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BODIPY-Cholesterol | CAS 878557-19-8
| Catalog Number | F01-0044 |
| Category | BODIPY |
| Molecular Formula | C36H51BF2N2O |
| Molecular Weight | 576.61 |
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Product Introduction
BODIPY-cholesterol is a cell-permeable analog of cholesterol that is tagged with BODIPY group. BODIPY-cholesterol mimics the membrane partitioning and trafficking of cholesterol, and it is often used to study the sterol distribution and transport in living cells.
Chemical Information
Product Specification
Application
Computed Properties
| Synonyms | TopFluor Cholesterol; BCh2; (T-4)-[(3β)-24-(3,5-dimethyl-1H-pyrrol-2-yl-κN)-24-(3,5-dimethyl-2H-pyrrol-2-ylidene-κN)chol-5-en-3-olato]difluoro-boron |
| Purity | ≥98% |
| Shelf Life | 4 years |
| IUPAC Name | (10R,13R)-17-[4-(2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)butan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol |
| Canonical SMILES | [B-]1(N2C(=CC(=C2C(=C3[N+]1=C(C=C3C)C)CCC(C)C4CCC5C4(CCC6C5CC=C7C6(CCC(C7)O)C)C)C)C)(F)F |
| InChI | InChI=1S/C36H51BF2N2O/c1-21(8-10-29-33-22(2)18-24(4)40(33)37(38,39)41-25(5)19-23(3)34(29)41)30-12-13-31-28-11-9-26-20-27(42)14-16-35(26,6)32(28)15-17-36(30,31)7/h9,18-19,21,27-28,30-32,42H,8,10-17,20H2,1-7H3/t21-,27+,28+,30-,31+,32+,35+,36-/m1/s1 |
| InChIKey | CFFWELDLDWZNRO-ZVEUZXBYSA-N |
| Appearance | Red Solid |
| Excitation | 480 nm |
| Emission | 508 nm |
| Storage | Store at -20°C |
BODIPY-Cholesterol, a widely utilized fluorescent cholesterol analog in bioscience research, finds diverse applications. Here are four key uses of BODIPY-Cholesterol:
Cell Membrane Studies: Delving into the intricacies of cholesterol dynamics within cell membranes, researchers employ BODIPY-Cholesterol to investigate its localization and movement. By integrating this fluorescent analog into cellular membranes, scientists can visually track cholesterol distribution using advanced microscopy techniques. This approach aids in unraveling cholesterol’s multifaceted roles in membrane organization, signaling cascades, and cellular trafficking pathways.
Lipid Raft Research: Serving as a valuable marker in studies focused on lipid rafts, BODIPY-Cholesterol enables exploration of these specialized microdomains’ composition and functions. Researchers leverage this fluorescent analog to probe the formation, stability, and protein constituents of lipid rafts in live cells. The insights gained shed light on lipid rafts’ pivotal involvement in cell signaling events, intracellular trafficking processes, and disease pathogenesis.
Cholesterol Metabolism: In the realm of cholesterol metabolism studies, BODIPY-Cholesterol emerges as a powerful tool for investigating cholesterol uptake, transport, and esterification within cells. By labeling cells with this fluorescent cholesterol analog, researchers can monitor and quantify real-time cholesterol metabolism. This application holds significant value in elucidating disorders associated with aberrant cholesterol processing, such as atherosclerosis and Niemann-Pick disease.
Drug Development: At the forefront of drug discovery endeavors, BODIPY-Cholesterol plays a crucial role in high-throughput screening assays aimed at evaluating the effects of pharmaceutical compounds on cholesterol homeostasis. Researchers leverage this fluorescent analog to assess the impact of drug candidates on cholesterol transport and distribution in cellular systems. This application is instrumental in the development of novel therapies targeting cholesterol-related disorders, showcasing the importance of BODIPY-Cholesterol in advancing drug development efforts.
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 4 |
| Exact Mass | 576.4062507 g/mol |
| Monoisotopic Mass | 576.4062507 g/mol |
| Topological Polar Surface Area | 28.2Ų |
| Heavy Atom Count | 42 |
| Formal Charge | 0 |
| Complexity | 1240 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 6 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
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