MitoPerOx, fluorescent mitochondria-targeted lipid peroxidation probe

Key facts

CAS number

1392820-50-6

Purity

>95%

Form

Solid

form

Molecular weight

760.46 g/mol

Molecular formula

C₄₂H₃₈BF₂N₃OP.Br

Nature

Synthetic

Solubility

Soluble in DMSO to 25 mM

Biological description

Ratiometric, fluorescent, mitochondria-targeted lipid peroxidation probe. Derived from the C11-BODIPY(581/591) probe, which contains a boron dipyromethane difluoride (BODIPY) fluorophore conjugated via a dienyl link to a phenyl group. An attached triphenylphosphonium lipophilic cation leads to selective uptake into mitochondria in living cells, driven by the mitochondrial membrane potential. In response to lipid peroxidation the fluorescence emission maximum shifts from ∼590 to ∼520 nm.

Isomeric smiles

[BR-].F[B-]7(F)[N+]=2C(C=CC=2\C=C\C=C\C1CCCCC1)=CC6CCC(CCC(=O)NCC[P+](C3CCCCC3)(C4CCCCC4)C5CCCCC5)N67

InChi

InChI=1S/C42H37BF2N3OP.BrH/c44-43(45)47-35(18-14-13-17-34-15-5-1-6-16-34)25-27-37(47)33-38-28-26-36(48(38)43)29-30-42(49)46-31-32-50(39-19-7-2-8-20-39,40-21-9-3-10-22-40)41-23-11-4-12-24-41;/h1-28,33H,29-32H2;1H/b17-13+,18-14+;

InChiKey

UDTNTHFRCJAKLR-GPSHETCQNA-N

IUPAC Name

4,4-Difluoro-5-(4-phenyl-1,3-butadienyl)-4-bora-3a,4a-diaza-s-indacene-3-(propionylaminoethylentriphenylphosphonium) bromide