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MedKoo Cat#: 585229 | Name: Splitomicin

Description:

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

Splitomicin is a cell-permeable lactone derived from naphthol and known to be a potent selective inhibitor of Sir2 (silent information regulator 2) and possesses an inhibitory effect on neutrophils.

Chemical Structure

Splitomicin
Splitomicin
CAS#4707-36-2

Theoretical Analysis

MedKoo Cat#: 585229

Name: Splitomicin

CAS#: 4707-36-2

Chemical Formula: C13H12O2

Exact Mass: 200.0837

Molecular Weight: 200.24

Elemental Analysis: C, 77.98; H, 6.04; O, 15.98

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Splitomicin
IUPAC/Chemical Name
1H-Naphtha(2,1-b)pyran-4-one, 2,3-dihydro-
InChi Key
UQEYDJJKWIEUTI-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H12O2/c14-15-9-3-6-12-11-5-2-1-4-10(11)7-8-13(12)15/h1-2,4-5,7-8H,3,6,9H2
SMILES Code
O=O1CCCC2=C3C=CC=CC3=CC=C21
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
Shelf Life
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 200.24 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
1: Liu FC, Day YJ, Liou JT, Yu HP, Liao HR. Splitomicin inhibits fMLP-induced superoxide anion production in human neutrophils by activate cAMP/PKA signaling inhibition of ERK pathway. Eur J Pharmacol. 2012 Aug 5;688(1-3):68-75. doi: 10.1016/j.ejphar.2012.05.006. Epub 2012 May 23. PubMed PMID: 22634165. 2: Posakony J, Hirao M, Stevens S, Simon JA, Bedalov A. Inhibitors of Sir2: evaluation of splitomicin analogues. J Med Chem. 2004 May 6;47(10):2635-44. PubMed PMID: 15115404. 3: Nadtochiy SM, Wang YT, Nehrke K, Munger J, Brookes PS. Cardioprotection by nicotinamide mononucleotide (NMN): Involvement of glycolysis and acidic pH. J Mol Cell Cardiol. 2018 Aug;121:155-162. doi: 10.1016/j.yjmcc.2018.06.007. Epub 2018 Jun 26. PubMed PMID: 29958828; PubMed Central PMCID: PMC6103815. 4: Freitag M, Schemies J, Larsen T, El Gaghlab K, Schulz F, Rumpf T, Jung M, Link A. Synthesis and biological activity of splitomicin analogs targeted at human NAD(+)-dependent histone deacetylases (sirtuins). Bioorg Med Chem. 2011 Jun 15;19(12):3669-77. doi: 10.1016/j.bmc.2011.01.026. Epub 2011 Jan 22. PubMed PMID: 21315612. 5: Villalba JM, Alcaín FJ. Sirtuin activators and inhibitors. Biofactors. 2012 Sep-Oct;38(5):349-59. doi: 10.1002/biof.1032. Epub 2012 Jun 25. Review. PubMed PMID: 22730114; PubMed Central PMCID: PMC3467333. 6: Liu FC, Liao CH, Chang YW, Liou JT, Day YJ. Splitomicin suppresses human platelet aggregation via inhibition of cyclic AMP phosphodiesterase and intracellular Ca++ release. Thromb Res. 2009 Jun;124(2):199-207. doi: 10.1016/j.thromres.2009.02.013. Epub 2009 Mar 26. PubMed PMID: 19327818. 7: Hori YS, Kuno A, Hosoda R, Horio Y. Regulation of FOXOs and p53 by SIRT1 modulators under oxidative stress. PLoS One. 2013 Sep 11;8(9):e73875. doi: 10.1371/journal.pone.0073875. eCollection 2013. PubMed PMID: 24040102; PubMed Central PMCID: PMC3770600. 8: Neugebauer RC, Uchiechowska U, Meier R, Hruby H, Valkov V, Verdin E, Sippl W, Jung M. Structure-activity studies on splitomicin derivatives as sirtuin inhibitors and computational prediction of binding mode. J Med Chem. 2008 Mar 13;51(5):1203-13. doi: 10.1021/jm700972e. Epub 2008 Feb 13. PubMed PMID: 18269226. 9: Charles S, Raj V, Arokiaraj J, Mala K. Caveolin1/protein arginine methyltransferase1/sirtuin1 axis as a potential target against endothelial dysfunction. Pharmacol Res. 2017 May;119:1-11. doi: 10.1016/j.phrs.2017.01.022. Epub 2017 Jan 23. Review. PubMed PMID: 28126510. 10: Iorio F, Shrestha RL, Levin N, Boilot V, Garnett MJ, Saez-Rodriguez J, Draviam VM. A Semi-Supervised Approach for Refining Transcriptional Signatures of Drug Response and Repositioning Predictions. PLoS One. 2015 Oct 9;10(10):e0139446. doi: 10.1371/journal.pone.0139446. eCollection 2015. PubMed PMID: 26452147; PubMed Central PMCID: PMC4599732. 11: Horio Y, Hisahara S, Sakamoto J. [Functional analysis of SIR2]. Nihon Yakurigaku Zasshi. 2003 Nov;122 Suppl:30P-32P. Japanese. PubMed PMID: 14727515. 12: Mitterberger MC, Zwerschke W. Mechanisms of resveratrol-induced inhibition of clonal expansion and terminal adipogenic differentiation in 3T3-L1 preadipocytes. J Gerontol A Biol Sci Med Sci. 2013 Nov;68(11):1356-76. doi: 10.1093/gerona/glt019. Epub 2013 Mar 22. PubMed PMID: 23525482. 13: Wang YH, Zheng GX, Li YJ. Giardia duodenalis GlSir2.2, homolog of SIRT1, is a nuclear-located and NAD(+)-dependent deacethylase. Exp Parasitol. 2016 Oct;169:28-33. doi: 10.1016/j.exppara.2016.07.002. Epub 2016 Jul 14. PubMed PMID: 27423969. 14: Kumari D, Usdin K. Polycomb group complexes are recruited to reactivated FMR1 alleles in Fragile X syndrome in response to FMR1 transcription. Hum Mol Genet. 2014 Dec 15;23(24):6575-83. doi: 10.1093/hmg/ddu378. Epub 2014 Jul 23. PubMed PMID: 25055869; PubMed Central PMCID: PMC4240206. 15: Hirao M, Posakony J, Nelson M, Hruby H, Jung M, Simon JA, Bedalov A. Identification of selective inhibitors of NAD+-dependent deacetylases using phenotypic screens in yeast. J Biol Chem. 2003 Dec 26;278(52):52773-82. Epub 2003 Oct 8. PubMed PMID: 14534292. 16: Denu JM. The Sir 2 family of protein deacetylases. Curr Opin Chem Biol. 2005 Oct;9(5):431-40. Review. PubMed PMID: 16122969. 17: Bedalov A, Gatbonton T, Irvine WP, Gottschling DE, Simon JA. Identification of a small molecule inhibitor of Sir2p. Proc Natl Acad Sci U S A. 2001 Dec 18;98(26):15113-8. PubMed PMID: 11752457; PubMed Central PMCID: PMC64992. 18: Stavrou EX, Fang C, Merkulova A, Alhalabi O, Grobe N, Antoniak S, Mackman N, Schmaier AH. Reduced thrombosis in Klkb1-/- mice is mediated by increased Mas receptor, prostacyclin, Sirt1, and KLF4 and decreased tissue factor. Blood. 2015 Jan 22;125(4):710-9. doi: 10.1182/blood-2014-01-550285. Epub 2014 Oct 22. PubMed PMID: 25339356; PubMed Central PMCID: PMC4304115. 19: Schemies J, Sippl W, Jung M. Histone deacetylase inhibitors that target tubulin. Cancer Lett. 2009 Aug 8;280(2):222-32. doi: 10.1016/j.canlet.2009.01.040. Epub 2009 Mar 5. Review. PubMed PMID: 19268440. 20: Pontiki E, Hadjipavlou-Litina D. Histone deacetylase inhibitors (HDACIs). Structure--activity relationships: history and new QSAR perspectives. Med Res Rev. 2012 Jan;32(1):1-165. doi: 10.1002/med.20200. Epub 2010 Feb 16. Review. PubMed PMID: 20162725.