WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 401920
CAS#: 77307-50-7
Description: SL0101 is a highly specific RSK inhibitor. SL0101 showed improved in vitro biological stability while maintaining specificity for RSK. These results should facilitate the development of RSK inhibitors derived from SL0101 as anticancer agents.
MedKoo Cat#: 401920
Name: SL0101
CAS#: 77307-50-7
Chemical Formula: C25H24O12
Exact Mass: 516.12678
Molecular Weight: 516.45
Elemental Analysis: C, 58.14; H, 4.68; O, 37.18
Synonym: SL0101; SL0101; SL 0101.
IUPAC/Chemical Name: (2S,3S,4S,5R,6S)-6-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-5-hydroxy-2-methyltetrahydro-2H-pyran-3,4-diyl diacetate
InChi Key: SXOZSDJHGMAEGZ-IGKKHSBFSA-N
InChi Code: InChI=1S/C25H24O12/c1-10-21(34-11(2)26)24(35-12(3)27)20(32)25(33-10)37-23-19(31)18-16(30)8-15(29)9-17(18)36-22(23)13-4-6-14(28)7-5-13/h4-10,20-21,24-25,28-30,32H,1-3H3/t10-,20+,21-,24-,25-/m0/s1
SMILES Code: C[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H](O)[C@H](OC2=C(C3=CC=C(O)C=C3)OC4=C(C(O)=CC(O)=C4)C2=O)O1
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: >5 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
The following data is based on the product molecular weight 516.45 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 |
1: Stratford AL, Reipas K, Hu K, Fotovati A, Brough R, Frankum J, Takhar M, Watson P, Ashworth A, Lord CJ, Lasham A, Print CG, Dunn SE. Targeting p90 Ribosomal S6 Kinase Eliminates Tumor-Initiating Cells by Inactivating Y-Box Binding Protein-1 in Triple-Negative Breast Cancers. Stem Cells. 2012 Jul;30(7):1338-48. doi: 10.1002/stem.1128. PubMed PMID: 22674792.
2: Hilinski MK, Mrozowski RM, Clark DE, Lannigan DA. Analogs of the RSK inhibitor SL0101: optimization of in vitro biological stability. Bioorg Med Chem Lett. 2012 May 1;22(9):3244-7. Epub 2012 Mar 13. PubMed PMID: 22464132; PubMed Central PMCID: PMC3331937.
3: Li T, Liu Z, Hu X, Ma K, Zhou C. Involvement of ERK-RSK cascade in phenylephrine-induced phosphorylation of GATA4. Biochim Biophys Acta. 2012 Feb;1823(2):582-92. Epub 2011 Dec 29. PubMed PMID: 22227582.
4: Lin JT, Stein EA, Wong MT, Kalpathy KJ, Su LL, Utz PJ, Robinson WH, Fathman CG. Differential mTOR and ERK pathway utilization by effector CD4 T cells suggests combinatorial drug therapy of arthritis. Clin Immunol. 2012 Feb;142(2):127-38. Epub 2011 Oct 1. PubMed PMID: 22075384; PubMed Central PMCID: PMC3273543.
5: Ma Q, Guin S, Padhye SS, Zhou YQ, Zhang RW, Wang MH. Ribosomal protein S6 kinase (RSK)-2 as a central effector molecule in RON receptor tyrosine kinase mediated epithelial to mesenchymal transition induced by macrophage-stimulating protein. Mol Cancer. 2011 May 28;10:66. PubMed PMID: 21619683; PubMed Central PMCID: PMC3117816.
6: Shan M, O'Doherty GA. Synthesis of SL0101 carbasugar analogues: carbasugars via Pd-catalyzed cyclitolization and post-cyclitolization transformations. Org Lett. 2010 Jul 2;12(13):2986-9. PubMed PMID: 20518547; PubMed Central PMCID: PMC2892554.
7: Harada K, Fukuda E, Hirohashi N, Chiba K. Regulation of intracellular pH by p90Rsk-dependent activation of an Na(+)/H(+) exchanger in starfish oocytes. J Biol Chem. 2010 Jul 30;285(31):24044-54. Epub 2010 May 27. PubMed PMID: 20507995; PubMed Central PMCID: PMC2911288.
8: Mauvoisin D, Prévost M, Ducheix S, Arnaud MP, Mounier C. Key role of the ERK1/2 MAPK pathway in the transcriptional regulation of the Stearoyl-CoA Desaturase (SCD1) gene expression in response to leptin. Mol Cell Endocrinol. 2010 May 5;319(1-2):116-28. Epub 2010 Jan 28. PubMed PMID: 20109524.
9: Chen S, Mackintosh C. Differential regulation of NHE1 phosphorylation and glucose uptake by inhibitors of the ERK pathway and p90RSK in 3T3-L1 adipocytes. Cell Signal. 2009 Dec;21(12):1984-93. Epub 2009 Sep 15. PubMed PMID: 19765648.
10: Stratford AL, Fry CJ, Desilets C, Davies AH, Cho YY, Li Y, Dong Z, Berquin IM, Roux PP, Dunn SE. Y-box binding protein-1 serine 102 is a downstream target of p90 ribosomal S6 kinase in basal-like breast cancer cells. Breast Cancer Res. 2008;10(6):R99. Epub 2008 Nov 27. PubMed PMID: 19036157; PubMed Central PMCID: PMC2656895.
11: Flynn JM, Lannigan DA, Clark DE, Garner MH, Cammarata PR. RNA suppression of ERK2 leads to collapse of mitochondrial membrane potential with acute oxidative stress in human lens epithelial cells. Am J Physiol Endocrinol Metab. 2008 Mar;294(3):E589-99. Epub 2008 Jan 2. PubMed PMID: 18171912.
12: Bain J, Plater L, Elliott M, Shpiro N, Hastie CJ, McLauchlan H, Klevernic I, Arthur JS, Alessi DR, Cohen P. The selectivity of protein kinase inhibitors: a further update. Biochem J. 2007 Dec 15;408(3):297-315. PubMed PMID: 17850214; PubMed Central PMCID: PMC2267365.
13: Smith JA, Maloney DJ, Hecht SM, Lannigan DA. Structural basis for the activity of the RSK-specific inhibitor, SL0101. Bioorg Med Chem. 2007 Jul 15;15(14):5018-34. Epub 2007 Apr 2. PubMed PMID: 17512736.
14: Shan M, O'Doherty GA. De novo asymmetric syntheses of SL0101 and its analogues via a palladium-catalyzed glycosylation. Org Lett. 2006 Oct 26;8(22):5149-52. PubMed PMID: 17048865; PubMed Central PMCID: PMC2529254.
15: Godeny MD, Sayeski PP. ERK1/2 regulates ANG II-dependent cell proliferation via cytoplasmic activation of RSK2 and nuclear activation of elk1. Am J Physiol Cell Physiol. 2006 Dec;291(6):C1308-17. Epub 2006 May 24. PubMed PMID: 16723511.
16: Nguyen TL, Gussio R, Smith JA, Lannigan DA, Hecht SM, Scudiero DA, Shoemaker RH, Zaharevitz DW. Homology model of RSK2 N-terminal kinase domain, structure-based identification of novel RSK2 inhibitors, and preliminary common pharmacophore. Bioorg Med Chem. 2006 Sep 1;14(17):6097-105. Epub 2006 May 24. PubMed PMID: 16723234.
17: Smith JA, Maloney DJ, Clark DE, Xu Y, Hecht SM, Lannigan DA. Influence of rhamnose substituents on the potency of SL0101, an inhibitor of the Ser/Thr kinase, RSK. Bioorg Med Chem. 2006 Sep 1;14(17):6034-42. Epub 2006 May 24. PubMed PMID: 16723233.
18: Clark DE, Errington TM, Smith JA, Frierson HF Jr, Weber MJ, Lannigan DA. The serine/threonine protein kinase, p90 ribosomal S6 kinase, is an important regulator of prostate cancer cell proliferation. Cancer Res. 2005 Apr 15;65(8):3108-16. PubMed PMID: 15833840.
19: Maloney DJ, Hecht SM. Synthesis of a potent and selective inhibitor of p90 Rsk. Org Lett. 2005 Mar 17;7(6):1097-9. Erratum in: Org Lett. 2006 Apr 13;8(8):1749. PubMed PMID: 15760148.
20: Smith JA, Poteet-Smith CE, Xu Y, Errington TM, Hecht SM, Lannigan DA. Identification of the first specific inhibitor of p90 ribosomal S6 kinase (RSK) reveals an unexpected role for RSK in cancer cell proliferation. Cancer Res. 2005 Feb 1;65(3):1027-34. PubMed PMID: 15705904.
