JP2014505685A5 - - Google Patents
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- Publication number
- JP2014505685A5 JP2014505685A5 JP2013547648A JP2013547648A JP2014505685A5 JP 2014505685 A5 JP2014505685 A5 JP 2014505685A5 JP 2013547648 A JP2013547648 A JP 2013547648A JP 2013547648 A JP2013547648 A JP 2013547648A JP 2014505685 A5 JP2014505685 A5 JP 2014505685A5
- Authority
- JP
- Japan
- Prior art keywords
- amino acid
- delivery polymer
- compound
- amidobenzyl
- polymer according
- 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
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- 229920000642 polymer Polymers 0.000 claims description 32
- 239000003446 ligand Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 22
- 229920000768 polyamine Polymers 0.000 claims description 21
- 239000012528 membrane Substances 0.000 claims description 20
- 108091033319 polynucleotide Proteins 0.000 claims description 16
- 102000040430 polynucleotide Human genes 0.000 claims description 16
- 239000002157 polynucleotide Substances 0.000 claims description 16
- 239000003381 stabilizer Substances 0.000 claims description 13
- 230000008685 targeting Effects 0.000 claims description 12
- 238000012228 RNA interference-mediated gene silencing Methods 0.000 claims description 11
- 230000009368 gene silencing by RNA Effects 0.000 claims description 11
- 102000005427 Asialoglycoprotein Receptor Human genes 0.000 claims description 10
- 108010006523 asialoglycoprotein receptor Proteins 0.000 claims description 10
- 239000002202 Polyethylene glycol Substances 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 230000002209 hydrophobic effect Effects 0.000 claims description 5
- 238000001727 in vivo Methods 0.000 claims description 5
- 150000003141 primary amines Chemical class 0.000 claims description 5
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 claims description 4
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 4
- OVRNDRQMDRJTHS-CBQIKETKSA-N N-Acetyl-D-Galactosamine Chemical compound CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@H](O)[C@@H]1O OVRNDRQMDRJTHS-CBQIKETKSA-N 0.000 claims description 4
- FVMMQJUBNMOPPR-WLDMJGECSA-N N-[(3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]formamide Chemical compound OC[C@H]1OC(O)[C@H](NC=O)[C@@H](O)[C@H]1O FVMMQJUBNMOPPR-WLDMJGECSA-N 0.000 claims description 4
- RTEOJYOKWPEKKN-HXQZNRNWSA-N N-[(3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]propanamide Chemical compound CCC(=O)N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O RTEOJYOKWPEKKN-HXQZNRNWSA-N 0.000 claims description 4
- MBLBDJOUHNCFQT-UHFFFAOYSA-N N-acetyl-D-galactosamine Natural products CC(=O)NC(C=O)C(O)C(O)C(O)CO MBLBDJOUHNCFQT-UHFFFAOYSA-N 0.000 claims description 4
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 4
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 4
- 229930182830 galactose Natural products 0.000 claims description 4
- 239000008101 lactose Substances 0.000 claims description 4
- KXTUJUVCAGXOBN-WQXQQRIOSA-N 2-methyl-N-[(3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]propanamide Chemical compound CC(C)C(=O)N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O KXTUJUVCAGXOBN-WQXQQRIOSA-N 0.000 claims description 3
- 108010036176 Melitten Proteins 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000000873 masking effect Effects 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229920001059 synthetic polymer Polymers 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims 12
- 235000001014 amino acid Nutrition 0.000 claims 10
- 229940024606 amino acid Drugs 0.000 claims 10
- 230000007935 neutral effect Effects 0.000 claims 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 4
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
- 239000004471 Glycine Substances 0.000 claims 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 2
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 claims 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 2
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 2
- 239000004473 Threonine Substances 0.000 claims 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 2
- 235000004279 alanine Nutrition 0.000 claims 2
- 229960001230 asparagine Drugs 0.000 claims 2
- 235000009582 asparagine Nutrition 0.000 claims 2
- 235000013477 citrulline Nutrition 0.000 claims 2
- 229960002173 citrulline Drugs 0.000 claims 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 2
- 229960000310 isoleucine Drugs 0.000 claims 2
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 2
- 102000005962 receptors Human genes 0.000 claims 2
- 108020003175 receptors Proteins 0.000 claims 2
- 229960002898 threonine Drugs 0.000 claims 2
- 239000004474 valine Substances 0.000 claims 2
- 102000040650 (ribonucleotides)n+m Human genes 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- 108020004414 DNA Proteins 0.000 claims 1
- 108010016626 Dipeptides Proteins 0.000 claims 1
- RYFOQDQDVYIEHN-ZETCQYMHSA-N N,N-Dimethyllysine Chemical compound CN(C)[C@H](C(O)=O)CCCCN RYFOQDQDVYIEHN-ZETCQYMHSA-N 0.000 claims 1
- 108020004459 Small interfering RNA Proteins 0.000 claims 1
- 229960002449 glycine Drugs 0.000 claims 1
- 108091070501 miRNA Proteins 0.000 claims 1
- 239000002679 microRNA Substances 0.000 claims 1
- 238000000034 method Methods 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JDFXJJLFADUZIY-UHFFFAOYSA-N CON(C(CC1)=O)C1=O Chemical compound CON(C(CC1)=O)C1=O JDFXJJLFADUZIY-UHFFFAOYSA-N 0.000 description 1
- ZRQUIRABLIQJRI-UHFFFAOYSA-N COc(c(F)c(c(F)c1F)F)c1F Chemical compound COc(c(F)c(c(F)c1F)F)c1F ZRQUIRABLIQJRI-UHFFFAOYSA-N 0.000 description 1
- RDWOLIZQAHPNKO-UHFFFAOYSA-N COc(cc1)ccc1[NH+]([O-])[O-] Chemical compound COc(cc1)ccc1[NH+]([O-])[O-] RDWOLIZQAHPNKO-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- -1 N-iso-butanoyl-galactosamine Compound Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 210000003494 hepatocyte Anatomy 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201061427936P | 2010-12-29 | 2010-12-29 | |
| US61/427,936 | 2010-12-29 | ||
| US13/336,028 US8426554B2 (en) | 2010-12-29 | 2011-12-23 | In vivo polynucleotide delivery conjugates having enzyme sensitive linkages |
| US13/336,028 | 2011-12-23 | ||
| PCT/US2011/067588 WO2012092373A2 (en) | 2010-12-29 | 2011-12-28 | In vivo polynucleotide delivery conjugates having enzyme sensitive linkages |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014505685A JP2014505685A (ja) | 2014-03-06 |
| JP2014505685A5 true JP2014505685A5 (enrdf_load_stackoverflow) | 2014-09-11 |
| JP5941926B2 JP5941926B2 (ja) | 2016-06-29 |
Family
ID=46383848
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013547648A Active JP5941926B2 (ja) | 2010-12-29 | 2011-12-28 | 酵素感受性連結を有するインビボポリヌクレオチド送達結合体 |
Country Status (15)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2653438C2 (ru) | 2012-11-15 | 2018-05-08 | Рош Инновейшен Сентер Копенгаген А/С | Конъюгаты олигонуклеотидов |
| EA201690051A1 (ru) * | 2013-08-07 | 2016-06-30 | Эрроухэд Рисерч Корпорейшн | Поликонъюгаты для доставки триггеров рнк интерференции в клетки опухоли in vivo |
| JOP20210043A1 (ar) | 2015-10-01 | 2017-06-16 | Arrowhead Pharmaceuticals Inc | تراكيب وأساليب لتثبيط تعبير جيني للـ lpa |
| MA45328A (fr) * | 2016-04-01 | 2019-02-06 | Avidity Biosciences Llc | Compositions acide nucléique-polypeptide et utilisations de celles-ci |
| US12173350B2 (en) | 2017-05-24 | 2024-12-24 | Ramot At Tel-Aviv University Ltd. | Chemiluminescent probes for imaging/detection of proteases |
| SG11202005022YA (en) | 2017-12-06 | 2020-06-29 | Avidity Biosciences Inc | Compositions and methods of treating muscle atrophy and myotonic dystrophy |
| JP2023501020A (ja) * | 2018-12-28 | 2023-01-18 | サーナオミクス インコーポレイテッド | 治療用分子の標的化送達 |
| US20200399660A1 (en) * | 2019-06-24 | 2020-12-24 | Promega Corporation | Modified polyamine polymers for delivery of biomolecules into cells |
| IL296387B2 (en) | 2020-03-19 | 2024-08-01 | Avidity Biosciences Inc | Preparations and methods for the treatment of facial, back and arm muscle atrophy |
| US20230390411A1 (en) * | 2021-01-28 | 2023-12-07 | Nanjing Chempion Biotechnology Co., Ltd. | Conjugate and use thereof |
| CA3219184A1 (en) * | 2021-06-24 | 2022-12-29 | Toru Nakazawa | Fluorescent probe |
| KR102712976B1 (ko) * | 2021-07-27 | 2024-10-07 | 국립안동대학교 산학협력단 | 등검은말벌 추출물을 유효성분으로 함유하는 혈전증의 예방 또는 치료용 약학적 조성물 및 건강 기능 식품 |
| CN113621003B (zh) * | 2021-09-10 | 2023-02-03 | 国科温州研究院(温州生物材料与工程研究所) | 一种制备有机分子共价修饰的功能化核酸材料的方法及其应用 |
| CA3231330A1 (en) | 2021-09-16 | 2023-03-23 | Avidity Biosciences, Inc. | Compositions and methods of treating facioscapulohumeral muscular dystrophy |
| WO2024237099A1 (ja) * | 2023-05-12 | 2024-11-21 | 五稜化薬株式会社 | 凍結乾燥製剤、凍結乾燥溶液、及びこれらの製造方法、並びに液剤 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6214345B1 (en) * | 1993-05-14 | 2001-04-10 | Bristol-Myers Squibb Co. | Lysosomal enzyme-cleavable antitumor drug conjugates |
| US6180095B1 (en) * | 1997-12-17 | 2001-01-30 | Enzon, Inc. | Polymeric prodrugs of amino- and hydroxyl-containing bioactive agents |
| EP1242609A2 (en) * | 1999-12-30 | 2002-09-25 | Novartis AG | Novel colloid synthetic vectors for gene therapy |
| PL358187A1 (en) * | 2000-02-24 | 2004-08-09 | Genentech, Inc. | Caspase activated prodrugs therapy |
| EP1243276A1 (en) * | 2001-03-23 | 2002-09-25 | Franciscus Marinus Hendrikus De Groot | Elongated and multiple spacers containing activatible prodrugs |
| US7091186B2 (en) * | 2001-09-24 | 2006-08-15 | Seattle Genetics, Inc. | p-Amidobenzylethers in drug delivery agents |
| US7541330B2 (en) * | 2004-06-15 | 2009-06-02 | Kosan Biosciences Incorporated | Conjugates with reduced adverse systemic effects |
| CA2627190A1 (en) * | 2005-11-10 | 2007-05-24 | Medarex, Inc. | Duocarmycin derivatives as novel cytotoxic compounds and conjugates |
| CN102614528B (zh) * | 2006-08-18 | 2014-02-26 | 箭头研究公司 | 用于体内递送多核苷酸的多缀合物 |
| RU2430740C2 (ru) * | 2006-08-18 | 2011-10-10 | Ф.Хоффманн-Ля Рош Аг | Поликонъюгаты для введения in vivo полинуклеотидов |
| CA2916671C (en) * | 2007-01-17 | 2018-01-09 | Immunomedics, Inc. | Polymeric carriers of therapeutic agents and recognition moieties for antibody-based targeting of disease sites |
| TW201004647A (en) * | 2008-05-20 | 2010-02-01 | Sigma Tau Ind Farmaceuti | Novel dual targeting antitumoural conjugates |
| US8501930B2 (en) * | 2010-12-17 | 2013-08-06 | Arrowhead Madison Inc. | Peptide-based in vivo siRNA delivery system |
-
2011
- 2011-12-28 EP EP11853858.6A patent/EP2658579A4/en not_active Withdrawn
- 2011-12-28 KR KR1020137017195A patent/KR20130136494A/ko not_active Ceased
- 2011-12-28 CA CA2816041A patent/CA2816041C/en active Active
- 2011-12-28 MX MX2016006733A patent/MX347298B/es unknown
- 2011-12-28 NZ NZ611656A patent/NZ611656A/en not_active IP Right Cessation
- 2011-12-28 PE PE2013001496A patent/PE20140198A1/es not_active Application Discontinuation
- 2011-12-28 WO PCT/US2011/067588 patent/WO2012092373A2/en active Application Filing
- 2011-12-28 BR BR112013014115A patent/BR112013014115A2/pt not_active IP Right Cessation
- 2011-12-28 CN CN201180061179.6A patent/CN103491982B/zh active Active
- 2011-12-28 JP JP2013547648A patent/JP5941926B2/ja active Active
- 2011-12-28 SG SG2013029830A patent/SG189942A1/en unknown
- 2011-12-28 MX MX2013007316A patent/MX341118B/es active IP Right Grant
- 2011-12-28 AU AU2011352204A patent/AU2011352204B2/en not_active Ceased
- 2011-12-28 RU RU2013117286A patent/RU2619453C2/ru active
-
2013
- 2013-04-22 ZA ZA2013/02896A patent/ZA201302896B/en unknown
- 2013-06-25 CL CL2013001876A patent/CL2013001876A1/es unknown
-
2015
- 2015-12-10 CL CL2015003580A patent/CL2015003580A1/es unknown
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