SKI-II
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MedKoo CAT#: 407255

CAS#: 312636-16-1

Description: SKI-II is a selective non-lipid inhibitor of sphingosine kinase (IC50 = 0.5 μM). nhibits acute myelogenous leukemia cell growth in vitro and in vivo. SKI-II was more efficient than two known SphK1 inhibitors SK1-I and FTY720 in inhibiting AML cells. Meanwhile, it induced dramatic apoptosis in above AML cells, and the cytotoxicity by SKI-II was almost reversed by the general caspase inhibitor z-VAD-fmk. SKI-II treatment inhibited SphK1 activation, and concomitantly increased level of sphingosine-1-phosphate (S1P) precursor ceramide in AML cells.


Price and Availability

Size Price Shipping out time Quantity
100mg USD 850 2 Weeks
200mg USD 1450 2 Weeks
500mg USD 2250 2 Weeks
1g USD 3250 2 Weeks
2g USD 4650 2 Weeks
5g USD 6550 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-27. Prices are subject to change without notice.

SKI-II, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 407255
Name: SKI-II
CAS#: 312636-16-1
Chemical Formula: C15H11ClN2OS
Exact Mass: 302.0281
Molecular Weight: 302.776
Elemental Analysis: C, 59.50; H, 3.66; Cl, 11.71; N, 9.25; O, 5.28; S, 10.59


Synonym: SKI-II; SKI II. Sphingosine kinase inhibitor II;

IUPAC/Chemical Name: 4-[[4-(4-Chlorophenyl)-2-thiazolyl]amino]phenol

InChi Key: ZFGXZJKLOFCECI-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H11ClN2OS/c16-11-3-1-10(2-4-11)14-9-20-15(18-14)17-12-5-7-13(19)8-6-12/h1-9,19H,(H,17,18)

SMILES Code: OC1=CC=C(NC2=NC(C3=CC=C(Cl)C=C3)=CS2)C=C1


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, not in water

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


References

1: Aurelio L, Scullino CV, Pitman MR, Sexton A, Oliver V, Davies L, Rebello RJ, Furic L, Creek DJ, Pitson SM, Flynn BL. From Sphingosine Kinase to Dihydroceramide Desaturase: A Structure-Activity Relationship (SAR) Study of the Enzyme Inhibitory and Anticancer Activity of 4-((4-(4-Chlorophenyl)thiazol-2-yl)amino)phenol (SKI-II). J Med Chem. 2016 Feb 3. [Epub ahead of print] PubMed PMID: 26780304.

2: Yang L, Weng W, Sun ZX, Fu XJ, Ma J, Zhuang WF. SphK1 inhibitor II (SKI-II) inhibits acute myelogenous leukemia cell growth in vitro and in vivo. Biochem Biophys Res Commun. 2015 May 15;460(4):903-8. doi: 10.1016/j.bbrc.2015.03.114. Epub 2015 Mar 28. PubMed PMID: 25824043.

3: Potì F, Ceglarek U, Burkhardt R, Simoni M, Nofer JR. SKI-II--a sphingosine kinase 1 inhibitor--exacerbates atherosclerosis in low-density lipoprotein receptor-deficient (LDL-R-/-) mice on high cholesterol diet. Atherosclerosis. 2015 May;240(1):212-5. doi: 10.1016/j.atherosclerosis.2015.03.020. Epub 2015 Mar 16. PubMed PMID: 25801013.

4: Li PH, Wu JX, Zheng JN, Pei DS. A sphingosine kinase-1 inhibitor, SKI-II, induces growth inhibition and apoptosis in human gastric cancer cells. Asian Pac J Cancer Prev. 2014;15(23):10381-5. PubMed PMID: 25556479.

5: Liu Y, Zhu Z, Cai H, Liu Q, Zhou H, Zhu Z. SKI-II reverses the chemoresistance of SGC7901/DDP gastric cancer cells. Oncol Lett. 2014 Jul;8(1):367-373. Epub 2014 Apr 25. PubMed PMID: 24959278; PubMed Central PMCID: PMC4063656.

6: Cingolani F, Casasampere M, Sanllehí P, Casas J, Bujons J, Fabrias G. Inhibition of dihydroceramide desaturase activity by the sphingosine kinase inhibitor SKI II. J Lipid Res. 2014 May 29;55(8):1711-1720. [Epub ahead of print] PubMed PMID: 24875537; PubMed Central PMCID: PMC4109765.

7: Zhang CX, Liu H, Gong YY, He HW, Shao RG. [Inhibitions of SphK1 inhibitor SKI II on cell cycle progression and cell invasion of hepatoma HepG2 cells]. Yao Xue Xue Bao. 2014 Feb;49(2):204-8. Chinese. PubMed PMID: 24761610.

8: Mercado N, Kizawa Y, Ueda K, Xiong Y, Kimura G, Moses A, Curtis JM, Ito K, Barnes PJ. Activation of transcription factor Nrf2 signalling by the sphingosine kinase inhibitor SKI-II is mediated by the formation of Keap1 dimers. PLoS One. 2014 Feb 5;9(2):e88168. doi: 10.1371/journal.pone.0088168. eCollection 2014. Erratum in: PLoS One. 2014;9(5):e97208. PubMed PMID: 24505412; PubMed Central PMCID: PMC3914928.

9: Zhang C, He H, Zhang H, Yu D, Zhao W, Chen Y, Shao R. The blockage of Ras/ERK pathway augments the sensitivity of SphK1 inhibitor SKI II in human hepatoma HepG2 cells. Biochem Biophys Res Commun. 2013 Apr 26;434(1):35-41. doi: 10.1016/j.bbrc.2013.03.070. Epub 2013 Mar 29. PubMed PMID: 23545258.

10: Zhu ZA, Zhu ZQ, Cai HX, Liu Y. Reversion of multidrug resistance by SKI-II in SGC7901/DDP cells and exploration of underlying mechanisms. Asian Pac J Cancer Prev. 2012;13(2):625-31. PubMed PMID: 22524836.

11: Chiba Y, Takeuchi H, Sakai H, Misawa M. SKI-II, an inhibitor of sphingosine kinase, ameliorates antigen-induced bronchial smooth muscle hyperresponsiveness, but not airway inflammation, in mice. J Pharmacol Sci. 2010;114(3):304-10. Epub 2010 Oct 8. PubMed PMID: 20948165.

12: Ren S, Xin C, Pfeilschifter J, Huwiler A. A novel mode of action of the putative sphingosine kinase inhibitor 2-(p-hydroxyanilino)-4-(p-chlorophenyl) thiazole (SKI II): induction of lysosomal sphingosine kinase 1 degradation. Cell Physiol Biochem. 2010;26(1):97-104. doi: 10.1159/000315110. Epub 2010 May 18. PubMed PMID: 20502009.

13: Leroux ME, Auzenne E, Evans R, Hail N Jr, Spohn W, Ghosh SC, Farquhar D, McDonnell T, Klostergaard J. Sphingolipids and the sphingosine kinase inhibitor, SKI II, induce BCL-2-independent apoptosis in human prostatic adenocarcinoma cells. Prostate. 2007 Nov 1;67(15):1699-717. PubMed PMID: 17879964.