Illudin M

Names

[ Name ]:
Illudin M

[Synonym ]:
illudin M
(3'S,6'R)-2',3'-Dihydro-3',6'-dihydroxy-2',2',4',6'-tetramethylspiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one
(3'S,6'R)-2',3'-Dihydro-2',2',4',6'-tetramethylspiro(cyclopropane-1,5'-[5H]inden)-7'(6'H)-one

Biological Activity

[Description]:

Illudin M is a cytotoxic fungal sesquiterpene that can be isolated from the culture medium of Omphalotus olearius mushrooms. Illudin M can alkylate DNA. Illudin M has anti-tumor activities[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA Alkylator/Crosslinker

[In Vitro]

Illudin M (0.01-10 μM; 24-120 hours) shows cytotoxicity and induction of apoptosis in vitro[1]. Apoptosis Analysis[1] Cell Line: Panc-1 pancreatic carcinoma, HT-29 colon adenocarcinoma, non-malignant human foreskin fibroblasts (HFs) Concentration: 0.01 μM, 1 μM, 10 μM Incubation Time: 24 hours, 48 hours,72 hours, 96 hours, 120 hours Result: Showed a comparable induction of apoptosis in the tumour cells (86% in Panc-1; 48% in HT-29), but an even greater one in the HF (89%).

[References]

[1]. Rainer Schobert, et al. Conjugates of the fungal cytotoxin illudin M with improved tumour specificity. Bioorg Med Chem. 2008 Sep 15;16(18):8592-7.

[2]. Dr. Philipp Le, et al. A Chemical Proteomic Analysis of Illudin‐Interacting Proteins. Chemistry. 2019 Sep 25; 25(54): 12644–12651.

Chemical & Physical Properties

[ Density]:
1.24g/cm3

[ Boiling Point ]:
452.4ºC at 760mmHg

[ Molecular Formula ]:
C₁₅H₂₀O₃

[ Molecular Weight ]:
248.31700

[ Flash Point ]:
241.5ºC

[ Exact Mass ]:
248.14100

[ PSA ]:
57.53000

[ LogP ]:
1.74390

[ Vapour Pressure ]:
4.36E-10mmHg at 25°C

[ Index of Refraction ]:
1.593

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: WH0204350

CHEMICAL NAME :: Spiro(cyclopropane-1,5'-(5H)inden)-7'(6'H)-one, 2',3'-dihydro-3'-beta,6'-alpha-dihydroxy-2',2 4',6'-tetramethyl-

CAS REGISTRY NUMBER :: 1146-04-9

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C15-H20-O3

MOLECULAR WEIGHT :: 248.35

WISWESSER LINE NOTATION :: L56 FV HXTJ BQ C1 C1 GQ G1 I1 H-& AL3XTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 15 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Rodent - hamster Lung

DOSE/DURATION :: 31250 ng/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 215,179,1989