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Key Documents

T8543

Sigma-Aldrich

O-Tricyclo[5.2.1.02,6]dec-9-yl dithiocarbonate potassium salt

≥95%, solid

Sinônimo(s):

D609

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About This Item

Fórmula empírica (Notação de Hill):
C11H15KOS2
Número CAS:
Peso molecular:
266.46
Número CE:
Número MDL:
Código UNSPSC:
41106300
ID de substância PubChem:
NACRES:
NA.77

fonte biológica

synthetic (organic)

Ensaio

≥95%

forma

solid

cor

off-white to yellow

solubilidade

H2O: soluble 50 mg/mL, clear to slightly hazy, colorless to faintly yellow
acetone: easily soluble
diethyl ether: insoluble
hydrocarbons: insoluble

cadeia de caracteres SMILES

[K]SC(=S)OC1CC2CC1C3CCCC23

InChI

1S/C11H16OS2.K/c13-11(14)12-10-5-6-4-9(10)8-3-1-2-7(6)8;/h6-10H,1-5H2,(H,13,14);/q;+1/p-1/t6-,7?,8?,9-,10?;/m1./s1

chave InChI

IGULCCCBGBDZKQ-HJPGVBIPSA-M

Aplicação

D609 has been used as a phosphatidylcholine-specific phospholipase C (PC-PLC) inhibitor in mouse bone marrow derived monocytes. D609 has also been reported to significantly reduce the elevated levels of phosphatidylethanolamine binding protein 1 (PEBP1) in apolipoprotein E-/- mice.

Ações bioquímicas/fisiológicas

D609 can block the production of diacylglycerol (DAG) in the cell. D609 functions by inhibiting the phospholipase C-mediated hydrolysis of the phosphate bond present in phosphatidylcholine and other glycerophospholipids.
Phosphatidylcholine-specific phospholipase C (PLC) and HIV-1 inhibitor. Xanthogenate derivative with in vitro anti-tumor activity.

Nota de preparo

O-Tricyclo[5.2.1.02,6]dec-9-yl dithiocarbonate or D609 is soluble in water at 50 mg/ml and yields a clear to slightly hazy, colorless to light yellow solution. It is also soluble in acetone. However, it is insoluble in ether and hydrocarbons.

Alcoholic solutions should not be prepared due to the possibility of transesterification. The product is very labile in solution (1.5 days half-life in tissue culture medium) and is readily hydrolyzed below pH 6.0. Hence, solutions should be prepared immediately before use and unused solutions must be discarded. For tissue culture preparations, the media should be buffered to pH 6.0-7.5. HEPES buffer must not be used as it renders this product toxic.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)


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Li Wang et al.
The Journal of physiology, 591(20), 5005-5015 (2013-08-21)
We previously found that phosphatidylcholine-specific phospholipase C (PC-PLC) was a key inducing element of atherosclerosis, and might negatively regulate human umbilical vein endothelial cell (HUVEC) autophagy. To further investigate the mechanism of PC-PLC action, we initially identified phosphatidylethanolamine binding protein
Laura Abalsamo et al.
Breast cancer research : BCR, 14(2), R50-R50 (2012-03-21)
Acquisition of mesenchymal characteristics confers to breast cancer (BC) cells the capability of invading tissues different from primary tumor site, allowing cell migration and metastasis. Regulators of the mesenchymal-epithelial transition (MET) may represent targets for anticancer agents. Accruing evidence supports
Chiharu Fujihara et al.
Journal of cellular physiology, 234(5), 7149-7160 (2018-10-30)
Fibroblast growth factor-2 (FGF-2) stimulates periodontal regeneration by a broad spectrum of effects on periodontal ligament (PDL) cells, such as proliferation, migration, and production of extracellular matrix. A critical factor in the success of periodontal regeneration is the rapid resolution
Ning Tang et al.
Journal of orofacial pain, 23(2), 167-173 (2009-06-06)
To evaluate possible effects of the intracerebroventricular (icv) injection of either O-Tricyclo [5.2.1.0(2,6)] dec-9-yl dithiocarbonate potassium salt (D609), a potent antioxidant and inhibitor of phosphatidylcholine specific phospholipase C (PtdCho-PLC) and acid sphingomyelinase (ASMase), or the spin trap/free radical scavenger N-tert-Butyl-alpha-phenylnitrone
Lu Zhang et al.
Arteriosclerosis, thrombosis, and vascular biology, 30(3), 411-418 (2010-02-09)
Atherosclerosis is considered to be a chronic inflammatory disease. Previous research has demonstrated that phosphatidylcholine-specific phospholipase C (PC-PLC) plays critical roles in various inflammatory responses. However, the association between PC-PLC and atherosclerosis is undetermined. Therefore, we sought to investigate whether

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