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MedKoo Cat#: 330052 | Name: Thailanstatin A
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Description:

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

Thailanstatin A, also known as TST-A, is a potent antiproliferative agent, which was isolated from the fermentation broth of B. thailandensis MSMB43

Chemical Structure

Thailanstatin A
Thailanstatin A
CAS#1426953-21-0

Theoretical Analysis

MedKoo Cat#: 330052

Name: Thailanstatin A

CAS#: 1426953-21-0

Chemical Formula: C28H41NO9

Exact Mass: 535.2781

Molecular Weight: 535.63

Elemental Analysis: C, 62.79; H, 7.72; N, 2.62; O, 26.88

Price and Availability

Size Price Availability Quantity
25mg USD 1,650.00 2 Weeks
50mg USD 2,950.00 2 Weeks
100mg USD 5,250.00 2 Weeks
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Related CAS #
No Data
Synonym
Thailanstatin A, TST-A;
IUPAC/Chemical Name
2-[(3R,4R,5R,7S)-5-[(1E,3E)-5-[(2S,3S,5R,6R)-5-[[(Z,4S)-4-acetyloxypent-2-enoyl]amino]-3,6-dimethyloxan-2-yl]-3-methylpenta-1,3-dienyl]-4-hydroxy-1,6-dioxaspiro[2.5]octan-7-yl]acetic acid
InChi Key
GJKQDOMCDFJANR-FUDLAKRJSA-N
InChi Code
InChI=1S/C28H41NO9/c1-16(7-10-24-27(34)28(15-35-28)14-21(38-24)13-26(32)33)6-9-23-17(2)12-22(19(4)37-23)29-25(31)11-8-18(3)36-20(5)30/h6-8,10-11,17-19,21-24,27,34H,9,12-15H2,1-5H3,(H,29,31)(H,32,33)/b10-7+,11-8-,16-6+/t17-,18-,19+,21+,22+,23-,24+,27+,28+/m0/s1
SMILES Code
O=C(O)C[C@H](C1)O[C@H](/C=C/C(C)=C/C[C@@H]2O[C@H](C)[C@H](NC(/C=C\[C@@H](OC(C)=O)C)=O)C[C@@H]2C)[C@@H](O)[C@@]31CO3
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 535.63 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: Nicolaou KC, Rhoades D, Kumar SM. Total Syntheses of Thailanstatins A-C, Spliceostatin D, and Analogues Thereof. Stereodivergent Synthesis of Tetrasubstituted Dihydro- and Tetrahydropyrans and Design, Synthesis, Biological Evaluation, and Discovery of Potent Antitumor Agents. J Am Chem Soc. 2018 Jul 5;140(26):8303-8320. doi: 10.1021/jacs.8b04634. Epub 2018 Jun 26. PMID: 29943984. 2: Ghosh AK, Veitschegger AM, Nie S, Relitti N, MacRae AJ, Jurica MS. Enantioselective Synthesis of Thailanstatin A Methyl Ester and Evaluation of in Vitro Splicing Inhibition. J Org Chem. 2018 May 4;83(9):5187-5198. doi: 10.1021/acs.joc.8b00593. Epub 2018 Apr 26. PMID: 29696980; PMCID: PMC5972027. 3: Wang B, Lo UG, Wu K, Kapur P, Liu X, Huang J, Chen W, Hernandez E, Santoyo J, Ma SH, Pong RC, He D, Cheng YQ, Hsieh JT. Developing new targeting strategy for androgen receptor variants in castration resistant prostate cancer. Int J Cancer. 2017 Nov 15;141(10):2121-2130. doi: 10.1002/ijc.30893. Epub 2017 Jul 31. PMID: 28722220; PMCID: PMC5777133. 4: Kulkarni C, Finley JE, Bessire AJ, Zhong X, Musto S, Graziani EI. Development of Fluorophore-Labeled Thailanstatin Antibody-Drug Conjugates for Cellular Trafficking Studies. Bioconjug Chem. 2017 Apr 19;28(4):1041-1047. doi: 10.1021/acs.bioconjchem.6b00718. Epub 2017 Mar 1. PMID: 28191936. 5: Puthenveetil S, Loganzo F, He H, Dirico K, Green M, Teske J, Musto S, Clark T, Rago B, Koehn F, Veneziale R, Falahaptisheh H, Han X, Barletta F, Lucas J, Subramanyam C, O'Donnell CJ, Tumey LN, Sapra P, Gerber HP, Ma D, Graziani EI. Natural Product Splicing Inhibitors: A New Class of Antibody-Drug Conjugate (ADC) Payloads. Bioconjug Chem. 2016 Aug 17;27(8):1880-8. doi: 10.1021/acs.bioconjchem.6b00291. Epub 2016 Jul 28. PMID: 27412791. 6: Nicolaou KC, Rhoades D, Lamani M, Pattanayak MR, Kumar SM. Total Synthesis of Thailanstatin A. J Am Chem Soc. 2016 Jun 22;138(24):7532-5. doi: 10.1021/jacs.6b04781. Epub 2016 Jun 13. PMID: 27266914. 7: Liu X, Zhu H, Biswas S, Cheng YQ. Improved production of cytotoxic thailanstatins A and D through metabolic engineering of Burkholderia thailandensis MSMB43 and pilot scale fermentation. Synth Syst Biotechnol. 2016 Apr 1;1(1):34-38. doi: 10.1016/j.synbio.2016.02.002. PMID: 29062925; PMCID: PMC5640593. 8: Eustáquio AS, Chang LP, Steele GL, O Donnell CJ, Koehn FE. Biosynthetic engineering and fermentation media development leads to gram-scale production of spliceostatin natural products in Burkholderia sp. Metab Eng. 2016 Jan;33:67-75. doi: 10.1016/j.ymben.2015.11.003. Epub 2015 Nov 24. PMID: 26620532. 9: Jain A, Liu X, Wordinger RJ, Yorio T, Cheng YQ, Clark AF. Effects of thailanstatins on glucocorticoid response in trabecular meshwork and steroid- induced glaucoma. Invest Ophthalmol Vis Sci. 2013 May 3;54(5):3137-42. doi: 10.1167/iovs.12-11480. PMID: 23548621; PMCID: PMC3645369. 10: Liu X, Biswas S, Berg MG, Antapli CM, Xie F, Wang Q, Tang MC, Tang GL, Zhang L, Dreyfuss G, Cheng YQ. Genomics-guided discovery of thailanstatins A, B, and C As pre-mRNA splicing inhibitors and antiproliferative agents from Burkholderia thailandensis MSMB43. J Nat Prod. 2013 Apr 26;76(4):685-93. doi: 10.1021/np300913h. Epub 2013 Mar 21. PMID: 23517093; PMCID: PMC3696399.