DASA-58 Chemical Properties

Boiling point:

681.5±65.0 °C(Predicted)

Density 

1.453±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

insoluble in EtOH; insoluble in H2O; ≥127.2 mg/mL in DMSO

form 

solid

pka

3.35±0.10(Predicted)

color 

White to off-white

InChI

1S/C19H23N3O6S2/c20-15-3-1-4-16(13-15)29(23,24)21-7-2-8-22(10-9-21)30(25,26)17-5-6-18-19(14-17)28-12-11-27-18/h1,3-6,13-14H,2,7-12,20H2

InChIKey

GMHIOMMKSMSRLY-UHFFFAOYSA-N

SMILES

NC1=CC=CC(S(N2CCN(S(C3=CC=C(OCCO4)C4=C3)(=O)=O)CCC2)(=O)=O)=C1

Safety Information

WGK Germany 

WGK 3

Storage Class

11 - Combustible Solids

DASA-58 Usage And Synthesis

Description

DASA-58 is a selective activator of pyruvate kinase M2 (PKM2; AC₅₀ = 38 nM in vitro, EC₅₀ = 19.6 μM in cells). DASA-58 converts PKM2 to a constitutively active enzyme state that is resistant to inhibition by tyrosine-phosphorylated proteins. Through its effects on PKM2, DASA-58 blocks the induction of HIF-1α by lipopolysaccharide in bone marrow-derived macrophages, suppressing the expression of several HIF-1α-dependent targets, including IL-1β. It also impairs metastatic dissemination of prostate cancer PCa cells in SCID mice.

Uses

DASA-58 is a potential pyruvate kinase isozyme (PKM2) allosteric activator. DASA-58 can be used for the research of metabolism and kinds of cancer[1].

Definition

ChEBI: 3-[[4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfonyl)-1,4-diazepan-1-yl]sulfonyl]aniline is a member of benzenes and a sulfonamide.

References

[1]. anastasiou d, yu y, israelsen wj, et al. pyruvate kinase m2 activators promote tetramer formation and suppress tumorigenesis. nature chemical biology, 2012, 8(10): 839-847.