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Key Documents

SML0599

Sigma-Aldrich

DIF-1

≥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

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

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

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. DIF-1 is more active when compared to DIF-2 in promoting stalk cell differentiation under submerged assay conditions.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000105066
0000070031
0000045201
023M4611V

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[Low molecular compounds that regulate cell differentiation and chemotaxis in Dictyostelium discoideum].
Yuzuru Kubohara et al.
Seikagaku. The Journal of Japanese Biochemical Society, 82(12), 1132-1137 (2011-02-26)
Jean-Paul Rieu et al.
Cell motility and the cytoskeleton, 66(12), 1073-1086 (2009-08-21)
The collective motion of cells in a biological tissue originates from their individual responses to chemical and mechanical signals. The Dictyostelium slug moves as a collective of up to 100,000 cells with prestalk cells in the anterior 10-30% and prespore
Marie-Françoise Luciani et al.
Autophagy, 7(5), 501-508 (2011-02-09)
We investigated the role of Atg1 in autophagic cell death (ACD) in a Dictyostelium monolayer model. The model is especially propitious, not only because of genetic tractability and absence of apoptosis machinery, but also because induction of ACD requires two
Danton H O'Day et al.
Cellular signalling, 21(2), 317-323 (2008-11-13)
The nucleomorphin gene numA1 from Dictyostelium codes for a multi-domain, calmodulin binding protein that regulates nuclear number. To gain insight into the regulation of numA, we assessed the effects of the stalk cell differentiation inducing factor-1 (DIF-1), an extracellular signalling
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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