2126-93-4

Basic information

• Product Name: cholesterylamine
• Synonyms: cholesterylamine;3-beta-aminocholesterol
• CAS NO: 2126-93-4
• Molecular Formula: C₂₇H₄₇N
• Molecular Weight: 385.67
• Mol File: 2126-93-4.mol

Chemical Properties

• Melting Point: 98 °C(Solv: methanol (67-56-1))
• Boiling Point: 470.8°Cat760mmHg
• Flash Point: 234.5°C
• Appearance: /
• Density: 0.96g/cm³
• Vapor Pressure: 4.93E-09mmHg at 25°C
• Refractive Index: 1.526
• PKA: 10?+-.0.70(Predicted)
• CAS DataBase Reference: cholesterylamine(CAS DataBase Reference)
• NIST Chemistry Reference: cholesterylamine(2126-93-4)
• EPA Substance Registry System: cholesterylamine(2126-93-4)

Safety Data

• Hazardous Substances Data: 2126-93-4(Hazardous Substances Data)

Usage

Uses

Used in Magnetic Resonance Applications:
Cholesterylamine is used as an enhancer for the magnetic susceptibility of lanthanide-chelating bicelles in bilayer structures. This application is particularly useful in the field of magnetic resonance imaging (MRI) and spectroscopy, where it can improve the quality of images and data obtained from these techniques.
Used in Antiviral Applications:
In the pharmaceutical industry, cholesterylamine is used as a potential antiviral agent. It shows a new mode of antiviral action by directly targeting the virus envelope and its biological functions, which could be beneficial in the development of new treatments for viral infections.
Used in Drug Delivery Systems:
Similar to gallotannin, cholesterylamine could also be employed in the development of novel drug delivery systems. Its unique properties might allow for improved targeting and delivery of therapeutic agents, potentially enhancing their efficacy and reducing side effects.

InChI:InChI=1/C27H47N/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25H,6-8,10-17,28H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

Upstream product

• 38759-57-8 cholest-5-en-3β-yl-isopropyliden-amine 
• 14412-92-1 N-acetyl-cholest-5-en-3β-amine 
• 1182-65-6 3β-Tosyloxy-Δ⁵-cholesten 
• 530-62-1 1,1'-carbonyldiimidazole 
• 123147-62-6 3β-methanesulfonyl-5-cholestene 
• 96290-22-1 (3S,8S,9S,10R,13R,14S,17R)-3-azido-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene 
• 907574-94-1 cholest-5-ene-3β-carboxylic acid hydrazide 
• 601-54-7 Cholest-5-en-3-one 
• 474-77-1 epicholesterol 
• 7144-08-3 Cholesteryl chloroformate 
• 390762-93-3 N-cholesteryl-2-nitrobenzenesulfonamide 
• 57-88-5 cholesterol 
• 1182-65-6 cholesteryl p-toluenesulfonate 
• 7664-41-7 ammonia 

Relevant articles and documents

Sterilizing Immunity against SARS-CoV-2 Infection in Mice by a Single-Shot and Lipid Amphiphile Imidazoquinoline TLR7/8 Agonist-Adjuvanted Recombinant Spike Protein Vaccine**

The search for vaccines that protect from severe morbidity and mortality because of infection with severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), the virus that causes coronavirus disease 2019 (COVID-19) is a race against the clock and the virus. Here we describe an amphiphilic imidazoquinoline (IMDQ-PEG-CHOL) TLR7/8 adjuvant, consisting of an imidazoquinoline conjugated to the chain end of a cholesterol-poly(ethylene glycol) macromolecular amphiphile. It is water-soluble and exhibits massive translocation to lymph nodes upon local administration through binding to albumin, affording localized innate immune activation and reduction in systemic inflammation. The adjuvanticity of IMDQ-PEG-CHOL was validated in a licensed vaccine setting (quadrivalent influenza vaccine) and an experimental trimeric recombinant SARS-CoV-2 spike protein vaccine, showing robust IgG2a and IgG1 antibody titers in mice that could neutralize viral infection in vitro and in vivo in a mouse model.

MODIFIED PIGMENT EPITHELIUM-DERIVED FACTOR (PEDF) PEPTIDES AND USES THEREOF FOR TREATING NEOVASCULAR DISEASES, INFLAMMATORY DISEASES, CANCER, AND FOR CYTOPROTECTION

Disclosed are modified pigment epithelium-derived factor (PEDF) peptides, particulate carrier prodrugs thereof, and pharmaceutical compositions comprising the peptides or particulate carrier prodrugs. The peptides, particulate carrier prodrugs, and pharmaceutical compositions may be used to treat diseases and disorders that are amenable to treatment with anti-angiogenic agents, anti-tumorigenic agents, anti-fibrotic agents, chemotherapy-protecting agents, and immune stimulating agents

Thermal Rearrangement of Sulfamoyl Azides: Reactivity and Mechanistic Study

The rearrangement of sulfamoyl azides under thermal conditions to form a C-C bond while breaking two C-N bonds is reported. Mechanistic study shows that this reaction goes through a Curtius-type rearrangement to form a 1,1-diazene, then which rearranges possibly through both a concerted rearrangement process and a stepwise radical process. This rearrangement could be used in the synthesis of complex biologically active molecules, such as sterols, and piperine derivatives.

Bivalent multifunctional ligands targeting Aβ oligomers as treatment for Alzheimer's disease

Bivalent multifunctional Aβ oligomerization inhibitors (BMAOIs) that target multiple risk factors involved in Alzheimer's disease are provided. The BMAOIs are useful for the treatment and/or prevention of Alzheimer's disease, as well as for diagnostic ima

Evaluation of steroidal amines as lipid raft modulators and potential anti-influenza agents

The influenza A virus (IFV) possesses a highly ordered cholesterol-rich lipid envelope. A specific composition and structure of this membrane raft envelope are essential for viral entry into cells and virus budding. Several steroidal amines were investigated for antiviral activity against IFV. Both, a positively charged amino function and the highly hydrophobic (C log P ≥ 5.9) ring system are required for IC50 values in the low μM range. An amino substituent is preferential to an azacyclic A-ring. We showed that these compounds either disrupt or augment membrane rafts and in some cases inactivate the free virus. Some of the compounds also interfere with virus budding. The antiviral selectivity improved in the series 3-amino, 3-aminomethyl, 3-aminoethyl, or by introducing an OH function in the A-ring. Steroidal amines show a new mode of antiviral action in directly targeting the virus envelope and its biological functions.

Derivatization of a bioorthogonal protected trisaccharide linker - Toward multimodal tools for chemical biology

When cross-linking biomolecules to surfaces or to other biomolecules, the use of appropriate spacer molecules is of great importance. Mimicking the naturally occurring spacer molecules will give further insight into their role and function, possibly unveil important issues regarding the importance of the specificity of carbohydrate-based anchor moieties, in e.g., glycoproteins and glycosylphosphatidylinositols. Herein, we present the synthesis of a lactoside-based trisaccharide, potentially suitable as a heterobifunctional bioorthogonal linker molecule whereon valuable chemical handles have been conjugated. An amino-derivative having thiol functionality shows promise as novel SPR-surfaces. Furthermore, the trisaccharide has been conjugated to a cholesterol moiety in combination with a fluorophore which successfully assemble on the cell surface in lipid microdomains, possibly lipid-rafts. Finally, a CuI-catalyzed azide-alkyne cycloaddition reaction (CuAAC) confirms the potential use of oligosaccharides as bioorthogonal linkers in chemical biology. (Chemical Equation Presented)

Practical synthesis of 3β-amino-5-cholestene and related 3β-halides involving i-steroid and retro-i-steroid rearrangements

(Equation Presented) Derivatives of 3β-amino-5-cholestene (3β-cholesterylamine) are of substantial interest as cellular probes and have potential medicinal applications. However, existing syntheses of 3β-amino-5-cholestene are of limited preparative utility. We report here a practical method for the stereoselective preparation of 3β-amino-5- cholestene, 3β-chloro-5-cholestene, 3β-bromo-5-cholestene, and 3β-iodo-5-cholestene from inexpensive cholesterol. A sequential i-steroid/retro-i-steroid rearrangement promoted by boron trifluoride etherate and trimethylsilyl azide converted cholest-5-en-3β-ol methanesulfonate to 3β-azido-cholest-5-ene with retention of configuration in 93% yield.

CHOLESTERYLAMINES FOR THE TREATMENT AND PREVENTION OF INFECTIOUS DISEASES

The present invention relates to the use of cholesterylamines in the preparation of pharmaceutical compositions. These pharmaceutical compositions are to be used in the medical intervention of infectious diseases, in particular diseases caused by a virus or a bacterium.

Synthetic mimics of mammalian cell surface receptors: method and compositions

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