A fluorescent cholesterol analog
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22-NBD Cholesterol

Item No. 30136

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
20S-methyl-21-[(7-nitro-2,1,3β-benzoxadiazol-4-yl)amino]-pregn-5-en-3-ol
CAS Number
78949-95-8
Molecular Formula
C28H38N4O4
Formula Weight
494.6
Purity
≥90%
Emission
540 nm
Excitation
472 nm
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: 1 mg/ml
SMILES
C[C@H](CNC1=CC=C([N+]([O-])=O)C2=NON=C12)[C@@]3([H])CC[C@@]4([H])[C@]5([H])CC=C6C[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@@]43C
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $75

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    1 mg

    $143

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    5 mg

    $369

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    Product Description

    22-NBD cholesterol is a fluorescent analog of cholesterol (Item No. 9003100) that contains a fluorescent nitrobenzoxadiazole (NBD) group.1 It has been used in a variety of in vitro and in vivo applications, including analysis of steroid uptake and esterification, intracellular localization and targeting, and metabolism in mammalian and bacterial cells, and intestinal absorption of cholesterol in hamsters.2,3,4 22-NBD cholesterol displays excitation/emission maxima of 472/540 nm, respectively, when incorporated into 1,2-dimyristoyl-sn-glycero-3-PC (DMPC; Item No. 15097) vesicles.5 The emission maximum of 22-NBD cholesterol is solvent-dependent and increases as solvent polarity increases.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Craig, I.F., Via, D.P., Mantulin, W.W., et al. Low density lipoproteins reconstituted with steroids containing the nitrobenzoxadiazole fluorophore. J. Lipid Res. 22(4), 687-696 (1981).

    2. Faletrov, Y., Brzostek, A., Plocinska, R., et al. Uptake and metabolism of fluorescent steroids by mycobacterial cells. Steroids 117, 29-37 (2017).

    3. Frolov, A., Petrescu, A., Atshaves, B.P., et al. High density lipoprotein-mediated cholesterol uptake and targeting to lipid droplets in intact L-cell fibroblasts. A single- and multiphoton fluorescence approach. The Journal of Biological Chemisty 275(17), 12769-12780 (2000).

    4. Sparrow, C.P., Patel, S., Baffic, J., et al. A fluorescent cholesterol analog traces cholesterol absorption in hamsters and is esterified in vivo and in vitro. J. Lipid Res. 40(10), 1747-1757 (1999).

    5. Ostašov, P., Sýkora, J., Brejchová, J., et al. FLIM studies of 22- and 25-NBD-cholesterol in living HEK293 cells: Plasma membrane change induced by cholesterol depletion. Chem. Phys. Lipids 167-168, 62-69 (2013).