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???S

???S
???S ??? ???
?? ??:
1149-99-1
???:
???S
???(??):
???S
???:
illudin S
???(??):
CS-1385;Illudin;Lampterol;Illusin S;Lunamycin;illudin S;NSC 400979;Illudine S;NSC-626369;(1R,2S,5R)-1,5-dihydroxy-2-(hydroxymethyl)-2,5,7-trimethylspiro[1H-indene-6,1'-cyclopropane]-4-one
CBNumber:
CB91318110
???:
C15H20O4
??? ??:
264.32
MOL ??:
1149-99-1.mol

???S ??

???
124-126℃
?? ?
327.55°C (rough estimate)
??
1.0583 (rough estimate)
???
1.4300 (estimate)
?? ??
-20°C, Inert atmosphere
???
DMSO(?? ???), ???(?? ???)
??? ??
A light yellow solid
?? ?? (pKa)
12.50±0.70(Predicted)
??
Off-white to yellow

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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.

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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.

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