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.

C11-BODIPY581/591是一种氧化敏感的荧光脂肪酸类似物，其荧光特性在可见光谱的红色范围内（发射峰值595nm），使其适用于荧光显微镜。 C11-BODIPY581/591容易被纳入膜中，在完整状态下呈现红色荧光，但在自由基诱导氧化时会转变为绿色。这个特点非常有优势，它使得可以在（亚）细胞水平上进行氧化剂活性比率成像。此外，C11-BODIPY581/591的荧光特性还可以利用多孔板/荧光读数器方法，在活体细胞和模型膜中快速筛选抗氧化剂^[1][2]。

荧光染料C11-BODIPY的最大激发和发射波长分别为581和591纳米。添加脂质氧化引发剂CumOOH/hemin后，激发和发射光谱向短波长移动，对应着绿色荧光（峰值激发500纳米，发射510纳米）。C11-BODIPY还容易被其他羟基、过氧化物和氧自由基产生系统如双氧水/Fe2+ 和 2,2'-偶氮丙烷等氧化。然而，这种探针对于生成一氧化氮和超氧阴离子的SIN-1相对不敏感[3]。