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C2832

Sigma-Aldrich

Cholesteryl 3β-N-(di­methyl­amino­ethyl)­carbamate hydrochloride

≥95%

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Synonym(s):
3β-[N-(Dimethylaminoethane)­carbamoyl]­cholesterol, DC-Chol
Empirical Formula (Hill Notation):
C32H57ClN2O2
CAS Number:
166023-21-8
Molecular Weight:
537.26
MDL number:
MFCD00467173
UNSPSC Code:
12352200
PubChem Substance ID:
24892536
NACRES:
NA.77

Quality Level

200

Assay

≥95%

form

powder

storage temp.

−20°C

SMILES string

Cl[H].[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)NCCN(C)C)[C@H](C)CCCC(C)C

InChI

1S/C32H56N2O2.ClH/c1-22(2)9-8-10-23(3)27-13-14-28-26-12-11-24-21-25(36-30(35)33-19-20-34(6)7)15-17-31(24,4)29(26)16-18-32(27,28)5;/h11,22-23,25-29H,8-10,12-21H2,1-7H3,(H,33,35);1H/t23-,25+,26+,27-,28+,29+,31+,32-;/m1./s1

InChI key

ISXSJGHXHUZXNF-LXZPIJOJSA-N

Application

Cholesteryl 3β-N-(di­methyl­amino­ethyl)­carbamate hydrochloride has been used as a bilayer-membrane stabiliser and for nucleic acid transfer.
This cationic cholesterol derivative forms liposomes with L-α-phosphatidylethanolamine, dioleoyl, that efficiently transfect mammalian cell lines.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Gene Targeting Protocols (2000)
S Szala et al.
Gene therapy, 3(11), 1026-1031 (1996-11-01)
An attempt was made to use simple cationic liposomes DC-Chol/DOPE and DDAB/DOPE (DC-Chol is 3 beta (N(N',N-dimethylaminoethane) carbamoyl) cholesterol, DDAB is dimethyldioctadecyl ammonium bromide and DOPE is dioleoylphosphatidylethanolamine) for transfer of Escherichia coli cytosine deaminase 'suicide' gene under the control
A Colosimo et al.
Biochimica et biophysica acta, 1419(2), 186-194 (1999-07-17)
We evaluated the transfection efficiency of five different cationic liposome/plasmid DNA complexes, during the in vitro gene transfer into human epithelial tracheal cell lines. A dramatic correlation between the transfection efficiency and the charge ratio (positive charge of liposome to
X Gao et al.
Biochemical and biophysical research communications, 179(1), 280-285 (1991-08-30)
A novel cationic derivative of cholesterol, 3 beta [N-(N',N'-dimethylaminoethane)-carbamoyl] cholesterol (DC-Chol), has been synthesized and used to prepare sonicated liposomes with dioleoylphosphatidylethanolamine. This novel cationic liposome reagent facilitates efficient DNA mediated transfection in A431 human epidermoid carcinoma cells, A549 human
M J Campbell
BioTechniques, 18(6), 1027-1032 (1995-06-01)
Cationic liposomes are being utilized for the delivery of DNA into mammalian cells both in vitro and in vivo. In this report, we describe a rapid, simple injection method for the preparation of cationic liposomes that requires no special equipment.
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