SML0599

DIF-1

Name: DIF-1
Brand: SIGMA
Price: 120.7 USD
Availability: InStock

≥98% (HPLC)

Synonym(s):

1-(3,5-Chloro-2,6-dihydroxy-4-methoxyphenyl)-1-Hexanone

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About This Item

Empirical Formula (Hill Notation):

C₁₃H₁₆Cl₂O₄

CAS Number:

111050-72-7

Molecular Weight:

307.17

UNSPSC Code:

12352200

NACRES:

NA.77

Key Documents

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Product Name

DIF-1, ≥98% (HPLC)

SMILES string

Clc1c(c(c(c(c1O)C(=O)CCCCC)O)Cl)OC

InChI

1S/C13H16Cl2O4/c1-3-4-5-6-7(16)8-11(17)9(14)13(19-2)10(15)12(8)18/h17-18H,3-6H2,1-2H3

InChI key

VUDQSRFCCHQIIU-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

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Show Differences

1 of 4

This Item	SML1274	D0567	SML2226
Sigma-Aldrich SML0599 DIF-1	Sigma-Aldrich SML1274 RI-1	Sigma-Aldrich D0567 DIF-3	Sigma-Aldrich SML2226 BC-LI-0186
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥99% (HPLC)	assay ≥98% (HPLC)
form powder	form powder	form solid	form powder
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level -
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. -	storage temp. 2-8°C
solubility DMSO: 20 mg/mL, clear	solubility DMSO: 10 mg/mL, clear	solubility DMSO: soluble 46 mg/mL	solubility DMSO: 2 mg/mL, clear
color white to beige	color yellow to orange	color -	color white to beige

Biochem/physiol Actions

DIF-1 (differentiation-inducing factor-1) is isolated from a Dictyostelium slime mold, and is used to inhibit proliferation/promote differentiation in various cell lines.

DIF-1 is a cell differentiation inducing factor.

DIF-1 is a cell differentiation inducing factor.
Differentiation-inducing factor-1 (DIF-1) blocks the migration and invasion of cells and decreases the expression of matrix metalloproteinase-2. It prevents the proliferation of cells using glycogen synthase kinase-3 (GSK-3)-dependent mechanism.[1] DIF-1 is more active when compared to DIF-2 in promoting stalk cell differentiation under submerged assay conditions.[2]

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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A flavin-dependent halogenase catalyzes the chlorination step in the biosynthesis of Dictyostelium differentiation-inducing factor 1.

Christopher S Neumann et al.

Proceedings of the National Academy of Sciences of the United States of America, 107(13), 5798-5803 (2010-03-17)

Differentiation-inducing factor 1 (DIF-1) is a polyketide-derived morphogen which drives stalk cell formation in the developmental cycle of Dictyostelium discoideum. Previous experiments demonstrated that the biosynthetic pathway proceeds via dichlorination of the precursor molecule THPH, but the enzyme responsible for

Glutathione S-transferase 4 is a putative DIF-binding protein that regulates the size of fruiting bodies in Dictyostelium discoideum.

Kuwayama H, et al.

Biochemistry and Biophysics Reports, 8, 219-226 (2016)

Perturbations of the actin cytoskeleton activate a Dictyostelium STAT signalling pathway.

Tsuyoshi Araki et al.

European journal of cell biology, 91(5), 420-425 (2012-03-01)

The Dictyostelium transcription factor STATc is tyrosine phosphorylated and accumulates in the nucleus when cells are exposed either to hyper-osmotic stress or to the prestalk-inducing polyketide DIF-1. In the case of stress STAT activation is mediated by regulated dephosphorylation; whereby

Differentiation-inducing factor-1 enhances 5-fluorouracil action on oral cancer cells inhibiting E2F1 and thymidylate synthase mRNAs accumulation.

Andrea Elio Sprio et al.

Cancer chemotherapy and pharmacology, 69(4), 983-989 (2011-12-06)

Differentiation-inducing factor-1 (DIF-1) is a morphogen originally identified in the amoebozoan Dictyostelium discoideum. In mammalian cells, it has been shown to activate GSK3β, which in turn is expected to reduce levels of β-catenin and cyclin D1, thus mediating DIF-1 antiproliferative

Biological activities of novel derivatives of DIF-1 isolated from Dictyostelium.

Haruhisa Kikuchi et al.

Biochemical and biophysical research communications, 377(3), 1012-1017 (2008-11-04)

The differentiation-inducing factor-1 (DIF-1) is a lipophilic signal molecule (chlorinated alkylphenone) that induces stalk cell differentiation in the cellular slime mold Dictyostelium discoideum. In addition, DIF-1 and its derivatives have been shown to possess anti-leukemic activity and glucose consumption-promoting activity

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DIF-1