| Identification | Back Directory | [Name]
6,8-Difluoro-4-pyridin-3-yl-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline | [CAS]
1139889-93-2 | [Synonyms]
Golgicide A
Golgicide A - CAS 1139889-93-2 - Calbiochem
6,8-Difluoro-4-pyridin-3-yl-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline
6,8-Difluoro-4-pyridin-3-yl-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline USP/EP/BP
rel-(3aR,9bS)-6,8-Difluoro-4-(pyridin-3-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline
3H-Cyclopenta[c]quinoline, 6,8-difluoro-3a,4,5,9b-tetrahydro-4-(3-pyridinyl)-, (3aR,9bS)-rel- | [Molecular Formula]
C17H14F2N2 | [MOL File]
1139889-93-2.mol | [Molecular Weight]
284 |
| Chemical Properties | Back Directory | [storage temp. ]
Store at RT | [solubility ]
insoluble in H2O; ≥12.95 mg/mL in DMSO; ≥2.27 mg/mL in EtOH with ultrasonic | [form ]
Off-white solid | [color ]
White to off-white | [CAS DataBase Reference]
1139889-93-2 |
| Hazard Information | Back Directory | [Uses]
Golgicide A, | [Definition]
ChEBI: Golgicide A is a diastereoisomeric mixture comprising racemic cis- and racemic trans-goglioside A in a 10:1 ratio. It is a potent and rapidly reversible GBF1 (Golgi-specific brefeldin A-resistance guanine nucleotide exchange factor 1) inhibitor. The (3aS,4R,9bR) isomer is the most active (see Bioorg. Med. Chem. Lett., 2012, 22, 5177-5181). It has a role as a cis-Golgi ArfGEF GBF inhibitor. It contains a cis-golgicide A and a trans-golgicide A. | [General Description]
A cell-permeable quinoline compound that selectively targets ArfGEF GBF1, but not BIG1/2, and attenuates GBF1-mediated cellular vesicle traffickings in a reversible manner. Phenotypic comparisons in Vero (African Green Monkey Kidney epithelial) cultures reveal that selective blockage of GBF1 function by GCA (10 μM) or by FGB1-E794K dominant-inactive expression affects medial- and cis-Golgi similarly to that seen with BFA (Cat. No. 203729), however, the non-GBF1-specific BFA (10 μg/ml or 35.6 μM) causes additional GBF1-independent morphologic effects on TGN, notably the rapid dispersal of Golgi-associated coat proteins AP-1 and GGA3, which are not seen with GCA treatment. Endocytic/retrograde transport studies using GCA establishes that GBF1 function is not required for the transport of bacterial toxins to the endosomes, however the retrograde transport of StxB (shiga toxin B subunit) from endosomes to TGN and Golgi is GBF1-dependent (100% inhibition of StxB sulfation at 10 μM), accounting for GCA′s (10 μM) ability to completely prevent Vera cells from Stx-induced (up to 100 ng/ml) inhibition of cellular protein synthesis. | [storage]
Store at -20°C |
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