1139889-93-2

Basic information

• Product Name: 6,8-Difluoro-4-pyridin-3-yl-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline
• Synonyms: 6,8-Difluoro-4-pyridin-3-yl-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline;Golgicide A;3H-Cyclopenta[c]quinoline, 6,8-difluoro-3a,4,5,9b-tetrahydro-4-(3-pyridinyl)-, (3aR,9bS)-rel-
• CAS NO: 1139889-93-2
• Molecular Formula: C17H14F2N2
• Molecular Weight: 284
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitors
• Mol File: 1139889-93-2.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: Store at RT
• Solubility: insoluble in H2O; ≥12.95 mg/mL in DMSO; ≥2.27 mg/mL in EtOH with ultrasonic
• CAS DataBase Reference: 6,8-Difluoro-4-pyridin-3-yl-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6,8-Difluoro-4-pyridin-3-yl-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline(1139889-93-2)
• EPA Substance Registry System: 6,8-Difluoro-4-pyridin-3-yl-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline(1139889-93-2)

Safety Data

• Hazardous Substances Data: 1139889-93-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 1139889-93-2 differently. You can refer to the following data:
1. Golgicide A,
2. Golgicide A, a potent, highly specific, reversible inhibitor of the cis-Golgi ArfGEF GBF1.

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.

Upstream product

• 500-22-1 3-pyridinecarboxaldehyde 
• 367-25-9 2,4-difluorophenylamine 
• 542-92-7 cyclopenta-1,3-diene 

Downstream Products

• 1394285-50-7 C₁₇H₁₄F₂N₂ 
• 1394285-49-4 C₁₇H₁₄F₂N₂ 

Relevant articles and documents

Distinct biological effects of golgicide a derivatives on larval and adult mosquitoes

A collection of Golgicide A (GCA) analogs has been synthesized and evaluated in larval and adult mosquito assays. Commercially available GCA is a mixture of four compounds. One enantiomer (GCA-2) of the major diastereomer in this mixture was shown to be responsible for the unique activity of GCA. Structure-activity studies (SAR) of the GCA architecture suggested that the pyridine ring was most easily manipulated without loss or gain in new activity. Eighteen GCA analogs were synthesized of which five displayed distinct behavior between larval and adult mosquitos, resulting in complete mortality of both Aedes aegypti and Anopheles stephensi larvae. Two analogs from the collection were shown to be distinct from the rest in displaying high selectivity and efficiency in killing An. stephensi larvae.