SML2041

CE3F4

≥98% (HPLC)

• Synonym(e): 5,7-Dibromo-6-fluoro-3,4-dihydro-2-methyl-1(2H)-quinolinecarboxaldehyde
• Empirische Formel (Hill-System): C₁₁H₁₀Br₂FNO
• CAS-Nummer: 143703-25-7
• Molekulargewicht: 351.01
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD30182244
• Assay: ≥98% (HPLC)
• Form: powder

Eigenschaften

• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 2 mg/mL, clear (warmed)
• storage temp.: −20°C
• SMILES string: Fc1c(c2c(cc1Br)N(C(CC2)C)C=O)Br
• InChI: 1S/C11H10Br2FNO/c1-6-2-3-7-9(15(6)5-16)4-8(12)11(14)10(7)13/h4-6H,2-3H2,1H3
• InChI key: ZZLQPWXVZCPUGC-UHFFFAOYSA-N

Beschreibung

Application

CE3F4 has been used as a selective exchange protein directly activated by cAMP isoform 1 (Epac1) inhibitor in cell proliferation assay to study the influence of Epac type I on cell proliferation of C6 cells (a model of glioma).[1]

Biochem/physiol Actions

CE3F4 is a tetrahydroquinoline derivative that blocks agonist-stimulated Epac1 (exchange protein directly activated by cAMP isoform 1) guanine nucleotide exchange activity toward its effector Rap1 (IC50 = 23 μM; Epac agonist = 2 μM 8-CPT-2′-O-Me-cAMP) by targeting agonist-bound Epac1 in an agonist-uncompetitive manner without affecting the GDP exchange on Rap1, Rap1-Epac1 interaction, or PKA type I/II activity (CβRIβ & CαRIIβ). CE3F4 (20 μM) effectively inhbits cellular Rap1 activation upon 10 μM Sp-8-pCPT-2′-O-Me-cAMPS (Epac1-transfected HEK293 and rat neonatal cardiac myocytes) or 10 μM β-adrenergic receptor agonist isoprenaline stimulation (β1AR & Epac1 dually transfected HEK293). The isolated CE3F4 R enantiomer is reported to display 10-fold Epac1 selectivity over Epac2, and is 10-times more potent than the CE3F S enantiomer against Epac1.

Epac1 is a downstream effector of the cyclic adenosine monophosphate (cAMP) pathway.[1]

Uncompetitive inhibitor against agonist-induced Epac1 (exchange protein directly activated by cAMP isoform 1) guanine nucleotide exchange activity.

Sicherheitshinweise

• pictograms: GHS07,GHS09
• signalword: Warning
• hcodes: H302,H411
• pcodes: P273 - P301 + P312 + P330
• Hazard Classifications: Acute Tox. 4 Oral - Aquatic Chronic 2
• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable