22-NBD Cholesterol

22-NBD cholesterol is a fluorescent analog of cholesterol 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 vesicles.⁵ The emission maximum of 22-NBD cholesterol is solvent-dependent and increases as solvent polarity increases.¹

1.Craig, I.F., Via, D.P., Mantulin, W.W., et al.Low density lipoproteins reconstituted with steroids containing the nitrobenzoxadiazole fluorophoreJ. Lipid Res.22(4)687-696(1981) 2.Faletrov, Y., Brzostek, A., Plocinska, R., et al.Uptake and metabolism of fluorescent steroids by mycobacterial cellsSteroids11729-37(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 approachJ. Biol. Chem.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 vitroJ. 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 depletionChem. Phys. Lipids167-16862-69(2013)