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
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Product Name
DIF-3, ≥99% (HPLC), solid
InChI key
JWBMZIJMSBFBIY-UHFFFAOYSA-N
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
assay
≥99% (HPLC)
form
solid
solubility
DMSO: soluble 46 mg/mL
Quality Level
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
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.
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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The search for morphogens in Dictyostelium.
L Bloom et al.
BioEssays : news and reviews in molecular, cellular and developmental biology, 9(6), 187-191 (1988-12-01)
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
Effects of Visfatin on Intracellular Mechanics and Catabolism in Human Primary Chondrocytes through Glycogen Synthase Kinase 3 beta Inactivation
Chang SF, et al.
International Journal of Molecular Sciences, 22(15), 8107-8107 (2021)
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
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
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