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D0567

Sigma-Aldrich

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
Pricing and availability is not currently available.

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.[1]

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[2], 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[3], as a GSK3β activator to study its effects on the cyclooxygenase 2 (COX2) expression levels in human primary chondrocytes in response to visfatin[4], 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[4]

Biochem/physiol Actions

DIF-3 Inhibits cell cycle by inducing G0/G1 arrest.
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.[1]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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R R Kay et al.
Seminars in cell & developmental biology, 10(6), 577-585 (2000-03-09)
The DIFs are a family of secreted chlorinated molecules that control cell fate during development of Dictyostelium cells in culture and probably during normal development too. They induce stalk cell differentiation and suppress spore cell formation. The biosynthetic and inactivation
A Early
Seminars in cell & developmental biology, 10(6), 587-595 (2000-03-09)
Prestalk cell differentiation in Dictyostelium is induced by DIF and two DIF-induced genes, ecmA and ecmB, have revealed the existence of multiple prestalk and stalk cell sub-types. These different sub-types are defined by the pattern of expression of subfragments derived
A Sobolewski et al.
Developmental biology, 127(2), 296-303 (1988-06-01)
In Dictyostelium discoideum stalk cell formation is induced by cyclic AMP and differentiation-inducing factor (DIF) when cells are plated in in vitro monolayers (Kay et al., 1979, Differentiation 13: 7-14). The in vivo developmental stages at which cells became independent
C R Thompson et al.
Developmental biology, 227(1), 56-64 (2000-11-15)
Cell fate in Dictyostelium development depends on intrinsic differences between cells, dating from their growth period, and on cell interactions occurring during development. We have sought for a mechanism linking these two influences on cell fate. First, we confirmed earlier
B Wurster et al.
Developmental biology, 140(1), 189-195 (1990-07-01)
The DIFs are unusual, chlorinated molecules which induce stalk cell differentiation during the later, multicellular phase of Dictyostelium development. Here we provide evidence that one or more DIFs have a role during early development, when small amounts are known to

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