A6563

Sigma-Aldrich

6-Anilinoquinoline-5,8-quinone

≥95% (TLC), solid

Synonym(s):
6-(Phenylamino)-5,8-quinolinedione, LY83583, LY-83,583
Empirical Formula (Hill Notation):
C15H10N2O2
CAS Number:
Molecular Weight:
250.25
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥95% (TLC)

form

solid

color

violet

solubility

0.1 M HCl: 1 mg/mL
methanol: 11 mg/mL
ethanol: 8 mg/mL

storage temp.

2-8°C

SMILES string

O=C1C=C(Nc2ccccc2)C(=O)c3cccnc13

InChI

1S/C15H10N2O2/c18-13-9-12(17-10-5-2-1-3-6-10)15(19)11-7-4-8-16-14(11)13/h1-9,17H

InChI key

GXIJYWUWLNHKNW-UHFFFAOYSA-N

Application

6-Anilinoquinoline-5,8-quinone inhibits soluble guanylate cyclase and cGMP production. 6-Anilinoquinoline-5,8-quinone also blocks the release of intracellular Ca2+ and antigen-induced leukotrienes.

Packaging

5 mg in glass bottle

Biochem/physiol Actions

Blocks cGMP production; inhibits intracellular Ca2+ release; blocks the effects of nitric oxide. Inhibits antigen-induced leukotriene release.

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Rajendra Patel et al.
Journal of vascular surgery, 43(2), 364-371 (2006-02-16)
Smooth muscle cells (SMCs) from prosthetic vascular grafts secrete higher levels of collagen than aortic SMCs under basal conditions and during incubation with oxidized low-density lipoprotein. We postulated that reactive oxygen species (ROS) contributed to the observed difference. The objective...
Vladimir A Snetkov et al.
Cardiovascular research, 89(1), 214-224 (2010-09-02)
the aim of this study was to determine the relative importance of Ca(2+) sensitization, ion channels, and intracellular Ca(2+) ([Ca(2+)](i)) in the mixed constrictor/relaxation actions of superoxide anion on systemic and pulmonary arteries. pulmonary and mesenteric arteries were obtained from...
Greg A Knock et al.
Free radical biology & medicine, 46(5), 633-642 (2008-12-24)
Reactive oxygen species play a key role in vascular disease, pulmonary hypertension, and hypoxic pulmonary vasoconstriction. We investigated contractile responses, intracellular Ca(2+) ([Ca(2+)](i)), Rho-kinase translocation, and phosphorylation of the regulatory subunit of myosin phosphatase (MYPT-1) and of myosin light chain...
Amaury de Montaigu et al.
The Plant cell, 22(5), 1532-1548 (2010-05-06)
Nitrate assimilation in plants and related organisms is a highly regulated and conserved pathway in which the enzyme nitrate reductase (NR) occupies a central position. Although some progress has been made in understanding the regulation of the protein, transcriptional regulation...
I Fleming et al.
British journal of pharmacology, 103(1), 1047-1052 (1991-05-01)
1. The aim of this investigation was to study the relationship between contractile responsiveness, activation of the L-arginine pathway and tissue levels of guanosine 3':5'cyclic monophosphate (cylic GMP) in aortic rings removed from rats 4 h after intraperitoneal administration of...

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