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MedKoo Cat#: 527901 | Name: D-609

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

D-609
D-609
CAS#83373-60-8

Theoretical Analysis

MedKoo Cat#: 527901

Name: D-609

CAS#: 83373-60-8

Chemical Formula: C11H15KOS2

Exact Mass:

Molecular Weight: 266.46

Elemental Analysis: C, 49.58; H, 5.67; K, 14.67; O, 6.00; S, 24.06

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 266.46 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.

Recalculate based on batch purity %
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
1: Sun C, Shao J, Su L, Zhao J, Bi J, Yang S, Zhang S, Gao J, Miao J. Cholinergic neuron-like cells derived from bone marrow stromal cells induced by tricyclodecane-9-yl-xanthogenate promote functional recovery and neural protection after spinal cord injury. Cell Transplant. 2013;22(6):961-75. doi: 10.3727/096368912X657413. PubMed PMID: 23031841. 2: Bonilla F, Minahk C, Ajmat MT, Toranzo GS, Bühler MI. Identification of phospholipase activity in Rhinella arenarum sperm extract capable of inducing oocyte activation. Zygote. 2014 Nov;22(4):483-95. doi: 10.1017/S0967199413000348. PubMed PMID: 24016596. 3: Wu CH, Chang CH, Lin HC, Chen CM, Lin CH, Lee HM. Role of protein kinase C in BSA-AGE-mediated inducible nitric oxide synthase expression in RAW 264.7 macrophages. Biochem Pharmacol. 2003 Jul 15;66(2):203-12. PubMed PMID: 12826263. 4: Mauban JR, Zacharia J, Fairfax S, Wier WG. PC-PLC/sphingomyelin synthase activity plays a central role in the development of myogenic tone in murine resistance arteries. Am J Physiol Heart Circ Physiol. 2015 Jun 15;308(12):H1517-24. doi: 10.1152/ajpheart.00594.2014. PubMed PMID: 25888510; PubMed Central PMCID: PMC4469871. 5: Dimitrova DZ, Dimitrov SD, Iliev I, Mladenov MI, Hristov KL, Mihov DN, Duridanova DB, Gagov HS. Ghrelin signaling in human mesenteric arteries. J Physiol Pharmacol. 2010 Aug;61(4):383-90. PubMed PMID: 20814065. 6: Rohra DK, Yamakuni T, Ito S, Saito SY, Ohizumi Y. Evidence for the involvement of protein kinase C in acidic pH-induced contraction in spontaneously hypertensive rat aorta. Pharmacology. 2004 May;71(1):10-6. PubMed PMID: 15051918. 7: Watanabe M, Kitano T, Kondo T, Yabu T, Taguchi Y, Tashima M, Umehara H, Domae N, Uchiyama T, Okazaki T. Increase of nuclear ceramide through caspase-3-dependent regulation of the "sphingomyelin cycle" in Fas-induced apoptosis. Cancer Res. 2004 Feb 1;64(3):1000-7. PubMed PMID: 14871831. 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. 9: Schäfer U, Burgdorf C, Engelhardt A, Kurz T, Richardt G. Presynaptic effects of moxonidine in isolated buffer perfused rat hearts: role of imidazoline-1 receptors and alpha2-adrenoceptors. J Pharmacol Exp Ther. 2002 Dec;303(3):1163-70. PubMed PMID: 12438540. 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. 16: Miwa M, Kozawa O, Tokuda H, Uematsu T. Mitogen-activated protein (MAP) kinases are involved in interleukin-1 (IL-1)-induced IL-6 synthesis in osteoblasts: modulation not of p38 MAP kinase, but of p42/p44 MAP kinase by IL-1-activated protein kinase C. Endocrinology. 1999 Nov;140(11):5120-5. PubMed PMID: 10537140. 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. 19: Chiang LL, Kuo CT, Wang CH, Chen TF, Ho YS, Kuo HP, Lin CH. Involvement of nuclear factor-kappaB in lipoteichoic acid-induced cyclooxygenase-2 expression in RAW 264.7 macrophages. J Pharm Pharmacol. 2003 Jan;55(1):115-23. PubMed PMID: 12625875. 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.