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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:
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

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.
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

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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
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)

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