WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 527901
Description: D-609, also known as D-609 free, is a phospholipase C inhibitor potentially for the treatment of pancreatic cancer. D-609, an inhibitor of PC-PLC and sphingomyelin synthase, strongly inhibited myogenic tone and had no effect on depolarization-induced contraction. D-609 appeared to act by lowering cytoplasmic Ca(2+) concentration to levels below those that activate contraction.
MedKoo Cat#: 527901
Chemical Formula: C11H15KOS2
Molecular Weight: 266.4583
Elemental Analysis: C, 49.58; H, 5.67; K, 14.67; O, 6.00; S, 24.06
This product is not in stock, which may be available by custom synthesis.
For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge).
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Related CAS #: 83373-60-8 (K+); 145764-52-9 (free)
Synonym: D-609; D 609; D609; D-609 free
IUPAC/Chemical Name: potassium O-(octahydro-1H-4,7-methanoinden-5-yl) carbonodithioate
InChi Key: IGULCCCBGBDZKQ-UHFFFAOYSA-M
InChi Code: 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
SMILES Code: [S-]C(OC1C(C2)C3CCCC3C2C1)=S.[K+]
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 266.4583 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
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8: Zholos AV, Tsytsyura YD, Gordienko DV, Tsvilovskyy VV, Bolton TB. Phospholipase C, but not InsP3 or DAG, -dependent activation of the muscarinic receptor-operated cation current in guinea-pig ileal smooth muscle cells. Br J Pharmacol. 2004 Jan;141(1):23-36. PubMed PMID: 14662735; PubMed Central PMCID: PMC1574170.
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10: Kozawa O, Suzuki A, Tokuda H, Kaida T, Uematsu T. Protein kinase C activation by interleukin (IL)-1 limits IL-1-induced IL-6 synthesis in osteoblast-like cells: involvement of phosphatidylcholine-specific phospholipase C. J Cell Biochem. 1997 Oct 1;67(1):103-11. PubMed PMID: 9328844.
11: Kozawa O, Suzuki A, Kaida T, Tokuda H, Uematsu T. Tumor necrosis factor-alpha autoregulates interleukin-6 synthesis via activation of protein kinase C. Function of sphingosine 1-phosphate and phosphatidylcholine-specific phospholipase C. J Biol Chem. 1997 Oct 3;272(40):25099-104. PubMed PMID: 9312119.
12: Vogt A, Pestell KE, Day BW, Lazo JS, Wipf P. The antisignaling agent SC-alpha alpha delta 9, 4-(benzyl-(2-[(2,5-diphenyloxazole-4-carbonyl)amino]ethyl)carbamoyl)- 2-decanoylaminobutyric acid, is a structurally unique phospholipid analogue with phospholipase C inhibitory activity. Mol Cancer Ther. 2002 Sep;1(11):885-92. PubMed PMID: 12481409.
13: Lin CH, Kuan IH, Lee HM, Lee WS, Sheu JR, Ho YS, Wang CH, Kuo HP. Induction of cyclooxygenase-2 protein by lipoteichoic acid from Staphylococcus aureus in human pulmonary epithelial cells: involvement of a nuclear factor-kappa B-dependent pathway. Br J Pharmacol. 2001 Oct;134(3):543-52. PubMed PMID: 11588108; PubMed Central PMCID: PMC1572984.
14: Wang N, Lv X, Su L, Zhao B, Zhang S, Miao J. D609 blocks cell survival and induces apoptosis in neural stem cells. Bioorg Med Chem Lett. 2006 Sep 15;16(18):4780-3. PubMed PMID: 16872828.
15: Huet E, Brassart B, Wallach J, Debelle L, Haye B, Emonard H, Hornebeck W. [Effect of elastin peptides on the production of matrix metalloproteinase 2 by human skin fibroblasts in culture]. J Soc Biol. 2001;195(2):165-72. French. PubMed PMID: 11723829.
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17: Wang N, Du CQ, Wang SS, Xie K, Zhang SL, Miao JY. D609 induces vascular endothelial cells and marrow stromal cells differentiation into neuron-like cells. Acta Pharmacol Sin. 2004 Apr;25(4):442-6. PubMed PMID: 15066210.
18: Kuo CT, Chiang LL, Lee CN, Yu MC, Bai KJ, Lee HM, Lee WS, Sheu JR, Lin CH. Induction of nitric oxide synthase in RAW 264.7 macrophages by lipoteichoic acid from Staphylococcus aureus: involvement of protein kinase C- and nuclear factor-kB-dependent mechanisms. J Biomed Sci. 2003 Jan-Feb;10(1):136-45. PubMed PMID: 12607534.
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20: Kato M, Hammam MA, Taniguchi T, Suga Y, Monde K. What Is the True Structure of D609, a Widely Used Lipid Related Enzyme Inhibitor? Org Lett. 2016 Feb 19;18(4):768-71. doi: 10.1021/acs.orglett.6b00025. PubMed PMID: 26854352.