical compound OC1=C(CC2=CC=CO2)N=C2N1C=C(N=C2CC1=CC=CC=C1)C1=CC=CC=C1 HTBLMRUZSCCOLL-UHFFFAOYSA-N 0.000 claims abstract description 168
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 141
- YHIPILPTUVMWQT-UHFFFAOYSA-N Oplophorus luciferin Chemical compound C1=CC(O)=CC=C1CC(C(N1C=C(N2)C=3C=CC(O)=CC=3)=O)=NC1=C2CC1=CC=CC=C1 YHIPILPTUVMWQT-UHFFFAOYSA-N 0.000 claims abstract description 128
- 239000003960 organic solvent Substances 0.000 claims abstract description 49
- NKOPQOSBROLOFP-UHFFFAOYSA-N 6-methyl-3-sulfanylidene-2h-1,2,4-triazin-5-one Chemical compound CC1=NNC(=S)NC1=O NKOPQOSBROLOFP-UHFFFAOYSA-N 0.000 claims description 219
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 108
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 106
- 150000001875 compounds Chemical class 0.000 claims description 83
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 42
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 150000002466 imines Chemical class 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 229910003827 NRaRb Inorganic materials 0.000 claims description 17
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 14
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 13
- 150000001735 carboxylic acids Chemical class 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- 108090000790 Enzymes Proteins 0.000 claims description 11
- 102000004190 Enzymes Human genes 0.000 claims description 11
- JEOQACOXAOEPLX-WCCKRBBISA-N (2s)-2-amino-5-(diaminomethylideneamino)pentanoic acid;1,3-thiazolidine-4-carboxylic acid Chemical compound OC(=O)C1CSCN1.OC(=O)[C@@H](N)CCCN=C(N)N JEOQACOXAOEPLX-WCCKRBBISA-N 0.000 claims description 8
- UDRLQUBSFWAFSO-UHFFFAOYSA-N 3-(4-amino-5-oxo-3-sulfanylidene-2h-1,2,4-triazin-6-yl)propanoic acid Chemical compound NN1C(=S)NN=C(CCC(O)=O)C1=O UDRLQUBSFWAFSO-UHFFFAOYSA-N 0.000 claims description 7
- YWUNWMADAOHUTF-UHFFFAOYSA-N 3-(5-oxo-3-sulfanylidene-2h-1,2,4-triazin-6-yl)propanoic acid Chemical compound OC(=O)CCC1=NNC(=S)NC1=O YWUNWMADAOHUTF-UHFFFAOYSA-N 0.000 claims description 7
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- FNIWYYXBXXNBTQ-UHFFFAOYSA-N 5-oxo-3-sulfanylidene-2h-1,2,4-triazine-6-carboxylic acid Chemical compound OC(=O)C1=NNC(=S)NC1=O FNIWYYXBXXNBTQ-UHFFFAOYSA-N 0.000 claims description 4
- BZUZUVWERCAEPE-UHFFFAOYSA-N 6-(hydroxymethyl)-3-sulfanylidene-2h-1,2,4-triazin-5-one Chemical compound OCC1=NNC(S)=NC1=O BZUZUVWERCAEPE-UHFFFAOYSA-N 0.000 claims description 4
- BMFVHRIQGZKRSH-UHFFFAOYSA-N 3-sulfanylidene-6-(trifluoromethyl)-2H-1,2,4-triazin-5-one Chemical compound S=C1NN=C(C(N1)=O)C(F)(F)F BMFVHRIQGZKRSH-UHFFFAOYSA-N 0.000 claims description 3
- 239000005450 thionucleoside Substances 0.000 abstract description 56
- 239000000243 solution Substances 0.000 description 65
- KAEGGIFPLJZUOZ-UHFFFAOYSA-N Renilla luciferin Chemical compound C1=CC(O)=CC=C1C(N1)=CN2C(=O)C(CC=3C=CC=CC=3)=NC2=C1CC1=CC=CC=C1 KAEGGIFPLJZUOZ-UHFFFAOYSA-N 0.000 description 42
- 125000003118 aryl group Chemical group 0.000 description 35
- -1 coelenterazine-h-h Chemical compound 0.000 description 32
- 238000004128 high performance liquid chromatography Methods 0.000 description 32
- 239000000047 product Substances 0.000 description 22
- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 description 21
- 125000001072 heteroaryl group Chemical group 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- 239000011550 stock solution Substances 0.000 description 14
- 238000002835 absorbance Methods 0.000 description 11
- 239000008380 degradant Substances 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 238000004020 luminiscence type Methods 0.000 description 11
- 230000014759 maintenance of location Effects 0.000 description 10
- 125000004043 oxo group Chemical group O=* 0.000 description 10
- 230000037361 pathway Effects 0.000 description 8
- 230000006641 stabilisation Effects 0.000 description 8
- 238000011105 stabilization Methods 0.000 description 8
- 125000000547 substituted alkyl group Chemical group 0.000 description 8
- 239000002202 Polyethylene glycol Substances 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 239000000654 additive Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 108060001084 Luciferase Proteins 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910003460 diamond Inorganic materials 0.000 description 4
- 239000010432 diamond Substances 0.000 description 4
- 239000012091 fetal bovine serum Substances 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- UMWWHOXOVPIGFD-UHFFFAOYSA-N 2-methyl-3-sulfanylidene-1,2,4-triazinane-5,6-dione Chemical compound CN1NC(=O)C(=O)N=C1S UMWWHOXOVPIGFD-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 238000004166 bioassay Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- 239000005089 Luciferase Substances 0.000 description 2
- 241001443978 Oplophorus Species 0.000 description 2
- 108010052090 Renilla Luciferases Proteins 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 230000031018 biological processes and functions Effects 0.000 description 2
- JIAUJOOGSKJAFH-UHFFFAOYSA-N coelenteramide Chemical compound C1=CC(O)=CC=C1CC(=O)NC(N=CC(N1)=C2C=CC(=O)C=C2)=C1CC1=CC=CC=C1 JIAUJOOGSKJAFH-UHFFFAOYSA-N 0.000 description 2
- CJIIERPDFZUYPI-UHFFFAOYSA-N coelenteramide Natural products C1=CC(O)=CC=C1CC(=O)NC1=NC=C(C=2C=CC(O)=CC=2)N=C1CC1=CC=CC=C1 CJIIERPDFZUYPI-UHFFFAOYSA-N 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000005347 halocycloalkyl group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000004404 heteroalkyl group Chemical group 0.000 description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 108700043045 nanoluc Proteins 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- GLNOCHFLWSMEDS-UHFFFAOYSA-N oxidized Renilla luciferin Chemical compound C1=CC(O)=CC=C1C(N=C1CC=2C=CC=CC=2)=CN=C1NC(=O)CC1=CC=CC=C1 GLNOCHFLWSMEDS-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 108010000239 Aequorin Proteins 0.000 description 1
- 241000158573 Aristeidae Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000243321 Cnidaria Species 0.000 description 1
- 241000239250 Copepoda Species 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 108090000331 Firefly luciferases Proteins 0.000 description 1
- 241001343649 Gaussia princeps (T. Scott, 1894) Species 0.000 description 1
- 241000158577 Luciferidae Species 0.000 description 1
- 108010047357 Luminescent Proteins Proteins 0.000 description 1
- 102000006830 Luminescent Proteins Human genes 0.000 description 1
- 241000186140 Metridia longa Species 0.000 description 1
- 241000202359 Oplophoroidea Species 0.000 description 1
- 229920001774 Perfluoroether Chemical group 0.000 description 1
- 241000158575 Sergestidae Species 0.000 description 1
- 241001660594 Solenoceridae Species 0.000 description 1
- 241001254485 Thalassocarididae Species 0.000 description 1
- 241000238584 Vargula Species 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 238000007876 drug discovery Methods 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000004475 heteroaralkyl group Chemical group 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000004850 protein–protein interaction Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
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- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/66—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving luciferase
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| PCT/US2015/032439 WO2015179864A1 (en) | 2014-05-23 | 2015-05-26 | Compositions and methods for stabilizing luminogenic substrates |
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| US11534504B2 (en) | 2018-10-03 | 2022-12-27 | Promega Corporation | Compositions and methods for stabilizing coelenterazine and analogs and derivatives thereof |
| CN111116594B (zh) * | 2019-12-03 | 2021-05-28 | 山东大学 | 一种C-6位改造NanoLuc类型类似物及其制备方法与应用 |
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| US7718389B2 (en) * | 2006-07-24 | 2010-05-18 | National Institute Of Advanced Industrial Science And Technology | Stabilizing composition and stabilizing method of coelenterazine solution for high-throughput measurement of luciferase activity |
| EP3141905B1 (en) * | 2008-03-27 | 2019-03-06 | Promega Corporation | Protein labeling with cyanobenzothiazole conjugates |
| SG10202103336SA (en) * | 2010-11-02 | 2021-04-29 | Promega Corp | Novel coelenterazine substrates and methods of use |
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