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Key Documents

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M1390

Sigma-Aldrich

3,3′-Methylene-bis(4-hydroxycoumarin)

Sinónimos:

Bishydroxycoumarin, Dicoumarol, Dicumarol

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About This Item

Fórmula empírica (notación de Hill):
C19H12O6
Número de CAS:
66-76-2
Peso molecular:
336.29
EC Number:
200-632-9
MDL number:
MFCD00006857
UNSPSC Code:
12352103
PubChem Substance ID:
24896643
NACRES:
NA.47

biological source

synthetic (organic)

assay

≥98% (TLC)

form

powder

mp

290-292 °C (lit.)

solubility

pyridine: 50 mg/mL, clear, faintly yellow to brownish-yellow

SMILES string

OC1=C(CC2=C(O)c3ccccc3OC2=O)C(=O)Oc4ccccc14

InChI

1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2

InChI key

DOBMPNYZJYQDGZ-UHFFFAOYSA-N

Gene Information

human ... CYP2C9(1559) , VKORC1(79001)

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Biochem/physiol Actions

Prototype of the 4-hydroxycoumarin class of anticoagulants, which act as vitamin K antagonists, preventing formation of prothrombin. There are many reports that dicumarol also inhibits NADPH:quinone oxidoreductase (NQO(1)). In one, it inhibited NQO(1) in a pancreatic cancer cell line, causing increased formation of superoxide and inhibiting cell growth.

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 2 - STOT RE 1 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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4-Nitroquinoline 1-oxide ≥98%

Sigma-Aldrich

N8141

4-Nitroquinoline 1-oxide

Resorufin sodium salt redox indicator

Sigma-Aldrich

R3257

Resorufin sodium salt

DT Diaphorase (NQO1) human lyophilized powder, recombinant, expressed in E. coli, ≥90% (SDS-PAGE)

Sigma-Aldrich

D1315

DT Diaphorase (NQO1) human

Alexandra Reichstein et al.
Journal of medicinal chemistry, 55(16), 7273-7284 (2012-08-01)
A series of linearly anellated lapacho quinone analogues substituted at the 2-position of the tricyclic naphtho[2,3-b]furan-4,9-dione system were synthesized and evaluated for their ability to suppress keratinocyte hyperproliferation using HaCaT cells as the primary test system. While very good in
Katherine Ann Scott et al.
Biochemical pharmacology, 81(3), 355-363 (2010-10-26)
The enzyme NAD(P)H quinone oxidoreductase (NQO1) can function both as a detoxifying enzyme as well as chaperone protein. The latter property has been extensively characterized by the use of dicoumarol which inhibits the chaperone properties of NQO1 in cells. However
Karen Ann Nolan et al.
Biochemical pharmacology, 80(7), 977-981 (2010-07-06)
NAD(P)H quinone oxidoreductase (NQO1) has multiple functions in the cell including an ability to act as a detoxifying enzyme and as a protein chaperone. The latter property is particularly important in oncology as one of the client proteins of NQO1
Ying Dong et al.
Cancer research, 70(20), 8088-8096 (2010-10-14)
The clinical experimental agent, β-lapachone (β-lap; Arq 501), can act as a potent radiosensitizer in vitro through an unknown mechanism. In this study, we analyzed the mechanism to determine whether β-lap may warrant clinical evaluation as a radiosensitizer. β-Lap killed
An S Tan et al.
Free radical biology & medicine, 48(3), 421-429 (2009-11-26)
2,3-Dimethoxy 1,4-naphthoquinone (DMNQ), which redox cycles via two-electron reduction, mediates reduction of the cell-impermeative tetrazolium dye WST-1 in kidney epithelial cells (MDCK), which express high levels of NQO1, but not in HL60 or CHO cells, which are NQO1 deficient. DMNQ-dependent
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