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92243

Sigma-Aldrich

Cholesteryl N-(2-dimethylaminoethyl)carbamate

≥98% (TLC)

Synonyme(s) :

3β-{N-[2-(Dimethylamino)ethyl]carbamoyl}cholesterol, DC-Chol

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About This Item

Formule empirique (notation de Hill):
C32H56N2O2
Numéro CAS:
137056-72-5
Poids moléculaire :
500.80
Code UNSPSC :
12352211
ID de substance PubChem :
329769879
Nomenclature NACRES :
NA.85

Niveau de qualité

100

Pureté

≥98% (TLC)

Forme

powder or crystals

Groupe fonctionnel

ester

Température de stockage

−20°C

Chaîne SMILES 

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(CC[C@]4(C)[C@H]3CC[C@]12C)OC(=O)NCCN(C)C

InChI

1S/C32H56N2O2/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)/t23-,25?,26+,27-,28+,29+,31+,32-/m1/s1

Clé InChI

HIHOWBSBBDRPDW-MTIZRNOUSA-N

Catégories apparentées

Application


  • Role of interleukin-6 in antigen-specific mucosal immunoglobulin A induction by cationic liposomes.: This study investigates the use of cholesteryl N-(2-dimethylaminoethyl)carbamate in cationic liposomes for enhancing mucosal immunoglobulin A production, highlighting its potential in vaccine development (Tada et al., 2021).

  • Nasal vaccination with pneumococcal surface protein A in combination with cationic liposomes consisting of DOTAP and DC-chol confers antigen-mediated protective immunity against Streptococcus pneumoniae infections in mice.: This research demonstrates the efficacy of cholesteryl N-(2-dimethylaminoethyl)carbamate in nasal vaccines, providing a promising strategy for respiratory infection prevention (Tada et al., 2018).


Actions biochimiques/physiologiques

Cationic liposome, investigated in cancer gene therapy, as vaccine delivery system/adjuvant.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Mentions de danger

H413

Classification des risques

Aquatic Chronic 4

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Malou Henriksen-Lacey et al.
Molecular pharmaceutics, 8(1), 153-161 (2010-12-02)
The immunostimulatory capacities of cationic liposomes are well-documented and are attributed both to inherent immunogenicity of the cationic lipid and more physical capacities such as the formation of antigen depots and antigen delivery. Very few studies have however been conducted
Gene therapy using DC-Chol liposomes.
Goyal, K. and Huang, L.
Journal of liposome research, 5, 49-60 (1995)
Jie Gao et al.
Biomaterials, 31(9), 2655-2664 (2009-12-29)
The development of a tumor-specific immunoliposome delivering small interfering RNA (siRNA) represents a practical way in cancer gene therapy. In this study, we developed PEGylated 3beta-[N-(N', N'-dimethylaminoethane) carbamoyl] cholesterol (DC-Chol)/dioleoylphosphatidyl ethanolamine (DOPE) immunoliposomes conjugated with the Fab' of recombinant humanized
Francesco Cardarelli et al.
Molecular pharmaceutics, 9(2), 334-340 (2011-12-27)
Here we investigate the cellular uptake mechanism and final intracellular fate of two cationic liposome formulations characterized by similar physicochemical properties but very different lipid composition and efficiency for intracellular delivery of DNA. The first formulation is made of cationic
Emmanuel A Ho et al.
Journal of pharmaceutical sciences, 99(6), 2839-2853 (2010-01-22)
Cationic liposomes exhibit a propensity to selectively target tumor-associated blood vessels demonstrating potential value as anti-cancer drug delivery vehicles. Their utility however, is hampered by their biological instability and rapid elimination following i.v. administration. Efforts to circumvent rapid plasma elimination
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