Name: Dios-Arg (trifluoroacetate salt)
Rating: 5 (10 reviews)

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HIT ID:HIT212972378
Cas No:1807353-31-6
常用名:Dios-Arg (trifluoroacetate salt)
常用名:Dios-Arg (trifluoroacetate salt)
IUPAC:[amino({[(4S)-4-azaniumyl-4-({6-oxo-6-[(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-en-16'-yloxy]hexyl}carbamoyl)butyl]amino})methylidene]azanium ditrifluoroacetate
IUPAC:[amino({[(4S)-4-azaniumyl-4-({6-oxo-6-[(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-en-16'-yloxy]hexyl}carbamoyl)butyl]amino})methylidene]azanium ditrifluoroacetate
InChI key:BUBYULRFSQOIII-XWXJGKJWSA-N

分子式:C43H67F6N5O9
分子量:912.025
氢键供体数 (HBD):5
氢键受体数 (HBA):6
LogP:4.412353
SMILES:[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F.C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC=C5C[C@H](CC[C@]5(C)[C@H]4CC[C@]23C)OC(=O)CCCCCNC(=O)[C@@H]([NH3+])CCCNC(N)=[NH2+])O[C@]11CC[C@@H](C)CO1 |t:20|
SMILES:[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F.C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC=C5C[C@H](CC[C@]5(C)[C@H]4CC[C@]23C)OC(=O)CCCCCNC(=O)[C@@H]([NH3+])CCCNC(N)=[NH2+])O[C@]11CC[C@@H](C)CO1 |t:20|

Dios-Arg is a steroid-based cationic lipid that contains a diosgenin skeleton coupled to an L-arginine head group. It forms a complex with plasmid DNA and decreases plasmid DNA migration in an agarose-gel retardant assay at charge ratio greater than or equal to 4. Dios-Arg facilitates transfection of plasmid DNA into H1299 and HeLa cells in the presence and absence of fetal bovine serum, an effect that is reversed by the lipid raft-mediated endocytosis inhibitor methyl-β-cyclodextrin and the caveolae-mediated endocytosis inhibitor genistein . It has been used, coupled to 1,2-dioleoyl-sn-glycero-3-PE , to bind siRNA and plasmid DNA to form cationic lipid nanoparticles for intracellular transport. Dios-Arg is cytotoxic to H1299 and HeLa cells (IC50s = 83.5 and 74.1 μg/ml, respectively).

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