A DNA alkylating agent
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Illudin S

Item No. 17451

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2'S,3'R,6'R)-2',3'-dihydro-3',6'-dihydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-spiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one
CAS Number
1149-99-1
Synonyms
  • Lampterol
  • NSC 400979
  • NSC 626369
Molecular Formula
C15H20O4
Formula Weight
264.3
Purity
≥98%
Formulation (Request formulation change)
A light yellow solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C1C2=C[C@](CO)(C)[C@H](O)C2=C(C)C3(CC3)[C@]1(O)C
InChi Code
InChI=1S/C15H20O4/c1-8-10-9(6-13(2,7-16)12(10)18)11(17)14(3,19)15(8)4-5-15/h6,12,16,18-19H,4-5,7H2,1-3H3/t12-,13+,14+/m1/s1
InChi Key
DDLLIYKVDWPHJI-RDBSUJKOSA-N
Origin
Fungus/Pleurotus lampas
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $334

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    Product Description

    Illudin S is a cytotoxic illudin that is converted, intracellularly, to metabolites that cause a complete block of cell cycling at the G1-S phase interface, particularly in myeloid and T-lymphocyte leukemia cells (IC50 = 6-11 nM).1 T-lymphocyte leukemia CEM cells that are resistant to doxorubicin (Item No. 15007), epipodophyllotoxins, and 1-β-D-arabinofuranosylcytosine display only 2-fold increased resistance to illudin S.1 Illudin S metabolites induce DNA damage that is not repaired by the processes that counter conventional DNA alkylating agents.2,3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kelner, M.J., McMorris, T.C., Beck, W.T., et al. Preclinical evaluation of illudins as anticancer agents. Cancer Res. 47(12), 3186-3189 (1987).

    2. Schobert, R., Knauer, S., Seibt, S., et al. Anticancer active illudins: Recent developments of a potent alkylating compound class. Curr. Med. Chem. 18, 790-807 (2011).

    3. Kelner, M.J., McMorris, T.C., Estes, L., et al. Characterization of illudin S sensitivity in DNA repair-deficient Chinese hamster cells. Unusually high sensitivity of ERCC2 and ERCC3 DNA helicase-deficient mutants in comparison to other chemotherapeutic agents. Biochem. Pharmacol. 48, 403-409 (1994).

    4. Jaspers, N.G.J., Raams, A., Kelner, M.J., et al. Anti-tumour compounds illudin S and Irofulven induce DNA lesions ignored by global repair and exclusively processed by transcription- and replication-coupled repair pathways. DNA Repair (Amst) 1(12), 1027-1038 (2002).