BODIPY 581/591 C11

Description

C11 BODIPY 581/591 is a lipid-soluble ratiometric fluorescent indicator of lipid oxidation. Upon oxidation, its excitation maximum shifts from 581 to 500 nm and the emission maximum shifts from 591 to 510 nm. C11 BODIPY 581/591 has been used in the quantitation of ferroptosis.

Definition

BODIPY 581/591 C11 is an oxidation-sensitive fluorescent fatty acid analog with fluorescent properties in the red range of the visible spectrum (emission maximum 595 nm), allowing its application in fluorescence microscopy. BODIPY 581/591 C11 is easily incorporated 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-BODIPY581/591 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.

Advantages

BODIPY 581/591 C11 is a fluorescent radio-probe for indexing lipid peroxidation and antioxidant efficacy in model membrane systems and living cells, with excellent characteristics: (i) emission in the visible range of the electromagnetic spectrum, with good spectral separation of the nonoxidized (595 nm) and oxidized (520 nm) forms; (ii) has a high quantum yield and because of this, low labeling concentrations can be used, ensuring minimal perturbation of the membrane whilst retaining favorable signal to noise ratios; (iii) has a good photo-stability and displays very few fluorescence artifacts; (iv) is virtually insensitive to environmental changes, i.e., pH or solvent polarity; (v) is lipophilic and as such quickly enters membranes; (vi) once oxidized, BODIPY 581/591 C11 remains lipophilic and does not spontaneously leave the lipid bilayer; (vii) BODIPY 581/591 C11 localizes in two distinct pools within the lipid bilayer, a shallow pool at 18 A and a deep pool at < 7.5 A from the center of the bilayer; (viii) is not cytotoxic to rat-1 fibroblasts up to 50 microM; (ix) is sensitive to a variety of oxy-radicals and peroxynitrite, but not to superoxide, nitric oxide, transition metal ions, and hydroperoxides per se; (x) its sensitivity to oxidation is comparable to that of endogenous fatty acyl moieties[1].

References

[1] Gregor P.C Drummen . “C11-BODIPY581/591, an oxidation-sensitive fluorescent lipid peroxidation probe: (micro)spectroscopic characterization and validation of methodology.” Free Radical Biology and Medicine 33 4 (2002): Pages 473-490.