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MedKoo Cat#: 401920 | Name: SL0101
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Description:

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

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.

Chemical Structure

SL0101
SL0101
CAS#77307-50-7

Theoretical Analysis

MedKoo Cat#: 401920

Name: SL0101

CAS#: 77307-50-7

Chemical Formula: C25H24O12

Exact Mass: 516.1268

Molecular Weight: 516.45

Elemental Analysis: C, 58.14; H, 4.68; O, 37.18

Price and Availability

Size Price Availability Quantity
1mg USD 400.00 2 Weeks
5mg USD 850.00 2 Weeks
10mg USD 1,150.00 2 Weeks
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Related CAS #
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Synonym
SL0101; SL0101; SL 0101; SL 0101-1; SL 0101 1; SL0101-1; SL0101 1
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
More Info
         
Product Data
Product Data
Instruction
View handling instruction
Biological target:
SL0101 is a selective RSK inhibitor (IC50 = 89 nM for RSK2). SL0101 does not inhibit upstream kinases such as MEK, Raf and PKC. SL0101 inhibits the growth of MCF-7 human breast cancer cells with no effect on the normal breast cell line.
In vitro activity:
SL0101 hinders the growth of the human breast cancer cell line MCF-7 by blocking the G(1) phase of the cell cycle; this effect is proportional to its inhibition of RSK. SL0101 does not impact the proliferation of normal human breast cells, despite inhibiting RSK in these cells. RSK is found to be overexpressed in around 50% of human breast cancer tissue samples, indicating a compromised regulation. Reference: Cancer Res. 2005 Feb 1;65(3):1027-34. https://pubmed.ncbi.nlm.nih.gov/15705904/
In vivo activity:
RSK plays a role in regulating light-induced adjustment of the internal circadian clock. When SL0101 is administered 30 minutes before light exposure during the early circadian night, it disrupts RSK signaling, resulting in a notable decrease in the light's ability to delay the circadian clock phase. Additionally, in slice cultures from a per1-Venus circadian reporter mouse line, chronic treatment with SL0101, suppressing RSK signaling, significantly extended the circadian period compared to vehicle-treated slices. Reference: Neuroscience. 2023 Apr 15;516:15-26. https://pubmed.ncbi.nlm.nih.gov/36796752/
Solvent mg/mL mM comments
Solubility
DMSO 5.2 10.00
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 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.

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. Roffé M, Lupinacci FC, Soares LC, Hajj GN, Martins VR. Two widely used RSK inhibitors, BI-D1870 and SL0101, alter mTORC1 signaling in a RSK-independent manner. Cell Signal. 2015 Aug;27(8):1630-42. doi: 10.1016/j.cellsig.2015.04.004. Epub 2015 Apr 16. PMID: 25889895. 2. 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. PMID: 15705904. 3. Hoyt KR, Li A, Yoon H, Weisenseel Z, Watkins J, Fischer A, Obrietan K. Ribosomal S6 Kinase Regulates the Timing and Entrainment of the Mammalian Circadian Clock Located in the Suprachiasmatic Nucleus. Neuroscience. 2023 Apr 15;516:15-26. doi: 10.1016/j.neuroscience.2023.02.003. Epub 2023 Feb 14. PMID: 36796752; PMCID: PMC10099606.
In vitro protocol:
1. Roffé M, Lupinacci FC, Soares LC, Hajj GN, Martins VR. Two widely used RSK inhibitors, BI-D1870 and SL0101, alter mTORC1 signaling in a RSK-independent manner. Cell Signal. 2015 Aug;27(8):1630-42. doi: 10.1016/j.cellsig.2015.04.004. Epub 2015 Apr 16. PMID: 25889895. 2. 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. PMID: 15705904.
In vivo protocol:
1. Hoyt KR, Li A, Yoon H, Weisenseel Z, Watkins J, Fischer A, Obrietan K. Ribosomal S6 Kinase Regulates the Timing and Entrainment of the Mammalian Circadian Clock Located in the Suprachiasmatic Nucleus. Neuroscience. 2023 Apr 15;516:15-26. doi: 10.1016/j.neuroscience.2023.02.003. Epub 2023 Feb 14. PMID: 36796752; PMCID: PMC10099606.
1: Wu T, Chen Z, Liu X, Wu X, Wang Z, Guo W. Targeting RSK2 in Cancer Therapy: A Review of Natural Products. Anticancer Agents Med Chem. 2024 Sep 6. doi: 10.2174/0118715206329546240830055233. Epub ahead of print. PMID: 39248063. 2: Hoyt KR, Horning P, Georgette Ang P, Karelina K, Obrietan K. Ribosomal S6 kinase signaling regulates neuronal viability during development and confers resistance to excitotoxic cell death in mature neurons. Neuroscience. 2024 Oct 18;558:1-10. doi: 10.1016/j.neuroscience.2024.08.012. Epub 2024 Aug 11. PMID: 39137868. 3: Wright EB, Lannigan DA. Therapeutic targeting of p90 ribosomal S6 kinase. Front Cell Dev Biol. 2023 Dec 19;11:1297292. doi: 10.3389/fcell.2023.1297292. PMID: 38169775; PMCID: PMC10758423. 4: Hoyt KR, Li A, Yoon H, Weisenseel Z, Watkins J, Fischer A, Obrietan K. Ribosomal S6 Kinase Regulates the Timing and Entrainment of the Mammalian Circadian Clock Located in the Suprachiasmatic Nucleus. Neuroscience. 2023 Apr 15;516:15-26. doi: 10.1016/j.neuroscience.2023.02.003. Epub 2023 Feb 14. PMID: 36796752; PMCID: PMC10099606. 5: Wright EB, Fukuda S, Li M, Li Y, O'Doherty GA, Lannigan DA. Identifying requirements for RSK2 specific inhibitors. J Enzyme Inhib Med Chem. 2021 Dec;36(1):1798-1809. doi: 10.1080/14756366.2021.1957862. PMID: 34348556; PMCID: PMC8344253. 6: Li Y, Seber P, Wright EB, Yasmin S, Lannigan DA, O'Doherty GA. The affinity of RSK for cylitol analogues of SL0101 is critically dependent on the B-ring C-4'-hydroxy. Chem Commun (Camb). 2020 Mar 10;56(20):3058-3060. doi: 10.1039/d0cc00128g. PMID: 32048692; PMCID: PMC7285658. 7: Li Y, Sandusky ZM, Vemula R, Zhang Q, Wu B, Fukuda S, Li M, Lannigan DA, O'Doherty GA. Regioselective Synthesis of a C-4'' Carbamate,C-6'' n-Pr Substituted Cyclitol Analogue of SL0101. Org Lett. 2020 Feb 21;22(4):1448-1452. doi: 10.1021/acs.orglett.0c00042. Epub 2020 Feb 3. PMID: 32009414; PMCID: PMC7292201. 8: Ding X, Krutzik PO, Ghaffari AA, Zhaozhi Y, Miranda D Jr, Cheng G, Ho CM, Nolan GP, Sanchez DJ. Cellular Signaling Analysis shows antiviral, ribavirin- mediated ribosomal signaling modulation. Antiviral Res. 2019 Nov;171:104598. doi: 10.1016/j.antiviral.2019.104598. Epub 2019 Sep 9. PMID: 31513822; PMCID: PMC7114107. 9: Stathopoulou K, Schobesberger S, Bork NI, Sprenger JU, Perera RK, Sotoud H, Geertz B, David JP, Christ T, Nikolaev VO, Cuello F. Divergent off-target effects of RSK N-terminal and C-terminal kinase inhibitors in cardiac myocytes. Cell Signal. 2019 Nov;63:109362. doi: 10.1016/j.cellsig.2019.109362. Epub 2019 Jul 22. PMID: 31344438. 10: Bao X, Hua Y, Keep RF, Xi G. Thrombin-induced tolerance against oxygen- glucose deprivation in astrocytes: role of protease-activated receptor-1. Cond Med. 2018 Feb;1(2):57-63. Epub 2018 Feb 15. PMID: 30123875; PMCID: PMC6097711. 11: Koizumi Y, Nagai K, Gao L, Koyota S, Yamaguchi T, Natsui M, Imai Y, Hasumi K, Sugiyama T, Kuba K. Involvement of RSK1 activation in malformin-enhanced cellular fibrinolytic activity. Sci Rep. 2018 Apr 3;8(1):5472. doi: 10.1038/s41598-018-23745-0. PMID: 29615689; PMCID: PMC5882963. 12: Pirbhoy PS, Farris S, Steward O. Synaptically driven phosphorylation of ribosomal protein S6 is differentially regulated at active synapses versus dendrites and cell bodies by MAPK and PI3K/mTOR signaling pathways. Learn Mem. 2017 Jul 17;24(8):341-357. doi: 10.1101/lm.044974.117. PMID: 28716954; PMCID: PMC5516686. 13: Li M, Li Y, Ludwik KA, Sandusky ZM, Lannigan DA, O'Doherty GA. Stereoselective Synthesis and Evaluation of C6″-Substituted 5a-Carbasugar Analogues of SL0101 as Inhibitors of RSK1/2. Org Lett. 2017 May 5;19(9):2410-2413. doi: 10.1021/acs.orglett.7b00945. Epub 2017 Apr 25. PMID: 28441024. 14: Gieseler-Halbach S, Meltendorf S, Pierau M, Weinert S, Heidel FH, Fischer T, Handschuh J, Braun-Dullaeus RC, Schrappe M, Lindquist JA, Mertens PR, Thomas U, Brunner-Weinzierl MC. RSK-mediated nuclear accumulation of the cold-shock Y-box protein-1 controls proliferation of T cells and T-ALL blasts. Cell Death Differ. 2017 Feb;24(2):371-383. doi: 10.1038/cdd.2016.141. Epub 2016 Dec 23. PMID: 28009354; PMCID: PMC5299718. 15: Ludwik KA, Campbell JP, Li M, Li Y, Sandusky ZM, Pasic L, Sowder ME, Brenin DR, Pietenpol JA, O'Doherty GA, Lannigan DA. Development of a RSK Inhibitor as a Novel Therapy for Triple-Negative Breast Cancer. Mol Cancer Ther. 2016 Nov;15(11):2598-2608. doi: 10.1158/1535-7163.MCT-16-0106. Epub 2016 Aug 15. PMID: 27528706; PMCID: PMC5807013. 16: Utepbergenov D, Hennig PM, Derewenda U, Artamonov MV, Somlyo AV, Derewenda ZS. Bacterial Expression, Purification and In Vitro Phosphorylation of Full- Length Ribosomal S6 Kinase 2 (RSK2). PLoS One. 2016 Oct 12;11(10):e0164343. doi: 10.1371/journal.pone.0164343. PMID: 27732676; PMCID: PMC5061434. 17: Ludwik KA, Lannigan DA. Ribosomal S6 kinase (RSK) modulators: a patent review. Expert Opin Ther Pat. 2016 Sep;26(9):1061-78. doi: 10.1080/13543776.2016.1212839. Epub 2016 Aug 1. PMID: 27410995. 18: Zhao H, Martin TA, Davies EL, Ruge F, Yu H, Zhang Y, Teng XU, Jiang WG. The Clinical Implications of RSK1-3 in Human Breast Cancer. Anticancer Res. 2016 Mar;36(3):1267-74. PMID: 26977024. 19: Roffé M, Lupinacci FC, Soares LC, Hajj GN, Martins VR. Two widely used RSK inhibitors, BI-D1870 and SL0101, alter mTORC1 signaling in a RSK-independent manner. Cell Signal. 2015 Aug;27(8):1630-42. doi: 10.1016/j.cellsig.2015.04.004. Epub 2015 Apr 16. PMID: 25889895. 20: Li M, Li Y, Mrozowski RM, Sandusky ZM, Shan M, Song X, Wu B, Zhang Q, Lannigan DA, O'Doherty GA. Synthesis and Structure-Activity Relationship Study of 5a-Carbasugar Analogues of SL0101. ACS Med Chem Lett. 2014 Nov 26;6(1):95-9. doi: 10.1021/ml5004525. PMID: 25589938; PMCID: PMC4291707.