1149-99-1

Basic information

• Product Name: illudin S
• Synonyms: illudin S;(2'S,3'R,6'R)-2',3'-Dihydro-3',6'-dihydroxy-2'-hydroxymethyl-2',4',6'-trimethylspiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one;Illusin S;Lampterol;NSC-626369;Illudin;Illudine S;Lunamycin
• CAS NO: 1149-99-1
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.35
• Mol File: 1149-99-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 124-126℃
• Boiling Point: 327.55°C (rough estimate)
• Flash Point: 276.1°C
• Appearance: /
• Density: 1.0583 (rough estimate)
• Vapor Pressure: 1.61E-12mmHg at 25°C
• Refractive Index: 1.4300 (estimate)
• Storage Temp.: -20°C, Inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: illudin S(CAS DataBase Reference)
• NIST Chemistry Reference: illudin S(1149-99-1)
• EPA Substance Registry System: illudin S(1149-99-1)

Safety Data

• Hazardous Substances Data: 1149-99-1(Hazardous Substances Data)

Usage

Description

Illudin S is a potent antitumor sesquiterpene derived from the fungus Clitocybe illudens, characterized by its unique DNA alkylating actions and cytotoxic properties. It is metabolically activated to reactive intermediates that bind to DNA, causing a complete block of cell cycling at the G1-S phase interface, particularly in myeloid and T-lymphocyte leukemia cells. Illudin S metabolites induce DNA damage that is not repaired by the processes that counter conventional DNA alkylating agents.

Uses

Used in Anticancer Applications:
Illudin S is used as an anticancer agent for its potent activity against multi-drug resistant tumors. It is particularly effective against myeloid and T-lymphocyte leukemia cells, even in cases where the cells display resistance to other chemotherapeutic agents. Illudin S's unique DNA damage mechanism makes it a valuable compound in the fight against cancer.
Used in Pharmaceutical Research:
Illudin S is used as a research compound for understanding the mechanisms of DNA alkylation and cell cycle inhibition. Its unique mode of action provides insights into the development of new anticancer drugs and potential strategies for overcoming drug resistance in cancer treatment.
Used in Drug Development:
Illudin S is used as a lead compound in the development of new antitumor drugs. Its potent activity against multi-drug resistant tumors and unique DNA damage mechanism make it an attractive candidate for further research and development in the pharmaceutical industry.

InChI:InChI=1/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

Upstream product

• 1099-42-9 ((2'S,3'R,6'R)-3'-acetoxy-6'-hydroxy-2',4',6'-trimethyl-7'-oxo-2',3',6',7'-tetrahydrospiro[cyclopropane-1,5'-inden]-2'-yl)methyl acetate 
• 127-09-3 sodium acetate 

Downstream Products

• 158440-71-2 [14C]-Irofulven 
• 3677-16-5 ((2'S,3'R,6'R)-3',6'-dihydroxy-2',4',6'-trimethyl-7'-oxo-2',3',6',7'-tetrahydrospiro[cyclopropane-1,5'-inden]-2'-yl)methyl 3,5-dinitrobenzoate 
• 33781-60-1 (R)-6’-hydroxy-2’,4’,6’-trimethylspiro[cyclopropane-1,5’-inden]-7’(6’H)-one 
• 25532-76-7 Dihydroilludin S 

Relevant articles and documents

AFFINITY ILLUDOFULVENE CONJUGATES

In an embodiment of the invention, a composition for treating a cell population comprises a medicant. The medicant moiety can be an illudofulvene analog. In an embodiment of the invention, a composition for treating a cell population comprises an Affinity Medicant Conjugate (AMC). The affinity moiety can be an antibody, an antibody fragment, a receptor protein, a peptidic growth factor, an anti-angiogenic protein, a specific binding peptide, protease cleavable peptide, a glycopeptide, a peptide, a peptidic toxin, a protein toxin and an oligonucleotide. The affinity moiety can be covalently bound to the medicant via a linker.