D0567
DIF-3
≥99% (HPLC), solid
Synonym(s):
1-(3-Chloro-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone, Differentiation-inducing factor 3
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About This Item
Empirical Formula (Hill Notation):
C13H17ClO4
CAS Number:
Molecular Weight:
272.72
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
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Assay
≥99% (HPLC)
form
solid
solubility
DMSO: soluble 46 mg/mL
SMILES string
CCCCCC(=O)c1c(O)cc(OC)c(Cl)c1O
InChI
1S/C13H17ClO4/c1-3-4-5-6-8(15)11-9(16)7-10(18-2)12(14)13(11)17/h7,16-17H,3-6H2,1-2H3
InChI key
JWBMZIJMSBFBIY-UHFFFAOYSA-N
General description
Differentiation-inducing factor-3 (DIF-3) is a monochlorinated metabolite of differentiation-inducing factor-1 (DIF-1), that belongs to the differentiation-inducing factor (DIF) family.
Application
DIF-3 has been used: as a glycogen synthase kinase-3β (GSK-3β) activator to determine if GSK-3β is required for the anti-inflammatory actions of VU0360172 (VuPAM) in murine microglia, as a phosphorylation inhibitor for GSK-3β to examine the links between activation of protein kinase B (PKB)/GSK-3β/Fyn axis and nuclear factor erythroid 2–related factor 2 (NRF2) retention, as a GSK3β activator to study its effects on the cyclooxygenase 2 (COX2) expression levels in human primary chondrocytes in response to visfatin, as a GSK3β activator to study its effects on the intracellular mechanics along with F-actin and β-tubulin fiber networks in human primary chondrocytes
Biochem/physiol Actions
Differentiation-inducing factor-3 (DIF-3) prevents the proliferation of intestinal cancer cells in vitro and in vivo. It may serve as a novel anti-cancer agent.
DIF-3 Inhibits cell cycle by inducing G0/G1 arrest.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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M S Masento et al.
The Biochemical journal, 256(1), 23-28 (1988-11-15)
Previous work has led to the identification of a novel class of effector molecules [DIFs (differentiation-inducing factors) 1-3] released from the slime mould Dictyostelium discoideum. These substances induce stalk-cell differentiation in Dictyostelium discoideum and are thought to act as morphogens
Y Kubohara
European journal of pharmacology, 381(1), 57-62 (1999-10-21)
DIF-1 (differentiation-inducing factor-1; 1-(3,5-dichloro-2, 6-dihydroxy-4-methoxyphenyl)hexan-1-one) is a putative morphogen that induces stalk cell formation in the cellular slime mold, Dictyostelium discoideum. It has been previously reported that DIF-1 exhibits anti-tumor activity in mammalian cells. In this study, we examined the
Fumi Takahashi-Yanaga et al.
The Journal of biological chemistry, 278(11), 9663-9670 (2003-01-11)
In search of chemical substances applicable for the treatment of cancer and other proliferative disorders, we studied the signal transduction of Dictyostelium differentiation-inducing factors (DIFs) in mammalian cells mainly using HeLa cells. Although DIF-1 and DIF-3 both strongly inhibited cell
Extracellular signals and intracellular transduction pathways regulating Dictyostelium development.
J G Williams
Current opinion in cell biology, 1(6), 1132-1138 (1989-12-01)
M Wang et al.
Developmental biology, 140(1), 182-188 (1990-07-01)
Stalk cell differentiation in Dictyostelium can be induced by the differentiation-inducing factor, DIF, or by conditions that decrease intracellular pH (pHi). We have investigated whether cytoplasmic acidification acts directly to induce expression of pDd56 and pDd63, two DIF-regulated genes, specifically
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