An inhibitor of FoxM1
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Siomycin A

Item No. 15378

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-valyl-2,3-didehydroalanyl-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
12656-09-6
Synonyms
  • NSC 285116
Molecular Formula
C71H81N19O18S5
Formula Weight
1648.9
Purity
≥85%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: Soluble
SMILES
O=C(NC(C(NC(C(N[C@@H](C)C(N[C@@]1(CCC(C2=NC(C(NC(C(NC(C(N)=O)=C)=O)=C)=O)=CS2)=N[C@]1([H])C3=CSC4=N3)C5=NC(C(NC(C(N/C(C6=NC(C(N[C@@](C7=NC8=CS7)([H])[C@@]([C@H](O)C)(O)C)=O)CS6)=C\C)=O)[C@H](O)C)=O)=CS5)=O)=O)=C)=O)=C)[C@H](C(C)C)NC9C(O)C%10=NC(C(O[C@H](C)[C@]4([H])NC8=O)=O)=CC([C@@H](O)C)=C%10C=C9
InChi Code
InChI=1S/C71H81N19O18S5/c1-14-37-64-83-44(22-109-64)61(103)89-52(70(13,107)34(12)93)67-85-43(23-112-67)59(101)88-48-33(11)108-68(106)40-19-36(31(9)91)35-15-16-38(50(94)49(35)79-40)78-46(25(2)3)62(104)77-29(7)56(98)74-27(5)55(97)75-30(8)57(99)90-71(69-86-45(24-113-69)60(102)87-47(32(10)92)63(105)81-37)18-17-39(80-51(71)41-20-111-66(48)82-41)65-84-42(21-110-65)58(100)76-28(6)54(96)73-26(4)53(72)95/h14-16,19-21,23-25,30-34,38,44,46-48,50-52,78,91-94,107H,4-7,17-18,22H2,1-3,8-13H3,(H2,72,95)(H,73,96)(H,74,98)(H,75,97)(H,76,100)(H,77,104)(H,81,105)(H,87,102)(H,88,101)(H,89,103)(H,90,99)/b37-14-/t30-,31-,32+,33+,34+,38?,44?,46-,47?,48-,50?,51+,52+,70+,71+/m0/s1
InChi Key
AKFVOKPQHFBYCA-OFENGFFDSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $436

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    Product Description

    The mammalian transcription factor forkhead box M1 (FoxM1) is induced during G1 phase, with expression continuing through S phase and mitosis. Siomycin A is a peptide thiazole antibiotic, first isolated from S. sioyaensis, that interacts with the 23S rRNA of bacteria.1 It inhibits FoxM1 (IC50 = ~5 μM), preventing the expression of FoxM1-regulated genes, which includes FoxM1 itself.2,3 Through this mechanism, siomycin A prevents proliferation and induces apoptosis in certain types of stem cells as well as cancer cells.4,5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tori, K., Tokura, K., Yoshimura, Y., et al. 1H NMR spectral evidence for the structure and conformation of peptide antibiotic siomycin-A. J. Antibiot. (Tokyo) 32(10), 1072-1077 (1979).

    2. Radhakrishnan, S.K., Bhat, U.G., Hughes, D.E., et al. Identification of a chemical inhibitor of the oncogenic transcription factor forkhead box M1. Cancer Res. 66(19), 9731-9735 (2006).

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

    4. Nakano, I., Joshi, K., Visnyei, K., et al. Siomycin A targets brain tumor stem cells partially through a MELK-mediated pathway. Neuro. Oncol. 13(6), 622-634 (2011).

    5. Joshi, K., Banasavadi-Siddegowda, Y., Mo, X., et al. MELK-dependent FOXM1 phosphorylation is essential for proliferation of glioma stem cells. Stem Cells 31(6), 1051-1063 (2013).

    6. 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).