JPH06506945A - ペプチド核酸 - Google Patents
ペプチド核酸Info
- Publication number
- JPH06506945A JPH06506945A JP4510434A JP51043492A JPH06506945A JP H06506945 A JPH06506945 A JP H06506945A JP 4510434 A JP4510434 A JP 4510434A JP 51043492 A JP51043492 A JP 51043492A JP H06506945 A JPH06506945 A JP H06506945A
- Authority
- JP
- Japan
- Prior art keywords
- group
- amino
- alkyl
- hydrogen
- taeg
- 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.)
- Granted
Links
- 108091093037 Peptide nucleic acid Proteins 0.000 title description 150
- 150000001875 compounds Chemical class 0.000 claims description 115
- 238000000034 method Methods 0.000 claims description 111
- -1 inserts Substances 0.000 claims description 63
- 239000000126 substance Substances 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 46
- 238000009739 binding Methods 0.000 claims description 43
- 230000027455 binding Effects 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- 235000001014 amino acid Nutrition 0.000 claims description 40
- 108091034117 Oligonucleotide Proteins 0.000 claims description 39
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 39
- 150000001413 amino acids Chemical class 0.000 claims description 38
- 125000003277 amino group Chemical group 0.000 claims description 37
- 108090000623 proteins and genes Proteins 0.000 claims description 34
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
- 125000006239 protecting group Chemical group 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 26
- 239000003446 ligand Substances 0.000 claims description 22
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 21
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 20
- 229940113082 thymine Drugs 0.000 claims description 20
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 claims description 18
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 102000004169 proteins and genes Human genes 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 16
- 229930024421 Adenine Natural products 0.000 claims description 15
- 229960000643 adenine Drugs 0.000 claims description 15
- 235000018102 proteins Nutrition 0.000 claims description 15
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 14
- 239000000872 buffer Substances 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 12
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 12
- 230000014616 translation Effects 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000006850 spacer group Chemical group 0.000 claims description 11
- 238000013518 transcription Methods 0.000 claims description 11
- 230000035897 transcription Effects 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 229940104302 cytosine Drugs 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 102000040430 polynucleotide Human genes 0.000 claims description 9
- 108091033319 polynucleotide Proteins 0.000 claims description 9
- 239000002157 polynucleotide Substances 0.000 claims description 9
- 241000700605 Viruses Species 0.000 claims description 8
- 239000002131 composite material Substances 0.000 claims description 8
- 229920002401 polyacrylamide Polymers 0.000 claims description 8
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 7
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000004793 Polystyrene Substances 0.000 claims description 6
- 238000004873 anchoring Methods 0.000 claims description 6
- 229940035893 uracil Drugs 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 229920002223 polystyrene Polymers 0.000 claims description 5
- 230000001105 regulatory effect Effects 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 150000001720 carbohydrates Chemical class 0.000 claims description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 239000002562 thickening agent Substances 0.000 claims description 4
- LQLQRFGHAALLLE-UHFFFAOYSA-N 5-bromouracil Chemical compound BrC1=CNC(=O)NC1=O LQLQRFGHAALLLE-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 235000014633 carbohydrates Nutrition 0.000 claims description 3
- 239000002773 nucleotide Substances 0.000 claims description 3
- 125000003729 nucleotide group Chemical group 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000002738 chelating agent Substances 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims description 2
- 230000002147 killing effect Effects 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920001184 polypeptide Polymers 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 150000003431 steroids Chemical class 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 150000001371 alpha-amino acids Chemical class 0.000 claims 6
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 3
- 125000003636 chemical group Chemical group 0.000 claims 3
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims 3
- 229910052711 selenium Inorganic materials 0.000 claims 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 229910006069 SO3H Inorganic materials 0.000 claims 2
- 230000000593 degrading effect Effects 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims 2
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims 1
- 230000015556 catabolic process Effects 0.000 claims 1
- 238000006731 degradation reaction Methods 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 150000004678 hydrides Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 239000010985 leather Substances 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 230000010076 replication Effects 0.000 claims 1
- 229960003087 tioguanine Drugs 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 346
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 200
- 229920005989 resin Polymers 0.000 description 165
- 239000011347 resin Substances 0.000 description 165
- 230000015572 biosynthetic process Effects 0.000 description 133
- 239000000243 solution Substances 0.000 description 124
- 238000003786 synthesis reaction Methods 0.000 description 124
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 114
- 229910001868 water Inorganic materials 0.000 description 112
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 96
- 238000006243 chemical reaction Methods 0.000 description 96
- 238000005859 coupling reaction Methods 0.000 description 92
- 239000000203 mixture Substances 0.000 description 91
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 80
- 108020004414 DNA Proteins 0.000 description 67
- 238000010168 coupling process Methods 0.000 description 67
- 230000008878 coupling Effects 0.000 description 65
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
- 239000007787 solid Substances 0.000 description 50
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 46
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
- 239000000178 monomer Substances 0.000 description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 38
- 238000003756 stirring Methods 0.000 description 38
- 238000001914 filtration Methods 0.000 description 37
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
- 238000003776 cleavage reaction Methods 0.000 description 36
- 238000005406 washing Methods 0.000 description 35
- 230000007017 scission Effects 0.000 description 34
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 33
- 238000004458 analytical method Methods 0.000 description 33
- 239000002244 precipitate Substances 0.000 description 33
- 239000000047 product Substances 0.000 description 32
- 210000004027 cell Anatomy 0.000 description 31
- 238000001035 drying Methods 0.000 description 31
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
- 238000012360 testing method Methods 0.000 description 30
- 238000000921 elemental analysis Methods 0.000 description 29
- 239000000463 material Substances 0.000 description 29
- 239000003921 oil Substances 0.000 description 29
- 238000010348 incorporation Methods 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 239000012043 crude product Substances 0.000 description 26
- 239000003153 chemical reaction reagent Substances 0.000 description 25
- 238000010511 deprotection reaction Methods 0.000 description 25
- 239000007864 aqueous solution Substances 0.000 description 23
- 238000005520 cutting process Methods 0.000 description 23
- 239000003208 petroleum Substances 0.000 description 23
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- 102000053602 DNA Human genes 0.000 description 21
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 239000012634 fragment Substances 0.000 description 20
- 239000000523 sample Substances 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 18
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 18
- 235000019341 magnesium sulphate Nutrition 0.000 description 18
- 239000012071 phase Substances 0.000 description 18
- 238000000746 purification Methods 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 239000013612 plasmid Substances 0.000 description 17
- 239000013058 crude material Substances 0.000 description 16
- 238000002474 experimental method Methods 0.000 description 16
- 238000011065 in-situ storage Methods 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 238000002835 absorbance Methods 0.000 description 14
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 235000017557 sodium bicarbonate Nutrition 0.000 description 14
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
- 239000007790 solid phase Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 13
- 229940079593 drug Drugs 0.000 description 13
- 239000003814 drug Substances 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 239000012535 impurity Substances 0.000 description 12
- 238000006386 neutralization reaction Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 12
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 11
- 239000011324 bead Substances 0.000 description 11
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- 230000021736 acetylation Effects 0.000 description 10
- 238000006640 acetylation reaction Methods 0.000 description 10
- 150000004985 diamines Chemical class 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
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- 238000001556 precipitation Methods 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 238000006467 substitution reaction Methods 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 9
- 238000007796 conventional method Methods 0.000 description 9
- 238000004807 desolvation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 239000000499 gel Substances 0.000 description 9
- 238000009396 hybridization Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 108020004999 messenger RNA Proteins 0.000 description 9
- 150000007523 nucleic acids Chemical group 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- 238000010532 solid phase synthesis reaction Methods 0.000 description 9
- 238000013519 translation Methods 0.000 description 9
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 8
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 238000010647 peptide synthesis reaction Methods 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- 101710163270 Nuclease Proteins 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 230000006870 function Effects 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 102000039446 nucleic acids Human genes 0.000 description 7
- 108020004707 nucleic acids Proteins 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 6
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Abstract
Description
Claims (33)
- 1.主鎖中に位置するアザ窒素原子に別個に結合した複数のリガンドを保有する ポリアミド主鎖からなる化合物であって、それらのリガンドのうち少なくとも1 個は天然核酸塩基、非天然核酸塩基、DNA挿入体、または核酸塩基結合性基で ある化合物。
- 2.アザ窒素原子が主鎖中において4−6個の介在原子により互いに分離されて いる、請求の範囲第1項に記載の化合物。
- 3.下記構造式を有する化合物: ▲数式、化学式、表等があります▼ 式中: nは少なくとも2であり; L1−Lnはそれぞれ、水素、ヒドロキシ、(C1−C4)アルカノイル、天然 核酸塩基、非天然核酸塩基、芳香族部分、DNA挿入体、核酸塩基結合性基、複 素環式部分、およびリポーターリガンドよりなる群から別個に選ばれ、少なくと も1個のL1−Lnは天然核酸塩基、非天然核酸塩基、DNA挿入体、または核 酸塩基結合性基であり; A1−Anはそれぞれ、単結合、メチレン基、または次式の基であり:▲数式、 化学式、表等があります▼もしくは▲数式、化学式、表等があります▼[これら の式中: XはO、S、Se、NR3、CH2またはC(CH3)2であり;Yは単結合、 O、SまたはNR4であり;pおよびqはそれぞれゼロまたは1−5の整数であ り、p+qの和は10を越えず; rおよびsはそれぞれゼロまたは1−5の整数であり、r+sの和は10を越え ず; R1およびR2はそれぞれ、水素、ヒドロキシ−またはアルコキシ−またはアル キルチオ−置換されていてもよい(C1−C4)アルキル、ヒドロキシ、アルコ キシ、アルキルチオ、アミノおよびハロゲンよりなる群から別個に選ばれ;そし て R3およびR4はそれぞれ、水素、(C1−C4)アルキル、ヒドロキシ−また はアルコキシ−またはアルキルチオ−置換された(C1−C4)アルキル、ヒド ロキシ、アルコキシ、アルキルチオおよびアミノよりなる群から別個に選ばれる ]; B1−BnはそれぞれNまたはR3N+であり、ここでR3は上記に定めたもの であり; C1−CnはそれぞれCR6R7、CHR6CHR7またはCR6R7CH2で あり、ここでR6は水素であり、かつR7は天然のα−アミノ酸の側鎖よりなる 群から選ばれるか、またはR6およびR7は、水素、(C2−C6)アルキル、 アリール、アルアルキル、ヘテロアリール、ヒドロキシ、(C1−C6)アルコ キシ、(C1−C6)アルキルチオ、NR3R4およびSR5[ここでR3およ びR4は上記に定めたものであり、R5は水素、(C1−C6)アルキル、ヒド ロキシ−、アルコキシ−またはアルキルチオ−置換された(C1−C6)アルキ ルである]よりなる群から別個に選ばれるか、またはR6とR7は一緒になって 脂環式もしくは複素環式の系を完成し; D1−DnはそれぞれCR6R7、CH2CR6R7またはCHR6CHR7で あり、ここでR6およびR7は上記に定めたものであり;G1−Gn−1はそれ ぞれ、いずれの向きであってもよい−NR3CO−、−NR3CS−、−NR3 SO−または−NR3SO7−であり、ここでR3は上記に定めたものであり; Qは−CO2H、−CONR′R′′、−SO3Hもしくは−SO2NR′R′ ′、または−CO7Hもしくは−SO3Hの活性化された誘導体であり;そして Iは−NHR′′′R′′′′または−NHR′′′C(O)R′′′′であり 、ここでR′、R′′、R′′′およびR′′′′は、水素、アルキル、アミノ 保護基、リポーターリガント、挿入体、キレーター、ペプチド、蛋白質、炭水化 物、脂質、ステロイド、オリゴヌクレオチド、ならびに可溶性および不溶性ポリ マーよりなる群から別個に選ばれる。
- 4.下記構造式を有する、請求の範囲第3項に記載の化合物:▲数式、化学式、 表等があります▼ 式中: Lはそれぞれ、水素、フェニル、複素環式部分、天然核酸塩基、非天然核酸塩基 よりなる群から別個に選ばれ: R7′はそれぞれ、水素、および天然のα−アミノ酸の側鎖よりなる群から別個 に選ばれ; nけ1−60の整数であり; kおよびmはそれぞれ別個にゼロまたは1であり;1はそれぞれゼロまたは1− 5の整数であり;RhはOH、NH2または−NHLysNH2であり;そして R1はHまたはCOCH3である。
- 5.下記構造式を有する、請求の範囲第4項に記載の化合物:▲数式、化学式、 表等があります▼ 式中: しはそれぞれ、核酸塩基チミン、アデニン、シトシン、グアニンおよびウラシル よりなる群から別個に選ばれ; R7′はそれぞれ水素であり;そして nは1−30の整数である。
- 6.下記構造式のいずれかを有する化合物:▲数式、化学式、表等があります▼ または▲数式、化学式、表等があります▼または▲数式、化学式、表等がありま す▼式中: Lは水素、ヒドロキシ、(C1−C4)アルカノイル、天然核酸塩基、非天然核 酸塩基、芳香族部分、DNA挿人体、核酸塩基結合性基、複素環式部分、および リポーターリガンドよりなる群から選ばれ、その際:少なくとも1個のL1−L nは天然核酸塩基、非天然核酸塩基、DNA挿入体、または核酸塩基結合性基で あり;そしてアミノ基は所望によりアミノ保護基により保護されており;Aは単 結合または次式の基であり: ▲数式、化学式、表等があります▼もしくは▲数式、化学式、表等があります▼ しこれらの式中: XはO、S、Se、NR3、CH2またはC(CH3)2であり;Yは革結合、 O、SまたはNR4であり;pおよびqはそれぞれゼロまたは1−5の整数であ り、p+qの和は10を越えず; rおよびsはそれぞれゼロまたは1−5の整数であり、r+sの和は10を越え ず; R1およびR2はそれぞれ、水素、(C1−C4)アルキル、ヒドロキシ−また はアルコキシ−またはアルキルチオ−置換された(C1−C4)アルキル、ヒド ロキシ、アルコキシ、アルキルチオ、アミノおよびハロゲンよりなる群から別個 に選ばれ;そして R3およびR4はそれぞれ、水素、(C1−C4)アルキル、ヒドロキシ−また はアルコキシ−またはアルキルチオ−置換された(C1−C4)アルキル、ヒド ロキシ、アルコキシ、アルキルチオおよびアミノよりなる群から別個に選ばれる ]; BはNまたはR3N+であり、ここでR3は上記に定めたものであり;Cはそれ ぞれCR6R7、CHR6CHR7またはCR6R7CH2であり、ここでR6 は水素であり、かつR7は天然のα−アミノ酸の側鎖よりなる群から選ばれるか 、またはR6およびR7は、水素、(C2−C6)アルキル、アリール、アルア ルキル、ヘテロアリール、ヒドロキシ、(C1−C6)アルコキシ、(C1−C 6)アルキルチオ、NR3R4およびSR5[ここでR3およびR4は上記に定 めたものであり、R5は水素、または(C1−C6)アルキル、ヒドロキシ−、 アルコキシ−もしくはアルキルチオ−置換された(C1−C6)アルキルである ]よりなる群から別個に選ばれるか、またはR6とR7は一緒になって脂環式も しくは複素環式の系を完成し; DはそれぞれCR6R7、CH2CR6R7またはCHR6CHR7であり、こ こでR6およびR7は上記に定めたものであり;Eはそれぞれ−COOH、CS OH、SOOH、SO2OHまたはそれらの活性化もしくは保護された誘導体で あり;そしてFはそれぞれNHR3またはNPgR3であり、これらにおいてR 3は前記に定めたものであり、Pgはアミノ保護基である。
- 7.下記構造式を有する、請求の範囲第6項に記載の化合物:▲数式、化学式、 表等があります▼ 式中: Lはそれぞれ、水素、フェニル、複素環式部分、天然核酸塩基、非天然核酸塩基 よりなる群から別個に選ばれ; R7′はそれぞれ、水素、および天然のα−アミノ酸の側鎖よりなる群から別個 に選ばれ;そして k、lおよびmはそれぞれ別個にゼロまたは1−5の整数である。
- 8.下記構造式を有する、請求の範囲第7項に記載の化合物:▲数式、化学式、 表等があります▼ 式中: Lは核酸塩基チミン、アデニン、シトシン、グアニン、ウラシル、5−メチルシ トシン、6−チオグアニンまたは5−ブロモウラシル、およびそれらの保護され た誘導体よりなる群から選ばれ; R7′は水素であり; EはCOOHまたはその活性化もしくは保護された誘導体であり;そしてFはN H2またはNHPgであり、ここでPgはアミノ保護基である。
- 9.下記構造式を有する化合物: ▲数式、化学式、表等があります▼ 式中: Lはそれぞれ、水素、フェニル、複素環式部分、天然核酸塩基、非天然核酸塩基 よりなる群から別個に選ばれ: R7′はそれぞれ、水素、および天然のα−アミノ酸の側鎖よりなる群から別個 に選ばれ; nは1−60の整数であり; k、lおよびmはそれぞれ別個にゼロまたは1−5の整数であり;RhはOH、 NHzまたは−NHLysNH2であり;そしてR1はHまたはCOCH3であ る。
- 10.下記工程を含む、請求の範囲第1項に記載の化合物の製造方法:A)ポリ マー系支持体を用意し、該ポリマーはアミノ酸との固定用結合を形成しうる化学 基により官能化されており;B)固定用結合を介して該ポリマーを第1アミノ酸 と結合させ、該第1アミノ酸は構造式(IV)を有するものであり:▲数式、化 学式、表等があります▼(IV){式中: Lは天然核酸塩基、非天然核酸塩基、芳香族部分、DNA挿入体、核酸塩基結合 性基、複素環式部分、およびリポーターリガンドよりなる群から選ばれ、これら においてアミノ基は所望によりアミノ保護基により保護されており;Aは単結合 または次式の基であり: ▲数式、化学式、表等があります▼もしくは▲数式、化学式、表等があります▼ [これらの式中: XはO、S、Se、NR3、CH2またはC(CH3)2であり:Yは単結合、 O、SまたはNR4であり;pおよびqはゼロまたは1−5の整数であり、p+ qの和は10を越えず;rおよびsはゼロまたは1−5の整数であり、r+sの 和は10を越えず;R1およびR2は、水素、(C1−C4)アルキル、ヒドロ キシ−またはアルコキシ−またはアルキルチオ−置換された(C1−C4)アル キル、ヒドロキシ、アルコキシ、アルキルチオ、アミノおよびハロゲンよりなる 群から別個に選ばれ;そして R3およびR4は、水素、(C1−C4)アルキル、ヒドロキシ−またはアルコ キシ−またはアルキルチオ−置換された(C1−C4)アルキル、ヒドロキシ、 アルコキシ、アルキルチオおよびアミノよりなる群から別個に選ばれる];Bは NまたはR3N+であり、ここでR3は上記に定めたものであり;CはCR6R 7、CHR6CHR7またはCR6R7CH2であり、ここでR6は水素であり 、かつR7は天然のα−アミノ酸の側鎖よりなる群から選ばれるか、またはR6 およびR7は、水素、(C2−C6)アルキル、アリール、アルアルキル、ヘテ ロアリール、ヒドロキシ、(C1−C6)アルコキシ、(C1−C6)アルキル チオ、NR3R4およびSR5[ここでR3およびR4は上記に定めたものであ り、R5は水素、または(C1−C6)アルキル、ヒドロキシ−、アルコキシ− もしくはアルキルチオ−置換された(C1−C6)アルキルである]よりなる群 から別個に選ばれるか、またはR6とR7は一緒になって脂環式もしくは複素環 式の系を完成し;DはCR6R7、CH2CR6R7またはCHR6CHR7で あり、ここでR6およびR7は上記に定めたものであり; EはCOOHまたはその活性化もしくは保護された誘導体であり;そしてFはN PgR3であり、ここでR3は前記に定めたものであり、Pgはアミノ保護基で ある}; C)結合した第1アミノ酸からアミノ保護基を除去して遊離アミノ基を生成させ ;そして D)この遊離アミノ基を式(IV)の第2アミノ酸と反応させて、ペプチド鎖を 形成する。
- 11.さらに下記の工程を含む、請求の範囲第10項に記載の方法:E)第2ア ミノ酸からアミノ保護基を除去して、ペプチド鎖上に末端遊離アミノ基を生成さ せ;そして F)ペプチド鎖上の遊離アミノ基をさらに式(IV)のアミノ酸と反応させて、 ペプチド鎖を延長する。
- 12.工程EおよびFが多数回実施される、請求の範囲第11項に記載の方法。
- 13.さらに、ペプチド鎖のアミノ酸部分に残存する少なくとも1個の保護基を 除去することを含む、請求の範囲第11項に記載の方法。
- 14.さらに、ペプチド鎖を実質的に分解することなく固定用結合を開裂させる ことを含む、請求の範囲第10項に記載の方法。
- 15.ポリマー系支持体がポリスチレン、ポリアクリルアミド、シリカ、複合材 料、木綿、またはそれらの誘導体を含有する、請求の範囲第10項に記載の方法 。
- 16.固定用結合を形成しうる化学基が、クロロ−、プロモーおよびヨード−直 換アルキル、アミノ−置換アルキル、アミノ−およびアリール−置換アルキル、 アミノ−およびアルキルアリール−置換アルキル、ヒドロキシ−置換アルキル、 またはポリペプチドを実質的に分解することな(開裂しうるスペーサー基を有す るそれらの誘導体である、請求の範囲第10項に記載の方法。
- 17.クロロ−置換アルキルがクロロメチルであり、アミノ−置換アルキルがア ミノメチルであり、アミノ−およびアルキル−置換アリールがα−アミノベンジ ルであり、アミノ−およびアルキルアリール−置換アルキルがα−アミノ−3− およびα−アミノ−4−メチルベンジルよりなる群から選ばれ、ヒドロキシ−置 換アルキルがヒドロキシメチルである、請求の範囲第16項に記載の方法。
- 18.化学基が、アミノ−置換アルキル、アミノ−およびアリール−置換アルキ ル、ならびにアミノ−およびアルキルアリール−置換アルキルより選ばれるアミ ノ含有部分から誘導され:そして 化学基が、4−(ハロアルキル)アリール−低級アルカン酸、Boc−アミノァ シル−4−(オキシメチル)アリール−低級アルカン酸、N−Boc−P−アシ ルベンゾヒドリルアミン、N−Boc−4′−(低級アルキル)−p−アシルベ ンゾヒドリルアミン、N−Boc−4′−(低級アルコキシ)−p−アシルベン ゾヒトリルアミン、および4−ヒドロキシメチルフェノキシ−低級アルカン酸よ りなる群から誘導されるスペーサー基を含有する、請求の範囲第16項に記載の 方法。
- 19.二本鎖ポリヌクレオチドの配列特異性認識法であって、天然RNAと異な り、かつ該ポリヌクレオチドの一方の鎖と結合し、これにより他方の鎖と置換す る化合物に、該ポリヌクレオチドを接触させることよりなる方法。
- 20.化合物が均質または不均質な主鎖からなるオリゴマーであり、これにポリ ヌクレオチド鎖中の少なくとも1個の天然核酸塩基に水素結合により別個に結合 する天然核酸塩基、非天然核酸塩基、または他のリガンドが結合したものである 、請求の範囲第19項に記載の方法。
- 21.化合物が請求の範囲第1項に記載の化合物である、請求の範囲第20項に 記載の方法。
- 22.化合物が請求の範囲第4項に記載の化合物である、請求の範囲第20項に 記載の方法。
- 23.生物の遺伝子の発現を調節する方法であって、該遺伝子から誘導されるD NAまたはRNAに特異的に結合する請求の範囲第1項に記載の化合物を該生物 に投与することよりなる方法。
- 24.化合物が請求の範囲第1項に記載の化合物である、請求の範囲第23項に 記載の方法。
- 25.化合物が請求の範囲第4項に記載の化合物である、請求の範囲第23項に 記載の方法。
- 26.調節が該遺伝子の転写を阻害することを含む、請求の範囲第23項に記載 の方法。
- 27.調節が該遺伝子の複製を阻害することを含む、請求の範囲第23項に記載 の方法。
- 28.生物における望ましくない蛋白質産生に伴う状態を処置する方法であって 、該蛋白質産生を制御する遺伝子から誘導されるDNAまたはRNAに特異的に 結合する、有効量の請求の範囲第1項に記載の化合物に、該生物を接触させるこ とよりなる方法。
- 29.化合物が請求の範囲第1項に記載の化合物である、請求の範囲第28項に 記載の方法。
- 30.化合物が請求の範囲第4項に記載の化合物である、請求の範囲第28項に 記載の方法。
- 31.生物の細胞中におけるDNAまたはRNAの分解を誘発する方法であって 、該DNAまたはRNAに特異的に結合する請求の範囲第1項に記載の化合物を 該生物に投与することよりなる方法。
- 32.細胞またはウイルスを死滅させる方法であって、該細胞またはウイルスの ゲノムの一部に特異的に結合する請求の範囲第1項に記載の化合物に、該細胞ま たはウイルスを接触させることよりなる方法。
- 33.請求の範囲第1項に記載の化合物、および少なくとも1種の薬剤学的に有 効なキャリヤー、結合剤、増粘剤、希釈剤、緩衝剤、防腐剤または界面活性剤を 含む薬剤組成物。
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1993
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1994
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1995
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2001
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JPS62502338A (ja) * | 1985-03-15 | 1987-09-10 | アンチバイラルズ インコーポレイテッド | 立体規則性ポリヌクレオチド結合ポリマ− |
JPH02156895A (ja) * | 1988-12-08 | 1990-06-15 | Sumitomo Heavy Ind Ltd | 好塩菌による5’‐ヌクレオチド類の製造法 |
JPH0399095A (ja) * | 1989-09-13 | 1991-04-24 | Makoto Takahashi | ジエチレントリアミン三酢酸化合物及びその製造中間体並びにそれらの製造法 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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WO1999002730A1 (fr) * | 1997-07-09 | 1999-01-21 | Dai Nippon Printing Co., Ltd. | Procede de detection d'adn au moyen d'une sonde de pna |
JP2003508062A (ja) * | 1999-08-30 | 2003-03-04 | バイオ−ラッド ラボラトリーズ,インコーポレイティド | ポリ(エーテル−チオエーテル)核酸、ポリ(エーテル−スルホキシド)核酸およびポリ(エーテル−スルホン)核酸 |
WO2005010181A1 (ja) * | 2003-07-25 | 2005-02-03 | Credia Japan Co., Ltd. | 核酸検出方法 |
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