illudin S Chemical Properties

Melting point:

124-126℃

Boiling point:

327.55°C (rough estimate)

Density 

1.0583 (rough estimate)

refractive index 

1.4300 (estimate)

storage temp. 

-20°C, Inert atmosphere

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

A light yellow solid

pka

12.50±0.70(Predicted)

color 

Off-white to yellow

InChI

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

InChIKey

DDLLIYKVDWPHJI-RDBSUJKOSA-N

SMILES

C12([C@](O)(C)C(=O)C3C(=C1C)[C@@H](O)[C@@](CO)(C)C=3)CC2

illudin S Usage And Synthesis

Description

Illudins are fungal sesquiterpenes that, through their unique DNA alkylating actions, have anticancer potential. 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). T-lymphocyte leukemia CEM cells that are resistant to doxorubicin , epipodophyllotoxins, and 1-β-D-arabinofuranosylcytosine display only 2-fold increased resistance to illudin S. Illudin S metabolites induce DNA damage that is not repaired by the processes that counter conventional DNA alkylating agents.

Uses

Illudin S is potent antitumor sesquiterpene, first isolated from the fungus, Clitocybe illudens, in 1963. Illudin S is metabolically activated to reactive intermediates that bind DNA. The DNA damage appears to differ from that of other reactive metabolites. Importantly, illudin S exhibits in vitro and in vivo potency against multi-drug resistant tumours.

Uses

Illudin S is a potent antitumor sesquiterpene.

Definition

ChEBI: Illudin S is a sesquiterpenoid.

References

[1] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[2] NICOLAAS G.J JASPERS . Anti-tumour compounds illudin S and Irofulven induce DNA lesions ignored by global repair and exclusively processed by transcription- and replication-coupled repair pathways[J]. DNA Repair, 2002, 1 12: Pages 1027-1038. DOI: 10.1016/s1568-7864(02)00166-0

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