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A6563

Sigma-Aldrich

6-Anilinoquinoline-5,8-quinone

≥95% (TLC), solid

Synonym(s):

6-(Phenylamino)-5,8-quinolinedione, LY-83,583, LY83583

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About This Item

Empirical Formula (Hill Notation):
C15H10N2O2
CAS Number:
91300-60-6
Molecular Weight:
250.25
MDL number:
MFCD00210756
UNSPSC Code:
41106305
PubChem Substance ID:
24891108
NACRES:
NA.77

Quality Level

200

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.

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

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
127H4726
108H47291
072H0830
057H1033
124H7702

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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
Yuanli Duan et al.
Developmental neurobiology, 69(1), 60-72 (2008-11-26)
Microglia migrate rapidly to lesions in the central nervous system (CNS), presumably in response to chemoattractants including ATP released directly or indirectly by the injury. Previous work on the leech has shown that nitric oxide (NO), generated at the lesion
M A Brandt et al.
Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), 196(1), 30-35 (1991-01-01)
Our main objective was to test the efficacy of 6-anilino-5,8-quinolinedione (LY83583) in vivo, a putative inhibitor of cyclic guanosine 3',5'-monophosphate (cGMP) production. If the drug proved capable of lowering plasma, vascular, and kidney levels of cGMP and of inhibiting the
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
Yao Teng et al.
Journal of plant physiology, 167(11), 885-889 (2010-02-23)
Cyclic guanosine 3',5'-monophosphate (cGMP) is an important second messenger in animals, and is emerging as a player in regulatory functions in plants. In this study, we investigated the role of cGMP in seed germination in Arabidopsis thaliana (Col-0). We demonstrated
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