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SML3831

Sigma-Aldrich

22-NBD Cholesterol

new

≥98% (HPLC)

Synonym(s):

(3β,20S)-20-Methyl-21-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]pregn-5-en-3-ol, 22-(N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-23,24-bisnor-5-cholen-3β-ol, 22-(N-(NBD)amino)-23,24-bisnorcholesterol, 22-NBD-Chol, Fluoresterol

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About This Item

Empirical Formula (Hill Notation):
C28H38N4O4
CAS Number:
78949-95-8
Molecular Weight:
494.63
MDL number:
MFCD00467337
UNSPSC Code:
12352200

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

, Yellow to dark orange

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

SMILES string

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]

Biochem/physiol Actions

Cell-permeant fluorescent tracer useful to study the distribution and dynamics of cholesterol.

22-NBD Cholesterol (22-NBD-Cho), a fluorescence-labeled cholesterol, is a lipid microenvironment-sensitive dye and localizes in the membrane’s interior. 22-NBD Cholesterol has proven useful for real-time imaging of HDL-mediated cholesterol uptake, efflux, and intracellular trafficking in living cells. 22-NBD-cholesterol′s fluorescence intensity is reported to enhance in response to phase changes of membrane lipids from rafts to non-raft fractions, and orient opposite to cholesterol in lipid bilayers. 22-NBD-Chol serves as a fluorescent substrate for cholesterol-converting oxidoreductases. λ ex/em ~ 470-490/500-600 nm (the fluorescence intensity and emission maximum depend on the medium’s polarity).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yaroslav Faletrov et al.
Steroids, 117, 29-37 (2016-10-27)
Fluorescent steroids BODIPY-cholesterol (BPCh) and 7-nitrobenzoxadiazole-4-amino-(NBD)-labeled 22-NBD-chelesterol (22NC) as well as synthesized 20-(NBD)-pregn-5-en-3β-ol (20NP) were found to undergo bioconversions by Mycobacterium tuberculosis H37Rv and M. smegmatis mc2 155. The major fluorescent products were determined to be 4-en-3-one derivatives of the
Cheng Zhang et al.
Frontiers in pharmacology, 14, 1066758-1066758 (2023-01-31)
Introduction: Atherosclerosis is the main cause of many cardiovascular diseases and contributes to morbidity and mortality worldwide. The formation of macrophage-derived foam cells plays a critical role in the early stage of atherosclerosis pathogenesis. Diterpenoids found in the flowers of
Spectrally and Time-Resolved Fluorescence Imaging of 22-NBD-Cholesterol in Human Peripheral Blood Mononuclear Cells in Chronic Kidney Disease Patients
Molecules (Basel), 26(22), 6800-6800 (2021)

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