InChI
1S/C28H38N4O4/c1-16(15-29-23-8-9-24(32(34)35)26-25(23)30-36-31-26)20-6-7-21-19-5-4-17-14-18(33)10-12-27(17,2)22(19)11-13-28(20,21)3/h4,8-9,16,18-22,29,33H,5-7,10-15H2,1-3H3/t16-,18+,19+,20-,21+,22+,27+,28-/m1/s1
InChI key
DLWLXTLRGQWGPC-XIWKFBMMSA-N
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]
assay
≥98% (HPLC)
form
powder
color
, Yellow to dark orange
solubility
DMSO: 2 mg/mL, clear
storage temp.
-10 to -25°C
Quality Level
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).
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).
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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)
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
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