C11 BODIPY 581/591

C11-BODIPY^581/591 is an oxidation-sensitive fluorescent fatty acid analogue with fluorescent properties in the red range of the visible spectrum (emission maximum 595 nm), allowing its application in fluorescence microscopy. C11-BODIPY^581/591 is easily incorporating into membranes and fluoresces red in the intact state but shifts to green upon free radical-induced oxidation. This characteristic is highly advantageous, it makes the ratio-imaging of oxidant activities at the (sub)cellular level feasible. In addition, the fluorescent properties of C11-BODIPY^581/591 allow the use of this probe in fast- and medium- throughput screening of antioxidants in living cells and model membranes in a multiwell/fluorescence reader approach^[1][2].

The wavelengths of maximal excitation and emission of fluorophore C11-BODIPY^581/591 corresponded to 581 and 591 nm, respectively. Addition of CumOOH/hemin, as an initiator of lipid oxidation, shifted the excitation and emission spectra to shorter wavelengths corresponding to green fluorescence (peak excitation 500 nm, emission 510 nm). C11-BODIPY^581/591 is also easily oxidized by other hydroxy-, peroxy- and oxy-radical generating systems such as hydrogen peroxide/Fe2+ and 2,2’-azobis. However, this probe is relatively insensitive to SIN-1, which generates nitric oxide and superoxide^[3]

References:
[1]. Drummen GP, et al. C11-BODIPY^581/591, an oxidation-sensitive fluorescent lipid peroxidation probe: (micro)spectroscopic characterization and validation of methodology. Free Radic Biol Med. 2002 Aug 15;33(4):473-90.
[2]. Partyka A, et al. Detection of lipid peroxidation in frozen-thawed avian spermatozoa using C11-BODIPY^581/591. Theriogenology. 2011 Jun;75(9):1623-9.
[3]. Pap EH, et al. Ratio-fluorescence microscopy of lipid oxidation in living cells using C11-BODIPY^581/591. FEBS Lett. 1999 Jun 25;453(3):278-82.