D-609

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

MedKoo CAT#: 527901

CAS#: 83373-60-8

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.


Price and Availability

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D-609 is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 527901
Name: D-609
CAS#: 83373-60-8
Chemical Formula: C11H15KOS2
Exact Mass:
Molecular Weight: 266.4583
Elemental Analysis: C, 49.58; H, 5.67; K, 14.67; O, 6.00; S, 24.06


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+]


Technical Data

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).

Harmonized System Code:
293490


References

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.