Spliceostatin A | CAS#391611-36-2 | potent splicing inhibitor

MedKoo Cat#: 333084 | Name: Spliceostatin A

Description:

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

Spliceostatin A is a potent splicing inhibitor. Spliceostatin A (SSA) causes cell cycle arrest at G1 and G2/M phases. Spliceostatin A treatment inhibits mitotic clonal expansion and adipogenesis. Spliceostatin A interaction with SF3B limits U1 snRNP availability and causes premature cleavage and polyadenylation. Spliceostatin A binds to the SF3B subcomplex of the U2 small nuclear ribonucleoprotein particle (snRNP), limits U1 snRNP availability in splicing, resulting in premature cleavage and polyadenylation of MALAT1, a nuclear lncRNA, as well as protein-coding mRNAs. Therefore, truncated transcripts are exported into the cytoplasm and translated, resulting in aberrant protein products.

Chemical Structure

Spliceostatin A

CAS#391611-36-2

Theoretical Analysis

MedKoo Cat#: 333084

Name: Spliceostatin A

CAS#: 391611-36-2

Chemical Formula: C28H43NO8

Exact Mass: 521.2989

Molecular Weight: 521.65

Elemental Analysis: C, 64.47; H, 8.31; N, 2.69; O, 24.54

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 3,950.00	2 Weeks

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Related CAS #

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Synonym

Spliceostatin A; Spliceostatin-A;

IUPAC/Chemical Name

(2Z,4S)-4-(Acetyloxy)-N-[(2R,3R,5S,6S)-tetrahydro-6-[(2E,4E)-5-[(3R,4R,5R,7S)-4-hydroxy-7-methoxy-7-methyl-1,6-dioxaspiro[2.5]oct-5-yl]-3-methyl-2,4-pentadien-1-yl]-2,5-dimethyl-2H-pyran-3-yl]-2-pentenamide

InChi Key

XKSGIJNRMWHQIQ-CGPJBNNXSA-N

InChi Code

InChI=1S/C28H43NO8/c1-17(9-12-24-26(32)28(16-34-28)15-27(6,33-7)37-24)8-11-23-18(2)14-22(20(4)36-23)29-25(31)13-10-19(3)35-21(5)30/h8-10,12-13,18-20,22-24,26,32H,11,14-16H2,1-7H3,(H,29,31)/b12-9+,13-10-,17-8+/t18-,19-,20+,22+,23-,24+,26+,27-,28+/m0/s1

SMILES Code

C[C@H](OC(C)=O)/C=C\C(N[C@H]1[C@@H](C)O[C@@H](C/C=C(C)/C=C/[C@@H](O[C@](C)(OC)C2)[C@@H](O)[C@@]32CO3)[C@@H](C)C1)=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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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 521.65 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: Kaida D, Shida K. Spliceostatin A stabilizes CDKN1B mRNA through the 3' UTR. Biochem Biophys Res Commun. 2022 Mar 29;608:39-44. doi: 10.1016/j.bbrc.2022.03.085. Epub ahead of print. PMID: 35381427. 2: Kikuchi K, Kaida D. CCNE1 and E2F1 Partially Suppress G1 Phase Arrest Caused by Spliceostatin A Treatment. Int J Mol Sci. 2021 Oct 27;22(21):11623. doi: 10.3390/ijms222111623. PMID: 34769053; PMCID: PMC8584075. 3: Yoshimoto R, Chhipi-Shrestha JK, Schneider-Poetsch T, Furuno M, Burroughs AM, Noma S, Suzuki H, Hayashizaki Y, Mayeda A, Nakagawa S, Kaida D, Iwasaki S, Yoshida M. Spliceostatin A interaction with SF3B limits U1 snRNP availability and causes premature cleavage and polyadenylation. Cell Chem Biol. 2021 Sep 16;28(9):1356-1365.e4. doi: 10.1016/j.chembiol.2021.03.002. Epub 2021 Mar 29. PMID: 33784500. 4: Yoshikawa Y, Ishibashi A, Takehara T, Suzuki T, Murai K, Kaneda Y, Nimura K, Arisawa M. Design and Synthesis of 1,2-Deoxy-pyranose Derivatives of Spliceostatin A toward Prostate Cancer Treatment. ACS Med Chem Lett. 2020 May 1;11(6):1310-1315. doi: 10.1021/acsmedchemlett.0c00153. PMID: 32551017; PMCID: PMC7294732. 5: Kaida D. Spliceostatin A treatment inhibits mitotic clonal expansion and adipogenesis. Biochem Biophys Res Commun. 2019 Jun 30;514(3):848-852. doi: 10.1016/j.bbrc.2019.04.180. Epub 2019 May 10. PMID: 31079922. 6: Ghosh AK, Reddy GC, Kovela S, Relitti N, Urabe VK, Prichard BE, Jurica MS. Enantioselective Synthesis of a Cyclopropane Derivative of Spliceostatin A and Evaluation of Bioactivity. Org Lett. 2018 Nov 16;20(22):7293-7297. doi: 10.1021/acs.orglett.8b03228. Epub 2018 Nov 5. PMID: 30394756; PMCID: PMC6519444. 7: Yoshimoto R, Kaida D, Furuno M, Burroughs AM, Noma S, Suzuki H, Kawamura Y, Hayashizaki Y, Mayeda A, Yoshida M. Global analysis of pre-mRNA subcellular localization following splicing inhibition by spliceostatin A. RNA. 2017 Jan;23(1):47-57. doi: 10.1261/rna.058065.116. Epub 2016 Oct 17. PMID: 27754875; PMCID: PMC5159648. 8: Larrayoz M, Blakemore SJ, Dobson RC, Blunt MD, Rose-Zerilli MJ, Walewska R, Duncombe A, Oscier D, Koide K, Forconi F, Packham G, Yoshida M, Cragg MS, Strefford JC, Steele AJ. The SF3B1 inhibitor spliceostatin A (SSA) elicits apoptosis in chronic lymphocytic leukaemia cells through downregulation of Mcl-1. Leukemia. 2016 Feb;30(2):351-60. doi: 10.1038/leu.2015.286. Epub 2015 Oct 21. PMID: 26488112. 9: Ghosh AK, Chen ZH, Effenberger KA, Jurica MS. Enantioselective total syntheses of FR901464 and spliceostatin A and evaluation of splicing activity of key derivatives. J Org Chem. 2014 Jun 20;79(12):5697-709. doi: 10.1021/jo500800k. Epub 2014 May 30. PMID: 24873648; PMCID: PMC4066912. 10: Ghosh AK, Chen ZH. Enantioselective syntheses of FR901464 and spliceostatin A: potent inhibitors of spliceosome. Org Lett. 2013 Oct 4;15(19):5088-91. doi: 10.1021/ol4024634. Epub 2013 Sep 19. PMID: 24050251; PMCID: PMC3827971. 11: Corrionero A, Miñana B, Valcárcel J. Reduced fidelity of branch point recognition and alternative splicing induced by the anti-tumor drug spliceostatin A. Genes Dev. 2011 Mar 1;25(5):445-59. doi: 10.1101/gad.2014311. PMID: 21363963; PMCID: PMC3049286. 12: Furumai R, Uchida K, Komi Y, Yoneyama M, Ishigami K, Watanabe H, Kojima S, Yoshida M. Spliceostatin A blocks angiogenesis by inhibiting global gene expression including VEGF. Cancer Sci. 2010 Nov;101(11):2483-9. doi: 10.1111/j.1349-7006.2010.01686.x. PMID: 20726856. 13: Roybal GA, Jurica MS. Spliceostatin A inhibits spliceosome assembly subsequent to prespliceosome formation. Nucleic Acids Res. 2010 Oct;38(19):6664-72. doi: 10.1093/nar/gkq494. Epub 2010 Jun 6. PMID: 20529876; PMCID: PMC2965229. 14: Lo CW, Kaida D, Nishimura S, Matsuyama A, Yashiroda Y, Taoka H, Ishigami K, Watanabe H, Nakajima H, Tani T, Horinouchi S, Yoshida M. Inhibition of splicing and nuclear retention of pre-mRNA by spliceostatin A in fission yeast. Biochem Biophys Res Commun. 2007 Dec 21;364(3):573-7. doi: 10.1016/j.bbrc.2007.10.029. Epub 2007 Oct 15. PMID: 17961508. 15: Kaida D, Motoyoshi H, Tashiro E, Nojima T, Hagiwara M, Ishigami K, Watanabe H, Kitahara T, Yoshida T, Nakajima H, Tani T, Horinouchi S, Yoshida M. Spliceostatin A targets SF3b and inhibits both splicing and nuclear retention of pre-mRNA. Nat Chem Biol. 2007 Sep;3(9):576-83. doi: 10.1038/nchembio.2007.18. Epub 2007 Jul 22. PMID: 17643111.