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

Properties

• 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]
• 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

Description

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).

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable