BODIPY 581/591 C11 is a BODIPY fluoroboronide analogue with good photostability and low fluorescence artifacts. BODIPY 581/591 C11 is often used to study lipid peroxidation and antioxidant properties in living cells, or to react with hydroxyl radicals and detect ferroptosis. The emission wavelength of BODIPY 581/591 C11 is 591 nm (reduced form), or red-shifted to 510 nm (oxidized form); the excitation wavelengths are 581 nm (reduced form) and 500 nm (oxidized form) respectively.

Physicochemical Properties

Molecular Formula	C30H35BF2N2O2
Molecular Weight	504.4189
Exact Mass	504.275
Elemental Analysis	C, 71.43; H, 6.99; B, 2.14; F, 7.53; N, 5.55; O, 6.34
CAS #	217075-36-0
PubChem CID	9914060
Appearance	Brown to black solid powder
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	14
Heavy Atom Count	37
Complexity	934
Defined Atom Stereocenter Count	0
SMILES	[B-]1(N2C(=CC=C2CCCCCCCCCCC(=O)O)C=C3[N+]1=C(C=C3)/C=C/C=C/C4=CC=CC=C4)(F)F
InChi Key	KXOYQMUYGHQCBT-CMQZKQKJSA-N
InChi Code	InChI=1S/C30H35BF2N2O2/c32-31(33)34-26(17-10-5-3-1-2-4-6-11-19-30(36)37)20-22-28(34)24-29-23-21-27(35(29)31)18-13-12-16-25-14-8-7-9-15-25/h7-9,12-16,18,20-24H,1-6,10-11,17,19H2,(H,36,37)/b16-12+,18-13+
Chemical Name	hydrogen 11-(5,5-difluoro-7-((1E,3E)-4-phenylbuta-1,3-dien-1-yl)-5H-5l4,6l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-3-yl)undecanoate
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	BODIPY borofluoroprene derivative
ln Vitro	Preparation of stock solution: The stock solution is prepared by dissolving 1 milligram of BODIPY 581/591 C11 in 0.1983 mL DMSO to produce 10 mM of the stock solution. Note: Store the stock solution at -20°C or -80°C, protect from light, and avoid repeated freeze and thaw cycles. 1.2 Preparing the BODIPY 581/591 C11 working solutions: Take the above BODIPY 581/591 C11 stock solution and dilute it to 2–10 μM with medium or PBS. Note: You may adjust the concentrations of BODIPY 581/591 C11 working solution based on your experimental needs. Cell staining: 2.1 Cell preparation: Suspension cells: Centrifuge 1000g at 4 ℃ for 3-5 minutes and discard the supernatant. Wash twice with PBS for 5 minutes each time. Adherent cells: Discard the cell culture medium, add trypsin to dissociate the cells, and prepare a single-cell suspension. Centrifuge at 1000 g at 4 ° C for 3-5 minutes, then discard the supernatant. Wash twice with PBS for 5 minutes each time. 2.2 Add 1 mL of BODIPY 581/591 C11 working solution and incubate at room temperature for 30 minutes. 2.3 Discard the supernatant after centrifuging at 400 g for three to four minutes at 4°C. 2.4 Use PBS twice, giving each wash five minutes. 2.5 Resuspend the cells for flow cytometry or fluorescence microscopy in PBS or serum-free cell culture media. Note: 1. It is advised that the stock solution be stored at -20°C or -80°C away from light and avoid repeated freeze and thaw cycles. 2. You may adjust the concentrations of BODIPY 581/591 C11 working solution based on your experimental needs. 3. This product is not to be used in human; it is only to be used for research and development. 4. Please wear a white lab-coat and disposable gloves for your health and safety.
Cell Assay	C11-BODIPY(581/591) 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 easily enters membranes; (vi) once oxidized, C11-BODIPY(581/591) remains lipophilic and does not spontaneously leave the lipid bilayer; (vii) C11-BODIPY(581/591) 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.
References	[1]. 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.

Solubility Data

Solubility (In Vitro)

DMSO : 12.5 mg/mL (24.78 mM)

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.9825 mL	9.9124 mL	19.8247 mL
	5 mM	0.3965 mL	1.9825 mL	3.9649 mL
	10 mM	0.1982 mL	0.9912 mL	1.9825 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.