SKI 5C | CAS#120005-55-2

SKI 5C
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 341201

CAS#: 120005-55-2

Description: SKI 5C is a selective Sphingosine Kinase 1 (SPHK1) inhibitor.

Chemical Structure

SKI 5C

CAS# 120005-55-2

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 341201
Name: SKI 5C
CAS#: 120005-55-2
Chemical Formula: C26H45NO4
Exact Mass: 435.33
Molecular Weight: 435.650
Elemental Analysis: C, 71.68; H, 10.41; N, 3.22; O, 14.69

Price and Availability

Size	Price	Availability
1mg	USD 250	2 weeks
5mg	USD 475	2 weeks
10mg	USD 675	2 Weeks
25mg	USD 1100	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: SKI 5C; SKI-5C; SKI5C.

IUPAC/Chemical Name: (4S)-2,2-dimethyl-4-(1-oxo-2-hexadecyn-1-yl)-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester

InChi Key: YGBSGZPIDCXNEH-QFIPXVFZSA-N

InChi Code: InChI=1S/C26H45NO4/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(28)22-21-30-26(5,6)27(22)24(29)31-25(2,3)4/h22H,7-18,21H2,1-6H3/t22-/m0/s1

SMILES Code: O=C(OC(C)(C)C)N1C(C)(OC[C@H]1C(C#CCCCCCCCCCCCCC)=O)C

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, DMF, and ethanol

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:

Product Data:

Product Data

Instruction:

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Biological target:	SKI 5C is an inhibitor of sphingosine kinase 1 (SPHK1; IC50 = 3.3 μM). It is selective for SPHK1 over SPHK2 at 10 μM and PKC at concentrations less than 100 μM. SKI 5C inhibits SPHK1 activity by 70% in U937 cells when used at a concentration of 5 μM.
In vitro activity:	SKI 5C may act as new candidate drug for Wilms' tumor. Treatment with SKI-5C inhibited proliferation and induced apoptosis of SK-NEP-1 and G401 cells in a dose-dependent manner. SKI 5C-treated SK-NEP-1 cells mostly downregulated PRKACA and significantly inhibited phosphorylation of ERK1/2 and NF-κB p65, implying that SKI 5C induces apoptosis of SK-NEP-1 cells through the PRKACA/MAPK/NF-κB pathway. Reference: Am J Transl Res. 2016 Nov 15;8(11):4548-4563. https://pubmed.ncbi.nlm.nih.gov/27904661/
In vivo activity:	SKI 5C has potential in the treatment of endometriotic lesions. In mice, SKI 5C significantly inhibited the development and vascularization of peritoneal endometriotic lesions, when compared to vehicle-treated controls. Endometriotic lesions in dorsal skinfold chambers of SKI 5C-treated mice exhibited a significantly smaller lesion size, lower functional microvessel density, smaller microvessel diameters and a reduced blood perfusion of the newly developing microvascular networks. Reference: Br J Pharmacol. 2021 Oct;178(20):4104-4118. https://pubmed.ncbi.nlm.nih.gov/34185874/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	3.0	6.82
	DMSO	2.0	4.55
	Ethanol	2.5	5.69

Preparing Stock Solutions

The following data is based on the product molecular weight 435.65 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

Formulation protocol:	1. Li ZH, Tao YF, Xu LX, Zhao H, Li XL, Fang F, Wu Y, Lu J, Li YH, Du WW, Ren JL, Li YP, Xu YY, Feng X, Wang J, He WQ, Pan J. A novel sphingosine kinase 1 inhibitor (SKI-5C) induces cell death of Wilms' tumor cells in vitro and in vivo. Am J Transl Res. 2016 Nov 15;8(11):4548-4563. PMID: 27904661; PMCID: PMC5126303. 2. Datta A, Loo SY, Huang B, Wong L, Tan SS, Tan TZ, Lee SC, Thiery JP, Lim YC, Yong WP, Lam Y, Kumar AP, Yap CT. SPHK1 regulates proliferation and survival responses in triple-negative breast cancer. Oncotarget. 2014 Aug 15;5(15):5920-33. doi: 10.18632/oncotarget.1874. PMID: 25153718; PMCID: PMC4171602. 3. Rudzitis-Auth J, Christoffel A, Menger MD, Laschke MW. Targeting sphingosine kinase-1 with the low MW inhibitor SKI-5C suppresses the development of endometriotic lesions in mice. Br J Pharmacol. 2021 Oct;178(20):4104-4118. doi: 10.1111/bph.15601. Epub 2021 Jul 27. PMID: 34185874.
In vitro protocol:	1. Li ZH, Tao YF, Xu LX, Zhao H, Li XL, Fang F, Wu Y, Lu J, Li YH, Du WW, Ren JL, Li YP, Xu YY, Feng X, Wang J, He WQ, Pan J. A novel sphingosine kinase 1 inhibitor (SKI-5C) induces cell death of Wilms' tumor cells in vitro and in vivo. Am J Transl Res. 2016 Nov 15;8(11):4548-4563. PMID: 27904661; PMCID: PMC5126303. 2. Datta A, Loo SY, Huang B, Wong L, Tan SS, Tan TZ, Lee SC, Thiery JP, Lim YC, Yong WP, Lam Y, Kumar AP, Yap CT. SPHK1 regulates proliferation and survival responses in triple-negative breast cancer. Oncotarget. 2014 Aug 15;5(15):5920-33. doi: 10.18632/oncotarget.1874. PMID: 25153718; PMCID: PMC4171602.
In vivo protocol:	1. Rudzitis-Auth J, Christoffel A, Menger MD, Laschke MW. Targeting sphingosine kinase-1 with the low MW inhibitor SKI-5C suppresses the development of endometriotic lesions in mice. Br J Pharmacol. 2021 Oct;178(20):4104-4118. doi: 10.1111/bph.15601. Epub 2021 Jul 27. PMID: 34185874.

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1: Li ZH, Tao YF, Xu LX, Zhao H, Li XL, Fang F, Wu Y, Lu J, Li YH, Du WW, Ren JL, Li YP, Xu YY, Feng X, Wang J, He WQ, Pan J. A novel sphingosine kinase 1 inhibitor (SKI-5C) induces cell death of Wilms' tumor cells in vitro and in vivo. Am J Transl Res. 2016 Nov 15;8(11):4548-4563. eCollection 2016. PubMed PMID: 27904661; PubMed Central PMCID: PMC5126303.

2: Tian T, Tian W, Yang F, Zhao R, Huang Q, Zhao Y. Sphingosine kinase 1 inhibition improves lipopolysaccharide/D-galactosamine-induced acute liver failure by inhibiting mitogen-activated protein kinases pathway. United European Gastroenterol J. 2016 Oct;4(5):677-685. Epub 2016 Mar 2. PubMed PMID: 27733910; PubMed Central PMCID: PMC5042311.

3: Datta A, Loo SY, Huang B, Wong L, Tan SS, Tan TZ, Lee SC, Thiery JP, Lim YC, Yong WP, Lam Y, Kumar AP, Yap CT. SPHK1 regulates proliferation and survival responses in triple-negative breast cancer. Oncotarget. 2014 Aug 15;5(15):5920-33. PubMed PMID: 25153718; PubMed Central PMCID: PMC4171602.

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