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MedKoo Cat#: 341201 | Name: SKI 5C
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Description:

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

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

Chemical Structure

SKI 5C
SKI 5C
CAS#120005-55-2

Theoretical Analysis

MedKoo Cat#: 341201

Name: SKI 5C

CAS#: 120005-55-2

Chemical Formula: C26H45NO4

Exact Mass: 435.3349

Molecular Weight: 435.65

Elemental Analysis: C, 71.68; H, 10.41; N, 3.22; O, 14.69

Price and Availability

Size Price Availability Quantity
1mg USD 300.00 2 weeks
5mg USD 550.00 2 weeks
10mg USD 750.00 2 Weeks
25mg USD 1,150.00 2 Weeks
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Related CAS #
No Data
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
View handling instruction
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/
Solvent mg/mL mM comments
Solubility
DMF 3.0 6.82
DMSO 2.0 4.55
Ethanol 2.5 5.69
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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
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.
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. 2: Sun D, Wang S. Sphingosine kinases are involved in the regulation of all- trans retinoic acid sensitivity of K562 chronic myeloid leukemia cells. Oncol Lett. 2021 Aug;22(2):581. doi: 10.3892/ol.2021.12842. Epub 2021 Jun 2. PMID: 34122632; PMCID: PMC8190775. 3: 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. 4: 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. doi: 10.1177/2050640616637968. Epub 2016 Mar 2. PMID: 27733910; PMCID: PMC5042311. 5: 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.