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Merck
CN

SML3831

Sigma-Aldrich

22-NBD Cholesterol

≥98% (HPLC)

别名:

(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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关于此项目

经验公式（希尔记法）:
C28H38N4O4
化学文摘社编号:
78949-95-8
分子量:
494.63
MDL编号:
MFCD00467337

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质量水平

100

方案

≥98% (HPLC)

表单

powder

颜色

, Yellow to dark orange

溶解性

DMSO: 2 mg/mL, clear

储存温度

-10 to -25°C

SMILES字符串

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]

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

生化/生理作用

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).

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000392451
0000392452
0000369557
0000369557
0000392452

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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
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
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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