Synonym
SK-216; SK 216; SK216.Plasminogen activator inhibitor-1 (PAI-1) inhibitor.
IUPAC/Chemical Name
2-[5-[[6-[5-(1,1-Dimethylethyl)-2-benzoxazolyl]-2-naphthalenyl]oxy]pentyl]propanedioic acid disodium salt
InChi Key
YYTGMMYYLGKWIK-UHFFFAOYSA-L
InChi Code
InChI=1S/C29H31NO6.2Na/c1-29(2,3)21-11-13-25-24(17-21)30-26(36-25)20-9-8-19-16-22(12-10-18(19)15-20)35-14-6-4-5-7-23(27(31)32)28(33)34;;/h8-13,15-17,23H,4-7,14H2,1-3H3,(H,31,32)(H,33,34);;/q;2*+1/p-2
SMILES Code
O=C([O-])C(CCCCCOC1=CC=C2C=C(C3=NC4=CC(C(C)(C)C)=CC=C4O3)C=CC2=C1)C([O-])=O.[Na+].[Na+]
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 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
More Info
lasminogen activator inhibitor-1 (PAI-1), which can be produced by host and tumor cells in the tumor microenvironment, is intimately involved in tumor progression.
Biological target:
SK-216 reduced the extent of angiogenesis in the tumors and inhibited VEGF-induced migration and tube formation by human umbilical vein endothelial cells in vitro. SK-216 reduced the degree of bleomycin-induced pulmonary fibrosis in mice. Targeting PAI-1 as a downstream effector of TGF-β could be a promising therapeutic strategy for pulmonary fibrosis.
In vitro activity:
SK-216 may be a novel drug to prevent lung metastasis in human osteosarcoma. SK-216 treatment suppressed invasion activity by inhibiting PAI-1 expression in 143B cells, but had no influence on their proliferation or migration. 143B cells treated with SK-216 exhibited reduced matrix metalloproteinase-13 (MMP-13) secretion in a dose-dependent manner.
Reference: Int J Mol Sci. 2018 Mar 5;19(3):736. https://pubmed.ncbi.nlm.nih.gov/29510576/
In vivo activity:
PAI-1 inactivation by SK-216 may represent a general strategy for inhibiting angiogenesis, including for the treatment of malignant pleural mesothelioma (MPM). In a mouse model of MPM, SK-216 reduced tumor weights and the degree of angiogenesis in intrapleural tumors, irrespective of their angiogenic expression profiles. Also, a combination of SK-216 and cisplatin significantly reduced tumor weights compared with monotherapy, prolonging the survival of mice compared with cisplatin treatment alone.
Reference: Cancer Res. 2016 Jun 1;76(11):3285-94. https://pubmed.ncbi.nlm.nih.gov/27197170/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| Water |
2.7 |
5.00 |
|
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
533.53
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. Tsuge M, Osaki M, Sasaki R, Hirahata M, Okada F. SK-216, a Novel Inhibitor of Plasminogen Activator Inhibitor-1, Suppresses Lung Metastasis of Human Osteosarcoma. Int J Mol Sci. 2018 Mar 5;19(3):736. doi: 10.3390/ijms19030736. PMID: 29510576; PMCID: PMC5877597.
2. Omori K, Hattori N, Senoo T, Takayama Y, Masuda T, Nakashima T, Iwamoto H, Fujitaka K, Hamada H, Kohno N. Inhibition of Plasminogen Activator Inhibitor-1 Attenuates Transforming Growth Factor-β-Dependent Epithelial Mesenchymal Transition and Differentiation of Fibroblasts to Myofibroblasts. PLoS One. 2016 Feb 9;11(2):e0148969. doi: 10.1371/journal.pone.0148969. PMID: 26859294; PMCID: PMC4747467.
3. Masuda T, Hattori N, Senoo T, Akita S, Ishikawa N, Fujitaka K, Haruta Y, Murai H, Kohno N. SK-216, an inhibitor of plasminogen activator inhibitor-1, limits tumor progression and angiogenesis. Mol Cancer Ther. 2013 Nov;12(11):2378-88. doi: 10.1158/1535-7163.MCT-13-0041. Epub 2013 Aug 29. PMID: 23990114.
4. Takayama Y, Hattori N, Hamada H, Masuda T, Omori K, Akita S, Iwamoto H, Fujitaka K, Kohno N. Inhibition of PAI-1 Limits Tumor Angiogenesis Regardless of Angiogenic Stimuli in Malignant Pleural Mesothelioma. Cancer Res. 2016 Jun 1;76(11):3285-94. doi: 10.1158/0008-5472.CAN-15-1796. Epub 2016 Apr 13. PMID: 27197170.
In vitro protocol:
1. Tsuge M, Osaki M, Sasaki R, Hirahata M, Okada F. SK-216, a Novel Inhibitor of Plasminogen Activator Inhibitor-1, Suppresses Lung Metastasis of Human Osteosarcoma. Int J Mol Sci. 2018 Mar 5;19(3):736. doi: 10.3390/ijms19030736. PMID: 29510576; PMCID: PMC5877597.
2. Omori K, Hattori N, Senoo T, Takayama Y, Masuda T, Nakashima T, Iwamoto H, Fujitaka K, Hamada H, Kohno N. Inhibition of Plasminogen Activator Inhibitor-1 Attenuates Transforming Growth Factor-β-Dependent Epithelial Mesenchymal Transition and Differentiation of Fibroblasts to Myofibroblasts. PLoS One. 2016 Feb 9;11(2):e0148969. doi: 10.1371/journal.pone.0148969. PMID: 26859294; PMCID: PMC4747467.
In vivo protocol:
1. Masuda T, Hattori N, Senoo T, Akita S, Ishikawa N, Fujitaka K, Haruta Y, Murai H, Kohno N. SK-216, an inhibitor of plasminogen activator inhibitor-1, limits tumor progression and angiogenesis. Mol Cancer Ther. 2013 Nov;12(11):2378-88. doi: 10.1158/1535-7163.MCT-13-0041. Epub 2013 Aug 29. PMID: 23990114.
2. Takayama Y, Hattori N, Hamada H, Masuda T, Omori K, Akita S, Iwamoto H, Fujitaka K, Kohno N. Inhibition of PAI-1 Limits Tumor Angiogenesis Regardless of Angiogenic Stimuli in Malignant Pleural Mesothelioma. Cancer Res. 2016 Jun 1;76(11):3285-94. doi: 10.1158/0008-5472.CAN-15-1796. Epub 2016 Apr 13. PMID: 27197170.
1: Takayama Y, Hattori N, Hamada H, Masuda T, Omori K, Akita S, Iwamoto H,
Fujitaka K, Kohno N. Inhibition of PAI-1 Limits Tumor Angiogenesis Regardless of
Angiogenic Stimuli in Malignant Pleural Mesothelioma. Cancer Res. 2016 Jun
1;76(11):3285-94. doi: 10.1158/0008-5472.CAN-15-1796. Epub 2016 Apr 13. PubMed
PMID: 27197170.
2: Omori K, Hattori N, Senoo T, Takayama Y, Masuda T, Nakashima T, Iwamoto H,
Fujitaka K, Hamada H, Kohno N. Inhibition of Plasminogen Activator Inhibitor-1
Attenuates Transforming Growth Factor-β-Dependent Epithelial Mesenchymal
Transition and Differentiation of Fibroblasts to Myofibroblasts. PLoS One. 2016
Feb 9;11(2):e0148969. doi: 10.1371/journal.pone.0148969. eCollection 2016. PubMed
PMID: 26859294; PubMed Central PMCID: PMC4747467.
3: Masuda T, Hattori N, Senoo T, Akita S, Ishikawa N, Fujitaka K, Haruta Y, Murai
H, Kohno N. SK-216, an inhibitor of plasminogen activator inhibitor-1, limits
tumor progression and angiogenesis. Mol Cancer Ther. 2013 Nov;12(11):2378-88.
doi: 10.1158/1535-7163.MCT-13-0041. Epub 2013 Aug 29. PubMed PMID: 23990114.
4: Mutoh M, Niho N, Komiya M, Takahashi M, Ohtsubo R, Nakatogawa K, Ueda K,
Sugimura T, Wakabayashi K. Plasminogen activator inhibitor-1 (Pai-1) blockers
suppress intestinal polyp formation in Min mice. Carcinogenesis. 2008
Apr;29(4):824-9. doi: 10.1093/carcin/bgn028. Epub 2008 Feb 6. PubMed PMID:
18258607.
5:Tsuge M, Osaki M, Sasaki R, Hirahata M, Okada F. SK-216, a Novel Inhibitor of Plasminogen Activator Inhibitor-1, Suppresses Lung Metastasis of Human Osteosarcoma. Int J Mol Sci. 2018 Mar 5;19(3):736. doi: 10.3390/ijms19030736. PMID: 29510576; PMCID: PMC5877597.
