Pladienolide B | CAS#445493-23-2

MedKoo Cat#: 525882 | Name: Pladienolide B

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Description:

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

Pladienolide B is an mRNA splicing inhibitor.

Chemical Structure

Pladienolide B

CAS#445493-23-2

Theoretical Analysis

MedKoo Cat#: 525882

Name: Pladienolide B

CAS#: 445493-23-2

Chemical Formula: C31H50O8

Exact Mass: 550.3506

Molecular Weight: 550.73

Elemental Analysis: C, 67.61; H, 9.15; O, 23.24

Price and Availability

Size	Price	Availability	Quantity
100µg	USD 350.00	2 Weeks

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Related CAS #

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Synonym

Pladienolide B

IUPAC/Chemical Name

(4R,7R,8S,9E,11S,12S)-8-(Acetyloxy)-4,7-dihydroxy-12-[(1E,3E,5S)-6-[(2R,3R)-3-[(1R,2S)-2-hydroxy-1-methylbutyl]-2-oxiranyl]-1,5-dimethyl-1,3-hexadien-1-yl]-7,11-dimethyloxacyclododec-9-en-2-one

InChi Key

OPXRWNGNSITCLV-KLRJOTOSSA-N

InChi Code

InChI=1S/C31H50O8/c1-8-10-25(34)22(5)30-26(38-30)17-19(2)11-9-12-20(3)29-21(4)13-14-27(37-23(6)32)31(7,36)16-15-24(33)18-28(35)39-29/h9,11-14,19,21-22,24-27,29-30,33-34,36H,8,10,15-18H2,1-7H3/b11-9+,14-13+,20-12+/t19-,21+,22-,24-,25+,26-,27+,29-,30-,31-/m1/s1

SMILES Code

O=C1O[C@H](/C(C)=C/C=C/[C@@H](C)C[C@@H](O2)[C@H]2[C@H](C)[C@@H](O)CCC)[C@@H](C)/C=C/[C@H](OC(C)=O)[C@](C)(O)CC[C@@H](O)C1

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 550.73 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

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Potential effect of spliceosome inhibition in small cell lung cancer irrespective of the MYC status. PLoS One. 2017 Feb 13;12(2):e0172209. doi: 10.1371/journal.pone.0172209. eCollection 2017. PubMed PMID: 28192473; PubMed Central PMCID: PMC5305228. 5: Tagishi K, Shimizu A, Endo K, Kito H, Niwa S, Fujii M, Ohya S. Defective splicing of the background K(+) channel K(2P)5.1 by the pre-mRNA splicing inhibitor, pladienolide B in lectin-activated mouse splenic CD4(+) T cells. J Pharmacol Sci. 2016 Nov;132(3):205-209. doi: 10.1016/j.jphs.2016.10.007. Epub 2016 Nov 3. PubMed PMID: 27865709. 6: Kumar D, Kashyap MK, La Clair JJ, Villa R, Spaanderman I, Chien S, Rassenti LZ, Kipps TJ, Burkart MD, Castro JE. Selectivity in Small Molecule Splicing Modulation. ACS Chem Biol. 2016 Oct 21;11(10):2716-2723. Epub 2016 Aug 8. PubMed PMID: 27499047. 7: Ling Y, Alshareef S, Butt H, Lozano-Juste J, Li L, Galal AA, Moustafa A, Momin AA, Tashkandi M, Richardson DN, Fujii H, Arold S, Rodriguez PL, Duque P, Mahfouz MM. Pre-mRNA splicing repression triggers abiotic stress signaling in plants. Plant J. 2017 Jan;89(2):291-309. doi: 10.1111/tpj.13383. Epub 2017 Jan 17. PubMed PMID: 27664942. 8: Dhar S, La Clair JJ, León B, Hammons JC, Yu Z, Kashyap MK, Castro JE, Burkart MD. A Carbohydrate-Derived Splice Modulator. J Am Chem Soc. 2016 Apr 20;138(15):5063-8. doi: 10.1021/jacs.5b13427. Epub 2016 Apr 8. PubMed PMID: 27058259. 9: Endo K, Kurokawa N, Kito H, Nakakura S, Fujii M, Ohya S. Molecular identification of the dominant-negative, splicing isoform of the two-pore domain K(+) channel K(2P)5.1 in lymphoid cells and enhancement of its expression by splicing inhibition. Biochem Pharmacol. 2015 Dec 1;98(3):440-52. doi: 10.1016/j.bcp.2015.10.002. Epub 2015 Oct 20. PubMed PMID: 26475531. 10: Koga M, Hayashi M, Kaida D. Splicing inhibition decreases phosphorylation level of Ser2 in Pol II CTD. Nucleic Acids Res. 2015 Sep 30;43(17):8258-67. doi: 10.1093/nar/gkv740. Epub 2015 Jul 21. PubMed PMID: 26202968; PubMed Central PMCID: PMC4787822. 11: Wan Y, Zheng X, Chen H, Guo Y, Jiang H, He X, Zhu X, Zheng Y. Splicing function of mitotic regulators links R-loop-mediated DNA damage to tumor cell killing. J Cell Biol. 2015 Apr 27;209(2):235-46. doi: 10.1083/jcb.201409073. PubMed PMID: 25918225; PubMed Central PMCID: PMC4411280. 12: Kashyap MK, Kumar D, Villa R, La Clair JJ, Benner C, Sasik R, Jones H, Ghia EM, Rassenti LZ, Kipps TJ, Burkart MD, Castro JE. Targeting the spliceosome in chronic lymphocytic leukemia with the macrolides FD-895 and pladienolide-B. Haematologica. 2015 Jul;100(7):945-54. doi: 10.3324/haematol.2014.122069. Epub 2015 Apr 10. PubMed PMID: 25862704; PubMed Central PMCID: PMC4486229. 13: Sato M, Muguruma N, Nakagawa T, Okamoto K, Kimura T, Kitamura S, Yano H, Sannomiya K, Goji T, Miyamoto H, Okahisa T, Mikasa H, Wada S, Iwata M, Takayama T. High antitumor activity of pladienolide B and its derivative in gastric cancer. Cancer Sci. 2014 Jan;105(1):110-6. doi: 10.1111/cas.12317. Epub 2013 Dec 4. PubMed PMID: 24635824; PubMed Central PMCID: PMC4317874. 14: Lagisetti C, Yermolina MV, Sharma LK, Palacios G, Prigaro BJ, Webb TR. Pre-mRNA splicing-modulatory pharmacophores: the total synthesis of herboxidiene, a pladienolide-herboxidiene hybrid analog and related derivatives. ACS Chem Biol. 2014 Mar 21;9(3):643-8. doi: 10.1021/cb400695j. Epub 2013 Dec 30. PubMed PMID: 24377313; PubMed Central PMCID: PMC3962696. 15: Effenberger KA, Anderson DD, Bray WM, Prichard BE, Ma N, Adams MS, Ghosh AK, Jurica MS. Coherence between cellular responses and in vitro splicing inhibition for the anti-tumor drug pladienolide B and its analogs. J Biol Chem. 2014 Jan 24;289(4):1938-47. doi: 10.1074/jbc.M113.515536. Epub 2013 Dec 3. PubMed PMID: 24302718; PubMed Central PMCID: PMC3900944. 16: Villa R, Kashyap MK, Kumar D, Kipps TJ, Castro JE, La Clair JJ, Burkart MD. Stabilized cyclopropane analogs of the splicing inhibitor FD-895. J Med Chem. 2013 Sep 12;56(17):6576-82. doi: 10.1021/jm400861t. Epub 2013 Aug 21. PubMed PMID: 23919277; PubMed Central PMCID: PMC3809018. 17: Kumar VP, Chandrasekhar S. Enantioselective synthesis of pladienolide B and truncated analogues as new anticancer agents. Org Lett. 2013 Jul 19;15(14):3610-3. doi: 10.1021/ol401458d. Epub 2013 Jul 3. PubMed PMID: 23822896. 18: Ghosh AK, Anderson DD. Enantioselective total synthesis of pladienolide B: a potent spliceosome inhibitor. Org Lett. 2012 Sep 21;14(18):4730-3. Epub 2012 Sep 6. PubMed PMID: 22954141; PubMed Central PMCID: PMC3482479. 19: Yokoi A, Kotake Y, Takahashi K, Kadowaki T, Matsumoto Y, Minoshima Y, Sugi NH, Sagane K, Hamaguchi M, Iwata M, Mizui Y. Biological validation that SF3b is a target of the antitumor macrolide pladienolide. FEBS J. 2011 Dec;278(24):4870-80. doi: 10.1111/j.1742-4658.2011.08387.x. Epub 2011 Oct 31. PubMed PMID: 21981285. 20: Müller S, Mayer T, Sasse F, Maier ME. Synthesis of a pladienolide B analogue with the fully functionalized core structure. Org Lett. 2011 Aug 5;13(15):3940-3. doi: 10.1021/ol201464m. Epub 2011 Jun 27. PubMed PMID: 21707025.