Spiruchostatin A | OBP-801 | YM-753 | CAS#328548-11-4 | Histone Deacetylase Inhibitor

MedKoo Cat#: 527402 | Name: Spiruchostatin A

Description:

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

Spiruchostatin A, also known as OBP-801 and YM-753, is a histone deacetylase (HDAC) inhibitor potentially for the treatment of solid tumors. When the U937 cells were treated with SP-A, evidence of apoptotic features, including increase in DNA fragmentation and changes in nuclear morphology, were obtained. Spiruchostatin A-induced acetylation of specific lysine residues within histones H3 and H4, and increased the expression of p21(cip1/waf1), but did not induce acetylation of alpha-tubulin.

Chemical Structure

Spiruchostatin A

CAS#328548-11-4

Theoretical Analysis

MedKoo Cat#: 527402

Name: Spiruchostatin A

CAS#: 328548-11-4

Chemical Formula: C20H31N3O6S2

Exact Mass: 473.1654

Molecular Weight: 473.60

Elemental Analysis: C, 50.72; H, 6.60; N, 8.87; O, 20.27; S, 13.54

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Spiruchostatin A; SpiruchostatinA; Spiruchostatin-A; OBP-801; OBP 801; OBP801; YM-753; YM 753; YM753

IUPAC/Chemical Name

(1S,5S,6R,9S,20R,E)-5-hydroxy-6-isopropyl-20-methyl-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docos-15-ene-3,8,18,21-tetraone

InChi Key

XFLBOEMFLGLWFF-HDXRNPEWSA-N

InChi Code

InChI=1S/C20H31N3O6S2/c1-11(2)18-15(24)9-17(26)29-13-6-4-5-7-30-31-10-14(20(28)23-18)22-19(27)12(3)21-16(25)8-13/h4,6,11-15,18,24H,5,7-10H2,1-3H3,(H,21,25)(H,22,27)(H,23,28)/b6-4+/t12-,13-,14-,15+,18-/m1/s1

SMILES Code

O=C1C[C@H](O2)/C=C/CCSSC[C@@H](NC([C@@H](C)N1)=O)C(N[C@H](C(C)C)[C@@H](O)CC2=O)=O

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

>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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 473.60 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: Rehman MU, Jawaid P, Yoshihisa Y, Li P, Zhao QL, Narita K, Katoh T, Kondo T, Shimizu T. Spiruchostatin A and B, novel histone deacetylase inhibitors, induce apoptosis through reactive oxygen species-mitochondria pathway in human lymphoma U937 cells. Chem Biol Interact. 2014 Sep 25;221:24-34. doi: 10.1016/j.cbi.2014.07.004. PubMed PMID: 25078973. 2: Crabb SJ, Howell M, Rogers H, Ishfaq M, Yurek-George A, Carey K, Pickering BM, East P, Mitter R, Maeda S, Johnson PW, Townsend P, Shin-ya K, Yoshida M, Ganesan A, Packham G. Characterisation of the in vitro activity of the depsipeptide histone deacetylase inhibitor spiruchostatin A. Biochem Pharmacol. 2008 Aug 15;76(4):463-75. doi: 10.1016/j.bcp.2008.06.004. PubMed PMID: 18611394. 3: Potharla VY, Wang C, Cheng YQ. Identification and characterization of the spiruchostatin biosynthetic gene cluster enable yield improvement by overexpressing a transcriptional activator. J Ind Microbiol Biotechnol. 2014 Sep;41(9):1457-65. doi: 10.1007/s10295-014-1474-8. PubMed PMID: 24973954; PubMed Central PMCID: PMC4134368. 4: Narita K, Kikuchi T, Watanabe K, Takizawa T, Oguchi T, Kudo K, Matsuhara K, Abe H, Yamori T, Yoshida M, Katoh T. Total synthesis of the bicyclic depsipeptide HDAC inhibitors spiruchostatins A and B, 5''-epi-spiruchostatin B, FK228 (FR901228) and preliminary evaluation of their biological activity. Chemistry. 2009 Oct 26;15(42):11174-86. doi: 10.1002/chem.200901552. PubMed PMID: 19760730. 5: Rehman MU, Jawaid P, Zhao QL, Li P, Narita K, Katoh T, Shimizu T, Kondo T. Low-dose spiruchostatin-B, a potent histone deacetylase inhibitor enhances radiation-induced apoptosis in human lymphoma U937 cells via modulation of redox signaling. Free Radic Res. 2016 Jun;50(6):596-610. doi: 10.3109/10715762.2015.1115029. PubMed PMID: 27108737. 6: Kanno S, Maeda N, Tomizawa A, Yomogida S, Katoh T, Ishikawa M. Characterization of cells resistant to the potent histone deacetylase inhibitor spiruchostatin B (SP-B) and effect of overexpressed p21waf1/cip1 on the SP-B resistance or susceptibility of human leukemia cells. Int J Oncol. 2012 Sep;41(3):862-8. doi: 10.3892/ijo.2012.1507. PubMed PMID: 22684370; PubMed Central PMCID: PMC3582725. 7: Davies ER, Haitchi HM, Thatcher TH, Sime PJ, Kottmann RM, Ganesan A, Packham G, O'Reilly KM, Davies DE. Spiruchostatin A inhibits proliferation and differentiation of fibroblasts from patients with pulmonary fibrosis. Am J Respir Cell Mol Biol. 2012 May;46(5):687-94. doi: 10.1165/rcmb.2011-0040OC. PubMed PMID: 22246864; PubMed Central PMCID: PMC4854311. 8: Kanno S, Maeda N, Tomizawa A, Yomogida S, Katoh T, Ishikawa M. Involvement of p21waf1/cip1 expression in the cytotoxicity of the potent histone deacetylase inhibitor spiruchostatin B towards susceptible NALM-6 human B cell leukemia cells. Int J Oncol. 2012 May;40(5):1391-6. doi: 10.3892/ijo.2011.1323. PubMed PMID: 22211246. 9: Fuse S, Okada K, Iijima Y, Munakata A, Machida K, Takahashi T, Takagi M, Shin-ya K, Doi T. Total synthesis of spiruchostatin B aided by an automated synthesizer. Org Biomol Chem. 2011 May 21;9(10):3825-33. doi: 10.1039/c0ob01169j. PubMed PMID: 21445425. 10: Calandra NA, Cheng YL, Kocak KA, Miller JS. Total synthesis of Spiruchostatin A via chemoselective macrocyclization using an accessible enantiomerically pure latent thioester. Org Lett. 2009 May 7;11(9):1971-4. doi: 10.1021/ol900436f. PubMed PMID: 19331423. 11: Takizawa T, Watanabe K, Narita K, Oguchi T, Abe H, Katoh T. Total synthesis of spiruchostatin B, a potent histone deacetylase inhibitor, from a microorganism. Chem Commun (Camb). 2008 Apr 14;(14):1677-9. doi: 10.1039/b718310k. PubMed PMID: 18368162. 12: Yurek-George A, Habens F, Brimmell M, Packham G, Ganesan A. Total synthesis of spiruchostatin A, a potent histone deacetylase inhibitor. J Am Chem Soc. 2004 Feb 4;126(4):1030-1. PubMed PMID: 14746465. 13: Klausmeyer P, Shipley SM, Zuck KM, McCloud TG. Histone deacetylase inhibitors from Burkholderia thailandensis. J Nat Prod. 2011 Oct 28;74(10):2039-44. doi: 10.1021/np200532d. PubMed PMID: 21967146; PubMed Central PMCID: PMC3204006. 14: Davidson SM, Townsend PA, Carroll C, Yurek-George A, Balasubramanyam K, Kundu TK, Stephanou A, Packham G, Ganesan A, Latchman DS. The transcriptional coactivator p300 plays a critical role in the hypertrophic and protective pathways induced by phenylephrine in cardiac cells but is specific to the hypertrophic effect of urocortin. Chembiochem. 2005 Jan;6(1):162-70. PubMed PMID: 15593114. 15: Narita K, Fukui Y, Sano Y, Yamori T, Ito A, Yoshida M, Katoh T. Total synthesis of bicyclic depsipeptides spiruchostatins C and D and investigation of their histone deacetylase inhibitory and antiproliferative activities. Eur J Med Chem. 2013 Feb;60:295-304. doi: 10.1016/j.ejmech.2012.12.023. PubMed PMID: 23313638.