Name: 2H-Cho-Arg (trifluoroacetate salt)
Rating: 5 (10 reviews)

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HIT ID:HIT212972365
Cas No:1609010-59-4
常用名:2H-Cho-Arg (trifluoroacetate salt)
常用名:2H-Cho-Arg (trifluoroacetate salt)
IUPAC:({[(4S)-4-[(6-{[(1R,3aS,3bR,5aS,7S,9aS,9bS,11aR)-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-hexadecahydro-1H-cyclopenta[a]phenanthren-7-yl]oxy}-6-oxohexyl)carbamoyl]-4-azaniumylbutyl]amino}(amino)methylidene)azanium ditrifluoroacetate
IUPAC:({[(4S)-4-[(6-{[(1R,3aS,3bR,5aS,7S,9aS,9bS,11aR)-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-hexadecahydro-1H-cyclopenta[a]phenanthren-7-yl]oxy}-6-oxohexyl)carbamoyl]-4-azaniumylbutyl]amino}(amino)methylidene)azanium ditrifluoroacetate
InChI key:VOJMFRVKQJJEJI-SKZSWDEZSA-N

分子式:C43H73F6N5O7
分子量:886.075
氢键供体数 (HBD):5
氢键受体数 (HBA):4
LogP:7.003516
SMILES:[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F.CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)OC(=O)CCCCCNC(=O)[C@@H]([NH3+])CCCNC(N)=[NH2+]
SMILES:[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F.CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)OC(=O)CCCCCNC(=O)[C@@H]([NH3+])CCCNC(N)=[NH2+]

2H-Cho-Arg is a steroid-based cationic lipid that contains a 2H-cholesterol skeleton coupled to an L-arginine head group and can be used to facilitate gene transfection. It forms a complex with plasmid DNA (pDNA) and decreases pDNA migration in an electrophoretic mobility shift assay at +/- charge ratios of 4 or higher. 2H-Cho-Arg facilitates transfection of a luciferase gene into H1299 cells, an effect that is reversed by the lipid raft-mediated endocytosis inhibitor methyl-β-cyclodextrin and the caveolae-mediated endocytosis inhibitor genistein , but not by inhibitors of clathrin- or micropinocytosis-mediated endocytosis. It induces cytotoxicity in H1299 cells (IC50 = 92.7 μg/ml).

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