BODIPY-aminoacetaldehyde diethyl acetal

BODIPY-aminoacetaldehyde diethyl acetal (BAAA-DA) is a stable precursor to BODIPY-aminoacetaldehyde, a cell-permeable fluorescent substrate for aldehyde dehydrogenase (ALDH). BODIPY-aminoacetaldehyde diethyl acetal is converted under acidic conditions to BODIPY-aminoacetaldehyde (BAAA). BAAA is cell-permeant and is converted intracellularly by ALDH to BODIPY aminoacetate (BAA), which is retained by cells and can be used to identify cells with high ALDH activity. BAA is a substrate for the efflux pump P-glycoprotein (P-gp) but co-application of BAAA with a P-gp inhibitor, such as verapamil (Cay-14288), inhibits BAA efflux. BAAA-DA has been used to isolate human hematopoietic progenitor cells, which have high ALDH activity, and via flow cytometry to sort cancer stem cells that contain high levels of ALDH. BAA used in cells can be excited at 488 nm and displays an emission maximum of 512 nm.Formal Name: (T-4)-[N-(2,2-diethoxyethyl)-5-[(3,5-dimethyl-2H-pyrrol-2-ylidene-kN)methyl]-1H-pyrrole-2-propanamidato-kappaN1]difluoro-boron. CAS Number: 247069-93-8. Synonyms: BAAA-DA. Molecular Formula: C20H28BF2N3O3. Formula Weight: 407.3. Purity: >95%. Emission: 512 nm. Formulation: (Request formulation change), A solution in methyl acetate. SMILES: [F][B-]1([N]2C(C=C(C(C)=C3)[N+]1=C3C)=CC=C2CCC(NCC(OCC)OCC)=O)[F]. InChi Code: InChI=1S/C20H28BF2N3O3/c1-5-28-20(29-6-2)13-24-19(27)10-9-16-7-8-17-12-18-14(3)11-15(4)25(18)21(22,23)26(16)17/h7-8,11-12,20H,5-6,9-10,13H2,1-4H3,(H,24,27). InChi Key: LHPURSCMUYRRRM-UHFFFAOYSA-N.