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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

Quality Level

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)

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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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
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)
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)
Junko Nakajima-Shimada et al.
Biochemical pharmacology, 85(11), 1603-1610 (2013-03-21)
Chagas disease (human American trypanosomiasis), which is caused by the protozoan parasite Trypanosoma cruzi, is responsible for numerous deaths each year; however, established treatments for the disease are limited. Differentiation-inducing factor-1 (DIF-1) and DIF-3 are chlorinated alkylphenones originally found in
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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