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N-2-[N'-(Nε-t-butyloxycarbonyl-L-Lysyl)]aminoethyl-N,N-di-n-tetradecylamine | 678975-65-0

中文名称
——
中文别名
——
英文名称
N-2-[N'-(Nε-t-butyloxycarbonyl-L-Lysyl)]aminoethyl-N,N-di-n-tetradecylamine
英文别名
N-2-[N'-(Nε-BOC-L-lysinyl)]aminoethyl-N,N-di-n-tetradecylamine;tert-butyl N-[(5S)-5-amino-6-[2-[di(tetradecyl)amino]ethylamino]-6-oxohexyl]carbamate
N-2-[N'-(N<sup>ε</sup>-t-butyloxycarbonyl-L-Lysyl)]aminoethyl-N,N-di-n-tetradecylamine化学式
CAS
678975-65-0
化学式
C41H84N4O3
mdl
——
分子量
681.143
InChiKey
RYSRPLQQIVNYMR-LHEWISCISA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    758.7±60.0 °C(Predicted)
  • 密度:
    0.926±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    13.8
  • 重原子数:
    48
  • 可旋转键数:
    37
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    0.95
  • 拓扑面积:
    96.7
  • 氢给体数:
    3
  • 氢受体数:
    5

反应信息

  • 作为反应物:
    描述:
    N-2-[N'-(Nε-t-butyloxycarbonyl-L-Lysyl)]aminoethyl-N,N-di-n-tetradecylamine 在 palladium on activated charcoal N-羟基丁二酰亚胺 、 ammonium formate 、 溶剂黄146N,N'-二环己基碳二亚胺 作用下, 以 甲醇二氯甲烷N,N-二甲基甲酰胺 为溶剂, 反应 53.0h, 生成 N-2-[N'-(Nα,Nε-di-tert-butyloxycarbonyl-L-Lys-Nε-tert-butyloxycarbonyl-L-Lys-Nε-tert-butyloxycarbonyl-L-Lys)]aminoethyl-N,N-di-n-tetradecylamine
    参考文献:
    名称:
    Design, Syntheses and In Vitro Gene Delivery Efficacies of Novel Mono-, Di- and Trilysinated Cationic Lipids:  A Structure−Activity Investigation
    摘要:
    Structure-activity investigation including design, syntheses, and evaluation of relative in vitro gene delivery efficacies of a novel series of cationic amphiphiles (1-10) containing mono-, di-, and trilysine headgroups are described in CHO, COS-1, and HepG2 cells. Several interesting and rather unexpected transfection profiles were observed. In general, lipid 1 with the myristyl tail used in combination with DOPE as colipid exhibited superior transfection properties compared to (a) the monolysinated analogues with longer hydrocarbon tails (lipids 2-4), (b) the dilysine (lipids 5-7) and the trilysine headgroup analogues (lipids 8-10), and (c) commercially available LipofectAmine with multiple positive charges in its polar region. As a preliminary estimate of the relative DNA-compacting efficacies of these new lysinated cationic lipids, the hydrodynamic diameters of representative lipoplexes were measured using dynamic laser light scattering technique. Our lipoplex size data are consistent with the notion that covalent grafting of an increasing number of positively charged functional groups in the headgroup region of cationic lipids need not necessarily result in more compacted lipoplexes. Both gel retardation and DNase I sensitivity assays indicated similar lipid/DNA binding interactions for all the novel mono-, di-, and trilysinated cationic lipids. MTT-assay-based cell viability results clearly demonstrate that the overall lower transfection properties of trilysine analogues (8-10) compared to their mono- (1-4) and dilysinated (5-7) counterparts are unlikely to originate from differential toxicity related effects. Taken together, the present findings support the notion that caution needs to be exercised in ensuring enhanced gene delivery efficacies of cationic lipids through covalent grafting of multiple lysine functionalities in the headgroup region.
    DOI:
    10.1021/jm030541+
  • 作为产物:
    描述:
    参考文献:
    名称:
    Design, Syntheses and In Vitro Gene Delivery Efficacies of Novel Mono-, Di- and Trilysinated Cationic Lipids:  A Structure−Activity Investigation
    摘要:
    Structure-activity investigation including design, syntheses, and evaluation of relative in vitro gene delivery efficacies of a novel series of cationic amphiphiles (1-10) containing mono-, di-, and trilysine headgroups are described in CHO, COS-1, and HepG2 cells. Several interesting and rather unexpected transfection profiles were observed. In general, lipid 1 with the myristyl tail used in combination with DOPE as colipid exhibited superior transfection properties compared to (a) the monolysinated analogues with longer hydrocarbon tails (lipids 2-4), (b) the dilysine (lipids 5-7) and the trilysine headgroup analogues (lipids 8-10), and (c) commercially available LipofectAmine with multiple positive charges in its polar region. As a preliminary estimate of the relative DNA-compacting efficacies of these new lysinated cationic lipids, the hydrodynamic diameters of representative lipoplexes were measured using dynamic laser light scattering technique. Our lipoplex size data are consistent with the notion that covalent grafting of an increasing number of positively charged functional groups in the headgroup region of cationic lipids need not necessarily result in more compacted lipoplexes. Both gel retardation and DNase I sensitivity assays indicated similar lipid/DNA binding interactions for all the novel mono-, di-, and trilysinated cationic lipids. MTT-assay-based cell viability results clearly demonstrate that the overall lower transfection properties of trilysine analogues (8-10) compared to their mono- (1-4) and dilysinated (5-7) counterparts are unlikely to originate from differential toxicity related effects. Taken together, the present findings support the notion that caution needs to be exercised in ensuring enhanced gene delivery efficacies of cationic lipids through covalent grafting of multiple lysine functionalities in the headgroup region.
    DOI:
    10.1021/jm030541+
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文献信息

  • [EN] METHODS AND COMPOSITIONS COMPRISING NOVEL CATIONIC LIPIDS<br/>[FR] PROCÉDÉS ET COMPOSITIONS COMPRENANT DE NOUVEAUX LIPIDES CATIONIQUES
    申请人:UNIV NORTH CAROLINA
    公开号:WO2009142892A1
    公开(公告)日:2009-11-26
    Provided herein are novel cationic lipids, compositions comprising the cationic lipids, and methods of using the cationic lipids. In some claims, the cationic lipids have cytotoxic activity and can be used alone or in combination with a cytotoxic bioactive compound to kill a cell. In some of these claims, the cationic lipid enhances the cytotoxic activity of the cytotoxic bioactive compound. Methods for treating a subject afflicted with a disease or unwanted condition are provided, wherein the method comprises administering a delivery system comprising a novel cationic lipid to the subject. The invention further provides methods for making delivery systems comprising the novel cationic lipids of the invention.
    本文提供了新型阳离子脂质、含有这些阳离子脂质的组合物,以及使用这些阳离子脂质的方法。在一些声明中,这些阳离子脂质具有细胞毒活性,可以单独使用或与细胞毒生物活性化合物结合使用以杀死细胞。在其中一些声明中,这些阳离子脂质增强了细胞毒生物活性化合物的细胞毒活性。提供了治疗患有疾病或不良状况的受试者的方法,其中该方法包括向受试者施用含有新型阳离子脂质的传递系统。该发明还提供了制备包含该发明的新型阳离子脂质的传递系统的方法。
  • US8389768B2
    申请人:——
    公开号:US8389768B2
    公开(公告)日:2013-03-05
  • Design, Syntheses and In Vitro Gene Delivery Efficacies of Novel Mono-, Di- and Trilysinated Cationic Lipids:  A Structure−Activity Investigation
    作者:Priya P. Karmali、Valluripalli V. Kumar、Arabinda Chaudhuri
    DOI:10.1021/jm030541+
    日期:2004.4.1
    Structure-activity investigation including design, syntheses, and evaluation of relative in vitro gene delivery efficacies of a novel series of cationic amphiphiles (1-10) containing mono-, di-, and trilysine headgroups are described in CHO, COS-1, and HepG2 cells. Several interesting and rather unexpected transfection profiles were observed. In general, lipid 1 with the myristyl tail used in combination with DOPE as colipid exhibited superior transfection properties compared to (a) the monolysinated analogues with longer hydrocarbon tails (lipids 2-4), (b) the dilysine (lipids 5-7) and the trilysine headgroup analogues (lipids 8-10), and (c) commercially available LipofectAmine with multiple positive charges in its polar region. As a preliminary estimate of the relative DNA-compacting efficacies of these new lysinated cationic lipids, the hydrodynamic diameters of representative lipoplexes were measured using dynamic laser light scattering technique. Our lipoplex size data are consistent with the notion that covalent grafting of an increasing number of positively charged functional groups in the headgroup region of cationic lipids need not necessarily result in more compacted lipoplexes. Both gel retardation and DNase I sensitivity assays indicated similar lipid/DNA binding interactions for all the novel mono-, di-, and trilysinated cationic lipids. MTT-assay-based cell viability results clearly demonstrate that the overall lower transfection properties of trilysine analogues (8-10) compared to their mono- (1-4) and dilysinated (5-7) counterparts are unlikely to originate from differential toxicity related effects. Taken together, the present findings support the notion that caution needs to be exercised in ensuring enhanced gene delivery efficacies of cationic lipids through covalent grafting of multiple lysine functionalities in the headgroup region.
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