1146-04-9

Usage

Uses

Used in Anticancer Applications:
Illudin M is utilized as a cytotoxic agent in the development of potential anticancer drugs. It is particularly effective against various types of cancer due to its ability to alkylate DNA, thereby inhibiting cell growth and replication. The compound has shown promise in the development of less toxic and more effective cancer treatments.
Used in Pharmaceutical Research:
Illudin M serves as a base structure for pharmaceutical research and development. Its alkylating properties and cytotoxic effects make it a valuable compound for the creation of new anticancer agents. Researchers are working on modifying the structure of illudin M to improve its efficacy and reduce potential side effects, with the ultimate goal of developing more effective cancer treatments.
Used in Drug Delivery Systems:
Similar to gallotannin, illudin M can also be incorporated into drug delivery systems to enhance its applications and efficacy against cancer cells. Various organic and metallic nanoparticles can be employed as carriers for illudin M delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes. This approach can potentially increase the effectiveness of illudin M as an anticancer agent and minimize any adverse effects associated with its use.

InChI:InChI=1/C15H20O3/c1-8-10-9(7-13(2,3)12(10)17)11(16)14(4,18)15(8)5-6-15/h7,12,17-18H,5-6H2,1-4H3/t12-,14+/m1/s1

Upstream product

• 127-09-3 sodium acetate 

Downstream Products

• 1075723-53-3 C₂₉H₃₇Cl₂NO₄ 
• 144156-48-9 (R)-4,6,6,8a-Tetramethyl-2,3,6,8a-tetrahydro-indeno[5,6-b]furan-8-one 
• 112953-12-5 Deoxyilludin M 
• 34338-99-3 Dihydroilludin M 
• 28282-65-7 dehydroilludin M 

Relevant academic research and scientific papers

Synthesis of [3H]-illudin S, [3H]-acylfulvene, [3H]and[14C]- hydroxymethylacylfulvene (MGI 114)

Tritiated derivatives of the toxic sesquiterpene illudin S (1) have been prepared by fermentation of Omphalotus illudens in the presence of [3H]- sodium acetate. [3H]-illudin S was converted to antitumor [3H]-acylfulvene (4) by treatment with dilute sulfuric acid. Antitumor [14C]- hydroxymethylacylfulvene (5) was best prepared by reacting acylfulvene with [14C]-paraformaldehyde in dilute sulfuric acid.

Total synthesis of (±)-illudin M

(+)-Illudin M (1) was synthesized in six steps starting from 1-acetyl-1-(diazoacetyl)cyclopropane (4) and 4-bromo-5,5-dimethyl-2-cyclopentenone (5). The key step of the synthesis featured a carbonyl ylide 1,3-dipolar cycloaddition reaction that was mediat

Cytotoxic Illudane Sesquiterpenes from the Fungus Granulobasidium vellereum (Ellis and Cragin) Jülich

Eight illudane sesquiterpenes were obtained from the wood-decomposing fungus Granulobasidium vellereum (Ellis and Cragin) Jülich; among them were the enantiomers of the known compounds illudin M (1) and dihydroilludin M (4) and the diastereomers of illudin M (2) and illudin S (3), as well as two previously undescribed illudanes (5, 6). The cytotoxicity of compounds 1-4 and 6 was evaluated against two tumor cell lines (Huh7 and MT4), which showed that compounds 1-3 had potent cytotoxic activity, whereas compounds 4 and 6 had no or only moderate effects at concentrations up to 400 μM. Surprisingly, both compounds 2 and 3 were about 10 times more potent than 1. When the chemical reactivity of 1 and 2 was tested, compound 2 was shown to have a substantially higher reaction rate when reacted both with 2 M HCl and with cysteine, indicating that the difference in cytotoxicity is probably due to chemical reactivity and not to enzymatic affinity.