| Identification | Back Directory | [Name]
22-NBD CHOLESTEROL | [CAS]
78949-95-8 | [Synonyms]
NBD cholesterol, 90%
N-(7-nitrobenz-2-oxa-1,3-diazole)-23,24-dinor-5-cholen-22-amine-3beta-ol
Pregn-5-en-3-ol, 20-methyl-21-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-, (3β,20S)-
NBD cholesterol [22-(N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)aMino)-23,24-bisnor-5-cholen-3b-ol] | [Molecular Formula]
C28H38N4O4 | [MDL Number]
MFCD00467337 | [MOL File]
78949-95-8.mol | [Molecular Weight]
494.63 |
| Chemical Properties | Back Directory | [Boiling point ]
650.5±65.0 °C(Predicted) | [density ]
1.27±0.1 g/cm3(Predicted) | [storage temp. ]
-10 to -25°C | [solubility ]
Methanol: 1 mg/ml | [form ]
A solid | [pka]
15.03±0.70(Predicted) | [color ]
Yellow to dark orange | [InChIKey]
DLWLXTLRGQWGPC-XIWKFBMMSA-N | [SMILES]
C[C@]12[C@]([H])([C@]3([C@@]([H])([C@]4(C)C(C[C@@H](O)CC4)=CC3)CC2)[H])CC[C@@]1([C@@H](CNC(C5=NON=C56)=CC=C6[N+]([O-])=O)C)[H] |
| Hazard Information | Back Directory | [Description]
22-NBD cholesterol is a fluorescent analog of cholesterol that contains a fluorescent nitrobenzoxadiazole (NBD) group. It has been used in a variety of in vitro and in vivo applications, including analysis of steroid uptake and esterification, intracellular localization and targeting, and metabolism in mammalian and bacterial cells, and intestinal absorption of cholesterol in hamsters. 22-NBD cholesterol displays excitation/emission maxima of 472/540 nm, respectively, when incorporated into 1,2-dimyristoyl-sn-glycero-3-PC (DMPC; ) vesicles. The emission maximum of 22-NBD cholesterol is solvent-dependent and increases as solvent polarity increases. | [Uses]
Fluoresterol is a fluorescently labeled cholesterol analog that can be used as a fluorescent probe to study the behavior and metabolism of cholesterol in cells, including lipid uptake and esterification analysis, intracellular localization and targeting, and lipid metabolism in mammalian and bacterial cells. Fluoresterol has an excitation maximum at 472 nm and an emission maximum at 540 nm. Fluoresterol is expected to be useful in the study of metabolic diseases[1][2]. | [References]
[1] Faletrov Y V, et al. 22-NBD-cholesterol as a novel fluorescent substrate for cholesterol-converting oxidoreductases[J]. The Journal of steroid biochemistry and molecular biology, 2013, 134: 59-66. DOI:10.1016/j.jsbmb.2012.09.035
[2] Lajdova I, et al. Spectrally and time-resolved fluorescence imaging of 22-NBD-cholesterol in human peripheral blood mononuclear cells in chronic kidney disease patients[J]. Molecules, 2021, 26(22): 6800. DOI:10.3390/molecules26226800 |
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| Company Name: |
Merck KGaA
|
| Tel: |
21-20338288 |
| Website: |
www.sigmaaldrich.cn |
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