M1390

Dicumarol

Name: Dicumarol
Brand: SIGMA
Price: 48.4 EUR

Synonym(e):

3,3′-Methylen-bis(4-hydroxycumarin), Bishydroxycumarin

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5 G

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Über diesen Artikel

Empirische Formel (Hill-System):

C₁₉H₁₂O₆

CAS-Nummer:

66-76-2

Molekulargewicht:

336.29

NACRES:

NA.47

PubChem Substance ID:

24896643

UNSPSC Code:

12352103

EC Number:

200-632-9

MDL number:

MFCD00006857

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Unterstützung erhalten

solubility

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

Quality Level

100

InChI key

DOBMPNYZJYQDGZ-UHFFFAOYSA-N

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

SMILES string

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

biological source

synthetic (organic)

assay

≥98% (TLC)

form

powder

mp

290-292 °C (lit.)

Gene Information

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

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Dieser Artikel	D5782	C9375	287897
Sigma-Aldrich M1390 3,3′-Methylene-bis(4-hydroxycoumarin)	Sigma-Aldrich D5782 2′,3′-Dideoxycytidine	Sigma-Aldrich C9375 5-Carboxy-2-thiouracil	Sigma-Aldrich 287897 Dicoumarol
biological source synthetic (organic)	biological source synthetic (organic)	biological source synthetic (organic)	biological source -
assay ≥98% (TLC)	assay ≥98% (HPLC)	assay ≥98% (TLC)	assay ≥98% (titration)
Gene Information human ... CYP2C9(1559), VKORC1(79001)	Gene Information -	Gene Information -	Gene Information -
Quality Level 100	Quality Level 200	Quality Level 200	Quality Level 100
form powder	form powder	form powder	form solid
solubility pyridine: 50 mg/mL, clear, faintly yellow to brownish-yellow	solubility water: 50 mg/mL, clear, colorless to faintly yellow	solubility 1 M NaOH: 50 mg/mL, clear, colorless to faintly yellow	solubility 0.1 M NaOH: 15 mg/mL, pyridine: 50 mg/mL

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.

pictograms

GHS06,GHS08,GHS09

signalword

Danger

hcodes

H301,H372,H411

pcodes

P260 - P264 - P273 - P301 + P310 - P314 - P391

Hazard Classifications

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

Lagerklasse

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Pharmacological inhibitors of NAD(P)H quinone oxidoreductase, NQO1: structure/activity relationships and functional activity in tumour cells.

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

Inhibitors of NQO1: identification of compounds more potent than dicoumarol without associated off-target effects.

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

Synthesis and structure-activity relationships of lapacho analogues. 1. Suppression of human keratinocyte hyperproliferation by 2-substituted naphtho[2,3-b]furan-4,9-diones, activation by enzymatic one- and two-electron reduction, and intracellular generation of superoxide.

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

Effect of cytochrome P450 and aldo-keto reductase inhibitors on progesterone inactivation in primary bovine hepatic cell cultures.

C O Lemley et al.

Journal of dairy science, 93(10), 4613-4624 (2010-09-22)

Progesterone is required for maintenance of pregnancy, and peripheral concentrations of progesterone are affected by both production and inactivation. Hepatic cytochrome P450 (EC 1.14.14.1) and aldo-keto reductase (EC 1.1.1.145-151) enzymes play a pivotal role in the first step of steroid

Evidence for NAD(P)H:quinone oxidoreductase 1 (NQO1)-mediated quinone-dependent redox cycling via plasma membrane electron transport: A sensitive cellular assay for NQO1.

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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