TW201021853A - Releasable cationic lipids for nucleic acids delivery systems - Google Patents

Info

Publication number

TW201021853A

TW201021853A TW098138946A TW98138946A TW201021853A TW 201021853 A TW201021853 A TW 201021853A TW 098138946 A TW098138946 A TW 098138946A TW 98138946 A TW98138946 A TW 98138946A TW 201021853 A TW201021853 A TW 201021853A

Authority

TW

Taiwan

Prior art keywords

group

substituted

compound

alkyl

ch2ch2

Prior art date

2008-11-17

Links

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• 150000007523 nucleic acids Chemical class 0.000 title claims abstract description 105
• 102000039446 nucleic acids Human genes 0.000 title claims abstract description 102
• 108020004707 nucleic acids Proteins 0.000 title claims abstract description 102
• 125000002091 cationic group Chemical group 0.000 title abstract description 28
• 239000002105 nanoparticle Substances 0.000 claims abstract description 257
• 239000000203 mixture Substances 0.000 claims abstract description 161
• 238000000034 method Methods 0.000 claims abstract description 72
• 108090000623 proteins and genes Proteins 0.000 claims abstract description 48
• 239000002253 acid Substances 0.000 claims abstract description 42
• 230000014509 gene expression Effects 0.000 claims abstract description 20
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 150
• 150000001875 compounds Chemical class 0.000 claims description 134
• 125000000217 alkyl group Chemical group 0.000 claims description 117
• -1 alkoxyoxy Chemical group 0.000 claims description 108
• 150000002632 lipids Chemical class 0.000 claims description 105
• 108091034117 Oligonucleotide Proteins 0.000 claims description 78
• 235000012000 cholesterol Nutrition 0.000 claims description 78
• 210000004027 cell Anatomy 0.000 claims description 74
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 72
• 239000002773 nucleotide Substances 0.000 claims description 60
• 125000003729 nucleotide group Chemical group 0.000 claims description 57
• 229910052739 hydrogen Inorganic materials 0.000 claims description 51
• 230000000692 anti-sense effect Effects 0.000 claims description 50
• 150000003904 phospholipids Chemical class 0.000 claims description 48
• 206010028980 Neoplasm Diseases 0.000 claims description 47
• 239000001257 hydrogen Substances 0.000 claims description 47
• 150000001412 amines Chemical class 0.000 claims description 45
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
• 125000003118 aryl group Chemical group 0.000 claims description 44
• 239000002585 base Substances 0.000 claims description 43
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 38
• 201000011510 cancer Diseases 0.000 claims description 37
• 150000002431 hydrogen Chemical class 0.000 claims description 35
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 34
• 125000003545 alkoxy group Chemical group 0.000 claims description 31
• 125000001072 heteroaryl group Chemical group 0.000 claims description 31
• 108020004414 DNA Proteins 0.000 claims description 25
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• 125000003107 substituted aryl group Chemical group 0.000 claims description 25
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• 125000003342 alkenyl group Chemical group 0.000 claims description 19
• 125000000304 alkynyl group Chemical group 0.000 claims description 19
• 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
• 229940106189 ceramide Drugs 0.000 claims description 18
• 229960001231 choline Drugs 0.000 claims description 17
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 17
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• 125000006850 spacer group Chemical group 0.000 claims description 16
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• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 15
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
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• 239000007789 gas Substances 0.000 claims description 12
• 125000004104 aryloxy group Chemical group 0.000 claims description 11
• 125000004405 heteroalkoxy group Chemical group 0.000 claims description 11
• 125000001424 substituent group Chemical group 0.000 claims description 11
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
• 201000010099 disease Diseases 0.000 claims description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
• 239000002777 nucleoside Substances 0.000 claims description 10
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
• YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 claims description 9
• CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 claims description 9
• ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 claims description 9
• VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 claims description 9
• RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 9
• 108010002687 Survivin Proteins 0.000 claims description 8
• 125000004093 cyano group Chemical class *C#N 0.000 claims description 8
• 150000003833 nucleoside derivatives Chemical class 0.000 claims description 8
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
• 102100021569 Apoptosis regulator Bcl-2 Human genes 0.000 claims description 7
• 102100021663 Baculoviral IAP repeat-containing protein 5 Human genes 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 7
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
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• 108010045100 HSP27 Heat-Shock Proteins Proteins 0.000 claims description 6
• 102100039165 Heat shock protein beta-1 Human genes 0.000 claims description 6
• 101000971171 Homo sapiens Apoptosis regulator Bcl-2 Proteins 0.000 claims description 6
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• 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 6
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• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• 101000605639 Homo sapiens Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform Proteins 0.000 claims description 4
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• 125000005055 alkyl alkoxy group Chemical group 0.000 claims description 4
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• WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 2
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