Title:
カチオン性脂質
Document Type and Number:
Japanese Patent JPWO2013065825
Kind Code:
A1
Abstract:
本発明は、核酸を、細胞内に導入することを容易にする、式(I)(式中、R1およびR2は同一または異なってアルケニル等であり、X1およびX2は水素原子であるか、または一緒になって単結合もしくはアルキレンを形成し、X3は存在しないか、アルキル等であり、Yは存在しないか、陰イオンであり、aおよびbは、同一または異なって0〜3であり、L3は単結合等であり、R3はアルキル等であり、L1およびL2は-O-、-CO-O-または-O-CO-である)で表されるカチオン性脂質、該カチオン性脂質および核酸を含有する組成物、該カチオン性脂質および核酸を含有する組成物を用いて核酸を細胞内に導入する方法等を提供する。
Inventors:
Takeyuki Kuboyama
Kimihiro Era
Tomoyuki Naoi
Nobuhiro Yagi
Kimihiro Era
Tomoyuki Naoi
Nobuhiro Yagi
Application Number:
JP2013541860A
Publication Date:
April 02, 2015
Filing Date:
November 02, 2012
Export Citation:
Assignee:
Kyowa Hakko Kirin Co., Ltd.
International Classes:
A61K31/713; C07C217/08; A61K47/48; A61K48/00; A61P29/00; A61P35/00; C07C219/08; C07C237/06; C07C271/16; C07D207/08; C07D207/12; C07D401/04; C07D491/056; C12N15/09
Domestic Patent References:
| JP2009536030A | 2009-10-08 | |||
| JP2000508642A | 2000-07-11 | |||
| JP5902616B2 | 2016-04-13 | |||
| JP5902617B2 | 2016-04-13 | |||
| JP2009536030A | 2009-10-08 | |||
| JP2000508642A | 2000-07-11 | |||
| JP5902616B2 | 2016-04-13 | |||
| JP5902617B2 | 2016-04-13 |
Foreign References:
| WO2010054384A1 | 2010-05-14 | |||
| WO2000040273A2 | 2000-07-13 | |||
| WO2000030444A1 | 2000-06-02 | |||
| WO2010054384A1 | 2010-05-14 | |||
| WO2000040273A2 | 2000-07-13 | |||
| WO2000030444A1 | 2000-06-02 |
Other References:
KATHRYN A WHITEHEAD ET AL.: "Synergistic Silencing: Combinations of Lipid-like Materials for Efficacious siRNA Delivery", MOLECULAR THERAPY, vol. 19, no. 9, JPN6013003083, September 2011 (2011-09-01), pages p.1688-1694, 特にAbstract及びFig.1, XP055067340, DOI: doi:10.1038/mt.2011.141
MUKTHAVARAM RAJESH ET AL.: "Dramatic Influence of the Orientation of Linker between Hydrophilic and Hydrophobic Lipid Moiety in", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 129, no. 37, JPN6013003084, 2007, pages p.11408-11420, 特にScheme 1, XP055067341, DOI: doi:10.1021/ja0704683
GOLLAPUDI VENKATA SRILAKSHMI ET AL.: "Anchor-dependent lipofection with non-glycerol based cytofections containing single 2-hydroxyethyl h", BIOCHIMICA ET BIOPHYSICA ACTA, BIOMENBRANES, vol. 1559, no. 2, JPN6013003085, 2002, pages p.87-95, 特にChart1, XP004341284, DOI: doi:10.1016/S0005-2736(01)00442-4
I. FLECHSLER ET AL.: "COMPARISON OF ANTISENSE VECTORS AND ANTISENSE OLIGONUCLEOTIDES DELIVERED BY MEANS OF THE NEW CATIONI", ADVANCES IN EXPERIMENTAL MEDICINE AND BIOLOGY, vol. Vol.451, JPN6013003086, 1998, pages 469 - 472, XP009048306
SANTANU BHATTACHARYA ET AL.: "The effects of cholesterol inclusion on the vesicular membranes of cationic lipids", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 1283, no. 1, JPN6013003087, 1996, pages p.21-30, 特にFig.1, XP055067345, DOI: doi:10.1016/0005-2736(96)00064-8
IGOR SOLODIN ET AL.: "Synthesis of Amphiphilic Derivatives of N-Methyldiethanolamine. Cationic Lipids 5", SYNLETT, vol. No.7, JPN6013003088, 1996, pages 6 - 0, XP002035804, DOI: doi:10.1055/s-1996-5577
IGOR SOLODIN ET AL.: "Synthesis of Novel Cationic Lipids with a Guanidine Group. Cationic Lipids 3", SYNLETT, vol. No.7, JPN6013003089, 1996, pages 617 - 618, XP055151450, DOI: doi:10.1055/s-1996-5575
KATHRYN A WHITEHEAD ET AL.: "Synergistic Silencing: Combinations of Lipid-like Materials for Efficacious siRNA Delivery", MOLECULAR THERAPY, vol. 19, no. 9, JPN6013003083, September 2011 (2011-09-01), pages p.1688-1694, 特にAbstract及びFig.1, XP055067340, DOI: doi:10.1038/mt.2011.141
MUKTHAVARAM RAJESH ET AL.: "Dramatic Influence of the Orientation of Linker between Hydrophilic and Hydrophobic Lipid Moiety in", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 129, no. 37, JPN6013003084, 2007, pages p.11408-11420, 特にScheme 1, XP055067341, DOI: doi:10.1021/ja0704683
GOLLAPUDI VENKATA SRILAKSHMI ET AL.: "Anchor-dependent lipofection with non-glycerol based cytofections containing single 2-hydroxyethyl h", BIOCHIMICA ET BIOPHYSICA ACTA, BIOMENBRANES, vol. 1559, no. 2, JPN6013003085, 2002, pages p.87-95, 特にChart1, XP004341284, DOI: doi:10.1016/S0005-2736(01)00442-4
I. FLECHSLER ET AL.: "COMPARISON OF ANTISENSE VECTORS AND ANTISENSE OLIGONUCLEOTIDES DELIVERED BY MEANS OF THE NEW CATIONI", ADVANCES IN EXPERIMENTAL MEDICINE AND BIOLOGY, vol. Vol.451, JPN6013003086, 1998, pages 469 - 472, XP009048306
SANTANU BHATTACHARYA ET AL.: "The effects of cholesterol inclusion on the vesicular membranes of cationic lipids", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 1283, no. 1, JPN6013003087, 1996, pages p.21-30, 特にFig.1, XP055067345, DOI: doi:10.1016/0005-2736(96)00064-8
IGOR SOLODIN ET AL.: "Synthesis of Amphiphilic Derivatives of N-Methyldiethanolamine. Cationic Lipids 5", SYNLETT, vol. No.7, JPN6013003088, 1996, pages 6 - 0, XP002035804, DOI: doi:10.1055/s-1996-5577
IGOR SOLODIN ET AL.: "Synthesis of Novel Cationic Lipids with a Guanidine Group. Cationic Lipids 3", SYNLETT, vol. No.7, JPN6013003089, 1996, pages 617 - 618, XP055151450, DOI: doi:10.1055/s-1996-5575
MUKTHAVARAM RAJESH ET AL.: "Dramatic Influence of the Orientation of Linker between Hydrophilic and Hydrophobic Lipid Moiety in", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 129, no. 37, JPN6013003084, 2007, pages p.11408-11420, 特にScheme 1, XP055067341, DOI: doi:10.1021/ja0704683
GOLLAPUDI VENKATA SRILAKSHMI ET AL.: "Anchor-dependent lipofection with non-glycerol based cytofections containing single 2-hydroxyethyl h", BIOCHIMICA ET BIOPHYSICA ACTA, BIOMENBRANES, vol. 1559, no. 2, JPN6013003085, 2002, pages p.87-95, 特にChart1, XP004341284, DOI: doi:10.1016/S0005-2736(01)00442-4
I. FLECHSLER ET AL.: "COMPARISON OF ANTISENSE VECTORS AND ANTISENSE OLIGONUCLEOTIDES DELIVERED BY MEANS OF THE NEW CATIONI", ADVANCES IN EXPERIMENTAL MEDICINE AND BIOLOGY, vol. Vol.451, JPN6013003086, 1998, pages 469 - 472, XP009048306
SANTANU BHATTACHARYA ET AL.: "The effects of cholesterol inclusion on the vesicular membranes of cationic lipids", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 1283, no. 1, JPN6013003087, 1996, pages p.21-30, 特にFig.1, XP055067345, DOI: doi:10.1016/0005-2736(96)00064-8
IGOR SOLODIN ET AL.: "Synthesis of Amphiphilic Derivatives of N-Methyldiethanolamine. Cationic Lipids 5", SYNLETT, vol. No.7, JPN6013003088, 1996, pages 6 - 0, XP002035804, DOI: doi:10.1055/s-1996-5577
IGOR SOLODIN ET AL.: "Synthesis of Novel Cationic Lipids with a Guanidine Group. Cationic Lipids 3", SYNLETT, vol. No.7, JPN6013003089, 1996, pages 617 - 618, XP055151450, DOI: doi:10.1055/s-1996-5575
KATHRYN A WHITEHEAD ET AL.: "Synergistic Silencing: Combinations of Lipid-like Materials for Efficacious siRNA Delivery", MOLECULAR THERAPY, vol. 19, no. 9, JPN6013003083, September 2011 (2011-09-01), pages p.1688-1694, 特にAbstract及びFig.1, XP055067340, DOI: doi:10.1038/mt.2011.141
MUKTHAVARAM RAJESH ET AL.: "Dramatic Influence of the Orientation of Linker between Hydrophilic and Hydrophobic Lipid Moiety in", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 129, no. 37, JPN6013003084, 2007, pages p.11408-11420, 特にScheme 1, XP055067341, DOI: doi:10.1021/ja0704683
GOLLAPUDI VENKATA SRILAKSHMI ET AL.: "Anchor-dependent lipofection with non-glycerol based cytofections containing single 2-hydroxyethyl h", BIOCHIMICA ET BIOPHYSICA ACTA, BIOMENBRANES, vol. 1559, no. 2, JPN6013003085, 2002, pages p.87-95, 特にChart1, XP004341284, DOI: doi:10.1016/S0005-2736(01)00442-4
I. FLECHSLER ET AL.: "COMPARISON OF ANTISENSE VECTORS AND ANTISENSE OLIGONUCLEOTIDES DELIVERED BY MEANS OF THE NEW CATIONI", ADVANCES IN EXPERIMENTAL MEDICINE AND BIOLOGY, vol. Vol.451, JPN6013003086, 1998, pages 469 - 472, XP009048306
SANTANU BHATTACHARYA ET AL.: "The effects of cholesterol inclusion on the vesicular membranes of cationic lipids", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 1283, no. 1, JPN6013003087, 1996, pages p.21-30, 特にFig.1, XP055067345, DOI: doi:10.1016/0005-2736(96)00064-8
IGOR SOLODIN ET AL.: "Synthesis of Amphiphilic Derivatives of N-Methyldiethanolamine. Cationic Lipids 5", SYNLETT, vol. No.7, JPN6013003088, 1996, pages 6 - 0, XP002035804, DOI: doi:10.1055/s-1996-5577
IGOR SOLODIN ET AL.: "Synthesis of Novel Cationic Lipids with a Guanidine Group. Cationic Lipids 3", SYNLETT, vol. No.7, JPN6013003089, 1996, pages 617 - 618, XP055151450, DOI: doi:10.1055/s-1996-5575
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