An inhibitor of FoxM1
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Thiostrepton

Item No. 19200

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(7R,8S)-2-carboxy-7,8-dihydro-8-hydroxy-4-[(1S)-1-hydroxyethyl]-7-quinolinyl]-L-isoleucyl-L-alanyl-2,3-didehydroalanyl-L-alanyl-2-[(4aR,11S,14Z,18S,21S,28S,32aS)-4a-amino-21-[(1S,2R)-1,2-dihydroxy-1-methylpropyl]-14-ethylidene-3,4,4a,9,10,11,12,13,14,18,19,20,21,27,28,32a-hexadecahydro-11,28-bis[(1R)-1-hydroxyethyl]-9,12,19,26-tetraoxo-17H,26H-8,5:18,15:25,22:32,29-tetranitrilo-5H,15H-pyrido[3,2-m][1,11,17,24,4,7,20,27]tetrathiatetraazacyclotriacontin-2-yl]-4-thiazolecarbonyl-2,3-didehydroalanyl-2,3-didehydro-alaninamide, (1→528)-lactone
CAS Number
1393-48-2
Synonyms
  • Bryamycin
  • NSC 81722
  • NSC 170365
  • Thiactin
  • Thiostreptin A
Molecular Formula
C72H85N19O18S5
Formula Weight
1664.9
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 1 mg/ml
SMILES
O=C([C@@H](NC(C(NC([C@@H](NC([C@@H](N[C@H](C=C1)[C@]2([H])O)[C@@H](C)CC)=O)C)=O)=C)=O)C)N[C@](C3=NC(C(N[C@H](C(N/C(C4=N[C@]5([H])CS4)=C\C)=O)[C@H](O)C)=O)=CS3)(CCC(C6=NC(C(NC(C(NC(C(N)=O)=C)=O)=C)=O)=CS6)=N7)[C@@]7([H])C8=CSC([C@@]([C@H](OC(C9=CC([C@@H](O)C)=C1C2=N9)=O)C)([H])NC(C%10=CSC([C@](NC5=O)([H])[C@](C)(O)[C@H](O)C)=N%10)=O)=N8
InChi Code
InChI=1S/C72H85N19O18S5/c1-14-26(3)47-63(105)78-30(7)57(99)75-28(5)56(98)76-31(8)58(100)91-72-19-18-40(66-85-43(22-111-66)59(101)77-29(6)55(97)74-27(4)54(73)96)81-52(72)42-21-112-67(83-42)49(34(11)109-69(107)41-20-37(32(9)92)36-16-17-39(79-47)51(95)5
InChi Key
NSFFHOGKXHRQEW-AIHSUZKVSA-N
Origin
Bacterium/Streptomyces laurentii
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Thiostrepton is a natural peptide thiazole antibiotic that inhibits FoxM1 in mammalian cells, preventing the expression of FoxM1-regulated genes, which includes FoxM1 itself.1,2 Through this mechanism, thiostrepton prevents proliferation and induces apoptosis in human cancer cells.1 These effects correlate with the ability of thiostrepton to act as a proteasome inhibitor.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bhat, U.G., Halasi, M., and Gartel, A.L. Thiazole antibiotics target FoxM1 and induce apoptosis in human cancer cells. PLoS One 4(5), e5592 (2009).

    2. Gartel, A.L. Thiazole antibiotics siomycin A and thiostrepton inhibit the transcriptional activity of FOXM1. Front. Oncol. 3, 150 (2013).

    3. Gartel, A.L. Suppression of the oncogenic transcription factor FOXM1 by proteasome inhibitors. Scientifica (Cairo) 2014:596528, (2014).

    Product Citations

    Marín, L., Gutiérrez-Del-Río, I., Villar, C.J., et al. De novo biosynthesis of garbanzol and fustin in Streptomyces albus based on a potential flavanone 3-hydroxylase with 2-hydroxylase side activity. Microb. Biotechnol. 14(5), 2009-2024 (2021).