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565725-M

SecinH3

A cell-permeable triazolo compound that acts as a Sec7 domain-binding, selective antagonist against cytohesin family small GEFs.

Synonym(s):

SecinH3, N-(4-(5-(1,3-Benzodioxol-5-yl)-3-methoxy-1H-1,2,4-triazol-1-yl)phenyl)-2-(phenylthio)acetamide, Cytohesin Inhibitor I

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About This Item

Empirical Formula (Hill Notation):
C24H20N4O4S
CAS Number:
853625-60-2
Molecular Weight:
460.51
MDL number:
MFCD10687099
UNSPSC Code:
12352202
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
solid
Storage condition:
OK to freeze, protect from light
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Quality Segment

100

assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

white

solubility

DMSO: 50 mg/mL

storage temp.

2-8°C

SMILES string

S(CC(=O)Nc2ccc(cc2)[n]3nc(nc3c4cc5c(cc4)OCO5)OC)c1ccccc1

InChI

1S/C24H20N4O4S/c1-30-24-26-23(16-7-12-20-21(13-16)32-15-31-20)28(27-24)18-10-8-17(9-11-18)25-22(29)14-33-19-5-3-2-4-6-19/h2-13H,14-15H2,1H3,(H,25,29)

InChI key

QPGYAMIHXLCFTJ-UHFFFAOYSA-N

General description

A cell-permeable triazolo compound that acts as a Sec7 domain-binding (Kd ≤250 nM for Sec7 from human cytohesins 1-3), selective antagonist against cytohesin family small GEFs (IC50 ≤5.6 µM in ARF1 GDP/GTP exchange assays using human cytohesin 3, as well as murine and Drosophila homologues). It inhibits large GEFs only at much higher concentrations (IC50 ≥65 µM in GDP/GTP exchange assays using hEFA6-S7 and yGea2-S7) and exhibits little activity against a panel of 10 commonly studied kinases or hSosII. Shown to effectively inhibit insulin signaling both in HepG2 cells in vitro and in Drosophila and mice in vivo.

Biochem/physiol Actions

Kd ≤250 nM for Sec7 from human cytohesins 1-3; IC50 ≤5.6 µM in ARF1 GDP/GTP exchange assays using human cytohesin 3, as well as murine and Drosophila homologues
Primary Target
Cytohesin

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Hafner, M., et al. 2006. Nature444, 941.
Fuss, B., et al. 2006. Nature444, 945.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Irritant (B)

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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