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SML3831

22-NBD Cholesterol

≥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:
Molecular Weight:
494.63
MDL number:
NACRES:
NA.21
Assay:
≥98% (HPLC)
Form:
powder
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Quality Segment

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]

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

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).


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pictograms

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

flash_point_f

Not applicable

flash_point_c

Not applicable



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